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Published: 4 June 2021
Last updated: 20 February 2023

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1

Deeb, Ali, Besher Bayoumy, Fathy Yasine, and Rida Fikry. "Pyridazine Derivatives and Related Compounds, Part 4. Pyrrolo[2,3-c]pyridazines and Furo[2,3-c]pyndazines, Synthesis and Some Reactions." Zeitschrift für Naturforschung B 47, no. 3 (March 1, 1992): 418–23. http://dx.doi.org/10.1515/znb-1992-0320.

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Ethyl 5-amino-3,4-diphenyl-7H-pyrrolo[2,3-c]pyridazine-6-carboxylate (1), ethyl 5-aminofuro[ 2,3-c]pyridazine-6-carboxylate (2) and 5-aminofuro[2,3-c]pyridazine-6-carboxamide (3), are obtained from 4-cyano-5,6-diphenyl-3(2H)-pyridazinone. 5-Acetamido and 5-chloroacetamido derivatives prepared from 1, undergo cyclization on heating to form 2-substituted pyridazino[4',3':4,5]pyrrolo[3,2-d]oxazin-4(5H)-one (5a, b). The reaction of 1 and 2 with hydrazine gave 6-carbohydrazide derivatives (7 a, b). Compound 3 undergoes condensation with acetyl chloride, chloroacetyl chloride, benzoyl chloride, formamide and carbon disulphide to furnish the corresponding pyrimido[4',5' :4,5]furo[2,3-c]pyridazin-4(3 H)-one derivatives. The reaction of 1 with o-aminophenol gave 3,4-diphenyl-11-oxo-10,11-dihydro-12H -pyridazino[ 4',3' :4,5]pyrrolo[3,2-b][1,5]benzoxazepine.
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2

Barlin, GB. "Imidazo[1,2-B]Pyridazines. I. Some 3-Alkoxy-6-Halogeno-2-Phenyl-(and 4′-Substituted Phenyl)Imidazo[1,2-B]Pyridazines and 3-Methoxy-2,6-Diphenylimidazo[1,2-B]Pyridazine." Australian Journal of Chemistry 39, no. 11 (1986): 1803. http://dx.doi.org/10.1071/ch9861803.

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A series of 3-alkoxy-6-halogeno-2-phenyl(and 4′-substituted phenyl) imidazo [1,2-b] pyridazines (1) and 3-methoxy-2,6- diphenylimidazo [1,2-b] pyridazine have been prepared from the relevant pyridazin-3-amines and arylglyoxals, followed by O- alkylation of the corresponding imidazo [1,2-b]pyridazin-3(5H)-ones with diazoalkanes. 6- Chloro-3-methoxy-2-phenylimidazo[2,1-a] phthal-azine was prepared similarly.
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3

Barlin, GB, LP Davies, PW Harrison, NW Jacobsen, and AC Willis. "Imidazo[1,2-b]Pyridazines. XVI. Synthesis and Central Nervous System Activities of Some 6-(Chloro, Alkylthio, Phenylthio, Benzylthio or Pyridinylmethylthio)-3-(unsubstituted, benzamidomethyl or methoxy)-2-(styryl or benzoyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 47, no. 11 (1994): 1989. http://dx.doi.org/10.1071/ch9941989.

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Some 6-( chloro, alkylthio, phenylthio, benzylthio or pyridinylmethylthio )-3-( unsubstituted , benzamidomethyl or methoxy )-2-styrylimidazo[1,2-b] pyridazines and 6-chloro-3-( unsubstituted and benzamidomethyl )-2-benzoylimidazo[1,2-b] pyridazines have been prepared and tested for their ability to displace [3H]diazepam from rat brain plasma membranes. The structures of 6-chloro-2-benzoyl[and 6-fluoro-2-(4′-tolyl)] imidazo [1,2-b] pyridazine have been confirmed by X-ray analyses. The reactions of 6-methylthio(and 6-phenylthio)pyridazin-3-amines with 3-bromo-1-phenylpropane-1,2-dione also have been investigated. The 6-substituted 3-unsubstituted 2-styryl(and benzoyl ) imidazo [1,2-b] pyridazines did not bind strongly to rat brain benzodiazepine receptors; nor did the 3-benzamidomethyl or 3-methoxy derivatives (cf. the 2-phenyl analogues). However, 3-benzamidomethyl-6-(pyridin-3-ylmethylthio)-2-styrylimidazo[1,2-b] pyridazine was an exception with IC50 68 nM.
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4

M., Sumakanth, V. Malla Reddy, V. S. H. Krishnan, and B. S. Sastry. "Synthesis of Some New Imidazo[1,2-b] Pyridazines." International Journal of Pharmaceutical Sciences and Nanotechnology 2, no. 1 (May 31, 2009): 471–76. http://dx.doi.org/10.37285/ijpsn.2009.2.1.14.

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Several 2,6-diaryl-imidazo[1,2-b]pyridazines (5 & 7) were prepared from 3-amino-6-aryl-pyridazines (3) which in turn were obtained from the corresponding 6-aryl-pyridazine-3(2H)-ones(1) via., 6-aryl-pyridazin-3(2H)-thiones (2) as intermediates, by a reaction with an appropriate a-halocarbonyl compounds (4) or a-haloacyl carbamates (6) in a suitable solvent at reflux temperature. The resulted products were characterized by their physical, analytical and spectral data.
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5

Kazimierczuk, Zygmunt, Jarosław Kamiński, and Flavio Meggio. "Studies on Improved Synthesis of 2'-Deoxyribonucleosides of Pyridazine Derivatives." Collection of Czechoslovak Chemical Communications 71, no. 6 (2006): 889–98. http://dx.doi.org/10.1135/cccc20060889.

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A number of 2'-deoxyribonucleosides of halogenated pyridazine derivatives were prepared by glycosylation of their respective potassium or DBU salts in acetone. The reaction yielded predominatly β-anomers that could be purified by simple crystallization or column chromatography. Of the studied pyridazines and deoxynucleosides, only 4-bromo-6-chloropyridazin-3-one and 6-chloro-2-(2'-deoxyribofuranosyl)pyridazin-3-one showed modest inhibition of CK2 kinase.
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6

Schmitt, Martine, Jean-Jacques Bourguignon, Gordon B. Barlin, and Les P. Davies. "Imidazo[1,2-b]pyridazines. XXIV Syntheses of Some 3-(Variously Substituted) Imidazo[1,2-b] pyridazines, 6-Substituted 2-Benzoyl- imidazo[1,2-b]pyridazines and Pyrimido[1,2-b]pyridazin- 5-ium-3-olates and their Interaction with Central and Mitochondrial Benzodiazepine Receptors." Australian Journal of Chemistry 50, no. 8 (1997): 779. http://dx.doi.org/10.1071/c97030.

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The syntheses of some ethyl 2-{2′-aryl-6′-(chloro, iodo and methoxy)imidazo[1,2-b]pyridazin-3′-yl}-2-(acetoxy, acylamino, hydroxy and methoxy)acetates, 6-methyl-2-(p-tolyl)- and 6-chloro-2-(4′-chlorophenyl)-3-trimethylammoniomethylimidazo[1,2-b]pyridazine iodides (and reactions thereof), 2-benzoyl 6-substituted imidazo[1,2-b]pyridazines and 7-(methoxy, chloro and phenylthio)-2-phenylpyrimido-[1,2-b]pyridazin-5-ium-3-olates are reported. The ability of these compounds to displace [3H]diazepam from rat forebrain membrane [central benzodiazepine receptor (BZR)] and rat kidney membrane [mitochondrial (peripheral-type) benzodiazepine receptor (PBR)] has been examined. The most active compound was ethyl 2-{6′-chloro-2′-(p-tolyl)imidazo[1,2-b]pyridazin-3′-yl}-2-hydroxyacetate with IC50 24 nM for displacement from the BZR and 91% displacement at 1000 nM from the PBR; the most selective for the PBR was 6-methyl-3-methylsulfonylmethyl-2-(p-tolyl)imidazo[1,2-b]pyridazine (PBR, IC50 92 nM; BZR, 15% inhibition of binding by [3H]diazepam at 1000 nM).
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7

Barlin, GB, LP Davies, SJ Ireland, and JK Zhang. "Imidazo[1,2-b]pyridazines. XIV. Syntheses and Central Nervous System Activities of Some 6-(Methoxy-, dimethoxy-, methylenedioxy-, chloro- and fluoro-)-3-alkoxy-2-phenyl(and substituted phenyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 46, no. 3 (1993): 353. http://dx.doi.org/10.1071/ch9930353.

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Syntheses are reported for 28 new 3-alkoxy-6-(3′-methoxy-,3′,4′-dimethoxy, 3′,4′-methylene-dioxy-, 2′- and 4′-chloro- and 4′-fluoro-benzylamino)-2-phenyl(and substituted phenyl) imidazo -[1,2-b] pyridazines from the corresponding 6-substituted pyridazin-3-amine 2-oxides with α- bromoacetophenones, followed by alkylation of the intermediate 3-hydroxyimidazo[1,2-b] pyridazines. In tests of the ability of these compounds to displace [3H]diazepam from rat brain membrane, 3-(2′-ethoxyethoxy)-6(3′-methoxybenzylamino)-2-phenyl- and 6(3′,4′-methylenedioxybenzylamino )-2-(3″,4″-methylenedioxyphenyl)-3-methoxy-imidazo[1,2-b] pyridazine bound most strongly, with IC50 values of 1nM.
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8

Sepsey Für, Csilla Sepsey, Gergő Riszter, Áron SzigetvárI, Miklós Dékány, György Keglevich, László HazaI, and Hedvig BölcskeI. "Novel Ring Systems: Spiro[Cycloalkane] Derivatives of Triazolo- and Tetrazolo-Pyridazines." Molecules 26, no. 8 (April 8, 2021): 2140. http://dx.doi.org/10.3390/molecules26082140.

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In orderto synthesize new pyridazine derivatives anellated with different nitrogen heterocyclic moieties, spiro[cycloalkane]pyridazinones were transformed into the corresponding thioxo derivatives via a reaction with phosphorus pentasulfide. The reaction of the formed 2,3-diazaspiro[5.5] undec-3-ene-1-thiones with hydrazine provided the corresponding 1-hydrazono-2,3-diazaspiro[5.5] undec-3-ene, whose diazotization led to the desired spiro[cyclohexane-1,8′-tetrazolo[1,5-b]pyridazines. The reaction of dihydropyridazinethiones with benzhydrazide afforded the corresponding 7H-spiro[[1,2,4]triazolo[4,3-b]pyridazin-8,1′-cyclohexanes]. As a result of our work, seven new pyridazinethione intermediates were prepared, which served as starting materials for the synthesis of two kinds of new ring systems: tetrazolo-pyridazines and triazolo-pyridazines. The six new annulated derivatives were characterized by physicochemical parameters. The new N-heterocycles are valuable members of the large family of pyridazines.
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9

Asif, Mohammad. "The Study of Pyridazine Compounds on Prostanoids: Inhibitors of COX, cAMP Phosphodiesterase, and TXA2Synthase." Journal of Chemistry 2014 (2014): 1–16. http://dx.doi.org/10.1155/2014/703238.

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The pyridazine moiety is an important structural feature of various pharmacological active compounds. Synthetic pyridazine compounds have been reported as effective antiprostaglandins (PGs), 5-lipoxygenase (5-LOX), and antiplatelet agents, that is, inhibitors of prostaglandin or cyclooxygenase (COX-I & COX-II) enzyme, platelet cAMP phosphodiesterase, and thromboxane A2 (TXA2) synthase. These compounds are selective and nonselective COX inhibitors and showed analgesic, anti-inflammatory, and antipyretic activity. Pyridazine compounds with antiplatelet agents inhibited TXA2enzyme. Pyridazines also exhibited antirheumatoid activity. These pyridazine compounds hold considerable interest relative to the preparation of organic intermediates and other anticipated biologically active compounds.
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10

Barlin, GB, LP Davies, SJ Ireland, and JK Zhang. "Imidazo[1,2-b]pyridazines. XI. Syntheses and Central Nervous System Activities of Some 6-(N-Benzyl-N-methylamino)-3-methoxy-2-phenyl(and substituted phenyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 45, no. 4 (1992): 751. http://dx.doi.org/10.1071/ch9920751.

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Syntheses are reported for 196-(N-benzyl-N-methylamino )-3-methoxy-2-phenyl(and substituted phenyl or pyridinyl ) imidazo [1,2-b] pyridazines from 6-(N-benzyl-N-methylamino)pyridazin-3- amine 2-oxide. The ability of each of these compounds to displace [3H]diazepam from rat brain membrane preparations was measured and the IC50 values (or percentage displacements) are reported and discussed. 6-(N-Benzyl-N-methylamino )-3-methoxy-2-phenylimido[1,2-b]pyridine was about half as active as its 6-bemylamino analogue, and the most active compound was 6-(N-benzyl-N-methylamino )-2-(2'-fluorophenyl)-3-methoxyimido[1,2-b] pyridazine with IC50 9.8 nM.
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11

El-Dean, Adel M. Kamal, Shaban M. Radwan, and Yasser A. Elosealy. "Synthesis of some new imidazo[3″,4″:1′,2′] pyrimido[4′,5′:4,5]thieno[2,3-c] pyridazines and other fused thieno[2,3-c]pyridazines." Journal of Chemical Research 2008, no. 11 (November 2008): 622–25. http://dx.doi.org/10.3184/030823408x371056.

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5-Amino-3,4-diphenylthieno[2,3-c]pyridazine-6-carboxamide was prepared and used as starting material to form the novel 6-chloromethyl-3,4-diphenylpyrimido[4′,5′:4,5]thieno[2,3-c]pyridazin-8(7H)-one (3), the 6-(arylaminomethyl) compounds (4a–c), 7-aryl-7,8-dihydro-3,4-diphenylimidazo[3″,4″:1′,2′]pyrimido[4′,5′:4,5]thieno[2,3-c]pyridazin-10(6H)-ones (5a–c), ethyl 7,8-dihydro-8-oxopyrimido[4′,5′:4,5]thieno[2,3-c]pyridazine-6-acetate (6) and its carbohydrazide (7). The pyridazinothienopyrimidotriazepinedione 8, pyridothienopyridazine 12 and pyridazinothienooxazepine 13 were also prepared.
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12

Abd El-Salam, Nasser M., Mohamed S. Mostafa, Gamal A. Ahmed, and Othman Y. Alothman. "Synthesis and Antimicrobial Activities of Some New Heterocyclic Compounds Based on 6-Chloropyridazine-3(2H)-thione." Journal of Chemistry 2013 (2013): 1–8. http://dx.doi.org/10.1155/2013/890617.

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Three tricyclic ring system, pyridazino[6,1-b]quinazolin-10-ones, benzimidazolo-pyridazine thione, and 1,2,4-benzotriazino-pyridazinethione along with imidazo-[1,2-b]-pyridazinethione, 1,2,4-triazolo[4,3-b]pyridazine-thione derivatives were synthesized starting from 6-chloropyridazin3-(2H)-thione. Some disulfide and sulfide derivatives were also prepared. The antimicrobial activity of the synthesized compounds was tested. Some of these compounds possess a highly response against gram-positive and gram-negative bacteria as well as fungi.
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13

Galtier, Christophe, Sylvie Mavel, Robert Snoeck, Graciela Andreï, Christophe Pannecouque, Myriam Witvrouw, Jan Balzarini, Erik De Clercq, and Alain Gueiffier. "Synthesis and Antiviral Activities of 3-Aralkyl-Thiomethylimidazo[1,2-b]Pyridazine Derivatives." Antiviral Chemistry and Chemotherapy 14, no. 4 (August 2003): 177–82. http://dx.doi.org/10.1177/095632020301400402.

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The synthesis of novel substituted 3-aralkylth-iomethylimidazo[1,2- b]pyridazines is reported. All of the synthesized compounds are devoid of antiviral activity against the replication of human immunodeficiency virus. However, compounds 6-chloro-8-methyl-3-phenethylthioimidazo[1,2- b]pyridazine and 6-chloro-2-methyl-3-phenethyl-thioimidazo[1,2- b]pyridazine are potent inhibitors of the replication of human cytomegalovirus in vitro, while compounds 6-chloro-2-methyl-3-benzylthiomethylimidazo[1,2- b]pyridazine and 6-chloro-2-methyl-3-phenethyl-thioimidazo[1,2- b]pyridazineare inhibitors of the replication of varicella-zoster virus. The results presented here suggest that compound 10 should be considered as a new lead in the development of antiviral agents.
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14

Abdullah, Ahmad H., Jalal A. Zahra, Salim S. Sabri, Firas F. Awwadi, Mohammed M. Abadleh, Qasem M. Abdallah, and Mustafa M. El-Abadelah. "Thiophene Ring-opening Reactions III: One-Pot Synthesis and Antitumor Activity of 1,3,4-Thiadiazoline–Benzothiazolo[3,2-b]pyridazine Hybrids†." Current Organic Synthesis 19, no. 2 (March 2022): 279–90. http://dx.doi.org/10.2174/1570179418666211109112148.

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Introduction: The preparation of model 6-chloro-5-nitrothieno[2,3-c]pyridazines incorporating (2'-halo-5'-nitrophenyl) entity is described. Interaction of these substrates with N'-(aryl)benzothiohydrazides, in the presence of triethylamine, followed a formal [4+1] annulation, furnishing the respective 1,3,4-thiadiazoline–benzothiazolo [3,2-b]pyridazine hybrids directly. This one-pot synthesis implies thiophene ring-opening and two consecutive intramolecular cyclizations. The structures of the synthesized new hybrids are supported by MS, NMR, and IR spectral data and further confirmed by single-crystal X-ray diffraction. These hybrids exhibit antiproliferative activity with notable selectivity against solid tumor cell lines (IC50: 4-18 μM). Aims: This study aimed at exploring the scope and applicability of thiophene ring-opening reaction towards the synthesis of new thiadiazoline–[fused]tricyclic conjugates. Background: α-Chloro-β-nitrothienopyridazine underwent ring-opening upon reacting with N'-(aryl)benzothiohydrazides generating 1,3,4-thiadiazoline–benzothiazolo[3,2-b]pyridazines. Objective: This new thiophene ring-opening reaction is applied to the one-pot synthesis of thiadiazoline–benzothiazolo[3,2-b]pyridazine couples. Method: A direct interaction of α-chloro-β-nitrothienopyridazine with N'-(aryl)benzothio-hydrazide at room temperature for 1-2 h occurred. Result: α-Chloro-β-nitrothieno[2,3-c]pyridazines are suitable substrates for the facile synthesis of thiadiazoline–benzothiazolo[3,2-b]pyridazine hybrids. Conclusion: This novel ring-opening reaction proceeds via formal [4+1] annulation and provides a versatile approach to various conjugated and/or fused five-membered heterocycles.
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15

Heinisch, G., E. Huber, C. Leitner, B. Matuszczak, A. Maurer, S. Pachler, and U. Prillinger. "Pyridazino[3,4-b][1,5]Benzodiazepin-5-Ones: Synthesis and Biological Evaluation." Antiviral Chemistry and Chemotherapy 8, no. 4 (August 1997): 371–79. http://dx.doi.org/10.1177/095632029700800410.

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Starting from 3,6-dichloropyridazine-4-carboxylic acid chloride, a series of pyridazino[3,4- b][1,5]benzodiazepin-5-ones bearing various substituents in positions 3, 6, 8 and 11 was prepared via N-alkyl-3-alkylamino-6-chloro- N-(2-chloro-5-nitrophenyl)-pyridazine-4-carboxamides. The latter were smoothly accessible by treatment of N-alkyl-3,6-dichloro-N-(2-fluorophenyl)-pyridazine-4-carboxamides with primary aliphatic amines. The new tricyclic compounds, which are structurally related to nevirapine and congeners were screened as human immunodeficiency virus type 1 reverse transcriptase inhibitors; the influence of the substitution pattern on inhibitory potency is discussed.
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16

Abdelrazek, Fathy M., Ahmed A. Fadda, and Akram N. Elsayed. "Novel Synthesis of Some New Pyridazine and Pyridazino[4,5-d]pyridazine Derivatives." Synthetic Communications 41, no. 8 (March 21, 2011): 1119–26. http://dx.doi.org/10.1080/00397911003797809.

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17

Czech, Karin, Norbert Haider, and Gottfried Heinisch. "Pyridazines, LIV: On the synthesis of pyridazine-fused S-heterocycles: Thieno[2,3-c]pyridazine, pyrimido[4?,5?:4,5]thieno[2,3-c]pyridazine, and pyridazino[3,4-b][1,4]benzothiazine." Monatshefte f�r Chemie Chemical Monthly 122, no. 5 (May 1991): 413–18. http://dx.doi.org/10.1007/bf00809662.

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18

CZECH, K., N. HAIDER, and G. HEINISCH. "ChemInform Abstract: Pyridazines. Part 54. Synthesis of Pyridazine-Fused S-Heterocycles: Thieno(2,3-c)pyridazine, Pyrimido(4′,5′:4,5)thieno(2,3-c)pyridazine, and Pyridazino(3,4-b)(1,4)benzothiazine." ChemInform 22, no. 35 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199135173.

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19

Wasfy, Ashraf A. F., Mohamed M. H. Arief, Mahassen S. Amine, Shafey G. Donia, and Aly A. Aly. "γ-Oxo Carboxylic Acids in Heterocyclic Synthesis, III. Synthesis of Biologically Active 4-Benzylamino-6-(5,5-dioxodibenzothiophen- 2-yl)-2,3,4,5-tetrahydropyridazin-3-ones." Zeitschrift für Naturforschung B 57, no. 6 (June 1, 2002): 668–76. http://dx.doi.org/10.1515/znb-2002-0613.

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α-Benzylamino-β-(5,5-dioxodibenzothiophen-2-carbonyl)propionic acid (1) has been synthesized by treating the corresponding β-aroylacrylic acid with benzylamine in dry benzene. On treatment with hydrazine hydrate the keto acid 1 furnishes the corresponding pyridazinone derivative 2. The behaviour of 2 towards carbon electrophiles, namely, ethyl chloroacetate, acrylonitrile, formaldehyde and secondary amines (under Mannich reaction conditions), aromatic aldehydes and carbon nucleophiles, namely, POCl3/PCl3 and P2S5 has been investigated. The 3-chloropyridazine derivative 13 reacts with hydrazine hydrate to give the 3-hydrazino derivative 14. On treatment with ethyl acetoacetate and/or acetylacetone the hydrazine 14 undergoes cyclization to afford pyrazolone derivative 16 and 3-(3,5-dimethylpyrazol- 1-yl)pyridazine derivative 17, respectively. On reaction with acetylhydrazine in boiling butanol and/or sodium azide in DMF the 3-chloropyridazine derivative 13 affords the triazolo[4,3-b]pyridazine 18 and the tetrazolo[1,5-b]pyridazine 19, respectively. The anti-microbial activity of the synthesized derivatives has been investigated.
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20

Youssef, A. SA, M. I. Marzouk, H. MF Madkour, A. MA El-Soll, and M. A. El-Hashash. "Synthesis of some heterocyclic systems of anticipated biological activities via 6-aryl-4-pyrazol-1-yl-pyridazin-3-one." Canadian Journal of Chemistry 83, no. 3 (March 1, 2005): 251–59. http://dx.doi.org/10.1139/v05-045.

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6-Aryl-4-pyrazol-1-yl-pyridazin-3-one (1) reacted with a PCl5–POCl3 mixture to give the 3-chloropyridazine derivative 3. Reaction of 3 with 2-hydroxybenzoylhydrazide and semicarbazide hydrochloride afforded 4 and 5. Reaction of 1 with ethyl chloroacetate gave 8. Reaction of 8 with hydrazine hydrate yielded the hydrazide 9. The hydrazide 9 condensed with the acetylenic ketones and esters 10a–10d and acetylacetone to give the adducts 11a, 11b, 12, 13, and 14. Reacting 1 with formaldehyde and piperidine, morpholine, or piperazine, 3-bromopropanoic acid, acetic anhydride, p-toluenesulphonyl chloride, succinyl chloride, oxalyl chloride, ethanolamine, or ethyl chloroacetate gave the adducts 15–22. The structures of all newly synthesized compounds were evidenced from their spectral and microanalytical data. Key words: 6-aryl-4-pyrazol-1-yl-pyridazinone derivative, 6-aryl-3-chloropyridazine derivative, 3,6-diaryl-1,2,4-triazino[4,3-b]pyridazine derivative, 6-aryl-3-ethoxycarbonylmethoxypyridazine derivative, 6-aryl-3-(ω-benzoylacetophenone)hydrazinocarbonylmethoxypyridazine.
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21

Rimaz, Mehdi, Jabbar Khalafy, Nader Noroozi Pesyan, and Rolf H. Prager. "A Simple One-Pot, Three Component Synthesis of 3-Arylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones and their Sulfur Analogues as Potential Monoamine Oxidase Inhibitors." Australian Journal of Chemistry 63, no. 3 (2010): 507. http://dx.doi.org/10.1071/ch09569.

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Several new 3-arylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones and 3-aryl-5-oxo-7-thioxo-7,8-dihydropyrimido[4,5-c]pyridazin-5(6H)-ones have been synthesized by a three-component reaction of barbituric acid or thiobarbituric acid with arylglyoxals in the presence of a catalytic amount of pyridine and hydrazine hydrate at room temperature in water.
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22

Abdelrazek, Fathy M., Ahmed A. Fadda, and Akram N. Elsayed. "ChemInform Abstract: Novel Synthesis of Some New Pyridazine and Pyridazino[4,5-d]pyridazine Derivatives." ChemInform 42, no. 38 (August 25, 2011): no. http://dx.doi.org/10.1002/chin.201138153.

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23

Barlin, GB, LP Davies, and SJ Ireland. "Imidazo[1,2-b]Pyridazines. XIX. Syntheses and Central Nervous System Activities of Some 6-Arylthio(aryloxy and alkylthio)-3-(acetamidomethyl, benzamidomethyl, methoxy and unsubstituted)-2-arylimidazo[1,2-b]pyridazines." Australian Journal of Chemistry 49, no. 4 (1996): 443. http://dx.doi.org/10.1071/ch9960443.

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Some 6-arylthio( aryloxy and alkylthio )-3-( acetamidomethyl , benzamidomethyl, methoxy and unsubstituted )-2-arylimidazo[1,2-b] pyridazines have been prepared and examined for their ability to displace [3H]diazepam from rat brain membranes. The most active compound was 3-acetamidomethyl-2-(3',4'-methylenedioxyphenyl)-6-phenylthioimidazo[1,2-b] pyridazine with IC50 4.4 nM. The 3-acylaminomethyl-6-(2- and 3-methoxyphenylthio)-2-phenylimidazo[1,2-b] pyridazines proved less active than their 6-phenylthio analogues, and larger substituents at the 2- and 6-positions markedly decreased binding. Significant differences in binding ability have been observed between 3-acylaminomethyl-2-aryl-6-phenylthioimidazo[1,2-b] pyridazines and the corresponding imidazo [1,2-a]pyridines.
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24

Barlin, GB, LP Davies, and MML Ngu. "Imidazo[1,2-b]Pyridazines. VIII. Syntheses and Central Nervous System Activities of Some 6-Benzylamino (and methoxybenzylamino)-3-methoxy-2-phenyl(Substituted phenyl or pyridinyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 42, no. 10 (1989): 1759. http://dx.doi.org/10.1071/ch9891759.

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Syntheses and IC50 values for the displacement of 3H-diazepam from rat brain plasma membrane are reported for a series of 6-benzylamino(and methoxybenzylamino )-3-methoxy-2-phenyl(substituted phenyl and pyridinyl )imidazo[l,2-b]pyridazines (and their 6-anilino and 6-phenethylamino analogues). The results are compared with those reported previously (by us) for the 6-chloro, 6-phenoxy, 6-benzylthio, and 6-benzyloxy compounds. In the imidazo[l,2-b]pyridazine ring system, 6-(o- and m- methoxybenzylamino ) groups were found to be beneficial to binding activity; eight compounds have been prepared with IC50 values less than 2 nM (cf. 3H-diazepam with IC50 of 4.2 nM ).2-(p-Aminopheny1)-3-methoxy- 6-(m- methoxybenzylamino )imidazo[1,2-b]pyridazine exhibited the highest activity with IC50 1.0 nM.
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25

Constable, Edwin C., Catherine E. Housecroft, Markus Neuburger, Sébastien Reymann, and Silvia Schaffner. "4-Substituted 3,6-Bis(2-pyridyl)pyridazines: Silver(I) Complexes of 4-Cyano- and 4-(4-Bromophenyl)-3,6-bis(2-pyridyl)pyridazine and Pseudopolymorphs of 1,3,5-Tris{3,6-bis(2-pyridyl)pyridazin-4-yl}benzene." Australian Journal of Chemistry 61, no. 11 (2008): 847. http://dx.doi.org/10.1071/ch08369.

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Metal:ligand complexes are crystallized from reaction mixtures of equimolar amounts of 4-cyano-3,6-bis(2-pyridyl)pyridazine 2 or 4-(4-bromophenyl)-3,6-bis(2-pyridyl)pyridazine 3 and silver(i) triflate. In [Ag2(2)2]2+, the two ligands adopt a head-to-tail arrangement, while a head-to-head motif is confirmed for the solid state structure of [Ag2(3)2]2+. In solution, one ligand environment is observed in each case. Silver(i) reacts with 1,3,5-tris{3,6-bis(2-pyridyl)pyridazin-4-yl}benzene 4 to give highly insoluble powders. The single crystal structures of the pseudopolymorphs (4)·Et2O and 2(4)·2MeCN·H2O are reported; in each structure, the ligand adopts the same conformation, derived from a Cs rather than C3v model structure.
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26

Barlin, GB, LP Davies, B. Glenn, PW Harrison, and SJ Ireland. "Imidazo[1,2-b]pyridazines. XV. Synthesis and Anxiolytic Activity of Some 3-(Benzamidomethyl and fluorobenzamidomethyl)-6-(fluoro, chloro and methylthio)-2-(4-tolyl and 3,4-methylenedioxyphenyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 47, no. 4 (1994): 609. http://dx.doi.org/10.1071/ch9940609.

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Syntheses are reported for some 3-( benzamido-and fluorobenzamido -methyl)-6-( fluoro , chloro and methylthio )-2(4-methyl-, 4-t-butyl-, 4-cyclohexyl- and 3,4-methylenedioxy-phenyl) imidazo-[1,2-b] pyridazines from the relevant 3-unsubstituted imidazo [1,2-b] pyridazines and the N-( hydroxymethyl ) benzamides. In tests of the ability of these compounds to displace [3H]diazepam from rat brain membrane, 3-(3- or 4-fluorobenzamidomethyl)-2-(3,4-methylenedioxyphenyl)-6-methylthioimidazo[1,2-b]- pyridazine bound most strongly, with IC50 2nM; but in behavioural tests in rats the most active compounds were 6-chloro(and methylthio )-3-(2-fluorobenzamidomethyl)-2-(3,4-methylenedioxyphenyl) imidazo [1,2-b] pyridazines which showed a significant anxiolytic activity at 2.5 mg/kg.
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27

Heinisch, Gottfried, and Wolfgang Holzer. "13C nuclear magnetic resonance spectra of 3,6-disubstituted pyridazines." Canadian Journal of Chemistry 69, no. 6 (June 1, 1991): 972–77. http://dx.doi.org/10.1139/v91-142.

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The 13C nuclear magnetic resonance spectra of 17 3,6-disubstituted pyridazine derivatives have been systematically analyzed. Chemical shifts and various 13C, 1H coupling constants are reported. Attempts were made to correlate these data with results obtained from semiempirical molecular orbital calculations as well as with substituent electronegativities and Taft's substituent constants σI and σR0. Key words: 3,6-disubstituted pyridazines, 13C NMR spectroscopy, 13C, 1H spin coupling constants.
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28

Ciccolini, Cecilia, Lucia De Crescentini, Fabio Mantellini, Giacomo Mari, Stefania Santeusanio, and Gianfranco Favi. "Construction of Unusual Indole-Based Heterocycles from Tetrahydro-1H-pyridazino[3,4-b]indoles." Molecules 25, no. 18 (September 9, 2020): 4124. http://dx.doi.org/10.3390/molecules25184124.

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Herein, we report the successful syntheses of scarcely represented indole-based heterocycles which have a structural connection with biologically active natural-like molecules. The selective oxidation of indoline nucleus to indole, hydrolysis of ester and carbamoyl residues followed by decarboxylation with concomitant aromatization of the pyridazine ring starting from tetrahydro-1H-pyridazino[3,4-b]indole derivatives lead to fused indole-pyridazine compounds. On the other hand, non-fused indole-pyrazol-5-one scaffolds are easily prepared by subjecting the same C2,C3-fused indoline tetrahydropyridazines to treatment with trifluoroacetic acid (TFA). These methods feature mild conditions, easy operation, high yields in most cases avoiding the chromatographic purification, and broad substrate scope. Interestingly, the formation of indole linked pyrazol-5-one system serves as a good example of the application of the umpolung strategy in the synthesis of C3-alkylated indoles.
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29

Daoui, Said, Emine Berrin Cinar, Fouad El Kalai, Rafik Saddik, Khalid Karrouchi, Noureddine Benchat, Cemile Baydere, and Necmi Dege. "Crystal structure and Hirshfeld surface analysis of 4-(4-methylbenzyl)-6-phenylpyridazin-3(2H)-one." Acta Crystallographica Section E Crystallographic Communications 75, no. 9 (August 23, 2019): 1352–56. http://dx.doi.org/10.1107/s2056989019011551.

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In this paper, we describe the synthesis of a new dihydro-2H-pyridazin-3-one derivative. The molecule, C18H16N2O, is not planar; the benzene and pyridazine rings are twisted with respect to each other, making a dihedral angle of 11.47 (2)°, and the toluene ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 89.624 (1)°. The molecular conformation is stabilized by weak intramolecular C—H...N contacts. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into inversion dimers with an R 2 2(8) ring motif. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional (2D) fingerprint plots, revealing that the most important contributions for the crystal packing are from H...H (56.6%), H...C/C...H (22.6%), O...H/H...O (10.0%) and N...C/C...N (3.5%) interactions.
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30

Mecadon, Hormi, and Bekington Myrboh. "Potassium Hydroxide Impregnated Alumina (KOH-Alumina) as a Recyclable Catalyst for the Solvent-Free Multicomponent Synthesis of Highly Functionalized Substituted Pyridazines and/or Substituted Pyridazin-3(2H)-ones under Microwave Irradiation." ISRN Organic Chemistry 2011 (April 12, 2011): 1–7. http://dx.doi.org/10.5402/2011/406427.

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The work described herein employs potassium hydroxide impregnated alumina (KOH-alumina) as a mild, efficient, and recyclable catalyst for a one-pot solvent-free and environmentally safer synthesis of 3,4,6-triarylpyridazines and some substituted pyridazines from active methylene carbonyl species, 1,2-dicarbonyls, and hydrazine hydrate by microwave (MW) irradiation. The method offers highly convergent, inexpensive, and functionality-tolerable procedure for rapid access to important pyridazine compounds in good yields.
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31

Degtyarenko, Anna S., and Konstantin V. Domasevitch. "Cadmium(II) iodide and thiocyanate complexes adopted by polycyclic 1,4-bis(pyridazin-4-yl)benzene: interplay of coordination and π–π stacking interactions." Acta Crystallographica Section C Crystal Structure Communications 69, no. 3 (February 5, 2013): 219–24. http://dx.doi.org/10.1107/s0108270113002801.

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New complexes containing the 1,4-bis(pyridazin-4-yl)benzene ligand, namely diaquatetrakis[1,4-bis(pyridazin-4-yl)benzene-κN2]cadmium(II) hexaiodidodicadmate(II), [Cd(C14H10N4)4(H2O)2][Cd2I6], (I), and poly[[μ-1,4-bis(pyridazin-4-yl)benzene-κ2N2:N2′]bis(μ-thiocyanato-κ2N:S)cadmium(II)], [Cd(NCS)2(C14H10N4)]n, (II), demonstrate the adaptability of the coordination geometries towards the demands of slipped π–π stacking interactions between the extended organic ligands. In (I), the discrete cationic [Cd—N = 2.408 (3) and 2.413 (3) Å] and anionic [Cd—I = 2.709 (2)–3.1201 (14) Å] entities are situated across centres of inversion. The cations associateviacomplementary O—H...N2′hydrogen bonding [O...N = 2.748 (4) and 2.765 (4) Å] and extensive triple π–π stacking interactions between pairs of pyridazine and phenylene rings [centroid–centroid distances (CCD) = 3.782 (4)–4.286 (3) Å] to yield two-dimensional square nets. The [Cd2I6]2−anions reside in channels generated by packing of successive nets. In (II), the CdIIcation lies on a centre of inversion and the ligand is situated across a centre of inversion. A two-dimensional coordination array is formed by crosslinking of linear [Cd(μ-NCS)2]nchains [Cd—N = 2.3004 (14) Å and Cd—S = 2.7804 (5) Å] withN2:N2′-bidentate organic bridges [Cd—N = 2.3893 (12) Å], which generate π–π stacks by double-slipped interactions between phenylene and pyridazine rings [CCD = 3.721 (2) Å].
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32

Barlin, Gordon B., Les P. Davies, Stephen J. Ireland, and Maria M. L. Ngu-Schwemlein. "Imidazo[1,2-b]pyridazines. XXII. Syntheses of Some 2-Aryl-3-methoxy-6-(pyridinylmethylthio and pyridinylmethylamino)imidazo[1,2-b]pyridazines and Their Interaction with Central and Mitochondrial (Peripheral-Type) Benzodiazepine Receptors." Australian Journal of Chemistry 50, no. 2 (1997): 91. http://dx.doi.org/10.1071/c96136.

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2-Aryl-3-methoxy-6-(pyridinylmethylthio and pyridinylmethylamino)imidazo[1,2-b]pyridazines have been prepared and examined as ligands for benzodiazepine receptors. Most were highly effective in displacing [3H]diazepam from central benzodiazepine receptors present in rat brain membranes but showed little capacity for its displacement from mitochondrial (peripheral-type) benzodiazepine receptors present in rat kidney membranes. For example, 3-methoxy-2-(3′,4′-methylenedioxyphenyl)-6-(pyridin-2′′-ylmethylthio)imidazo[1,2-b]pyridazine had an IC50 value of 1 · 7 nM for central receptors but gave only 39% displacement at 1000 nM for mitochondrial receptors. Of all the compounds described in this series of papers, 3-methoxy-6-(2′-methoxybenzylamino)-2-(3′′,4′′-methylenedioxyphenyl)imidazo[1,2-b]pyridazine was the most active in displacing [3H]diazepam from central receptors (IC50 0·3 nM), and it had a low affinity for mitochondrial receptors (40% displacement of [3H]diazepam at 1000 nM).
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33

Norman, Rebecca E., Michael V. Perkins, Andris J. Liepa, and Craig L. Francis. "N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part X. The First Pyrazolo[1,5-b][1,2,4,6]thiatriazine Derivatives and their Unusual Reactions with Acylating Agents." Australian Journal of Chemistry 66, no. 11 (2013): 1323. http://dx.doi.org/10.1071/ch13282.

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N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 underwent a regioselective reaction with 3-aminopyrazoles 2 to produce pyrazolo[1,5-b][1,2,4,6]thiatriazines 3, representatives of a new ring system. Attempted N-acylation of compounds 3 with acetic anhydride (or chloride) and benzoyl chloride in pyridine, only afforded 5-(pyridin-4-yl)-pyrazolo[1,5-b][1,2,4,6]thiatriazine derivatives 11. The analogous reaction with pyridazine led to the corresponding pyridazin-4-yl derivative.
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34

El Kalai, Fouad, Cemile Baydere, Said Daoui, Rafik Saddik, Necmi Dege, Khalid Karrouchi, and Noureddine Benchat. "Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate." Acta Crystallographica Section E Crystallographic Communications 75, no. 6 (May 24, 2019): 892–95. http://dx.doi.org/10.1107/s2056989019007424.

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The title pyridazinone derivative, C21H19ClN2O3, is not planar. The unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41 (13)° whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19 (13)°]. In the crystal, C—H...O hydrogen bonds generate dimers with R 2 2(10) and R 2 2(24) ring motifs which are linked by C—H...O interactions, forming chains extending parallel to the c-axis direction. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most significant contributions to the crystal packing are from H...H (44.5%), C...H/H...C (18.5%), H...O/H...O (15.6%), Cl...H/H...Cl (10.6%) and C...C (2.8%) contacts.
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35

Aziz, Suzan Ibrahim, Hany Fakhry Anwar, Morsy Ahmed El-Apasery, and Mohamed Hilmy Elnagdi. "Studies with pyridazines and condensed pyridazines: Routes for synthesis of 3-amino-5-aryl-2,5-dihydro-pyridazine, 10aH-pyridazino[1,6-a]quinazoline and thieno[3,4-d]pyridazinone." Journal of Heterocyclic Chemistry 44, no. 4 (July 2007): 877–81. http://dx.doi.org/10.1002/jhet.5570440421.

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36

Chen, Liqin, Laurence K. Thompson, and John N. Bridson. "Coordination chemistry of thioether–pyridazine macrocycles. I. Synthetic, structural, and spectroscopic studies of Cu(II) and Cu(I) complexes of novel thioether–pyridazine macrocycles that contain two or three pyridazine subunits." Canadian Journal of Chemistry 70, no. 7 (July 1, 1992): 1886–96. http://dx.doi.org/10.1139/v92-236.

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The preparations of thioether–pyridazine macrocycles containing three (L1) and two (L2) pyridazine subunits and their copper complexes are described. The ligands are characterized by 1H nuclear magnetic resonance and mass spectrometry and in one case by X-ray crystallography, and the complexes by infrared, electronic, and electron spin resonance (esr) spectra and in some cases by X-ray crystallography. The complex [Cu3(L1)2Cl6]•2CHCl3 (1) crystallized in the triclinic system, space group [Formula: see text] with a = 13.661(2) Å, b = 14.174(3) Å, c = 9.412(2) Å, α = 101.08(2)°, β = 96.94(2)°, γ = 75.76(2)°, V = 1728.2(6) Å3, and Z = 2 (R = 0.056, Rw = 0.048 for 2080 reflections). Two monodentate pyridazine rings in each ligand bind to one square-planar copper centre with the third monodentate pyridazine in each ligand linking the two to the central square-planar copper. The complex [Cu(L2)Cl2] (2) crystallized in the orthorhombic system, space group Pnma, with a = 8.571(1) Å, b = 16.104(3) Å, c = 13.961(2) Å, V = 1927(1) Å3, and Z = 4 (R = 0.037, Rw = 0.033 for 1070 reflections). A cis square-planar structure exists for 2 with monodentate pyridazines. [Cu(L2)2]•(ClO4)2•CH3CN•CHCl3 (5) crystallized in the triclinic system, space group [Formula: see text] with a = 12.888(4) Å, b = 17.462(6) Å, c = 10.906(1) Å, α = 96.07(2)°, β = 104.18(2)°, γ = 94.51(2)°, V = 2352(1) Å3, and Z = 2 (R = 0.053, Rw = 0.044 for 2941 reflections). Two ligands involving monodentate pyridazine rings bind to a square-planar copper(II) centre. The protonated ligand salt [L2H](ClO4)•H2O (6) crystallized in the monoclinic system, space group P21/n, with a = 14.762(4) Å, b = 8.637(5) Å, c = 16.267(4) Å, β = 92.78(2)°, V = 2072(1) Å3, and Z = 4 (R = 0.064, Rw = 0.053 for 1456 reflections). No sulfur coordination is observed in these complexes and there is no apparent spin exchange in the trinuclear derivative.
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37

Chen, Liqin, Laurence K. Thompson, and John N. Bridson. "Coordination chemistry of thioether–pyridazine macrocycles. III. Synthetic, structural, and spectroscopic studies of Cu(II), Cu(II)Cu(I), and Cu(I) complexes of a hexathiapyridazinophane macrocyclic ligand." Canadian Journal of Chemistry 71, no. 7 (July 1, 1993): 1086–93. http://dx.doi.org/10.1139/v93-144.

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The preparation and properties of the thioether–pyridazine macrocycle (L4; C16H20S6N4) containing two pyridazine subunits, and its Cu(II), Cu(II)Cu(I), and Cu(I) complexes are described. The ligand is characterized by 1H nuclear magnetic resonance and mass spectrometry, and the complexes by infrared, eleetronic spectra, and magnetism, and in some cases by X-ray crystallography. The complex [Cu2(L4)Cl4]x, (1) crystallized in the triclinic system, space group [Formula: see text] with a = 8.6204(8) Å, b = 9.850(1) Å, c = 8.348(1) Å, α = 111.46(1)°, β = 102.50(1)°, γ = 71.818(9)°, V = 622.6(1) Å3, and Z = 1 (R = 0.043, Rw = 0.042 for 1312 reflections). Two monodentate pyridazine rings in the same ligand bind to one trans square-planar copper centre (CuN2Cl2) with two sulfurs from each ligand binding to another trans square-planar copper centre (CuS2Cl2) to form a polynuclear chain. The complex [Cu(L4)Cl2] (3) crystallized in the triclinic system, space group [Formula: see text] with a = 11.001(1) Å, b = 12.888(2) Å, c = 8.704(1) Å, α = 102.89(1)°, β = 103.36(1)°,γ = 75.84(1)°, V = 1145.8(3) Å3 and Z = 2 (R = 0.056, Rw = 0.044 for 2059 reflections). A trans square-planar structure (CuN2Cl2) exists for 3 with monodentate pyridazines. [Cu(L4)(NO3)2] (4) crystallized in the orthorhombic system, space group P212121, with a = 15.148(2) Å, b = 15.562(3) Å, c = 11.064(1) Å, V = 2608.2(7) Å3 and Z = 4 (R = 0.039, Rw = 0.034 for 1864 reflections). Two monodentate pyridazine rings and two bidentate nitrates bind to a pseudo-octahedral copper(II) centre.
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38

El-Din, Harb. "Synthesis and reactions of 4-(p-methoxybenzyl)-6-[5,6,7,8-tetrahydro-2-naphthyl]-pyridazin-3(2H-one." Journal of the Serbian Chemical Society 64, no. 11 (1999): 663–72. http://dx.doi.org/10.2298/jsc9911663e.

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The condensation of 4-(p-methoxybenzyl)-6-[5,6,7,8-tetrahydro-2-naphthyl]- pyridazin-3(2H)-one (3), prepared by the reaction of 6-[5,6,7,8-tetrahydro-2-naphthyl]-4,5-dihydropyridazin-3(2H)-one (1) and anisaldehyde, with dimethyl sulphate, formal-dehyde and acrylonitrile, and also the formation of the Mannich base, proceeded smoothly at the 2-position to give compounds 4,5,6,7, respectively. 4-p-Methoxybenzyl-3-chloro-6-[5,6,7,8-tetrahydro-2-naphthyl]-pyridazine (9) was prepared in law yield by the action of phosphorus oxychloride on 3. The reaction of 9 with benzylamine, aniline and piperidine gave 10a,b,c, respectively. 4-p-Methoxybenzyl-6-[5,6,7,8-tetrahydro-2-napthyl]pyridazine-3(2H)-thione (12) was prepared either by the action of thiourea on 9, or by the reaction of 3 with phosphorus pentasulphide. The reaction of these thiones with acrylonitrile, morpholine and piperidine to give 13 and 14 a,b, respectively, were also investigated.
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39

Deeb, Ali, Abdel Naby Essawy, Fathy Yasine, and Rida Fikry. "Pyridazine Derivatives and Related Compounds, Part 3 [1] Some Reactions with 4-Cyano-3(2H)-pyridazinethione." Zeitschrift für Naturforschung B 46, no. 6 (June 1, 1991): 835. http://dx.doi.org/10.1515/znb-1991-0620.

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The reaction of 5-amino-3,4-diphenylthieno[2,3-c]pyridazine-6-carboxamide 2 with formamide, acetic anhydride and carbon disulphide yielded pyrimido[4′,5′ :4,5]thieno[2,3-c]-pyridazin-4-one derivatives. Pyrimido[4,5-c]pyridazinethione and dithione derivatives were obtained by cyclocondensation of 3-amino-5,6-diphenylpyridazine-4-carbonitrile (8) with phenyl isothiocyanate and carbon disulphide, respectively. Tetrahydropyridazino[3,4-b]-quinoline (11) was prepared by reaction of 8 with cyclohexanone in presence of zinc chloride.
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40

Barlin, Gordon B., Les P. Davies, and Peter W. Harrison. "Imidazo[1,2-b]pyridazines. XXI. Syntheses of some 3-Acylaminomethyl-6-(chloro and iodo)- 2-(substituted phenyl)-imidazo[1,2-b]pyridazines and -imidazo[1,2-a]pyridines and their Interaction with Central and Mitochondrial Benzodiazepine." Australian Journal of Chemistry 50, no. 1 (1997): 61. http://dx.doi.org/10.1071/c96130.

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A series of 3-acylaminomethyl-6-(chloro, iodo and methyl)-2-(phenyl, 4′-t-butylphenyl, 4′-cyclohexyl- phenyl, biphenyl-4′-yl, 4′-chlorophenyl and 4′-iodophenyl)imidazo[1,2-b]pyridazines and imidazo[1,2- a]pyridines has been prepared and examined for interaction with central and mitochondrial (peripheral- type) benzodiazepine receptors. The imidazo[1,2-b]pyridazines were generally more selective for the mitochondrial receptors than the corresponding imidazo[1,2-a]pyridines. Of these compounds, 3- acetamidomethyl-2-(biphenyl-4′-yl)-6-chloroimidazo[1,2-b]pyridazine (9) proved to be the most selective in studies of the displacement of [3H]diazepam from peripheral-type and central benzodiazepine receptors (IC50 2·8 nM and 0% displacement at 1000 nM, respectively).
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41

Barlin, GB, LP Davies, RA Davis, and PW Harrison. "Imidazo[1,2-b]pyridazines. XVII. Synthesis and Central Nervous System Activity of Some 6-(Alkylthio and chloro)-3-(methoxy, unsubstituted and benzamidomethyl)-2-arylimidazo[1,2-b]pyridazines Containing Methoxy, Methylenedioxy and Methyl Substituents." Australian Journal of Chemistry 47, no. 11 (1994): 2001. http://dx.doi.org/10.1071/ch9942001.

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Syntheses are reported for 6-( methylthio, ethylthio, propylthio, substituted benzylthio and chloro )-3-( methoxy, unsubstituted and benzamidomethyl )-2-arylimidazo[1,2-b] pyridazines containing methoxy, methylenedioxy and methyl groups attached to phenyl substituents . In tests of the ability of these compounds to displace [3H]diazepam from rat brain membranes, 3-methoxy-6-(3′,4′-methylenedioxybenzylthio)-2- (3′,4′-methylenedioxyphenyl) imidazo [1,2-b] pyridazine (IC50 1 nM) bound most strongly; methylenedioxy groups were beneficial to activity whereas polymethoxy or dimethyl substituents were generally detrimental.
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42

Okamura, Hidenori, Giang Hoang Trinh, Zhuoxin Dong, Yoshiaki Masaki, Kohji Seio, and Fumi Nagatsugi. "Selective and stable base pairing by alkynylated nucleosides featuring a spatially-separated recognition interface." Nucleic Acids Research 50, no. 6 (March 2, 2022): 3042–55. http://dx.doi.org/10.1093/nar/gkac140.

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Abstract Unnatural base pairs (UBPs) which exhibit a selectivity against pairing with canonical nucleobases provide a powerful tool for the development of nucleic acid-based technologies. As an alternative strategy to the conventional UBP designs, which involve utility of different recognition modes at the Watson–Crick interface, we now report that the exclusive base pairing can be achieved through the spatial separation of recognition units. The design concept was demonstrated with the alkynylated purine (NPu, OPu) and pyridazine (NPz, OPz) nucleosides endowed with nucleobase-like 2-aminopyrimidine or 2-pyridone (‘pseudo-nucleobases’) on their major groove side. These alkynylated purines and pyridazines exhibited exclusive and stable pairing properties by the formation of complementary hydrogen bonds between the pseudo-nucleobases in the DNA major groove as revealed by comprehensive Tm measurements, 2D-NMR analyses, and MD simulations. Moreover, the alkynylated purine-pyridazine pairs enabled dramatic stabilization of the DNA duplex upon consecutive incorporation while maintaining a high sequence-specificity. The present study showcases the separation of the recognition interface as a promising strategy for developing new types of UBPs.
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43

Daoui, Said, Cemile Baydere, Fouad El Kalai, Lhassane Mahi, Necmi Dege, Khalid Karrouchi, and Noureddine Benchat. "Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[5-(4-methylbenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetic acid." Acta Crystallographica Section E Crystallographic Communications 75, no. 12 (November 26, 2019): 1925–29. http://dx.doi.org/10.1107/s2056989019015317.

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The title pyridazinone derivative, C20H18N2O3, is not planar. The phenyl ring and the pyridazine ring are inclined to each other by 10.55 (12)°, whereas the 4-methylbenzyl ring is nearly orthogonal to the pyridazine ring, with a dihedral angle of 72.97 (10)°. In the crystal, molecules are linked by pairs of O—H...O hydrogen bonds, forming inversion dimers with an R 2 2(14) ring motif. The dimers are linked by C—H...O hydrogen bonds, generating ribbons propagating along the c-axis direction. The intermolecular interactions were additionally investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots. They revealed that the most significant contributions to the crystal packing are from H...H (48.4%), H...O/O...H (21.8%) and H...C/C...H (20.4%) contacts. Molecular orbital calculations providing electron-density plots of HOMO and LUMO molecular orbitals and molecular electrostatic potentials (MEP) were also computed, both with the DFT/B3LYP/6–311 G++(d,p) basis set.
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44

Degtyarenko, Anna S., and Konstantin V. Domasevitch. "Anion...π interactions in copper(I) chloride and bromide coordination polymers bearing 1,4-bis(pyridazin-4-yl)benzene ligands." Acta Crystallographica Section C Structural Chemistry 70, no. 2 (January 11, 2014): 173–77. http://dx.doi.org/10.1107/s2053229613034840.

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In poly[[μ4-1,4-bis(pyridazin-4-yl)benzene-1:2:3:4κ4N1:N2:N1′:N2′]di-μ2-chlorido-dicopper(I)], [Cu2Cl2(C14H10N4)]n, (I), and its isomorphous bromide analogue, [Cu2Br2(C14H10N4)]n, (II), the organic ligand is situated across a centre of inversion. The CuIcations adopt a distorted tetrahedral [CuN2X2] [X= Cl in (I) or Br in (II)] environment [Cu—N = 2.0183 (14)–2.0936 (14) Å; Cu—Cl = 2.2686 (6) and 2.4241 (5) Å; Cu—Br = 2.4002 (6) and 2.5284 (5) Å] and the primary coordination motif consists of cuprohalogenide chains accommodating μ-pyridazine groups. The organic ligands are tetradentate and link the inorganic chains into corrugated layers. Their packing is influenced by interlayer anion...π interactions [Cl...π = 3.540 (2) Å and Br...π = 3.593 (2) Å] with the electron-deficient pyridazine rings. This kind of interaction precludes the characteristic slipped π–π stacking and close parallel alignment of the organic tectons; it may be involved as a structure-defining factor for coordination layers based upon lengthy polyaromatic linkers.
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45

Barlin, GB, LP Davies, SJ Ireland, MML Ngu, and JK Zhang. "Imidazo[1,2-b]pyridazines. X. Syntheses and Central Nervous System Activities of Some 3-(Acetamido, benzamido, substituted benzamido or dimethylamino)methyl-2-(phenyl or substituted phenyl)-6-(halogeno, alkylthio, alkoxy, phenylthio, phenoxy, benzylthio or benzyloxy)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 45, no. 4 (1992): 731. http://dx.doi.org/10.1071/ch9920731.

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Syntheses of some 3-( acetamido, benzamido , substituted benzamido or dimethylamino)methyl-2-(phenyl or substituted phenyl)-6( halogeno, alkylthio, alkoxy, phenylthio, phenoxy , benzylthio or benzyloxy ) imidazo [1,2-b] pyridazines from the 3-unsubstituted analogues are described. The IC50 values (or percentage displacements) are reported and discussed for the displacement of [3H]diazepam from rat brain membrane by each of these compounds. .The 3-benzamidomethyl compounds were generally the most active; of these, 3-benzamidomethyl-2-(3',4'-methylenedioxyphenyl)-6-methylthioimido[1,2-b] pyridazine showed outstanding activity with IC50 2 nM .
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46

Barlin, GB, LP Davies, SJ Ireland, and JK Zhang. "Imidazo[1,2-b]pyridazines. XIII. Syntheses and Central Nervous System Activities of Some 2-Benzyl(phenethyl, biphenyl-4'-yl, 6'-methylnaphthalen-2'-yl, t-Butyl and cyclohexyl)-3-methoxy(acylaminomethyl and dimethylaminomethyl)-6-(variously substituted)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 45, no. 8 (1992): 1281. http://dx.doi.org/10.1071/ch9921281.

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6-(Variously substituted)-3-methoxy(unsubstituted, dimethylaminomethyl, acetamidomethyl and benzamidomethy1)-2-benzyl(phenethyl, biphenyl-4'-yl, 6'-methylnaphthalen-2'-yl, t-butyl and cyclohexyl)imidazo[1,2-b] pyridazines have been prepared and examined for activity in the central nervous system. Of these, 2-benzyl-3-methoxy-6-(3'-methoxybenzylamino) imidazo[1,2-b]pyridazine (IC50 88nM) bound most strongly to rat brain membrane. In general, the order of activity for groups at the 2-position was Ph > PhCH2 > PhCH2CH2 > C6H4Ph-p, 6'-methylnaphthalen-2'-yl, c-C6H11 or But.
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47

Hensen, Karl, and Jens Gaede. "Thermodynamische Interpretation der Schmelzdiagramme binärer Systeme aus Methylchlorsilanen und Pyridazin bzw. Pyrazin." Zeitschrift für Naturforschung A 42, no. 4 (April 1, 1987): 341–51. http://dx.doi.org/10.1515/zna-1987-0402.

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By analyzing the cooling curves and the resulting melting point diagrams of the chloromethylsilane- pyridazine and pyrazine systems the existence of the incongruently melting addition compounds CH3SiCl3 • Pyridazine, (CH3)2SiCl2 • (Pyridazine)2, (CH3)3SiCl • (Pyridazine)2, CH3SiCl3 • (Pyrazine)2, (CH3)2SiCl2 • (Pyrazine)2 , (CH3)3SiCl • (Pyrazine)2 was proved. By electro-optical measurements of the turbidity point it was proved that the system (CH3)3SiCl- Pyridazine exhibits a miscibility gap which intersects the liquidus curve of the amine. Based on certain approximations it was possible to fit thermodynamic functions to the experimental results to obtain the excess data of mixing of the corresponding systems. These data allow for a more profound understanding of the Lewis-acid base behaviour of the silanes and amines.Chloromethylsilanes, Pyridazine, Pyrazine, Phase Diagrams, Addition Compounds, Thermodynamic Excess Functions
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48

Yengoyan, Aleksandr P., Roza S. Shainova, Tiruhi A. Gomktsyan, and Armen V. Karapetyan. "Synthesis of Novel 6-(3,5-Dimethyl-1H-Pyrazol-1-yl)Pyridazin-3(2H)-One Derivatives and their Preliminary Biological Evaluation." Journal of Chemical Research 42, no. 10 (October 2018): 535–39. http://dx.doi.org/10.3184/174751918x15389922302823.

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Simple and accessible pathways for the synthesis of a series of novel 6-(3,5-dimethyl-1H-pyrazol-1-yl)pyridazin-3(2H)-one derivatives including compounds with a combination of a pyrazolyl-pyridazine moiety with pyrimidine, 1,3,5-triazine and 1,3,4-oxadiazole rings in the same molecules were established. The tautomeric structures of 3-oxopyridazine and 5-thioxo-1,3,4-oxadiazole rings and also the position of their alkylation were shown. At preliminary screening the synthesised compounds showed pronounced plant growth stimulant activity. The most active compounds were selected for deeper studies and further field trials.
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49

Xie, Xiao Hua, Wei Shen, Rong Xing He, and Ming Li. "A Class of Semiconducting Polymers as Potential Materials for Polymer Solar Cells." Advanced Materials Research 716 (July 2013): 177–84. http://dx.doi.org/10.4028/www.scientific.net/amr.716.177.

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In this work, fifteen polymers have been studied to test their potential as donors for polymer solar cells by density functional theory. Those polymers contained five homopolymers based on pyridazine, [1,2,thiadiazolo [3,4-pyridazine, [1,2,oxadiazole [3,4-pyridazine, isothiazolo [3,4-pyridazine and isoxazolo [3,4-pyridazine, and ten copolymers composed of the above compounds and thiophene incorporated with 1:1 and 1:2 ratios. The fifteen polymers have been examined in terms of the abilities of absorbing sunlight, stabilities in the environment, and photovoltaic properties. The results suggest that the copolymes DTHP, DTHTP, DTHOP, DTHITP, and DTHIXP are good material candidates of polymer donor for polymer solar cells.
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50

Wöhlert, Susanne, Mario Wriedt, Inke Jess, and Christian Näther. "Tetrakis(pyridazine-κN)bis(thiocyanato-κN)nickel(II) pyridazine disolvate." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 26, 2012): m793. http://dx.doi.org/10.1107/s1600536812023306.

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The reaction of nickel(II) thiocyanate with an excess of pyridazine leads to single crystals of the title compound, [Ni(NCS)2(C4H4N2)4]·2C4H4N2. The NiII cations are coordinated by two terminal N-bonded thiocyanate anions (trans) and four pyridazine ligands in a slightly distorted octahedral geometry. The discrete complexes are arranged into layers parallel to the ab plane which are separated by additional non-coordinated pyridazine ligands.
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