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Journal articles on the topic 'Pyrazolo[5,1 b]thiazole'

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Author: Grafiati

Published: 1 July 2022

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1

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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2

Sawusch, Stefan, and Uwe Schilde. "Ligandenaustauschreaktionen von NiCl2 (PPh3)2 mit O(S)⌒N⌒S-Liganden / Ligand Exchange Reactions of NiCl2(PPh3)2 with O(S )⌒ N ⌒ S Ligands." Zeitschrift für Naturforschung B 54, no. 7 (July 1, 1999): 881–86. http://dx.doi.org/10.1515/znb-1999-0710.

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Ligand exchange reactions of NiCl2(PPh3)2 with O (S )⌒N⌒S ligands were studied. Oxidation products of O⌒N⌒S ligands have been characterized and their structures determined: 3-methyl-4H-benzo[b] [ 1,4]thiazin-2-yl-phenylmethanone / 2-methyl-benzo[d] [ 1,3]thiazole (mixed crystal); [2-iminoisopropyl-thiophenolato(2-)](triphenyl-phosphane)-nickel(II); 1 -phenyl-3-methyl-4-(benzoyl-thiobenzoylhydrazono)-pyrazol-5-thione; [ 1 -phenyl-3-methyl- 4-(benzoyl-thiobenzoylhydrazono)-pyrazol-5-thionato](triphenyl-phosphane)-nickel(II).

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3

Thorimbert, Serge, Candice Botuha, and Kevin Passador. "‘Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space." Synthesis 51, no. 02 (November 7, 2018): 384–98. http://dx.doi.org/10.1055/s-0037-1611279.

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William Pitt and co-workers have created a virtual exploratory heterocyclic library ‘VEHICLe’ containing over 200 unconquered bicyclic heteroaromatic rings, synthetically feasible with potential medicinal interest. Since the publication of the 22 ‘heteroaromatic rings of the future’ by Pitt in 2009, 15 of them have been successfully synthesized as bicyclic or polycyclic forms and evaluated for applications in both biology and material science. This short review presents the critical synthesis associated with innovative synthetic methodologies of the synthetically conquered ring scaffolds from the list of 22 with a spotlight on the scientific contribution of this fascinating article for the expansion of the chemical diversity.1 Introduction2 Heteroaromatic Rings of the Future: The Synthetic challenge?2.1 4-Pyrido[1,3]oxazin-4-one-P1 2.2 Pyrrolo[2,1-b][1,3]oxazin-4-one-P4 2.3 Furo[2,1-e]pyridazin-4(1H)-one-P5 2.4 Isoxazolo[3,4-c]pyridin-7-one-P6 2.5 5H,6H-[1,2]Thiazolo[5,4-c]pyridin-5-one-P7 2.6 4H,5H-Furo[3,2-b]pyridin-5-one-P8 2.7 1H,5H,6H-Pyrazolo[3,4-c]pyridin-5-one-P9 2.8 Thieno[3,4-c]pyridazine-P10 2.9 Pyrrolo[1,2-c][1,2,3]triazine-P11 2.10 Thieno[3,4-a]oxazole-P12 2.11 2,4-Dihydropyrrolo[3,2-c]pyrazole-P13 2.12 Pyrazolo[1,5-b]isoxazole-P14 2.13 Imidazo[1,5-c]pyrimidin-3(2H)-one-P16 2.14 Cyclopenta[b][1,4]oxazin-5(4H)-one-P17 2.15 2,3-Dihydro-2,6-naphthyridin-3-one-P18 3 Conclusion

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4

Abdel-motaal, Marwa, E. M. Kandeel, M. Abou-Elzahab, and F. Elghareeb. "Synthesis and Evaluation of Antioxidant Activity of Some New Heterocyclic Compounds Bearing the Benzo[B]Furan Moiety." European Scientific Journal, ESJ 13, no. 30 (October 31, 2017): 297. http://dx.doi.org/10.19044/esj.2017.v13n30p297.

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New compounds were synthesized by the reaction of 3-acetyl-5- methoxy-2-methylbenzofuran (1) with cyanoacetylhydrazine which afforded the hydrazide hydrazone derivative 2. Compound 2 underwent a series of heterocyclization reactions to give the new pyrazole, isoxazole, cyclopentanothiophene, thiazole, triazole, 2H-chromene and pyridone derivatives (3-13). The elemental and spectral data (IR, 1H NMR and MS) characterized their structures. Screening for some selected compounds was carried for their potential antioxidant activities using ABTS. Among the tested samples compounds 9, 11, 5 and 10 exhibited promising activity.

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5

Mohareb, Rafat M., Nadia Y. Megally Abdo, and Wagnat W. Wardakhan. "Synthesis and evaluation of pyrazolo[5,1-b]quinazoline-2-carboxylate, and its thiazole derivatives as potential antiproliferative agents and Pim-1 kinase inhibitors." Medicinal Chemistry Research 26, no. 10 (June 17, 2017): 2520–37. http://dx.doi.org/10.1007/s00044-017-1951-5.

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6

Ghabbour, Hazem A., Bakr F. Abdel-Wahab, Mesfer Alamri, Mohamed A. Al-Omar, and Gamal A. El-Hiti. "Crystal structure of 2-(5-(4-fluorophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)-4-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)thiazole, C29H25FN6S." Zeitschrift für Kristallographie - New Crystal Structures 232, no. 1 (January 1, 2017): 21–23. http://dx.doi.org/10.1515/ncrs-2016-0110.

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AbstractC29H25FN6S, triclinic, P1̅, a = 7.5726(8) Å, b = 11.1428(13) Å, c = 16.412(2) Å, α = 91.823(5)°, β = 102.277(5)°, γ = 106.692(4)°, V = 1289.8(3) Å3, Z = 2, Rgt(F) = 0.079, wRref(F2) = 0.205, T = 296 K.

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7

El-Hiti, Gamal A., Bakr F. Abdel-Wahab, Mohammed Baashen, and Hazem A. Ghabbour. "Crystal structure of 2-(3-(benzofuran-2-yl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-chlorophenyl)thiazole, C26H17ClFN3OS." Zeitschrift für Kristallographie - New Crystal Structures 231, no. 3 (September 1, 2016): 911–12. http://dx.doi.org/10.1515/ncrs-2016-0004.

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8

Baashen, Mohammed A., Bakr F. Abdel-Wahab, Amany S. Hegazy, Benson M. Kariuki, and Gamal A. El-Hiti. "The crystal structure of 4-(4-bromophenyl)-2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole, C24H16Br2FN3S." Zeitschrift für Kristallographie - New Crystal Structures 236, no. 2 (January 8, 2021): 425–27. http://dx.doi.org/10.1515/ncrs-2020-0605.

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9

Sheikhi-Mohammareh, Seddigheh, Ali Shiri, Mehdi Bakavoli, and Joel Mague. "A Straightforward Approach for the Synthesis of Novel Derivatives of Benzo[b]pyrazolo[5′,1′:2,3]pyrimido[4,5-e][1,4]thiazine." Journal of Heterocyclic Chemistry 53, no. 4 (July 21, 2015): 1231–35. http://dx.doi.org/10.1002/jhet.2432.

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10

Alotaibi, Abdullah A., Bakr F. Abdel-Wahab, Amany S. Hegazy, Benson M. Kariuki, and Gamal A. El-Hiti. "The crystal structure of 2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-8H-indeno[1,2-d]thiazole, C25H17BrFN3S." Zeitschrift für Kristallographie - New Crystal Structures 235, no. 4 (June 25, 2020): 897–99. http://dx.doi.org/10.1515/ncrs-2020-0088.

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AbstractC25H17BrFN3S, triclinic, P1̄ (no. 2), a = 11.2926(6) Å, b = 11.5832(4) Å, c = 16.9974(9) Å, α = 109.211(4)°, β = 90.211(4)°, γ = 95.290(4))°, V = 2089.21(18) Å3, Z = 4, Rgt(F) = 0.0580, wRref(F2) = 0.1797, T = 296 K.

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11

Hafez, Hend N., and Abdel-Rahman B. A. El-Gazzar. "Synthesis of Novel Pyridine Bearing Biologically Active Imidiazolyl, Pyrazolyl, Oxa/thiadiazolyl and Urea Derivatives as Promising Anticancer Agents." Current Organic Synthesis 17, no. 1 (February 24, 2020): 55–64. http://dx.doi.org/10.2174/1570179417666191223163225.

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Background: A novel series of pyridine containing 1,3,4-oxa/thiadiazol derivatives 4a,b, pyrazole derivatives 5-7, thiazole derivatives 9a,b and 17a-c, urea derivatives 12a-c, imidiazole derivative 16, imidazo[1,2-a]pyridine derivatives 18a, b, tetrazole 19, pyrane 20 and pyridine derivatives 21 has been synthesized. Objective: This research aims to synthesize 6-(Trifluoromethyl)-2-[3-(trifluoromethyl)phenyl] amino nicotinohydrazide 2 and 6-(trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]amino pyridin-3-carboaldhyde 15 as key intermediate for the synthesis of novel pyridine derivatives bearing different heterocyclic rings in order to study the additive effect of this ring toward tumor cell lines. Methods: 6-(Trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]amino nicotinohydrazide 2 was synthesized in a series of synthetic steps and was used as key intermediate for the synthesis of compounds 3-(1,3,4- oxa/thiadiazol-2-yl)-6-(trifluoromethyl)-N-(3- trifluoromethyl) phenyl) pyridin-2-amine 4a,b, (3,5-dimethyl- 1H-pyrazol-1-yl derivatives) [6-(trifluoromethyl)-2-[3- trifluoromethyl) phenyl] amino pyridin-3- yl]methanone 5a,b, 6-8, 9a,b and 12a-c. Also, 6-(trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]amino pyridin-3-carboaldhyde (15) was used as a key intermediate for the synthesis of novel series of pyridine derivatives with different heterocyclic ring (16-21). Results: Structures of the newly synthesized compounds were established by elemental analysis and spectral data. All the synthesized compounds were screened for their in vitro anticancer activity against liver cancer (HepG2), human colon cancer (HT-29) and human breast adenocarcinoma cell lines (MCF-7). Conclusion: All the synthesized compounds were investigated for their in vitro antitumor activity. Compounds 4b, 9a,b and 19 showed higher antitumor activity than the doxorubicin. Interestingly, pyridine with pfluorophenyl urea 12a demonstrated the most potent antitumor activity. The activity of these compounds is strongly dependent on the basic skeleton of the molecules and the nature of the heterocyclic ring attached to the pyridine moiety.

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12

Mostafa, Mohamed S., Nasser M. Abd El-Salam, and Othman Y. Alothman. "Synthesis and Microbial Activity of Novel 3-Methyl-2-pyrazolin-5-one Derivatives." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/183130.

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2-Oxo-2H-chromene-3-carbohydrazide derivatives2a,breact with 2-{[4-(substituted thiazol-2-yl)iminoethyl)-phenyl]hydrazono}-3-oxo-butyric acid ethyl esters4a–cto give 3-methyl-1-[(2-oxo-2H-chromen-3-yl) carbonyl]-4-{[4-(substituted thiazol-2-yl)iminoethyl)-phenyl]hydrazono}]-2-pyrazolin-5-one derivatives5a–f. A considerable increase in the reaction rate had been observed with better yield using microwave irradiation for the synthesis of compounds2a,b,3a–c, and5a–f. The synthesized products were tested againstB. subtilis,S. aureus, andE. colias well asC. albicanscompared with tetracycline and nystatin as reference drugs.

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13

Toplak, Renata, Jurij Svete, Simona Golič Grdadolnik, and Branko Stanovnik. "Methyl (Z)-2-[(Benzyloxycarbonyl)amino]-3-dimethyl- aminopropenoate in the Synthesis of Heterocyclic Systems. Synthesis of (Benzyloxycarbonyl)amino Substituted Fused Pyrimidinones." Collection of Czechoslovak Chemical Communications 64, no. 2 (1999): 177–89. http://dx.doi.org/10.1135/cccc19990177.

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Methyl (Z)-2-[(benzyloxycarbonyl)amino]-3-dimethylaminopropenoate (1) was used as a reagent for preparation of 3-[(benzyloxycarbonyl)amino] substituted 4H-pyrido[1,2-a]pyrimidin-4-ones 17-21, 4H-pyrimido[1,2-b]pyridazin-4-ones 22 and 23, 5H-[1,2,4]triazolo[2,3-a]- pyrimidin-5-one 24, 5H-thiazolo[3,2-a]pyrimidin-5-one 25, and 4H-pyrazino[1,2-a]pyrimidin-4-one 26. Removal of the benzyloxycarbonyl group by catalytical transfer hydrogenation with Pd/C in the presence of cyclohexene is selective to give 3-amino-4H-pyrido[1,2-a]- pyrimidin-4-ones 27-30 in 85-92% yields, or with hydrogen bromide in acetic acid to give 3-amino-4H-pyrimido[1,2-b]pyridazin-4-one (31) and 6-amino-5H-thiazolo[3,2-a]pyrimidin-5-one (32) in 80% yields.

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14

Shaker, R. M. "Synthesis of 1-(2,3-Dimethyl-1-phenyl-pyrazolone-5-yl-4)-2-mercapto-1′,5-cycloalkane-spiro[1,3]thiazolo[3,4-b]-1,2,4-triazole Derivatives." Phosphorus, Sulfur, and Silicon and the Related Elements 178, no. 5 (May 1, 2003): 1175–82. http://dx.doi.org/10.1080/10426500307854.

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15

Gad-Elkareem, Mohamed A. M., Azza M. Abdel-Fattah, and Mohamed A. A. Elneairy. "Pyrazolo[3,4-b]pyridine in heterocyclic synthesis: synthesis of new pyrazolo[3,4-b]pyridines, imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines, and pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines." Canadian Journal of Chemistry 85, no. 9 (September 1, 2007): 592–99. http://dx.doi.org/10.1139/v07-089.

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Pyrazolo[3,4-b]pyridine derivatives 7 and 9 were synthesized via the reaction of 3-amino-1H-pyrazolo-[3,4-b]pyridine derivative 2 with ω-bromoacetophenones. Reaction of 7 and 9 with Ac2O afforded the imidazo[1',2':1,5]py razolo[3,4-b]pyridine derivative 8 and pyrazolo[3,4-b]pyridine derivative 10, respectively. Reaction of 2 with chloroacetonitrile followed by DMF-DMA gave imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines 4 and 5, respectively. Acetyl acetone and 1,1-dicyano-2,2-dimethylthioethene were reacted with 2 to afford the pyrido[2',3':3,4]pyrazolo-[1,5-a]-pyrimidines 11 and 14, respectively. Also, 2 reacted with DMF-DMA to yield the formamidine 15, which in turn, reacted with active methylene reagents, yielding the corresponding pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines 18 and 23a-23d.Key words: 1H-pyrazolo[3,4-b]pyridines, imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines, pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines.

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Abd El Latif, Fawi M., Magda A. Barsy, Eman A. Elrady, and M. Hassan. "New Routes for Novel Pyrazolo[3,4-b][1,6]-naphthyridine, Pyrazolo[3,4-b]pyridine and Pyrazolo[3,4:2,3]pyrido[6,1-a]benzimidazole Derivatives." Journal of Chemical Research 23, no. 12 (December 1999): 696–97. http://dx.doi.org/10.1177/174751989902301206.

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Pyrazolo[3,4- b] [1,6] naphthyridine, pyrazolo[3,4- b] pyridine and pyrazolo[3,4:2,3] pyrido [6,1 -a] benzimidazole derivatives are synthesized starting from the isomeric 3-substituted 5-chloro-1-phenylpyrazole-4-carbaldehyde.

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17

Lynch, Daniel E., and Ian McClenaghan. "Ethyl 2-amino-4-tert-butyl-1,3-thiazole-5-carboxylate and 6-methylimidazo[2,1-b]thiazole–2-amino-1,3-thiazole (1/1)." Acta Crystallographica Section C Crystal Structure Communications 60, no. 8 (July 21, 2004): o592—o594. http://dx.doi.org/10.1107/s0108270104015471.

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18

S. AL-Rawi, Muna, Huda A. Hassan, Dheefaf F. Hassan, and Ismaeel Y. Majeed. "New Series of Substituted Heterocyclics Derived from α , β – Unsaturated Ketone and Their Cytotoxic Activity Tumor Cell Lines." Oriental Journal of Chemistry 34, no. 6 (November 10, 2018): 2826–31. http://dx.doi.org/10.13005/ojc/340620.

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The aldol condensation of 2-acetylnaphthalene with 9-anthracene carboxaldehyde afforded α, β-unsaturated keton (1) . New heterocyclic compounds containing: cyclohexenone[2], indazole[3], pyrimidinethion [4], thiazolo fused pyrimidine[5], isoxazoline[6], substituted pyrazoline[7]a-d and pyrimidinone[8] rings system were synthesized from α, β-unsaturated keton[1]. Cyclization of [1] with ethylacetoacetate gave the mentioned heterocycle cyclohexanone [2]. The cyclo condensation of [2] with hydrazine gave the new indazole derivative [3]. furthermore, the reation of [1]with thiourea gives thiopyrmidine derivative [4]. The cyclo condensation of [4] with chloroacetic acid gave the fused rings [5]. Then reacted compound[1] with hydroxylamine to produce isoxazoline [6]. Also the reaction of [1]with hydrazine and hydrazide derivatives to produce pyrazole [7]a-d. All the newly synthesized derivatives[2-7a-d] were characterized via the CHN-S, FT- IR, 1H NMR, and13C NMR (of some of theme). The antibacterial and cytotoxic activities were evaluated for these derivatives[2-7a-d] . The study of antibacterial displayed good to moderate activity and the study of anticancer activity showed that were effective for inhibition of L20 B the mice intestines carcinoma cell line and RD human pelvic rhabdomyosarcoma cell line. Treated.

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19

Norman, Rebecca E., Michael V. Perkins, Andris J. Liepa, and Craig L. Francis. "N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIII. Cleavage and Rearrangement Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine 1,1-Dioxides." Australian Journal of Chemistry 69, no. 1 (2016): 61. http://dx.doi.org/10.1071/ch15445.

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Treatment of pyrazolo[1,5-b][1,2,4,6]thiatriazines 1 with the Vilsmeier–Haack reagent afforded pyrazolo[1,5-a][1,3,5]triazines 5. Reaction of compounds 1 with trifluoroacetic anhydride, dimethyl sulfoxide, and triethylamine afforded 5-dimethylsulfanylidene derivatives 8. The guanidino-pyrazole-sulfonic acid 9 was produced from treatment of compounds 1 with trifluoroacetic acid under anhydrous conditions. Similar treatment in the presence of water afforded the desulfonated pyrazolo-guanidine 6. Reactions of 6 with one-carbon electrophiles provided various 4-substituted pyrazolo[1,5-a][1,3,5]triazines 5. Attempted catalytic hydrogenolysis of N7-benzyl pyrazolo[1,5-b][1,2,4,6]thiatriazines 2 in alcohols led to sulfamates 12 from thiatriazine ring cleavage. Ethyl acetate or tert-butanol as solvent allowed successful debenzylation to provide compounds 1. Aminolysis of compounds 2 gave sulfamides 13. Thermal rearrangement of compounds 2 afforded 6-benzyl-pyrazolo[3,4-e][1,2,4]thiadiazines 14.

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Forsyth, Craig M., Craig L. Francis, Saba Jahangiri, Andris J. Liepa, Michael V. Perkins, and Anna P. Young. "N,N-Dialkyl-N'-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part VIII. Novel Pyrazolo-Fused Oxathiadiazines and Thiatriazoles." Australian Journal of Chemistry 63, no. 4 (2010): 659. http://dx.doi.org/10.1071/ch09581.

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N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted with pyrazol-3-ones 2 under a variety of conditions to give pyrazolo[2,3-e][1,2,3,5]oxathiadiazine dioxides 3 and pyrazolo[3,2-b][1,4,3,5]oxathiadiazine dioxides 5, and frequently, one or both of pyrazolo[1,2-b][1,2,3,5]thiatriazole 1,1,5-trioxides 4 and 1,1,7-trioxides 6. In all reactions, the pyrazolo[3,2-b][1,4,3,5]oxathiadiazine 5 was the major product, with the pyrazolo[2,3-e][1,2,3,5]oxathiadiazine 3 being a significant product in the absence of base. Prior to our recent work, the core ring systems of compounds 3 and 5 had not been reported and compounds 4 and 6 are new derivatives of a rare ring system.

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21

Ghabbour, Hazem A., Adnan A. Kadi, Hussein I. El-Subbagh, Tze Shyang Chia, and Hoong-Kun Fun. "1-(5-Bromo-4-phenyl-1,3-thiazol-2-yl)pyrrolidin-2-one." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 16, 2012): o1738—o1739. http://dx.doi.org/10.1107/s160053681201954x.

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The asymmetric unit of the title compound, C13H11BrN2OS, consists of two crystallographically independent molecules (A and B). In each molecule, the pyrrolidine ring adopts an envelope conformation with a methylene C atom as the flap atom. In molecule A, the central thiazole ring makes a dihedral angle of 36.69 (11)° with the adjacent phenyl ring, whereas the corresponding angle is 36.85 (12)° in molecule B. The pyrrolidine ring is slightly twisted from the thiazole ring, with C—N—C—N torsion angles of 4.8 (3) and 3.0 (4)° in molecules A and B, respectively. In the crystal, C—H...π and π–π [centroid-to-centroid distance = 3.7539 (14) Å] interactions are observed. The crystal studied was a pseudo-merohedral twin with twin law (-100 0-10 101) and a refined component ratio of 0.7188 (5):0.2812 (5).

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22

Shukla, Upendra K., Raieshwar Singh, J. M. Khanna, Anil K. Saxena, Hemant K. Singh, Ravindra N. Sur, Bhola N. Dhawan, and Nitya Anand. "Synthesis of trans-2-[N-(2-Hydroxy-1,2,3,4-tetrahydronaphthalene-1-yl)]iminothiazolidine and Related Compounds - A New Class of Antidepressants." Collection of Czechoslovak Chemical Communications 57, no. 2 (1992): 415–24. http://dx.doi.org/10.1135/cccc19920415.

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Antiparasitic and antidepressant activities exhibited by tetramisole (I) and its enantiomers prompted the study of its structural analogs trans-2-[N-(2-hydroxy-1,2,3,4-tetrahydronaphthalene/indane-1-yl)]iminothiazolidine (VIII/IX) and 2,3,4a,5,6,10b-hexahydronaphtho[1',2':4,5]-imidazo[2,1-b]thiazole (XII), 2,3,4a,5-tetrahydro-9bH-indeno[1',2':4,5]imidazo[2,1-b]thiazole (XIII), and 2,3,4a,5-tetrahydro-9bH-indeno[1',2':4,5]imidazo[2,1-b]thiazole (XVI), and a homolog 3,4,6,7-tetrahydro-7-phenyl-2H-imidazo[2,1-b]-1,3-thiazine (XX). While none of these compounds showed any noteworthy antiparasitic activity, the trans-2-[N-(2-hydroxy-1,2,3,4-tetrahydronaphthalene-1-yl)]iminothiazolidine (VIII) has shown marked antidepressant activity, better than imipramine in the tests used, and provides a new structural lead for antidepressants.

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23

Abd El-Aal, Hassan A. K., and Ali A. Khalaf. "Friedel–Crafts Chemistry. Part 46. Unprecedented Construction of Tricyclic Pyrazolo[3,4-b]quinolines, -[1,8]naphthyridines, -azepines, -azocines, -pyrido[3,2-g]azocines, and pyrazolo[3,4-b]azonines via Friedel–Crafts Ring Closures." Australian Journal of Chemistry 69, no. 6 (2016): 652. http://dx.doi.org/10.1071/ch15526.

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A series of keto-substituted pyrazolo[3,4-b]quinolines, pyrazolo[3,4-b][1,8]naphthyridines, benzo[e]pyrazolo[3,4-b]azepines, benzo[g]pyrazolo[3,4-b]azocines, pyrazolo[3,4-b]pyrido[3,2-g]azocines, and benzo[g]pyrazolo[3,4-b]azonines scaffolds were synthesized via a Friedel–Crafts cyclialkylation approach. The precursor acids were obtained by utilizing the modified Ullman coupling reactions of 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid with different aryl amines followed by ring closures in the presence of AlCl3/CH3NO2 or P2O5 or polyphosphoric acid catalysts. Particular attention is given to the novel structures especially in regard to the promising pharmaceutical and therapeutic values associated with their skeletons.

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24

Hu, Hua-nan, You Peng, Hua-nan Huang, Tao Yang, Fu-shan Chen, and Ping Yan. "Deacylation during the Synthesis of New 4-Amino-1H-Pyrazolo [3,4-B] Pyridines Catalysed by Sncl4." Journal of Chemical Research 42, no. 8 (August 2018): 412–15. http://dx.doi.org/10.3184/174751918x15337230783041.

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A series of novel 1-(4-amino-6-methyl-1-aryl-1H-pyrazolo[3,4-b]pyridin-5-yl)-ethanones and 6-methyl-1-aryl-1H-pyrazolo[3,4-b]pyridin-4-amines were prepared by the annulation of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles with acetylacetone in the presence of tin(IV) chloride. The results demonstrated that the ethanones are the precursors of second compounds.

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25

Romo, Pablo E., Braulio Insuasty, Jairo Quiroga, and Rodrigo Abonia. "3′-Methyl-2-oxo-1′,5′-diphenyl-1′,7′-dihydrospiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-6′-carboxylic Acid." Molbank 2021, no. 2 (May 21, 2021): M1214. http://dx.doi.org/10.3390/m1214.

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3′-methyl-2-oxo-1′,5′-diphenyl-1′,7′-dihydrospiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-6′-carboxylic acid was synthesized using diverse conditions. The best reaction condition consisted of using water as solvent under microwave irradiation, affording product in 76% yield.

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26

Polo, Efrain, Karoll Ferrer-Pertuz, Jorge Trilleras, Jairo Quiroga, and Margarita Gutiérrez. "Microwave-assisted one-pot synthesis in water of carbonylpyrazolo[3,4-b]pyridine derivatives catalyzed by InCl3 and sonochemical assisted condensation with aldehydes to obtain new chalcone derivatives containing the pyrazolopyridinic moiety." RSC Adv. 7, no. 79 (2017): 50044–55. http://dx.doi.org/10.1039/c7ra10127a.

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Pyrazolo[3,4-b]pyridines derivatives have been synthesized via one-pot condensation of 3-methyl-1-phenyl-1H-pyrazolo-5-amine (1), paraformaldehyde (2) and β-diketones (3) under microwave irradiation in aqueous media catalyzed by InCl₃.

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Akkurt, Mehmet, Sema Öztürk Yıldırım, Fusun Ur, Zafer Cesur, Nesrin Cesur, and Orhan Büyükgüngör. "6-Methyl-N'-(1-methylethylidene)imidazo[2,1-b][1,3]thiazole-5-carbohydrazide monohydrate." Acta Crystallographica Section E Structure Reports Online 61, no. 3 (February 19, 2005): o718—o720. http://dx.doi.org/10.1107/s160053680500509x.

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28

Low, John Nicolson, Jaime Mera, Jairo Quiroga, and Justo Cobo. "3,7,7-Trimethyl-1-phenyl-1,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one." Acta Crystallographica Section E Structure Reports Online 59, no. 11 (October 23, 2003): o1804—o1806. http://dx.doi.org/10.1107/s1600536803023675.

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29

Hrynyshyn, Yevhenii V., Nazar M. Tsizorik, Anna R. Musiychuk, Andriy V. Bol’but, and Mykhailo V. Vovk. "Synthesis of 8Н-pyrazolo[5',1':3,4]pyrazino[2,1-b]quinazolin-8-ones." Chemistry of Heterocyclic Compounds 53, no. 11 (November 2017): 1242–47. http://dx.doi.org/10.1007/s10593-018-2196-z.

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30

Alotibi, Mohammed F., Bakr F. Abdel-Wahab, Emad Yousif, Amany S. Hegazy, Benson M. Kariuki, and Gamal A. El-Hiti. "Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S." Zeitschrift für Kristallographie - New Crystal Structures 235, no. 2 (February 25, 2020): 469–71. http://dx.doi.org/10.1515/ncrs-2019-0776.

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AbstractC28H20FN3O2S, triclinic, P1̄ (no. 2), a = 9.1325(7) Å, b = 11.5184(9) Å, c = 11.6535(9) Å, α = 74.682(7)°, β = 84.253(6)°, γ = 76.720(6)°, V = 1149.68(15) Å3, Z = 2, Rgt(F) = 0.0574, wRref(F2) = 0.1438, T = 296(2) K.

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31

Essassi, E. M., and M. Salem. "Synthèse Des Pyrazolo [2, 3-b] Benzotriazepines-1, 3, 5 A Partir Des Alkyl-1 Benzodiazepine 1, 5 Ones-2." Bulletin des Sociétés Chimiques Belges 97, no. 5 (September 1, 2010): 387–94. http://dx.doi.org/10.1002/bscb.19880970511.

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32

ZAHRAN, M. A., A. A. HASSANIEN, H. A. EMAM, M. Z. EL-SAID, and Y. A. AMMAR. "ChemInform Abstract: Synthesis of New Pyrazolo[1,5-a]-s-triazine, Pyrazolo[5,1-c]-as-triazines, Pyrazolo[1′,5′:1,2]imidazo[4,5-b]quinoxaline, and Pyrazolo[1,5-a]pyrimidines." ChemInform 29, no. 10 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199810139.

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33

Jaberi, Hamid Reza, and Hadi Noorizadeh. "Synthesis of Some Novel Fused Imidazo [2, 1-b] [1, 3] Thiazole and Imidazo [2, 1-b] Thiazolo [5, 4-d] Isoxazole Derivatives." E-Journal of Chemistry 9, no. 3 (2012): 1518–25. http://dx.doi.org/10.1155/2012/896454.

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In this work we describe the synthesis of some novel fused imidazo [2, 1-b] [1, 3] thiazole derivatives. The reaction of 1, 2-diaminoethane 1 with carbon disulphide in H2O/ETOH as solvent furnishes 4, 5-dihydro-1H-imidazol-2-thiol 2 under reflux condition. the reaction of 4,5-dihydro-1H-imidazol-2-thiol on treatment with ethylchloro acetate and aromatic aldehyde in presence of anhydrous sodium acetate and acetic acid as solvent to give (Z)-2-(arylidene)-5,6-dihydroimidazo [2,1-b] [1,3] thiazol-3(2H)-one 3a-j. Compounds 3a-j was condensed with hydroxylamine to give 3-(aryl)-2, 3, 6, 7-tetrahydroimidazo [2, 1-b] [1,3] thiazolo [5, 4-d] isoxazole 4a-j. The structures of the new compounds were established by elemental analyses, IR,1H NMR and13C NMR data.

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34

Nezhad, Shefa Mirani, Seied Ali Pourmousavi, and Ehsan Nazarzadeh Zare. "Superparamagnetic Poly(aniline-co-m-phenylenediamine)@Fe3O4 Nanocomposite as an Efficient Heterogeneous Catalyst for the Synthesis of 1H-pyrazolo[1,2-a]pyridazine-5,8-diones & 1H-pyrazolo[1,2-b]phthalazine-5, 10-diones Derivatives." Current Organic Synthesis 19, no. 2 (March 2022): 246–66. http://dx.doi.org/10.2174/1570179418666211104143736.

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Background: The use of polymer-based catalysts has increased because of their high potential application as an effective catalyst in organic reactions. They have benefits such as high efficiency and reactivity, simple separation, and safety compared to other heterogeneous catalysts. Aim and Objective: The objective of the current research is to prepare solid polymer-based catalysts, poly(aniline-co-m-phenylenediamine) (PAmPDA), and its superparamagnetic nanocomposite. Then, the catalytic activity of the resulting superparamagnetic nanocomposite was investigated in the synthesis of 1H-pyrazolo[1,2-b]phetalazine-5,10-diones and 1H-pyrazolo[1,2-a]pyridazine-5,8-dione derivatives. A series of some 1H-pyrazolo[1,2-b]phetalazine-5,10-diones and 1H-pyrazolo[1,2-a]pyridazine-5,8-dione derivatives was tested for its antibacterial properties against the Staphylococcus aureus and E. coli bacteria. Materials and Methods: PAmPDA copolymer was synthesized in a 1:2 molar ratio of Ani to mPDA via radical oxidative polymerization at room temperature. Superparamagnetic PAmPDA@Fe3O4 nanocompo-site was synthesized from a mixture of Fe(II), Fe(III) solution, and PAmPDA copolymer via the in-situ co-precipitation technique. 1H-pyrazolo[1,2-b]phetalazine-5,10-diones were synthesized via one-pot three-component condensation reaction of Phthalhydrazide, aromatic aldehyde derivatives, and malono-nitrile in the presence of PAmPDA under solvent-free conditions at 80 °C. The synthesis of 1H-pyrazolo[1,2-a]pyridazine-5,8-dione derivatives was carried out via a one-pot three-component condensa-tion reaction of maleic hydrazide, aromatic aldehyde derivatives, and malononitrile in the presence of PAmPDA under reflux conditions at EtOH/H2O 1:1. The antibacterial activity of some derivatives was tested against Gram-positive and Gram-negative bacteria. Results: First, superparamagnetic PAmPDA@Fe3O4 nanocomposite was synthesized and characterized successfully, and then the resulting nanocatalyst was used for the synthesis of pyrazolo[1,2-b]phthalazine and pyrazolo[1,2-a]pyridazine. We obtained the maximum yield of the desired 1H-pyrazolo[1,2-b]phthalazine-5,10 dione derivatives with 0.05 g of catalyst at 80°C, under solvent free conditions, whereby the reaction was complete within 30 min. A wide range of 1H-pyrazolo[1,2-b]phthalazine-5,10 dione derivatives were synthesized in good to excellent yield. On the other hand, pyrazolo[1,2-a]pyridazine derivative was synthesized successfully in high yield using PAmPDA as a nanocatalyst. The antibacterial activity of some derivatives, according to the data (inhibition zone%), showed good ac-tivity against Staphylococcus aureus and E. coli. Conclusion: In this research, PAmPDA was used for mild preparation of 1H-pyrazolo [1,2-a]pyridazine-5,8-diones & 1H-pyrazolo[1,2-b]phetalazine-5,10-diones derivatives with excellent yields and short reac-tion times. The attractive features of this protocol are simple procedure, cleaner reaction, and the use of recyclable nanocatalyst. Satisfactory yields of products and easy workup make this a useful protocol for the green synthesis of this class of compounds. The antibacterial activity of some derivatives, according to the data (inhibition zone%), showed good activity against Staphylococcus aureus and E. coli.

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35

Norman, Rebecca E., Michael V. Perkins, Andris J. Liepa, and Craig L. Francis. "N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XI. Some Substitution Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine 1,1-Dioxides." Australian Journal of Chemistry 68, no. 7 (2015): 1011. http://dx.doi.org/10.1071/ch14547.

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The recently discovered pyrazolo[1,5-b][1,2,4,6]thiatriazine template was shown to possess four nucleophilic sites (N2, N4, C5, N7) that underwent a range of substitution reactions. Methylation occurred at both N4 and N7. Alkylation with benzylic halides occurred preferentially at N7, regardless of the solvent, but also occurred at C5, N4, and N2. Similar alkylation with α-halo esters occurred at both N4 and N7, but the latter derivatives underwent a novel pyrazole ring expansion to afford pyrimido[1,6-b][1,2,4,6]thiatriazine derivatives. Bromination of pyrazolo[1,5-b][1,2,4,6]thiatriazines afforded unstable 5-bromo derivatives. Tosylation occurred selectively at C5, but in modest yield; catalysis with 1-methylimidazole also led to a low yield of the 5,5′-dimer. The action of HCl on N7-benzylated pyrazolo[1,5-b][1,2,4,6]thiatriazines readily caused extrusion of sulfur dioxide to produce pyrazolo-guanidines.

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36

Deeb, Ali, Medhat El-Mobayed, Abdel Naby Essawy, Adel Abd El-Hamid, and Atef Mohamid Abd El-Hamid. "Heterocyclic synthesis from 3-amino-4-cyanopyrazole." Collection of Czechoslovak Chemical Communications 55, no. 3 (1990): 728–33. http://dx.doi.org/10.1135/cccc19900728.

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3-Amino-4-cyanopyrazole I reacts with hydroxylamine and with hydrazine to yield 1H,6H-3-aminopyrazolo[3,4-c]pyrazole (III and IV). Diazotized IV couples with 2-naphthol to give the arylazo derivative VI which cyclizes to 9H-naphthol[2,1-e]pyrazolo[3',4':3,4]pyrazolo[5,1-c]-[1,2,4]triazine VII by means of acetic acid. The pyrazol-5-ylthiourea obtained from I and phenyl isothiocyanate undergoes base-catalyzed cyclization to give pyrazolo[3,4-d]pyrimidinethione derivative IX. Compound I reacts with cyclohexane in the presence of zinc chloride to give the tetrahydropyrazolo[3,4-b]quinoline derivative XI. The reaction of I with pyridine 1-oxide affords 4H,5H-pyrazolo[5',1':2,3] [1,2,4]triazolo[1,5-a]pyridine-3-carbonitrile XII.

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37

Halim, Shimaa Abdel, and Magdy A. Ibrahim. "Synthesis, spectral analysis, quantum studies, NLO, and thermodynamic properties of the novel 5-(6-hydroxy-4-methoxy-1-benzofuran-5-ylcarbonyl)-6-amino-3-methyl-1H-pyrazolo[3,4-b] pyridine (HMBPP)." RSC Advances 12, no. 21 (2022): 13135–53. http://dx.doi.org/10.1039/d2ra01469f.

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Ring opening followed by ring closure reactions of 4-methoxy-5-oxo-5H-furo[3,2-g] chromene-6-carbonitrile with 5-amino-3-methyl-1H-pyrazole gave the novel 5-(6-hydroxy-4-methoxy-1-benzofuran-5-ylcarbonyl)-6-amino-3-methyl-1H-pyrazolo[3,4-b] pyridine.

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38

Bondock, Samir, Abd El-Gaber Tarhoni, and Ahmed A. Fadda. "Heterocyclic Synthesis with 4-Benzoyl-1-cyanoacetylthiosemicarbazide: Selective Synthesis of Some Thiazole, Triazole, Thiadiazine, Pyrrylthiazole, and Pyrazolo[1,5-a]triazine Derivatives." Monatshefte für Chemie - Chemical Monthly 139, no. 2 (January 11, 2008): 153–59. http://dx.doi.org/10.1007/s00706-007-0764-5.

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39

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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40

Abdelhamid, Abdou O., and Sobhi M. Gomha. "Synthesis of New Pyrazolo[1,5-a]pyrimidine, Triazolo[4,3-a]pyrimidine Derivatives, and Thieno[2,3-b]pyridine Derivatives from Sodium 3-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-oxoprop-1-en-1-olate." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/327095.

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Condensation of sodium 3-oxo-3-(1-phenyl-1H-pyrazol-4-yl)prop-1-en-1-olate (2) with several heterocyclic amines, cyanoacetamide, cyanothioacetamide, and 2-cyanoacetohydrazide gives pyrazolo[1,5-a]pyrimidines (5a–d), pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine (9), benzo[4,5]imidazo[1,2-a]pyrimidine (10), [1,2,4]triazolo[1,5-a]pyrimidine (11), and pyridine derivatives (12–14). Also, thieno[2,3-b]pyridines (15–18) were synthesized via pyridinethione (13) withα-halo ketones andα-halo ester. Structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, alternative synthetic routes, and chemical transformation whenever possible.

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41

Rajni Swamy, V., P. Müller, N. Srinivasan, S. Perumal, and R. V. Krishnakumar. "Isomorphous methyl- and chloro-substituted small heterocyclic analogues obeying the chlorine–methyl (Cl–Me) exchange rule." Acta Crystallographica Section C Crystal Structure Communications 69, no. 4 (March 6, 2013): 412–15. http://dx.doi.org/10.1107/s0108270113004812.

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The two new isomorphous structures [3-methyl-4-(4-methylphenyl)-1-phenyl-6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridin-5-yl](thiophen-2-yl)methanone, C26H18F3N3OS, (I), and [4-(4-chlorophenyl)-3-methyl-1-phenyl-6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridin-5-yl](thiophen-2-yl)methanone, C25H15ClF3N3OS, (II), are shown to obey the chlorine–methyl exchange rule. Both structures show extensive disorder, treatment of which greatly improves the quality of the description of the structures. In addition, it is worth noting that the presence of extensive disorder may make it difficult to detect the isomorphism automatically during data-mining procedures (such as searches of the Cambridge Structural Database).

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42

Bhukya, Bhadru, and Hanmanthu Guguloth. "Synthesis and Anticancer Activity of Novel Oxadiazole Functionalized Pyrazolo[3,4-b]pyridine Derivatives." Asian Journal of Chemistry 33, no. 6 (2021): 1331–35. http://dx.doi.org/10.14233/ajchem.2021.23183.

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A series of novel oxadiazole functionalized pyrazolo[3,4-b]pyridine derivatives (6a-n)was synthesized using 6-thiophenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-3-amine (1) through reaction with 2-bromoethyl acetate, followed by hydrazine hydrate to afford hydrazide derivatives (5). These compounds were further treated with aromatic acids in the presence of phosphoryl chloride and obtained oxadiazole functionalized pyrazolo[3,4-b]pyridine derivatives (6a-n). All the synthesized compounds 6a-n were screened for anticancer activity against four cancer cell lines such as HeLa - cervical cancer (CCL-2); COLO 205-colon cancer (CCL-222); HepG2-liver cancer (HB-8065); MCF7-breast cancer (HTB-22). Compounds 6i, 6m and 6n were found to have more prominent anticancer activity at micromolar concentration.

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43

Murat Saracoglu, Murat Saracoglu, Zulbiye Kokbudak Zulbiye Kokbudak, and Zeynep imen and Fatma Kandemirli Zeynep imen and Fatma Kandemirli. "Synthesis and DFT Quantum Chemical Calculations of Novel Pyrazolo[1,5-c]pyrimidin-7(1H)-one Derivatives." Journal of the chemical society of pakistan 41, no. 3 (2019): 479. http://dx.doi.org/10.52568/000746/jcsp/41.03.2019.

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In this study, a convenient procedure for the preparation of pyrazolo[1,5-c]pyrimidin-7(1H)-one derivatives is described. The new pyrazolo[1,5-c]pyrimidin-7(1H)-one derivatives (2a, b) were synthesized from the cyclocondensation reaction of the compounds 1-amino-5-(4-methoxybenzoyl)-4-(4-methoxyphenyl)pyrimidin-2(1H)-one (1a) and 1-amino-5-(4-methylbenzoyl)-4-(4-methylphenyl)pyrimidin-2(1H)-one (1b) with α-chloroacetone. The structures of the compounds (2a, b) were characterized by elemental analysis, FT-IR, 1H-NMR and 13C-NMR spectroscopic techniques. In addition to experimental study in order to find molecular properties, quantum-chemical calculations of the new pyrazolo[1,5-c]pyrimidin-7(1H)-one derivatives (2a, b) were carried out by using DFT/B3LYP method with the 6-311G(d,p) and 6-311++G(2d,2p) basic sets. Quantum chemical features such as HOMO, LUMO, HOMO-LUMO energy gap, chemical hardness, chemical softness, electronegativity, chemical potential, dipole moment etc. values for gas and solvent phase of neutral molecules were calculated and discussed.

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44

Dias, Luiza Rosaria S., Maria JoséF Alvim, Antonio Carlos C. Freitas, Eliezer J. Barreiro, and Ana Luisa P. Miranda. "Synthesis and analgesic properties of 5-acyl-arylhydrazone 1-H pyrazolo [3,4-b] pyridine derivatives." Pharmaceutica Acta Helvetiae 69, no. 3 (December 1994): 163–69. http://dx.doi.org/10.1016/0031-6865(94)90019-1.

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45

Yakovenko, G. G., and M. V. Vovk. "Convenient approaches to the synthesis of 6-amino- and 6-oxoimidazo[4,5-b]pyrazolo[3,4-e]pyridines." Journal of Organic and Pharmaceutical Chemistry 19, no. 1(73) (March 15, 2021): 10–15. http://dx.doi.org/10.24959/ophcj.21.224583.

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Aim. To develop convenient approaches to the synthesis of 6-amino- and 6-oxoimidazo[4,5-b]pyrazolo[3,4-e]pyridines as promising biologically active scaﬀolds.Results and discussion. It has been found that cyclocondensation of N-Boc-4-aminopyrazole-5-carbaldehydes with creatinine can be used as an eﬀective method for obtaining 6-aminoimidazo[4,5-b]pyrazolo[3,4-e]pyridines previously unknown. For the synthesis of their 6-oxoanalogs, the reaction of 5-aminopyrazolo[4,3-b]pyridine-6-carboxylic acids used in a modifed Curtius rearrangement with diphenylphosphorylazide was successful. This method was implemented through the stage of the intermediate aminoisocyanates formation.Experimental part. The reaction of N-Boc-4-aminopyrazole-5-carbaldehydes with creatinine in the presence of pyrrolidine as a catalyst in reﬂuxing acetic acid allowed to obtain 6-aminoimidazo[4,5-b]pirazolo[3,4-e]pyridines with the yields of 54 – 70 %. The structure of the compounds synthesized was proven by spectral measurements. In the 1H NMR spectra there were singlets of H-3 (7.63 – 7.88 ppm) and H-8 (7.87 – 8.26 ppm) protons, as well as broad singlets of the NH2 group in the range of 7.05 – 7.21 ppm. Heating of 5-aminopyrazolo[4,3-b]pyridine-6-carboxylic acids with triethylamine and diphenylphosphorylazide in dioxane for 6 hours gave 1-substituted imidazo[4,5-b]pyrazolo[3,4-е]pyridine-6(5Н)-ones with the yields of 67 – 80 %. The IR-spectra of the compounds synthesized were characterized by the absorption bands of the C=O (1705 – 1708 cm-1) and NH (3275 – 3281 cm-1) groups. 1H NMR-spectra were characterized by singlets of H-3 and H-8 protons in the intervals of 7.43 – 8.08 ppm and 7.92 – 8.32 ppm respectively, as well as by two broad singlets of NH-protons in the ranges of 10.90 – 11.12 ppm and 11.25 – 11.37 ppm.Conclusions. Eﬀective approaches to the synthesis of new promising heterocyclic systems of 6-amino- and6-oxoimidazo[4,5-b]pirazolo[3,4-e]pyridines have been developed. Cyclocondensations of N-Boc-4-aminopyrazole-5-carbaldehydes with creatinine and 5-aminopyrazolo[4,3-b]pyridine-6-carboxylic acids with diphenylphosphorylazide have been proven to be convenient ways to obtain these compounds with good yields.Key words: N-Boc-4-aminopyrazole-5-carbaldehyde; creatinine; 5-aminopyrazolo[4,3-b]pyridine-6-carboxylic acid; diphenylphosphorylazide; 6-amino(oxo)imidazo[4,5-b]pyrazolo[3,4-e]pyridines;cyclocondensation

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46

Jasinski, Jerry P., Mehmet Akkurt, Shaaban K. Mohamed, Hajjaj H. M. Abdu-Allah, and Mustafa R. Albayati. "Crystal structure of 3-methyl-1-phenyl-6-propylamino-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (September 17, 2015): o766—o767. http://dx.doi.org/10.1107/s2056989015017004.

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In the title compound, C17H17N5, the dihedral angle between the 1H-pyrazolo[3,4-b]pyridine ring system (r.m.s. deviation = 0.001 Å) and the attached phenyl group is 2.56 (6)°. The propylamino side chain has a contorted conformation [Car—N—C—C = −77.97 (16)° and N—C—C—C = −57.37 (17)°]. An intramolecular C—H...N interaction closes anS(6) ring. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generateR22(12) loops. Aromatic π–π stacking interactions [centroid–centroid distance = 3.5726 (8) Å] are also observed.

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47

El-Kashef, Hussein, Talaat El-Emary, Pierre Verhaeghe, Patrice Vanelle, and Maha Samy. "Anticancer and Anti-Inflammatory Activities of Some New Pyrazolo[3,4-b]pyrazines." Molecules 23, no. 10 (October 16, 2018): 2657. http://dx.doi.org/10.3390/molecules23102657.

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Abstract:

New derivatives of pyrazolo[3,4-b]pyrazines and related heterocycles were synthesized using 5-amino-3-methyl-4-nitroso-1-phenyl-pyrazole (1) as a starting material. The 5-acetyl derivative 15 was shown to be a useful key intermediate for the synthesis of several derivatives of pyrazolopyrazines. Some of the prepared compounds were evaluated for their anti-inflammatory and anti-breast cancer MCF-7 cell line activities. SAR study showed that compounds 15 and 29 exhibited remarkable anti-inflammatory activity, where 15 showed the same activity as that of the reference drug indomethacin. On the other hand, compounds 25i, 25j showed very significant inhibitory activity (p < 0.001) against MCF-7 breast cancer cell line.

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48

Ibrahim, Yusria R. "Synthesis of imidazo- and pyrazolothiadiazoles from dithiobiureas and dimethyl ethynedicarboxylate." Journal of Chemical Research 2009, no. 10 (October 2009): 602–6. http://dx.doi.org/10.3184/030823409x12510192920270.

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Abstract:

Microwave irradiation of 1-substituted-2, 5-dithiobiureas and 1, 6-disubstituted-2, 5-dithiobiureas with dimethyl ethynedicarboxylate gave methyl 2-{6-oxo-2-(substituted amino)imidazo-[2, 1- b][1, 3, 5]thiadiazol-5(6 H)-ylidene} acetate and methyl 7-oxo-1, 3-bis(substituted imino)-3, 7-dihydro-1 H-pyrazolo[1, 2- c][1, 3, 4]thiadiazole-5-carboxylate. Rationales for these transformations are presented.

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49

Aly, Ashraf A., Talaat I. El‐Emary, Aboul‐Fetouh E. Mourad, Zainab Khallaf Alyan, Stefan Bräse, and Martin Nieger. "Synthesis of New Heterocycles from Reactions of 1‐Phenyl‐1 H ‐pyrazolo[3,4‐ b ]pyridine‐5‐carbonyl Azides." Journal of Heterocyclic Chemistry 56, no. 4 (February 10, 2019): 1369–75. http://dx.doi.org/10.1002/jhet.3511.

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50

Vidali, Veroniki P., Georgia Nigianni, Georgia D. Athanassopoulou, Aleksander Canko, Barbara Mavroidi, Dimitris Matiadis, Maria Pelecanou, and Marina Sagnou. "Synthesis of Novel Pyrazolo[3,4-b]pyridines with Affinity for β-Amyloid Plaques." Molbank 2022, no. 1 (February 22, 2022): M1343. http://dx.doi.org/10.3390/m1343.

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Abstract:

Three novel pyrazolo[3,4-b]pyridines were synthesized via the cyclization of 5-amino-1-phenylpyrazole with the corresponding unsaturated ketone in the catalytic presence of ZrCl4. The ketones were afforded by modifying a stabilized ylide facilitated Wittig reaction in fairly high yields. The novel compounds exhibited exciting photophysical properties with the dimethylamine phenyl-bearing pyrazolopyridine showing exceptionally large Stoke’s shifts. Finally, both the dimethylamino- and the pyrene-substituted compounds demonstrated high and selective binding to amyloid plaques of Alzheimer’s disease (AD) patient brain slices upon fluorescent confocal microscopy observation. These results reveal the potential application of pyrazolo[3,4-b]pyridines in the development of AD amyloid plaque probes of various modalities for AD diagnosis.

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