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Journal articles on the topic '4-d]pyridazine'

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Published: 4 June 2021

Last updated: 8 February 2022

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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

Chmovzh, Knyazeva, mlv@ioc ac ru Tanaka, Popov, Mikhalchenko, Robertson, and Rakitin. "[1,2,5]Thiadiazolo[3,4-d]Pyridazine as an Internal Acceptor in the D-A-π-A Organic Sensitizers for Dye-Sensitized Solar Cells." Molecules 24, no. 8 (April 22, 2019): 1588. http://dx.doi.org/10.3390/molecules24081588.

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Four new D-A-π-A metal-free organic sensitizers for dye-sensitized solar cells (DSSCs), with [1,2,5]thiadiazolo[3 ,4-d]pyridazine as internal acceptor, thiophene unit as π-spacer and cyanoacrylate as anchoring electron acceptor, have been synthesized. The donor moiety was introduced into [1,2,5]thiadiazolo[3,4-d]pyridazine by nucleophilic aromatic substitution and Suzuki cross-coupling reactions, allowing design of D-A-π-A sensitizers with the donor attached to the internal heterocyclic acceptor not only by the carbon atom, as it is in a majority of DSSCs, but by the nitrogen atom also. Although low values of power conversion efficiency (PCE) were found, a few important consequences were identified: (i) poor PCE data can be attributed to high electron deficiency of the internal [1,2,5]thiadiazolo[3,4-d]pyridazine acceptor due to lower light harvesting by the dye; (ii) the manner in which the donor was attached to the internal acceptor (by carbon or nitrogen) did not play an essential role in the photovoltaic properties of the dyes; (iii) dyes based on the novel donor 2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazolyl and 9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H- carbazole moieties showed similar photovoltaic properties to dyes based on the well-known 4-(p-tolyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indolyl building block, which opens the door for further optimization potential of new dye families.

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3

Richter, Marianne, and Gunther Seitz. "4-(β-D-Ribofuranosyl)pyridazine: Neue C-Nukleoside durch [4+2]-Cycloaddition mit inversem Elektronenbedarf." Archiv der Pharmazie 327, no. 6 (1994): 365–70. http://dx.doi.org/10.1002/ardp.19943270604.

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4

Bussolari, Jacqueline C., Johanna D. Stoeckler, and Raymond P. Panzica. "The synthesis and biological evaluation of 4-p-nitrobenzylthio-v-triazolo [4,5-d]pyridazine and imidazo[4,5-d]pyridazine ribosides as potential nucleoside transport inhibitors." Bioorganic & Medicinal Chemistry 4, no. 10 (October 1996): 1725–31. http://dx.doi.org/10.1016/0968-0896(96)00188-5.

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5

Ramesh, Kakarla, and Raymond Panzica. "Synthesis and Biological Activity of Certain 4-Substituted Imidazo[4,5-d]Pyridazine Nucleosides." Nucleosides, Nucleotides and Nucleic Acids 8, no. 5 (1989): 1141–42. http://dx.doi.org/10.1080/07328318908054311.

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6

Filali, Mouad, Nada Kheira Sebbar, Tuncer Hökelek, Joel T. Mague, Said Chakroune, Abdessalam Ben-Tama, and El Mestafa El Hadrami. "Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 4-[(prop-2-en-1-yloxy)methyl]-3,6-bis(pyridin-2-yl)pyridazine." Acta Crystallographica Section E Crystallographic Communications 75, no. 9 (August 20, 2019): 1321–26. http://dx.doi.org/10.1107/s2056989019011186.

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The title compound, C18H16N4O, consists of a 3,6-bis(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yloxy)methyl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C—HPyrd...NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C—HPrpoxy...π (Prpoxy = prop-2-en-1-yloxy) interactions link the molecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (48.5%), H...C/C...H (26.0%) and H...N/N...H (17.1%) contacts, hydrogen bonding and van der Waals interactions being the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the C—HPyrd...NPyrdz hydrogen-bond energy is 64.3 kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

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7

Chmovzh, Timofey N., and Oleg A. Rakitin. "7-Bromo-[1,2,5]selenadiazolo[3,4-d]pyridazin-4(5H)-one." Molbank 2021, no. 2 (June 5, 2021): M1229. http://dx.doi.org/10.3390/m1229.

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New heterocyclic systems containing 1,2,5-chalcogenadiazoles are of great interest for the creation of organic photovoltaic materials and biologically active compounds. In this communication, 3,6-dibromopyridazine-4,5-diamine was investigated in reaction with selenium dioxide in order to obtain 4,7-dibromo-[1,2,5]selenadiazolo[3,4-d]pyridazine. We found that 7-bromo-[1,2,5]selenadiazolo[3,4-d]pyridazin-4(5H)-one, the first representative of the new heterocyclic system, was isolated as a hydrolysis product of the corresponding 4,7-dibromoderivative. The structure of the newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, 1H, 13C NMR, IR and UV spectroscopy, and mass spectrometry.

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8

Patra, Gopal Chandra, Sankar Chandra Bhunia, Monoj Kumar Roy, and Sudhir Chandra Pal. "Synthesis of 4-Aryl-4,6-dihydropyrimido[4,5-d]pyridazine-2,5(1H,3H)-diones fromBiginelliCompounds." Helvetica Chimica Acta 96, no. 1 (January 2013): 130–34. http://dx.doi.org/10.1002/hlca.201200109.

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9

Chen, Shi-Quan, Kai Jiang, and Shi-Fan Wang. "Ethyl 3-methyl-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-d]pyridazine-2-carboxylate." Acta Crystallographica Section E Structure Reports Online 66, no. 2 (January 9, 2010): o259. http://dx.doi.org/10.1107/s1600536809055081.

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10

OISHI, ETSUO, HIDEKI MATSUBARA, and EISAKU HAYASHI. "Condensed Pyridazines. III. Reaction of 4, 7-Dichloro-1-phenyl-1H-pyrazolo [3, 4-d] pyridazine with Carbanions." YAKUGAKU ZASSHI 105, no. 2 (1985): 119–28. http://dx.doi.org/10.1248/yakushi1947.105.2_119.

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11

Abdelhamid, Abdou O., Zeineb H. Ismail, and Anhar Abdel-Aziem. "Reactions with Hydrazonoyl Halides 601: Synthesis of Thieno[2′,3′:4,5] Pyrimidino[1,2-b][1,2,4,5]tetrazines, [1]benzothieno[2′,3′:4,5]pyrimidino [1,2-b][1,2,4,5]tetrazines, Pyrazolo[3′,4′:4,5]pyrimidino[1,2-b] [1,2,4,5]tetrazines and Pyrazolo[3,4-d]pyridazines." Journal of Chemical Research 2007, no. 10 (October 2007): 609–16. http://dx.doi.org/10.3184/030823407x256118.

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Thieno[2′,3′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, [1]benzothieno-[2′,3′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, pyrazolo [3′,4′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, triazolo[4,3- a]pyrimidin-5(1 H)-one, 1-{[2-(1-benzofuran-2-yl)-5-phenyl-4,5-dihydro-1 H-pyrazol-1-yl]-4-substituted-1,3-thiazol-5-yl}-2-phenyldiazene, 3-acyl-4-(1-benzofuran-2-ylcarbonyl) pyrazole and pyrazolo[3,4- d]pyridazine derivatives could be obtained via reactions of hydrazonoyl halides with the appropriate pyrimidine-2-thione, 3-amino-5,6-dimethyl-2-sulfanylthieno[2,3- d]pyrimidin-4(3 H)-one, 5-amino-6-mercapto-1-phenyl-1,5-dihydropyrazolo[3,4- d]pyrimidin-4-one and 1-(benzofuran-2-yl)-3-(dimethylamino)prop-2-en-1-one. Structures of the products have been determined by elemental analyses, spectral data studies and alternative synthesis whenever possible.

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12

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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13

Annam, Sri Charitha, K. V. Padmavathi, N. Murali Krishna, and Mannam Subbarao. "Computational Designing of Low Energy Band Gap of New Donor-Acceptor (D-A) Copolymer Monomers for Organic Solar Cells: DFT and TD-DFT Study." Science & Technology Journal 8, no. 2 (July 1, 2020): 44–54. http://dx.doi.org/10.22232/stj.2020.08.02.08.

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Via this look at efforts have been made to increase a chain of latest donor-acceptor (D-A) systems through the usage of 4-methoxy-2,7,nine-trimethyl-9H-carbazole (2,7-MMCB) as a electron donor and benzo[c][1,2,5] oxadiazole (BCO); benzo[c] [1,2,5] thiadiazole (BCT); benzo[c][1,2,5]selenadiazole (BCS); [1,2,5]oxadiazolo[3,4-c]pyridine (OCP); [1,2,5] thiadiazolo [3,4-c]pyridine (TCP); [1,2,5] selenadiazolo [3,4-c]pyridine (SCP); [1,2,5] oxadiazolo[3,4-d]pyridazine (ODP); [1,2,5] thiadiazolo[3,4-d]pyridazine (TDP) as electron acceptors. In this work, we executed calculations of DFT and TD-DFT/B3LYPmethod with /6-31G basis. Calculated and explored theoretical expertise of the HOMO, LUMO oenergies, the band gap (Eg), and the open-circuit voltage (Voc) of the studied compounds. To take a look at the relationship between molecularstructure and optoelectronic properties, the consequences of the extraordinary acceptor effect on the geometries and optoelectronic residences of those substances were discussed. The outcomes acquired show how the digital residences can be modified with many lessons of acceptors through the substituent and suggest that 2,7MMCB-ODP, 2,7MM CB-TDP, and 2,7MM CB-SDP are these compounds as suitable candidates for optoelectronic packages in solar cells inclusive of BHJ.

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14

Renoud-Grappin, M., C. Fossey, G. Fontaine, D. Ladurée, AM Aubertin, and A. Kirn. "Imidazo[1,5-b]Pyridazine-D4T Conjugates: Synthesis and Anti-Human Immunodeficiency Virus Evaluation." Antiviral Chemistry and Chemotherapy 9, no. 3 (June 1998): 205–23. http://dx.doi.org/10.1177/095632029800900302.

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In an attempt to combine the human immunodeficiency virus type 1 (HIV-D-inhibitory capacity of 2′,3 -dideoxy-2,3 -didehydronucleoside analogues [nucleoside reverse transcriptase (RT) inhibitors; NRTI] and non-nucleoside RT inhibitors (NNRTI), we have designed, synthesized and evaluated for their anti-HIV activity several heterodimers of the general formula [d4T]-NH-(CH2)n-NH-[imidazo[1,5–b]pyridazine]. The synthesis of these heterodimers was conducted in three parts. The first part focused on the synthesis of the NRTI. The second part was devoted to the NNRTI and the NNRTI linked to appropriate spacers; [NNRTI]-NH-(CH2)n-NH2. In the third part, the condensation between the NRTI and the [NNRTI]-NH-(CH2)n-NH2 was performed. The in vitro inhibitory activities against HIV-1 of the [d4T]-NH-(CH2)n-NH-[imidazo[1,5–b]pyridazine] heterodimers were found to be comparable to that of d4T (stavudine) in HIV-infected cells. Moreover, the heterodimers were endowed with anti-HlV-2 activity and with anti-nevirapine-resistant HIV-1 activity. None of the heterodimers proved markedly cytotoxic to CEM-SS or MT-4 cells. There was not a clear trend toward antiviral potency on lengthening the methylene spacer in the [d4T]-NH-(CH2)n-NH-[imidazo[1,5–b]pyridazine] heterodimers.

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15

Tominaga, Yoshinori, Noriko Yoshioka, Hiroki Minematsu, and Seigo Kataoka. "Synthesis and Chemiluminescence of 1,3-Disubstituted 4-Hydroxypyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones." HETEROCYCLES 44, no. 1 (1997): 85. http://dx.doi.org/10.3987/com-96-s17.

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16

Haider, Norbert, Kurt Mereiter, and Richard Wanko. "[4+2]Cycloaddition Reactions of 1,4-Bis(trifluoromethyl)pyrido[3,4-d]pyridazine with Indole-Type Dienophiles." HETEROCYCLES 41, no. 7 (1995): 1445. http://dx.doi.org/10.3987/com-95-7063.

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17

OISHI, ETSUO, TAKESHI ENDO, YOSHIKAZU ASAHINA, and EISAKU HAYASHI. "Condensed Pyridazines. IV. Chemical Properties of 7-Methoxy-1-phenyl-1H-pyrazolo [3, 4-d] pyridazine 5-Oxide." YAKUGAKU ZASSHI 105, no. 2 (1985): 129–41. http://dx.doi.org/10.1248/yakushi1947.105.2_129.

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18

Meade, Eric A., and Leroy B. Townsend. "Synthesis of 4-Amino-1-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyridazine; an entry into a novel series of adenosine analogs." Bioorganic & Medicinal Chemistry Letters 1, no. 2 (January 1991): 111–14. http://dx.doi.org/10.1016/s0960-894x(00)80242-5.

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19

Al-Mehizia, Abdulrahman A., Ahmed H. Bakheit, Seema Zargar, Mashooq A. Bhat, Majid Mohammed Asmari, and Tanveer A. Wani. "Evaluation of Biophysical Interaction between Newly Synthesized Pyrazoline Pyridazine Derivative and Bovine Serum Albumin by Spectroscopic and Molecular Docking Studies." Journal of Spectroscopy 2019 (June 16, 2019): 1–12. http://dx.doi.org/10.1155/2019/3848670.

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In this research, the pyrazoline pyridazine derivative 7-methyl-2-phenyl-4-(3,4,5-trimethoxyphenyl)-2H-pyrazolo[3,4-d]pyridazine (5d) was studied for its interaction with bovine serum albumin (BSA). Various spectroscopic techniques along with molecular docking analysis were utilized to understand the mechanism of interaction. The quenching of BSA fluorescence by using investigational drug 5d was the basic principle for the methodology. Spectrofluorometric methods and UV-absorption studies were conducted for exploration of the 5d and BSA binding mechanism. The fluorescence quenching mechanism involved in BSA and 5d interaction was static quenching, and a complex formation also occurred between them. Both enthalpy and entropy attained positive values suggesting involvement of hydrophobic forces in BSA and 5d interaction. The Förster distance of 2.23 nm was calculated by fluorescence resonance energy transfer (FRET). An alteration in BSA secondary structure was proven from the conformational studies of BSA-5d interaction. This binding interaction study provided a basis to comprehend the binding interaction between 5d and BSA. These results provided information about sites of BSA involved in its interaction with 5d.

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20

TOMINAGA, Y., N. YOSHIOKA, H. MINEMATSU, and S. KATAOKA. "ChemInform Abstract: Synthesis and Chemiluminescence of 1,3-Disubstituted 4-Hydroxypyrazolo( 4′,3′:5,6)pyrido(2,3-d)pyridazine-5,8(6H,7H)diones." ChemInform 28, no. 21 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199721163.

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21

THEOCHARIS, A. B., N. E. ALEXANDROU, and A. TERZIS. "ChemInform Abstract: Generation and Dienophilic Properties of 1-Benzyl-1H-1,2,3-triazolo(4, 5-d)pyridazine-4,7-dione." ChemInform 22, no. 11 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199111204.

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22

Patra, Gopal Chandra, Sankar Chandra Bhunia, Monoj Kumar Roy, and Sudhir Chandra Pal. "ChemInform Abstract: Synthesis of 4-Aryl-4,6-dihydropyrimido[4,5-d]pyridazine-2,5(1H,3H)-diones from Biginelli Compounds." ChemInform 44, no. 22 (May 13, 2013): no. http://dx.doi.org/10.1002/chin.201322183.

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23

Quintela, J. M., M. C. Veiga, R. Alvarez-Sarand�s, L. Gonz�lez, and C. Peinador. "Synthesis of new pyridazino[4?,3?:4,5]-thieno[3,2-d]-1,2,3-triazine and pyrimido[4?,5?:4,5]thieno[2,3-c]pyridazine derivatives." Monatshefte f�r Chemie Chemical Monthly 127, no. 10 (October 1996): 1037–43. http://dx.doi.org/10.1007/bf00807576.

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24

MEADE, E. A., and L. B. TOWNSEND. "ChemInform Abstract: Synthesis of 4-Amino-1-(β-D-ribofuranosyl)pyrrolo(2,3-d)pyridazine. An Entry into a Novel Series of Adenosine Analogs." ChemInform 22, no. 35 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199135262.

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25

Pita, Beatriz, Eddy Sotelo, Margarita Suárez, Enrique Raviña, Estael Ochoa, Yamila Verdecia, Héctor Novoa, Norbert Blaton, Caimle de Ranter, and Oswald M. Peeters. "Pyridazine Derivatives. Part 21: Synthesis and Structural Study of Novel 4-Aryl-2,5-dioxo-8-phenylpyrido[2,3-d]pyridazines." Tetrahedron 56, no. 16 (April 2000): 2473–79. http://dx.doi.org/10.1016/s0040-4020(00)00082-x.

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26

Deeb, Ali, Mahmoud Kotb, and Mohamed El-Abbasy. "Pyridazine Derivatives and Related Compounds, Part 12: Synthesis of Some Pyridazino [4′,3′:4,5]thieno[3,2-d]1,2,3-triazines." Phosphorus, Sulfur, and Silicon and the Related Elements 180, no. 2 (February 2005): 591–99. http://dx.doi.org/10.1080/104265090517398.

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27

Amer, F. A., M. Hammouda, A. A. S. El-Ahl, and B. F. Abdel-Wahab. "Synthesis of new pyrrolo-[3,4-c]isoxazole, pyrrolo[2,3-d]-[1,2,3]triazole, triazolo[4,5-c]-pyridazine, and dipyrrolo-[3,2-b:3′,4′-d]pyran derivatives." Chemistry of Heterocyclic Compounds 43, no. 12 (December 2007): 1559–66. http://dx.doi.org/10.1007/s10593-007-0241-4.

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28

QUINTELA, J. M., M. C. VEIGA, R. ALVAREZ-SARANDES, L. GONZALEZ, and C. PEINADOR. "ChemInform Abstract: Synthesis of New Pyridazino(4′,3′:4,5)thieno(3,2-d)-1,2,3-triazine and Pyrimido(4′,5′:4,5)thieno(2,3-c)pyridazine Derivatives." ChemInform 28, no. 12 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199712151.

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29

Tominaga, Yoshinori, Noriko Yoshioka, Seigo Kataoka, Norihito Aoyama, Toshiyuki Masunari, and Akira Miike. "Synthesis and chemiluminescence of 1,3-disubstituted pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyridazine-5,8(6h,7h)-diones and related compounds." Tetrahedron Letters 36, no. 47 (November 1995): 8641–44. http://dx.doi.org/10.1016/0040-4039(95)01862-c.

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30

Pita, Beatriz, Eddy Sotelo, Margarita Suarez, Enrique Ravina, Estael Ochoa, Yamila Verdecia, Hector Novoa, Norbert Blaton, Caimle de Ranter, and Oswald M. Peeters. "ChemInform Abstract: Pyridazine Derivatives. Part 21. Synthesis and Structural Study of Novel 4-Aryl-2,5-dioxo-8-phenylpyrido[2,3-d]pyridazines." ChemInform 31, no. 30 (June 7, 2010): no. http://dx.doi.org/10.1002/chin.200030131.

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31

Haider, Norbert, Kurt Mereiter, and Richard Wanko. "Inverse-Electron-Demand Diels-Alder Reactions of Condensed Pyridazines, 4. Synthesis and Cycloaddition Reactions of 1,4-Bis(trifluoromethyl)pyrido[3,4-d]pyridazine." HETEROCYCLES 38, no. 8 (1994): 1845. http://dx.doi.org/10.3987/com-94-6753.

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32

Abdel-Rehem, Esam, and Norbert Haider. "Unsubstituted pyrido[3,4-d]pyridazine as an electron-deficient azadiene in [4+2] cycloaddition reactions: a short route to g-fused isoquinolines." Arkivoc 2001, no. 2 (November 5, 2001): 21–27. http://dx.doi.org/10.3998/ark.5550190.0002.203.

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33

Meade, Eric A., Linda L. Wotring, John C. Drach, and Leroy B. Townsend. "Synthesis, antiproliferative, and antiviral activity of certain 4-aminopyrrolo[2,3-d]pyridazine nucleosides: an entry into a novel series of adenosine analogs." Journal of Medicinal Chemistry 35, no. 3 (February 1992): 526–33. http://dx.doi.org/10.1021/jm00081a014.

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34

Deeb, Ali, and Mohamed El-Abbasy. "Pyridazine Derivatives and Related Compounds, Part 21:1 Synthesis of Different Heterocycles from 2-Methyl-4H- pyridazino[4′,3′:4,5]thieno[3,2-d]-1,3-oxazin-4-one." Phosphorus, Sulfur, and Silicon and the Related Elements 181, no. 1 (January 1, 2006): 15–23. http://dx.doi.org/10.1080/104265090968451.

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35

Wang, Ke, Xiao-long Fu, Qiu-fan Tang, Huan Li, Yuan-jie Shu, Jun-qiang Li, and Wei-piang Pang. "Theoretical investigations on novel energetic salts composed of 4-nitro-7-(4-nitro-1,2,3-triazol-1-olate)-furazano[3,4-d]pyridazine-based anions and ammonium-based cations." Computational Materials Science 146 (April 2018): 230–39. http://dx.doi.org/10.1016/j.commatsci.2018.01.016.

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36

Merslavič, Marjo, Andrej Petrič, Branko Stanovnik, and Miha Tišler. "1, 3-dipolar cycloaddition of diazomethane to azolopyridazines. The synthesis of 8-methyl-8H- and 9-methyl-9H-pyrazolo[3, 4-d]-s-triazolo[4, 3-b]pyridazine and 1-methyl-1H- and 2-methyl-2H-imidazo[1, 2-b]pyrazolo[3, 4-b]pyridazine derivatives." Journal of Heterocyclic Chemistry 26, no. 3 (May 1989): 581–83. http://dx.doi.org/10.1002/jhet.5570260311.

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37

Zohdi, Hussein F., Tabia A. Osman, and Abdou O. Abdelhamid. "Heterocycles from Pyrazoloylhydroximoyl Chloride: Synthesis of Certain Quinoxaline, Benzothiadiazine, Benzoxadiazine, Quinazolinone, Imidazo[1,2-a]pyridine, Imidazo[1,2-a]pyrimidine, Isoxazole, Pyrazolo[3,4-d]pyridazine and Pyrrolidino[3,4-d]isoxazolin-4,." Journal of the Chinese Chemical Society 44, no. 6 (December 1997): 617–23. http://dx.doi.org/10.1002/jccs.199700095.

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38

MEADE, E. A., L. L. WOTRING, J. C. DRACH, and L. B. TOWNSEND. "ChemInform Abstract: Synthesis, Antiproliferative, and Antiviral Activity of Certain 4-Aminopyrrolo(2,3-d)pyridazine Nucleosides: An Entry into a Novel Series of Adenosine Analogues." ChemInform 23, no. 23 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199223266.

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39

TOMINAGA, Y., N. YOSHIOKA, S. KATAOKA, N. AOYAMA, T. MASUNARI, and A. MIIKE. "ChemInform Abstract: Synthesis and Chemiluminescence of 1,3-Disubstituted Pyrazolo(4′,3′:5, 6)pyrido(2,3-d)pyridazine-5,8(6H,7H)-diones and Related Compounds." ChemInform 27, no. 12 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199612172.

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40

Zohdi, Hussein F., Rafat M. Mohareb, and Wagnat W. Wardakhan. "HETEROCYCLIC SYNTHESIS WITH ISOTHIOCYANATE AND SULFUR: A NOVEL ROUTE FOR THE SYNTHESIS OF PYRIDINO[2,3-d]THIAZOLE, THIAZOLO[4′,5′:2,3] PYRIDINO[4,3-d]PYRIDAZINE AND THIAZOLO[4,5-b]ISOQUINOLINE DERIVATIVES." Phosphorus, Sulfur, and Silicon and the Related Elements 101, no. 1-4 (April 1995): 179–87. http://dx.doi.org/10.1080/10426509508042515.

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41

HAIDER, N., K. MEREITER, and R. WANKO. "ChemInform Abstract: Inverse-Electron-Demand Diels-Alder Reactions of Condensed Pyridazines, Part 4. Synthesis and Cycloaddition Reactions of 1,4-Bis( Trifluoromethyl)pyrido(3,4-d)pyridazine." ChemInform 25, no. 46 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199446175.

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42

Boraei, Ahmed T. A., Ahmed A. M. Sarhan, Sammer Yousuf, and Assem Barakat. "Synthesis of a New Series of Nitrogen/Sulfur Heterocycles by Linking Four Rings: Indole; 1,2,4-Triazole; Pyridazine; and Quinoxaline." Molecules 25, no. 3 (January 21, 2020): 450. http://dx.doi.org/10.3390/molecules25030450.

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Abstract:

A new series of nitrogen and sulfur heterocyclic systems were efficiently synthesized by linking the following four rings: indole; 1,2,4-triazole; pyridazine; and quinoxaline hybrids. The strength of the acid that catalyzes the condensation of 4-amino-5-(1H-indol-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 1 with aromatic aldehydes controlled the final product. Reflux in glacial acetic acid yielded Schiff bases 2–6, whereas concentrated HCl in ethanol resulted in a cyclization product at C-3 of the indole ring to create indolo-triazolo-pyridazinethiones 7–16. This fascinating cyclization approach was applicable with a wide range of aromatic aldehydes to create the target cyclized compounds in excellent yield. Additionally, the coupling of the new indolo-triazolo-pyridazinethiones 7–13 with 2,3-bis(bromomethyl)quinoxaline, as a linker in acetone and K2CO3, yielded 2,3-bis((5,6-dihydro-14H-indolo[2,3-d]-6-aryl-[1,2,4-triazolo][4,3-b]pyridazin-3 ylsulfanyl)methyl)quinoxalines 19–25 in a high yield. The formation of this new class of heterocyclic compounds in high yields warrants their use for further research. The new compounds were characterized using nuclear magnetic resonance (NMR) and mass spectral analysis. Compound 6 was further confirmed by the single crystal X-ray diffraction technique.

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KOERMENDY, K., and F. RUFF. "ChemInform Abstract: Pyridazines Condensed with a Hetero Ring. Part 4. Formation of Pyrazino(2,3-d(c))pyridazine Skeletons by Cyclocondensation of 4,5- Diamino- and 3,4,5-Triaminopyridazinones." ChemInform 22, no. 15 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199115196.

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44

Ito, Keiichi, Kazuya Kinoshita, Atsuyuki Tomizawa, Fumi Inaba, Yuka Morikawa-Inomata, Mitsuko Makino, Keiichi Tabata, and Nobuhiko Shibakawa. "Pharmacological Profile of Novel Acid Pump Antagonist 7-(4-Fluorobenzyloxy)-2,3-dimethyl-1-{[(1S,2S)-2-methyl cyclopropyl]methyl}-1H-pyrrolo[2,3-d]pyridazine (CS-526)." Journal of Pharmacology and Experimental Therapeutics 323, no. 1 (July 13, 2007): 308–17. http://dx.doi.org/10.1124/jpet.107.121350.

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45

TOMINAGA, Y., J. K. LUO, L. W. CASTLE, and R. N. CASTLE. "ChemInform Abstract: Polycyclic Pyridazines. Part 2. Synthesis of Pyrazolo(4′,3′:5,6)pyrido( 2,3-d)pyridazine Derivatives from Dimethyl Pyrazolo(3,4-b)pyridine-5,6- dicarboxylates as the Key Intermediates." ChemInform 24, no. 38 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199338218.

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46

HAIDER, N., K. MEREITER, and R. WANKO. "ChemInform Abstract: Inverse-Electron-Demand Diels-Alder Reactions of Condensed Pyridazines. Part 7. (4 + 2) Cycloaddition Reactions of 1,4-Bis(trifluoromethyl) pyrido(3,4-d)pyridazine with Indole-Type Dienophiles." ChemInform 26, no. 43 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199543170.

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47

Filali, Mouad, Hicham Elmsellem, Tuncer Hökelek, Abdelkrim El-Ghayoury, Oleh Stetsiuk, El Mestafa El Hadrami, and Abdessalam Ben-Tama. "Crystal structure, Hirshfeld surface analysis and corrosion inhibition study of 3,6-bis(pyridin-2-yl)-4-{[(3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-5H-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl)methoxy]methyl}pyridazine monohydrate." Acta Crystallographica Section E Crystallographic Communications 75, no. 8 (July 12, 2019): 1169–74. http://dx.doi.org/10.1107/s2056989019009848.

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Abstract:

In the title compound, C27H30N4O6·H2O, the two dioxolo rings are in envelope conformations, while the pyran ring is in a twisted-boat conformation. The pyradizine ring is oriented at dihedral angles of 9.23 (6) and 12.98 (9)° with respect to the pyridine rings, while the dihedral angle between the two pyridine rings is 13.45 (10)°. In the crystal, O—Hwater...Opyran, O—Hwater...Omethoxymethyl and O—Hwater...Npyridazine hydrogen bonds link the molecules into chains along [010]. In addition, weak C—Hdioxolo...Odioxolo hydrogen bonds and a weak C—Hmethoxymethyl...π interaction complete the three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (55.7%), H...C/C...H (14.6%), H...O/O...H (14.5%) and H...N/N...H (9.6%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Electrochemical measurements are also reported.

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48

Attaby, Fawzy A., Sanaa M. Eldin, and Mohamed B. Abou-abdou. "REACTIONS OF α-THIOCARBOXAMIDOCINNA-MONITRILE DERIVATIVES WITH DIETHYL MALONATE: SYNTHESIS OF PYRAZOLO-[3,4-b]-α-PYRIDINONE, THIENO[2,3-b]-α-PYRIDINONE, PYRIDO[2,3:4′,5′]THIENO[2,3-c]PYRIDAZINE AND PYRIDO[2,3:4′,5′]-THIENO[2,3-d]PYRIMIDINONETHIONE DERIVATIVES." Phosphorus, Sulfur, and Silicon and the Related Elements 129, no. 1 (October 1, 1997): 121–33. http://dx.doi.org/10.1080/10426509708031587.

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49

Furlan, Borut, Branko Stanovnik, and Miha Tišler. "1,3-Dipolar Cycloadditions of 2-Diazopropane to 1-Phenyl-bis-s-triazolo[4,3-b:3′,4′-f]pyridazine. The Synthesis of 11,11-Dimethyl-11H-pyrazolo [3,4-d]bis-s-triazolo[4,3-b:3′,4′-f]pyridazines, Derivatives of a Novel Heterocyclic System." Synthesis 1986, no. 01 (1986): 78–80. http://dx.doi.org/10.1055/s-1986-31486.

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50

Ito, Keiichi, Kazuya Kinoshita, Atsuyuki Tomizawa, Yuka Morikawa-Inomata, Fumi Inaba, Yoshifumi Fujita, Keiichi Tabata, and Nobuhiko Shibakawa. "The Effect of Subchronic Administration of 7-(4-Fluorobenzyloxy)-2,3-dimethyl-1-{[(1S,2S)-2-methylcyclopropyl]methyl}-1H-pyrrolo[2,3-d]pyridazine (CS-526), a Novel Acid Pump Antagonist, on Gastric Acid Secretion and Gastrin Levels in Rats." Journal of Pharmacology and Experimental Therapeutics 326, no. 1 (April 14, 2008): 163–70. http://dx.doi.org/10.1124/jpet.108.137299.

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