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Journal articles on the topic 'Pyrazolo[3,4-d]pyrimidine derivatives'

Author: Grafiati

Published: 10 September 2021

Last updated: 29 July 2025

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1

Edrees, Mastoura M. "Synthesis of 4-hydrazinopyrazolo[3,4-d]pyrimidines and their Reactions with Carbonyl Compounds." Journal of Chemical Research 37, no. 1 (2013): 6–10. http://dx.doi.org/10.3184/174751912x13543818811749.

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Synthesis of a new 4-hydrazinopyrazolo[3,4- d]pyrimidine was achieved via heating (4,6-dithioxo-1 H-pyrazolo[3,4- d] pyrimidin-3-yl)acetonitrile with hydrazine hydrate. Reactions of the latter product with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues afforded the corresponding hydrazone and pyrazole derivatives, respectively. Similarly, condensation of 2-[6-(benzylsulfanyl)-4-hydrazino-1 H-pyrazolo[3,4- d]pyrimidin-3-yl]acetonitrile with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues gave the respective hydrazone and pyrazolone derivatives. Alkylation

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2

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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3

Azam, Mohammed Afzal, Loganathan Dharanya, Charu Chandrakant Mehta, and Sumit Sachdeva. "Synthesis and biological evaluation of some novel pyrazolopyrimidines incorporating a benzothiazole ring system." Acta Pharmaceutica 63, no. 1 (2013): 19–30. http://dx.doi.org/10.2478/acph-2013-0001.

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In the present study, a series of benzothiazol derivatives 3a-l containing pyrazolo[3,4-d]pyrimidine moiety at the second position were synthesized and characterized by analytical and spectral data. The compounds were tested for their in vitro antimicrobial activity. Compounds 1-(1,3-benzothiazol-2- yl)-3-methyl-4-phenyl-1H-pyrazolo[3,4-d]pyrimidine (3a), 1- (1,3-benzothiazol-2-yl)-4-(4-chlorophenyl)-3-methyl-1H-pyrazolo[ 3,4-d]pyrimidine (3d) and 1-(1,3-benzothiazol-2-yl)- 3-methyl-4-substituted phenyl-1H-pyrazolo[3,4-d]pyrimidines (3h-j) showed significant inhibitory activity against P. aeru

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4

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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5

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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6

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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7

Velihina, Y. S., S. G. Pilyo, I. V. Ivanova, and V. S. Brovarets. "Synthesis of pyrazolo[1,5-a][1,3,5]triazine and oxazolo[4,5-d]pyrimidine derivatives and study of their vasodilator activity." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 2 (May 2023): 51–60. http://dx.doi.org/10.32434/0321-4095-2023-147-2-51-60.

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A number of pyrazolo[1,5-a][1,3,5]triazine and oxazolo[4,5-d]pyrimidine derivatives were synthesized and characterized. Pyrazolo[1,5-a][1,3,5]triazines with various substituents in the fourth position and a dichloromethyl group in the second position were obtained by the heterocyclization reaction of available N-(2,2-dichloro-1-cyanoethenyl)carboxamides and 5-aminopyrazoles. Oxazolo[4,5-d]pyrimidines were obtained by treating 2-phenyl-4-dichloromethylene-1,3-oxazol-5(4H)-one with the corresponding arylamidine hydrochloride in the presence of triethylamine. The resulting 4,5-dihydro-1H-imidazol

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8

Kordian, Marcus, Holger Feist, and Klaus Peseke. "Anellation and Ring Transformations of Push-pull-functionalized Deoxypyranosiduloses." Zeitschrift für Naturforschung B 64, no. 6 (2009): 676–82. http://dx.doi.org/10.1515/znb-2009-0613.

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Reaction of (E)-3-aminomethylene-α-D-erythro-hexopyranosid-2-ulose 5 with substituted 5- aminopyrazoles afforded the pyrano-anellated pyrazolo[1,5-a]pyrimidines 8. The treatment of the corresponding (E)-2-aminomethylene-α-D-erythro-hexopyranosid-3-ulose 6 with 5-aminopyrazoles and (benzimidazol-2-yl)acetonitrile yielded in a ring transformation process the D-erythronoyl-pyrazolo[ 1,5-a]pyrimidine-3-carbonic acid derivatives 10 and D-erythronoyl-pyrido[1,2-a]benzimidazole- 4-carbonitrile (12), respectively

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9

Hassaneen, Hamdi M., Fatma M. Saleh, Tayseer A. Abdallah, et al. "Synthesis, Cytotoxicity, Antimicrobial and Docking Simulation of Novel Pyrazolo[3,4-d]pyrimidine and pyrazolo[4,3-e][1,2,4]triazolo[3,4-c] pyrimidine Derivatives." Mini-Reviews in Medicinal Chemistry 19, no. 8 (2019): 657–70. http://dx.doi.org/10.2174/1389557518666181017162459.

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Background:Isobutyrohydrazonoyl bromide 1 was used as a precursor for the synthesis of 4-imino-3-isopropyl-1-(4-nitrophenyl)-1,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-amine 4, which was converted into hydrazino derivative 5 by heating with hydrazine hydrate at reflux. Hydrazino, as well as imino-amino derivatives, underwent condensation and cyclization reactions to give pyrazolo[ 3,4-d]pyrimidine and pyrazolo[4,3-e][1,2,4]triazolo[3,4-c]pyrimidine derivatives, respectively.Method:Antimicrobial studies are performed using two-gram positive bacteria and two-gram negative bacteria.Results:Data re

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10

Otero, Iran, Holger Feist, Dirk Michalik, Manfred Michalik, José Quincoces та Klaus Peseke. "Synthesis of Iso-C-nucleoside Analogues from 1-(Methyl 2-O-benzyl-4,6- O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-ones". Zeitschrift für Naturforschung B 60, № 11 (2005): 1175–85. http://dx.doi.org/10.1515/znb-2005-1110.

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1-(Methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-one (3a) reacted with 3-amino-1H-1,2,4-triazole and 5-aminopyrazole-4-carboxylic acid derivatives in the presence of base to furnish the triazolo[1,5-a]pyrimidine (5) and the pyrazolo[1,5- a]pyrimidines (8a - d), respectively. Treatment of 1-(methyl 2-O-benzyl-4,6-O-benzylidene-3- deoxy-α-D-altropyranosid-3-yl)-4-phenyl-but-3-yn-2-one (3b) with cyanacetamide, 2-cyano-N- (4-methoxyphenyl)acetamide und N-aryl-3-oxo-butyramides afforded the substituted nicotinonitriles (11a - d). Furthermore, reaction of 3b with 2-b

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11

Swelam, Samira, Abd El-Salam, and Magdi Zaki. "Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives." Journal of the Serbian Chemical Society 64, no. 11 (1999): 655–62. http://dx.doi.org/10.2298/jsc9911655s.

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Reaction of 2 with different reagents, namely formic acid, acetic anhydride and trichloroacetonitrile, yielded pyrazolo[3,4-d]pyrimidine derivatives 3, 5 and 6, respectively. Pyrazolo[3,4-d]pyrimidine m-thiazine(7) and 2,4-(1H,3H)dithione (8) derivatives were formed by the action of carbon disulfide on 2, depending on the reaction medium. Interaction of 7 with hydrazine hydrate yielded the aminoimino derivative 9 which reacted with acetic anhydride, triethyl orthoacetate and/or appropriate aldehydes to give 11, 12 and 13a,b, respectively. Methylation of compound 8 gave 14, which reacted with h

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12

Ho, Yuh-Wen, and Maw Cherng Suen. "Thioxopyrimidine in Heterocyclic Synthesis I: Synthesis of Some Novel 6-(Heteroatom-substituted)-(thio)pyrimidine Derivatives." Journal of Chemistry 2013 (2013): 1–15. http://dx.doi.org/10.1155/2013/765243.

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A series of novel N-cycloalkanes, morpholine, piperazines, pyrazole, pyrimidine, benzimidazolo[1,2-a]pyrimidine, 1,2,3,4-tetrazolo[1,5-a]pyrimidine, azopyrazolo[1,5- a]pyrimidine, pyrimido[4', 5':3,4]pyrazolo[1,5-a]pyrimidines and pyridine derivatives incorporating a 5-cyano-4-methyl-2-phenyl-(thio)pyrimidine moiety were obtained by the intramolecular cyclization of 6-methylthio-pyrimidine, 6-(benzoylmethyl)thio- pyrimidine and 2-[(5-cyano-4-methyl-2-phenylpyrimidin-6-yl)thio]-3-dimethyl- amino-1-phenyl-prop-2-en-1-one with appropriate amines and enaminone compounds, respectively. The structur

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13

Ibrahim, Yusria R. "Synthesis of spiro(cyclohexa-diene-pyrazolo[1,5-a]pyrimidine-4-ylidene)-malononitrile derivatives." Journal of Chemical Research 2009, no. 8 (2009): 495–98. http://dx.doi.org/10.3184/030823409x466717.

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The reaction of 4-substituted aryldiazenyl-1 H-pyrazole-3,5-diamines with 7,7′,8,8′-tetra-cyanoquinodimethane gave 2-(2′,7′-diamino-6′-cyano-3′-(aryldiazenyl)-4′ H-spiro(cyclohexa[2,5]-diene-1,5′-pyrazolo[1,5- a]pyrimidine-4-ylidene) malononitriles in 63–79% yield, while, by reaction of 2-aminobenzimidazole with 7,7′,8,8′-tetracyanoquinodimethane, 2-(3′-amino-4′-cyano-6′ H-spiro-(cyclohexa[2′,5′]diene-1,5′-benzo( d)-imidazo[1,2- a]pyrimidine)-4-ylidene)malononitrile was formed in 71% yield. Rationales for these transformations are presented.

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14

Huppatz, JL. "Systemic Fungicides. The Synthesis of Pyrazolo[1,5-a]pyrimidine Analogues of Carboxin." Australian Journal of Chemistry 38, no. 1 (1985): 221. http://dx.doi.org/10.1071/ch9850221.

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The synthesis of a series of pyrazolo [1,5-a] pyrimidine derivatives, structural analogues of the systemic fungicide carboxin, is described. A common intermediate incorporating structural features desirable for fungicidal activity, N-phenyl-3(5)-amino-5(3)-methylpyrazole-4- carboxamide (6), was used to prepare pyrazolo [1,5-a] pyrimidines variously substituted in positions 5 and 7 of the ring system. Bromination of N-phenyl-2-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide (8) occurred preferentially in the phenyl ring and the 6-bromo derivative was prepared by bromination of the corresponding 3

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15

Ebrahimpour, Zahra, Ali Shiri, Mehdi Bakavoli, Seyed Mohammad Seyedi, Masoumeh Bahreini, and Fatemeh Oroojalian. "Microwave-assisted synthesis and antibacterial evaluation of new derivatives of 1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one." Heterocyclic Communications 22, no. 1 (2016): 49–53. http://dx.doi.org/10.1515/hc-2015-0145.

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AbstractSynthesis of new 1,2-dihydro-3H-pyrazolo[3,4-d] pyrimidin-3-ones4–6starting with ethyl 4-hydroxy-2-methylthio-pyrimidine-5-carboxylate (1) under classical heating and microwave-induced conditions is reported. The antibacterial activities of the synthesized compounds were evaluated using chloramphenicol and streptomycin as reference drugs.

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16

K., R. JYOTHJKUMARI, N. RAJASEKHARAN K., and K.DHEVENDRAN. "Synthesis of some New Pyrazolo[3',4-d]-pyrimidine Derivatives and their Antibacterial Activity." Journal of Indian Chemical Society Vol. 68, Oct 1991 (1991): 578–80. https://doi.org/10.5281/zenodo.6154774.

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Department of Chemistry Department of Aquatic Biology, University of Kera!a. Thiruvauanthapuram-695 034 <em>Manuscript received 4 June 1991, revised 96 September 1991, accepted 4 October 1991</em> Synthesis of some New Pyrazolo[3',4-d]-pyrimidine Derivatives and their Antibacterial Activity.

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17

Yuan, Jun, Michael Gulianello, Stéphane De Lombaert, Robbin Brodbeck, Andrzej Kieltyka, and Kevin J. Hodgetts. "3-Aryl pyrazolo[4,3-d]pyrimidine derivatives." Bioorganic & Medicinal Chemistry Letters 12, no. 16 (2002): 2133–36. http://dx.doi.org/10.1016/s0960-894x(02)00358-x.

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18

Chavda, Mukesh M., Manoj F. Dhaduk, and Jatin M. Upadhyay. "Synthesis, characterization and biological study of some new substituted pyrazolo[3,4-d] thiazolo[3,2-a] pyrimidine derivatives." Current Chemistry Letters 12, no. 4 (2023): 831–38. http://dx.doi.org/10.5267/j.ccl.2023.3.010.

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Fused pyrimidines play an imperative role in our life due to their biological importance in the struggle of microorganisms. A series of 4-aryl-3-methyl-1-phenyl-1,4,6,7-tetrahydropyrazolo[3,4-d] thiazolo[3,2-a]pyrimidine (4a-j) were synthesized by cyclization of 3-methyl-1-phenyl-4-aryl-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-d]pyrimidine-6-thiones (3a-j) with 1,2-dibromoethane in presence of anhydrous potassium carbonate. Earlier, compounds (3a-j) were synthesized by the condensation of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (2), different substituted benzaldehyde and thiourea with catalyt

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19

Arshia, Parveen. "Green Synthesis of Bioactive Pyrazolo[3,4-d]-pyrimidine Thiones." International Journal of Advance and Applied Research 3, no. 6 (2022): 66–71. https://doi.org/10.5281/zenodo.7421057.

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An efficient and green method for the preparation of 3- phenyl-1H-pyrazolo [3, 4-d] pyrimidine Thiones derivatives in minutes of time with high yields is accomplished by the mixture of ethyl acetoacetate, hydrazine hydrate, thiourea, and different benzaldehydes. The reaction is accomplished in the presence of ionic liquid [HBim}BF<sub>4</sub> in an excellent yield.

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20

Hosny, Mona A., Yasser H. Zaki, Wafaa A. Mokbel, and Abdou O. Abdelhamid. "Synthesis, Characterization, Antimicrobial Activity and Anticancer of Some New Pyrazolo[1,5-a]pyrimidines and Pyrazolo[5,1-c]1,2,4-triazines." Medicinal Chemistry 16, no. 6 (2020): 750–60. http://dx.doi.org/10.2174/1573406415666190620144404.

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Background: Pyrazole and its derivatives are known to exhibit significant biological and pharmacological activities such as anticancer, anti-inflammatory, antioxidant, antibacterial, analgesic, antiviral, antimicrobial, antifungal, anti-glycemic, antiamoebic, and antidepressive. Considering the immense biological properties, pyrazole is one of the most widely studied nitrogen- containing heterocyclic nuclei. Fused pyrazole derivatives are composed of the pyrazole nucleus attached to other heterocyclic moieties. Objective: The objective of this article is the synthesis of some new pyrazolo[1,5-

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21

Hafez, Hend N., and Abdel-Rhman B. A. El-Gazzar. "Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents." Acta Pharmaceutica 65, no. 3 (2015): 215–33. http://dx.doi.org/10.1515/acph-2015-0022.

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Abstract As a part of systematic investigation of the synthesis and biological activities of pyrazole analogues linked to various heterocyclic systems, a new series of pyrazolo-N-glycoside derivatives, pyrazolopyranopyrimidine and C-glycoside of pyrazolopyranotriazolo-pyrimidine derivatives was synthesized through the reaction of the key intermediate 6-amino-3-methyl-4-(substituted-phenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (3a,b) with different reagents. Structures of the newly synthesized compounds were elucidated by elemental microanalysis and spectroscopic methods. The compoun

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22

I.H. El-Qaliei, Mohamed, Sayed A.S. Mousa, Esam A. Ishak, Hamdi M.D. Nasr, Modather F Hussein, and Abdallah M.A. Hassane. "Synthesis, characterization, antimicrobial, antioxidant activities, and in silico study of new azo disperse dyes containing pyrazole and pyrazolo[1,5-a]pyrimidine rings." Bulletin of the Chemical Society of Ethiopia 39, no. 7 (2025): 1411–24. https://doi.org/10.4314/bcse.v39i7.13.

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New N,N-dimethyl-N'-(5-oxo-4-(aryldiazenyl)-2,5-dihydro-1H-pyrazol-3-yl)formimidamide 5a-c are formed by reaction of 5-amino-1H-pyrazol-3(2H)-one derivatives 4a-c with N,N-dimethylformamide dimethyl acetal (DMF-DMA). Compounds 5a-c serve as excellent precursors for the synthesis of new disazo pyrazole disperse dyes, When refluxed with hydrazine hydrate or active methylene reagents 8a,b, leading to N''-(3-hydroxy-4-(arylaza)-1H-pyrazol-5-yl)formimidohydrazide 7a-c or pyrazolo[1,5-a]. pyrimidines 11a–e. In vitro studies were carried out to evaluate antioxidant properties of the produced compound

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23

Kaping, Shunan, Philippe Helissey, and Jai Narain Vishwakarma. "A three step one-pot regioselective synthesis of highly substituted pyrazolo[1,5-a]pyrimidines assisted by KHSO4 in aqueous media under ultrasound irradiation." European Journal of Chemistry 11, no. 3 (2020): 179–86. http://dx.doi.org/10.5155/eurjchem.11.3.179-186.1977.

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A simple and efficient synthesis of substituted pyrazolo[1,5-a]pyrimidine derivatives has been developed by the use of ultrasound. 5-Methyl-4-phenyl-1H-pyrazol-3-amine required for the synthesis of pyrazolo[1,5-a]pyrimidine derivatives has been easily obtained by the reaction of 3-(dimethylamino)-2-phenylacrylonitrile (formed from readily available 2-phenylacetonitrile) with hydrazine hydrate in refluxing ethanol. The 5-aminopyrazole was then reacted with various formylated active proton compounds in presence of KHSO4 in aqueous medium under ultrasound irradiation to give the desired products.

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24

Z h a o, J., Z. M u r t a z a e v a, A. B u r o n o v, D. B Tukhtaev, K. h. A Bozorov, and H. A Aisa. "NEUROPROTECTIVE PROPERTIES OF THE PYRAZOLO[3,4-D]PYRIMIDINONES." 2022-yil, 3-son (133/1) ANIQ FANLAR SERIYASI 5, no. 135/2 (2022): 1–7. http://dx.doi.org/10.59251/2181-1296.v5.1352.1163.

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Two series of the novel an aryl(heteryl)idene containing pyrazolo[3,4-d]pyrimidin-4-one targets (5a-o and 6a−o) were performed applying by the condensation of tricyclic pyrazolo[3,4-d]pyrimidin-4-ones (3 and 4) with the appropriate aromatic aldehydes in the basic condition. Some derivatives demonstrated AChE and BuChE inhibition

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25

Hafez, Hend N., Abdel-Rhman B. A. El-Gazzar, and Magdi E. A. Zaki. "Simple approach to thieno[3,2-d]pyrimidines as new scaffolds of antimicrobial activities." Acta Pharmaceutica 66, no. 3 (2016): 331–51. http://dx.doi.org/10.1515/acph-2016-0029.

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Abstract 6ʹ-(4-Chlorophenyl)-spiro[cyclohexane-1,2ʹ-thieno[3,2-d][1,3] oxazin]-4ʹ(1ʹH)-one (1) was synthesized and used as a starting material for the synthesis of a novel series of spiro compounds having biologically active sulfonamide 2a-e and 3ʹ-(4-acetylphenyl)-6ʹ- (4-chlorophenyl)-1ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d] pyrimidine-4ʹ(3ʹH)-one (3). Compound 2a was used as a key intermediate for the synthesis of sulfonyl carbothioamide derivatives 4a-c. Also, compound 3 was used as an intermediate for the synthesis of 3ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d]pyrimidin]-3ʹ-yl] phenyl}-2-imin

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S, M. HASSAN, M. KHAFAGY M., A. EMAM H., and A. EL-MAGHRABY A. "Synthesis of New 2-Substituted-pyrazolo[4',3':5,6]pyrano[3,2-e][1,2,4]triazolo[ 1,5 -c ]pyrimidine Derivatives." Journal of Indian Chemical Society Vol. 74, Jan 1997 (1997): 27–29. https://doi.org/10.5281/zenodo.5876741.

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Chemistry Department. Faculty of Science. Al-Azhar University, Nasr City, Cairo, Egypt <em>Manuscript received 3 November 1994, revised 3 April 1995 accepted 31 May 1995</em> 1,3-Diphenylpyrazol-5-one has been reacted with arylidenemalononitriles (la d) to afford pyrano[2,3-cipyrazoles (2a-d). Reaction of 2d with triethyl orthoformate gives compound 4 which on hydrazinolysis yields aminoiminopyrhnidine derivative (5) Interaction of diffeient carboxylic acid derivatives with compound 5 gives 2-substituted-1,2,4-triazolopyrimidine derivatives (6-11).

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Panchal, Ishan I., Sandip N. Badeliya, Rakesh Patel, Ashish Patel, and Animesh Devaligar. "In silico Analysis and Molecular Docking Studies of Novel 4-Amino-3- (Isoquinolin-4-yl)-1H-Pyrazolo[3,4-d]Pyrimidine Derivatives as Dual PI3-K/mTOR Inhibitors." Current Drug Discovery Technologies 16, no. 3 (2019): 297–306. http://dx.doi.org/10.2174/1568009618666181102144934.

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Background: mTORC1/ PI3K control multiple anabolic pathways, including protein synthesis, ribosome production, lipogenesis, and nucleotide synthesis, are all important for cell and tissue growth. Sapanisertib and Dactolisib inhibit PI3K/AKT/mTOR pathway, an important signaling pathway for many cellular functions such as growth control, metabolism and translation initiation. Methods: Dactolisib contains quinolin-3-yl-2,3-dihydroimidazo[4,5-c]quinolin scaffold and Sapanisertib contains benzo[d]oxazol-5-yl-1-ethyl-1H-pyrazolo[3,4-d]pyrimidinnucleous. From the reference to both of drug novel serie

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Mahmoud, Naglaa F. H., Eman A. El-Bordany, and Galal A. Elsayed. "Synthesis and Pharmacological Activities of Pyrano[2,3-d]pyrimidine and Pyrano[2,3-d]pyrimidine-5-one Derivatives as New Fused Heterocyclic Systems." Journal of Chemistry 2017 (2017): 1–7. http://dx.doi.org/10.1155/2017/5373049.

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Various fused oxazine such as 4-(4-methoxyphenyl)-3,7-dimethyl-1,4-dihydro-5H-pyrazolo [4′,3′:5,6]pyrano[2,3-d][1,3]oxazin-5-one2has been prepared and utilized as a starting material for novel pyrazolopyranopyrimidinones3,5,6, and7a–cand pyrazolopyranopyrimidines4,9,10, and11which are expected to possess considerable chemical and pharmacological activities. The structures of the new compounds have been elucidated by spectroscopic data and elemental analysis. The antioxidant and anticancer activities of synthesized products have been evaluated.

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Moustafa, Moustafa Sherif, Ahmed Moukhtar Nour-Eldeen, Saleh Mohamed Al-Mousawi, Afaf Abd El-Hameed, Michael Magdy, and Kamal Usef Sadek. "Regioselectivity in the reaction of 5-amino-3-anilino-1H-pyrazole-4-carbonitrile with cinnamonitriles and enaminones: Synthesis of functionally substituted pyrazolo[1,5-a]pyrimidine derivatives." Green Processing and Synthesis 11, no. 1 (2022): 116–28. http://dx.doi.org/10.1515/gps-2022-0009.

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Abstract The development of efficient methods for the synthesis of polyfunctional N-heterocycles is an important area of research in organic and medicinal chemistry. Pyrazolo[1,5-a]pyrimidine derivatives are purine analogous of biomedical importance and have been extremely studied for their broad spectrum of biological activities. Recently, they have attracted great interest in materials science owing to their photophysical properties. 3(5)-Aminopyrazoles are extensively utilized in the synthesis of condensed heterocyclic systems, particularly pyrazolo[1,5-a]pyrimidines via the reaction with 1

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30

El Hafi, Mohamed, El Hassane Anouar, Sanae Lahmidi, et al. "Synthesis of New Pyrazolo[3,4-d]pyrimidine Derivatives: NMR Spectroscopic Characterization, X-Ray, Hirshfeld Surface Analysis, DFT, Molecular Docking, and Antiproliferative Activity Investigations." Molecules 29, no. 21 (2024): 5020. http://dx.doi.org/10.3390/molecules29215020.

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Four new pyrazolo[3,4-d]pyrimidines (P1–P4) were successfully synthesized in good relative yields by reacting 3-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ol with various alkylating agents (methyl iodide, propargyl bromide, and phenacyl bromide) at room temperature in DMF solvent, employing liquid–solid phase transfer catalysis. The P1–P4 structures were elucidated using NMR spectroscopy and X-ray diffraction. Intermolecular interactions in P1–P4 were analyzed via Hirshfeld surface analysis and 2D fingerprint plots. Geometrical parameters were accurately modeled by DFT calculations using th

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31

Youssef, Ahmed Said Ahmed. "Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile and 6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazole-5-carbonitrile with substituted benzylidenemalononitriles, α,β-acetylenic esters and ketones". Journal of Chemical Research 2009, № 4 (2009): 214–17. http://dx.doi.org/10.3184/030823409x435874.

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Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile (1a) with substituted benzylidenemalononitriles gave 4-amino-2-(1-cyano-2-arylvinyl)benzothieno[2,3- d]pyrimidine derivatives (3) as ( E,Z)-mixtures and in one case (2c) as separated ( Z)- and ( E)-isomers. Similar treatment of 6-amino-1,4-dihydro-3-methyl-1,4-diphenyl-pyrano[2,3- c]pyrazole-5-carbonitrile (4) yielded similarly-formed pyrazolopyranopyrimidine derivatives (5a, b) as ( Z)-and ( E)-stereoisomers. Attempted acetylation of the aminobenzothienopyrimidines resulted in degradation of the pyrimidine ring and the fo

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32

El-Sayed, Wael A., Mahmoud M. M. Ramiz та Adel A. H. Abdel-Rahman. "Anti-Hepatitis B Virus Activity of New N4-β-D-Glycoside Pyrazolo[3,4-d]pyrimidine Derivatives". Zeitschrift für Naturforschung C 64, № 5-6 (2009): 323–28. http://dx.doi.org/10.1515/znc-2009-5-603.

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1The reaction of 6-hydrazinyl-1,3-dimethylpyrimidine-2,4-(1H,3H)-dione () with ethoxymethylenemalononitrile afforded 5-amino-1-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin- 6-yl)-1H-pyrazole-4-carbonitrile (2). The latter was reacted with formamide and urea affording the corresponding 4-aminopyrazolo[3,4-d]pyrimidines 3 and 4. The reaction of monosaccharide aldoses with 3 and 4 gave stereoselectively the β-N-glycosides 5a - d and 6a - d which were treated with acetic anhydride in pyridine to afford the corresponding acetylated derivatives 7a - d and 8a - d. The prepared compounds were t

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33

Shamroukh, Ahmed H., Magdi E. A. Zaki, Eman M. H. Morsy, Faiza M. Abdel-Motti, and Farouk M. E. Abdel-Megeid. "Synthesis of Pyrazolo[4′,3′:5,6]pyrano[2,3-d]pyrimidine Derivatives for Antiviral Evaluation." Archiv der Pharmazie 340, no. 5 (2007): 236–43. http://dx.doi.org/10.1002/ardp.200700005.

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34

Mcfadden, HG, JL Huppatz, and PK Halladay. "Synthesis of Pyrazoles and Pyrazolo[1,5-a]pyrimidines From 3-Arylsulfonylaminoacrylates." Australian Journal of Chemistry 46, no. 6 (1993): 873. http://dx.doi.org/10.1071/ch9930873.

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3-Arylsulfonylaminopyrazole-4-carboxamides and -carboxylates were synthesized from 3-arylsulfonylamino-3-methylthiocyanoacrylate derivatives as potential herbicidal inhibitors of the enzyme acetohydroxyacetic acid synthase (AHAS). Some of these compounds were reacted further with acetylacetone, giving 3-arylsulfonylaminopyrazolo[1,5-a]pyrimidine-3-carboxamides by a novel route. During the synthesis of the 3-arylsulfonylaminopyrazole-4-carboxylates, the arylsulfonylamino group was observed to function as a leaving group. This phenomenon is of potential synthetic utility and was found to be sens

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35

Ahmed, Hatem Abdel Moniem. "A Facile One-pot Synthesis of New Pyrazolopyrimidines and Pyrazolo Pyridines Derivatives." JOURNAL OF ADVANCES IN CHEMISTRY 8, no. 1 (2014): 1533–38. http://dx.doi.org/10.24297/jac.v8i1.6789.

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A Simple Facile One-pot reaction, novel and efficient rout for the synthesis of substituted pyrazolo [3, 4-d] pyrimidines, and pyrazolo [3, 4-b] pyridines, results from reaction of substituted-5-amino-4-cyanopyrazoles with malononitrile and diethylmalonate respectively. The structures of the products and conceivable mechanisms are discussed. The antibacterial activity of some new synthesized compounds was evaluated and seemed to be significant.

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36

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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37

FAWI, M., and EL-LATIF ABD. "A Study on 1-Phenyl-3-methyl-5-chloropyrazole-4-carboxaldehyde. Synthesis of fused Pyrazole, Isoxazole, Pyrimidine and Pyridine-[2,3-d]pyrazoline Derivatives." Journal of Indian Chemical Society Vol. 71, Oct 1994 (1994): 631–33. https://doi.org/10.5281/zenodo.5896706.

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Chemistry Department, Aswan Faculty of Science, Aswan, Egypt <em>Manuscript received 28 February 1992, revised 29 March 1993, accepted 30 July 1993</em> A Study on 1-Phenyl-3-methyl-5-chloropyrazole-4-carboxaldehyde. Synthesis of fused Pyrazole, Isoxazole, Pyrimidine and Pyridine-[2,3-<em>d</em>]pyrazoline Derivatives.

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NOGUCHI, MICHIHIKO, SEIJI NAGATA, and SHOJI KAJIGAESHI. "Studies on pyridopyrimidines. I Synthesis of pyrazolo(3',4':4,5)pyrido(2,3-d)pyrimidine derivatives." CHEMICAL & PHARMACEUTICAL BULLETIN 34, no. 10 (1986): 3994–4000. http://dx.doi.org/10.1248/cpb.34.3994.

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Zaki, Remon M., Adel M. Kamal El-Dean, Shaban M. Radwan, and Ahmed F. Saber. "Efficient synthesis, reactions and spectral characterization of pyrazolo[4’,3’:4,5]thieno[3,2-d] pyrimidines and related heterocycles." Heterocyclic Communications 25, no. 1 (2019): 39–46. http://dx.doi.org/10.1515/hc-2019-0004.

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AbstractNew pyrazolothienopyrimidines were synthesized. The key intermediate 4-aminothieno[2,3-c]pyrazole-5-carbonitrile 1 was converted to the chloroacetyl amino derivative 2 followed by nucleophilic substitution and Dimorth rearrangement upon treatment with nitrogen nucleophiles to give the pyrimidinones 3a-c. Treatment of 3a with formaldehyde and with triethyl orthoformate afforded the respective tetracyclic derivatives 4 and 5. Condensation of the amino group in the o-aminocarbonitrile 1 with triethyl orthoformate followed by cycloaddition reaction with hydrazine led to the formation of py

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40

Shamroukh, A. H., A. E. Rashad, and H. H. Sayed. "Synthesis of Some Pyrazolo[3, 4]pyrimidine Derivatives for Biological Evaluation." Phosphorus, Sulfur, and Silicon and the Related Elements 180, no. 10 (2005): 2347–60. http://dx.doi.org/10.1080/104265090921074.

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41

Otero, Iran, Holger Feist, Lidcay Herrera, Manfred Michalik, José Quincoces, and Klaus Peseke. "Nucleoside Analogues from Branched-Chain Pyranosides." Australian Journal of Chemistry 58, no. 2 (2005): 104. http://dx.doi.org/10.1071/ch04168.

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Reaction of (pyranosid-3-yl)ethanal 2 with ethynylmagnesium bromide or lithium phenylacetylide in THF afforded (2R,S)-1-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-yl)but-3-yn-2-ols 3a and 3b, respectively. Oxidation of 3a and 3b yielded the 1-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-yl)but-3-yn-2-ones 4a and 4b, which upon treatment with hydrazine and hydrazine derivatives formed the 3-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-ylmethyl)pyrazoles 5a–5d. Compounds 4a and 4b also underwent reaction with amidinium and guanidin

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42

Hayat, Faisal, Attar Salahuddin, and Amir Azam. "Synthesis, characterization, antiamoebic activity and cytotoxicity of new pyrazolo[3, 4-d]pyrimidine-6-one derivatives." Journal of Enzyme Inhibition and Medicinal Chemistry 26, no. 4 (2010): 472–79. http://dx.doi.org/10.3109/14756366.2010.528414.

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43

Roudbaraki, Seyyed Jalal, Morteza Ziyaadini, and Majid Ghashang. "Multi-component Preparation of Pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines Using Solvent-free and HSBM Techniques." Letters in Organic Chemistry 17, no. 7 (2020): 512–16. http://dx.doi.org/10.2174/1570178616666190319155522.

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Simple and clean access to pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidine derivatives using solvent- free and HSBM techniques through the multi-component reaction of 3-methyl-1-phenyl-1Hpyrazol- 5-amine, 1-aryl-2-thiocyanatoethan-1-one and aromatic aldehydes are reported. Using 2-hydroxyethan-1-aminium acetate as an ionic liquid, the product in high yields is obtained.

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44

Bahashwan, Saleh A. "Pharmacological activities of some triazinopyrazolothieno pyrimidine derivatives." Acta Pharmaceutica 67, no. 3 (2017): 407–14. http://dx.doi.org/10.1515/acph-2017-0022.

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Abstract Triazinopyrazolothieno pyrimidine derivatives 1–5 were evaluated for their anti-inflammatory, analgesic and anticancer activities and acute toxicity. Anti-inflammatory activity of the compounds was studied using the carrageenan test. All tested compounds showed analgesic activity, 3-methoxycarbonyl-4,6-dimethyl-8-[(N-methylindolyl)methyl] pyrimido [5′,4′:4,5]thieno [3′,2′-3,4]pyrazolo [5,1-c]triazine (4) showed activity comparable to that of diclofenac. Compounds 1–5 were also screened for anticancer activity on a human lung cancer cell line (A549) and a human prostate cancer cell lin

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45

Gong, Tang, Liu та Liu. "Synthesis and Evaluation of Novel 2H-Benzo[e]-[1,2,4]thiadiazine 1,1-Dioxide Derivatives as PI3Kδ Inhibitors". Molecules 24, № 23 (2019): 4299. http://dx.doi.org/10.3390/molecules24234299.

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In previous work, we applied the rotation-limiting strategy and introduced a substituent at the 3-position of the pyrazolo [3,4-d]pyrimidin-4-amine as the affinity element to interact with the deeper hydrophobic pocket, discovered a series of novel quinazolinones as potent PI3Kδ inhibitors. Among them, the indole derivative 3 is one of the most selective PI3Kδ inhibitors and the 3,4-dimethoxyphenyl derivative 4 is a potent and selective dual PI3Kδ/γ inhibitor. In this study, we replaced the carbonyl group in the quinazolinone core with a sulfonyl group, designed a series of novel 2H-benzo[e][1

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46

Gharib, Ali, Manouchehr Jahangir, Mina Roshani, Sara Moghadasi, and Reza Safee. "Catalytic Synthesis of Pyrazolo[3,4-d]pyrimidin-6-ol and Pyrazolo[3,4-d]pyrimidine-6-thiol Derivatives Using Nanoparticles of NaX Zeolite as Green Catalyst." Journal of Catalysts 2013 (April 4, 2013): 1–4. http://dx.doi.org/10.1155/2013/657409.

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An efficient and environmental benign method is reported for the synthesis of some pyrazolopyrimidine derivatives using 3-methyl-1-phenyl-5-pyrazolone with carbonyl compounds in the presence of nanozeolite Nax catalysts, solvent-free and at reflux conditions. It is noteworthy to mention that this method of the synthesis requires less time, less temperature, and better yield.

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47

Rajesh, Kumar, and C. Joshi Y. "A highly efficient synthesis of 3H-1,5-benzodiazepine derivatives using lanthanum(III) nitrate hexahydrate as a catalyst." Journal of Indian Chemical Society Vol. 85, Oct 2008 (2008): 1045–49. https://doi.org/10.5281/zenodo.5820698.

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Department of Chemistry, University of Rajasthan, Jaipur-302 004, Rajasthan, India <em>E-mail</em> : rnunia@yahoo.com <em>Manuscript received 22 April 2008, accepted 16 July 2008</em> Sulphonation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7<em>H</em>-pyrazolo[4,3-<em>d</em>]pyrimidin-7-one (1) with chlorosulphonic acid affords 5-[(5-chlorosulphonyl-2-ethoxy)pyrimidin]-1-methyl-3-propyl-1 ,6-dihydro-7 <em>H</em>-pyrazolo[ 4,3-d]pyrimidin- 7-one (2). Compound (2) condensed with different β-diketones/β-ketoesters (3a-e) to obtain new β-diketones/ β-ketoesters (4a-e).

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48

Anand, Aditi, Navjeet Kaur, and Dharma Kishore. "An Efficient One Pot Protocol to the Annulation of Face “d” of Benzazepinone Ring with Pyrazole, Isoxazole, and Pyrimidine Nucleus through the Corresponding Oxoketene Dithioacetal Derivative." Advances in Chemistry 2014 (August 6, 2014): 1–5. http://dx.doi.org/10.1155/2014/358153.

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A highly facile single step approach to the annulation of face “d” of benzazepinone nucleus with pyrazole, isoxazole, and pyrimidine ring has been described. The annulation proceeded smoothly on the reaction of oxoketene dithioacetal derivative 3 with (i) NH2–NH2·H2O, (ii) NH2OH·HCl, (iii) acetamidine hydrochloride, (iv) guanidine nitrate, (v) urea, and (vi) thiourea which yielded the pyrazolo, isoxazolo, and pyrimido annulated analogues of benzazepinone 4–9, respectively, in acceptable yields. The 4-ketene dithioacetal analogue of 7-fluorobenzo[b]azepine-2,5-dione (3) was in turn obtained fro

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Bazgir, Ayoob, Maryam Mohammadi Khanaposhtani, and Ali Abolhasani Soorki. "One-pot synthesis and antibacterial activities of pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-dione derivatives." Bioorganic & Medicinal Chemistry Letters 18, no. 21 (2008): 5800–5803. http://dx.doi.org/10.1016/j.bmcl.2008.09.057.

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Yuan, Jun, Michael Gulianello, Stephane De Lombaert, Robbin Brodbeck, Andrzej Kieltyka, and Kevin J. Hodgetts. "ChemInform Abstract: 3-Aryl-pyrazolo[4,3-d]pyrimidine Derivatives: Nonpeptide CRF-1 Antagonists." ChemInform 33, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.200249140.

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