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

Author: Grafiati

Published: 1 July 2022

Last updated: 28 July 2025

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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 (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

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2

Al-Abboodi1, Doaa Hashim, and Naeemah Al-lami. "NEW METHDOLOGY OF SYNTHESIS PYRAZOLO- THIAZOLO DERIVATIVES WITH STUDY ANTIMICROBAL ACTIVITIES." iraqi journal of market research and consumer protection 16, no. 1 (2024): 1–12. http://dx.doi.org/10.28936/jmracpc16.1.2024.(1).

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In this contribution, new derivatives of thiosemicarbazon, cyclic thiazolidinone, yilidine thiazolidinone, and parazolo-thiazole were synthesized, starting from the reaction of 2 -aminobenzothiazole with p-bromo phenacyl bromide to give the first step of 2(4-bromo phenyl) imidazole (2,1 -b) benzo thiazole (1). Compound (1) then was subjected under Viels Myer Haack to yield 3-carbaldehyde linking with imidazo-benzothiazol (2). Compound (2) condensed with thiosemicarbazide togivenewsynthesis of thiosemicarbazon derivative (3). Compound 4-Oxo-1,3-thiazolidine (4) was constituted from reacting com

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3

Sultan Alwan, Ensaf, and Rafat Milad Mohareb. "Synthesis of bioactive heterocyclic compounds using camphor." Bulletin of the Chemical Society of Ethiopia 38, no. 4 (2024): 1069–76. http://dx.doi.org/10.4314/bcse.v38i4.20.

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The aim of the work was to synthesize novel heterocyclic compounds derived from camphor with antibacterial activity. The pyridazine, xanthene, pyranothiazole, pyridinothiazole, thiophene and pyrazole derivatives were produced from 4,11,11-trimethyl-9-phenyl-7-(2-phenylhydrazono)-3,4,5,6,7,9-hexahydro-1H-1,4-methanoxanthen-8(2H)-one (1). Thiophene derivatives 6a,b were produced according to the Gewald’s reaction for thiophene synthesis. On the other hand, pyranothiazol derivatives 8a,b were synthesized by the multicomponent reactions between xanthene derivative 5, benzaldehyde and ethylcyanoace

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4

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 (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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5

Thorimbert, Serge, Candice Botuha, and Kevin Passador. "‘Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space." Synthesis 51, no. 02 (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

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6

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 (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 ex

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7

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 (2017): 2520–37. http://dx.doi.org/10.1007/s00044-017-1951-5.

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8

Srinivas, Avula. "Microwave Asisted Synthesis of Methylene Bisthiazolo Arylvinyl Pyrazoles as Potential Biological Agents." Acta Chimica Slovenica 71, no. 4 (2024): 660–67. https://doi.org/10.17344/acsi.2024.8876.

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(2E,2’E)-1,1’-(5,5’-(5,5’-methylenebis(2-methoxy-5,1-phenylene))bis(3-(4-fluorophenyl)-6-phenyl-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d]thiazole-5,2-diyl))bis(3-phenylprop-2-en-1-ones) 5a–e were synthesized from (5Z,5’Z)-2,2’-(5,5’-methylenebis(2-methoxy-5,1-phenylene))bis(5-(4-fluorobenzylidene)-3-phenylthiazolidin-4-ones) 4a–e through cycloaddition reaction with cinnamic acid hydrazide and evaluated for their antibacterial, antifungal and antinematicidal activity. Among the tested compounds 5b and 5d containing chloro and nitro groups were shown to be the most effective against Ditylenchus myc

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9

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 (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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10

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 (2016): 911–12. http://dx.doi.org/10.1515/ncrs-2016-0004.

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11

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 (2021): 425–27. http://dx.doi.org/10.1515/ncrs-2020-0605.

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12

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 (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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13

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 (2015): 1231–35. http://dx.doi.org/10.1002/jhet.2432.

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14

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 (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

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15

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 ny

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16

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 a

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17

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 (2003): 1175–82. http://dx.doi.org/10.1080/10426500307854.

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18

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 (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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19

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 (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.

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20

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]tri

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21

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 be

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22

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

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23

Shukla, Upendra K., Raieshwar Singh, J. M. Khanna, et al. "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

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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 (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

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 InCl<sub>3</sub>.

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26

S. AL-Rawi, Muna, Huda A. Hassan, Dheefaf F. Hassan та 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, № 6 (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 thiopyrmi

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27

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 (2004): o592—o594. http://dx.doi.org/10.1107/s0108270104015471.

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28

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 (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 [ce

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29

Kalampaliki, Amalia D., Sofia Kanellopoulou, and Ioannis K. Kostakis. "3,6-Dihydro-5H-pyrazolo [4’,3’:5,6]pyrano[3,4-b]indol-5-one." Molbank 2022, no. 3 (2022): M1412. http://dx.doi.org/10.3390/m1412.

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Pyrano [3,4-b]indol-1(9H)-ones and indolo [2,3-c]coumarins are important classes of heterocyclic compounds with versatile biological activities. Herein, we describe a straightforward and scalable synthesis of 3,6-dihydro-5H-pyrazolo [4’,3’:5,6]pyrano [3,4-b]indol-5-one, a pyrazolo-fused pyrano [3,4-b]indolone, via a three step approach including Fischer-indole synthesis and intramolecular esterification. The compound is fully characterized by means of 1H and 13C NMR spectra, using direct and long-range heteronuclear correlation experiments (HMBC and HMQC).

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30

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 derivat

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31

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 af

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32

Yin, Xuelian, and Yang-Heon Song. "5-Methyl-1-phenyl-3-(thieno[2,3-d]pyrimidin-4-yl)chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one." Molbank 2022, no. 4 (2022): M1469. http://dx.doi.org/10.3390/m1469.

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A chromeno[4,3-d]pyrazolo[3,4-b]pyridinone derivative 3 bearing thieno[2,3-d]pyrimidine moiety, 5-methyl-1-phenyl-3-(thieno[2,3-d]pyrimidin-4-yl)chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one, was efficiently prepared in 75% yield by the reaction of 3-phenyl-1-(thieno[2,3-d]pyrimidin-4-yl)-1H-pyrazol-5-amine 1 with 3-acetyl-2H-chromen-2-one 2 in the presence of FeCl3-SiO2 as a catalyst in refluxing ethanol for 6 h. The structure of the new synthesized compound was characterized by 1H-, 13C- NMR, IR spectroscopy, mass-spectrometry, and elemental analysis.

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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

M., K. A. IBRAHIM, H. H. ELGHANDOUR A., ABOU-HADEED K., and S. ABDELHAFIZ I. "Utility of Hydrazidoyl Chlorides : Synthesis of New Pyrazoles, Pyrazolo[ 3,4-d]pyridazines, Pyrazolo[4,5-b]pyridines and Pyrazolo[ 4,5-d]pyrimidine Derivatives." Journal of Indian Chemical Society Vol. 69, Jul 1992 (1992): 378–80. https://doi.org/10.5281/zenodo.6004337.

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Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt Chemistry Department, Faculty of Science. Suez-Canal University, Ismalia, Egypt <em>Manuscript received 28 October 1991 revised 26 May 1992, accepted 3 June 1992</em> Hydrazidoyl chlorides (1) were reacted with a variety of active methylene compounds and arylidemnialononitriles .1 medium, to produce polyfunctionally substituted pyrazole derivatives (2-6 and 10). The pyrazoles (2, 3, 6 and 10) were converted into the corresponding pyrazolo[3, 4-<em>d</em>]pyridazine derivatives (7 - 9 and 14), respectively. The aminopyraiol

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35

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 (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[

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36

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 (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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37

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 (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 isomor

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38

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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39

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 can

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40

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 orde

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41

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 (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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42

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) (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

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43

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

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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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44

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-tetrahydr

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45

KRISHNA, C. JOSHI, N. PATHAK VIJAI, SAREEN V., and GARG U. "Synthesis of some New Fluorine containing 1H-Pyrazolo[3,4-b]pyridines." Journal of Indian Chemical Society Vol. 64, Jun 1987 (1987): 372–73. https://doi.org/10.5281/zenodo.6235986.

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Department of Chemistry, University of RajasthanJaipur-302 004 <em>Manuscript received 2 September 1986, revised 14 May 1987, </em><em>accepted 5 June 1987</em> Synthesis of some New Fluorine containing<em> </em>1<em>H-</em>Pyrazolo[3,4-b]pyridines.

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46

Alshaye, Najla A., Al-Shimaa Badran, and Magdy A. Ibrahim. "Linear and Angular Heteroannulated Pyridines Tethered 6-Hydroxy-4,7-Dimethoxybenzofuran: Synthesis and Antimicrobial Activity." Molecules 29, no. 18 (2024): 4496. http://dx.doi.org/10.3390/molecules29184496.

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2-Chloropyridine-3-carbonitrile derivative 1 was utilized as a key precursor to build a series of linear and angular annulated pyridines linked to a 6-hydroxy-4,7-dimethoxybenzofuran moiety. Reaction of substrate 1 with various hydrazines afforded pyrazolo[3,4-b]pyridines. Treatment of substrate 1 with 1,3-N,N-binucleophiles including 3-amino-1,2,4-triazole, 5-amino-1H-tetrazole, 3-amino-6-methyl-1,2,4-triazin-5(4H)-one and 2-aminobenzimidazole produced the novel angular pyrido[3,2-e][1,2,4]triazolo[4,3-a]pyrimidine, pyrido[3,2-e][1,2,4]tetrazolo[1,5-a]pyrimidine, pyrido[3′,2′:5,6] pyrimido[2,

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47

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, alternat

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48

Danel, Andrzej, Elżbieta Porębska, Kacper Markiel, et al. "Multicomponent Synthesis of 4-Aryl-4,9-dihydro-1H-pyrazolo[3,4-b]quinolines Using L-Proline as a Catalyst—Does It Really Proceed?" Molecules 28, no. 22 (2023): 7612. http://dx.doi.org/10.3390/molecules28227612.

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Looking for effective synthetic methods for 1H-pyrazolo[3,4-b]quinolines preparation, we came across a procedure where, in a three-component reaction catalysed by L-proline, 4-aryl-4,9-dihydro-1H-pyrazolo[3,4-b]quinolines are formed. These compounds can be easily oxidised to a fully aromatic system, which gives hope for a synthetic method that could replace, e.g., Friedländer condensation, often used for this purpose, even though severely limited by the availability of suitable substrates. However, after careful repetition of the procedures described in the publication, it turned out that the

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49

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 (2003): o1804—o1806. http://dx.doi.org/10.1107/s1600536803023675.

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50

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

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