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Journal articles on the topic '4-oxopyrido[2,3-d]pyrimidines synthesis'

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Published: 4 June 2021

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1

Borrell, José I., Jordi Teixidó, Blanca Martínez-Teipel, Blanca Serra, Josep Lluís Matallana, Marta Costa, and Xavier Batllori. "An Unequivocal Synthesis of 4-Amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones and 2-Amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones." Collection of Czechoslovak Chemical Communications 61, no. 6 (1996): 901–9. http://dx.doi.org/10.1135/cccc19960901.

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An unequivocal set of procedures for the synthesis of 4-amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones (7) and 2-amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones (8), in a maximum of four steps from an α,β-unsaturated ester 1, is reported. Thus, the acid hydrolysis of the 2,4-diaminopyrido[2,3-d]pyrimidines 3 yields the 4-amino-2-oxopyrido[2,3-d]pyrimidines 7 while the cyclization of the Michael adducts 9 (formed by reaction of 1 and methyl cyanoacetate) with guanidine affords the corresponding 2-amino-4-oxopyrido[2,3-d]pyrimidines 8. Both isomers were also obtained by hydrolysis of the 4-amino-2-bromo- and 2-amino-4-bromo-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones 5 and 6, respectively.

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2

Mohamed, Mosaad, Ramdan El-Domany, and Rania Abd El-Hameed. "Synthesis of certain pyrrole derivatives as antimicro-bial agents." Acta Pharmaceutica 59, no. 2 (June 1, 2009): 145–58. http://dx.doi.org/10.2478/v10007-009-0016-9.

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Synthesis of certain pyrrole derivatives as antimicro-bial agentsIn an effort to establish new pyrroles and pyrrolo[2,3-d] pyrimidines with improved antimicrobial activity we report here the synthesis andin vitromicrobiological evaluation of a series of pyrrole derivatives. A series of new 2-aminopyrrole-3-carbonitriles (1a-d) were synthesized from the reaction of benzoin, primary aromatic amines and malononitrile, from which a number of pyrrole derivatives (2a-dto5a-d) and pyrrolo[2,3-d]pyrimidines (6a-dto10a, d) were synthesized. Thein vitroantimicrobial testing of the synthesized compounds was carried out against Gram-positive, Gram-negative bacteria and fungi. Some of the prepared compounds, [2-amino-1-(2-methylphenyl)-4,5-diphenyl-1H-pyrrole-3-carbonitriles (1b), 2-amino-3-carbamoyl-1-(3-methylphenyl)-4,5-diphenyl-1H-pyrroles (2b),N-(3-cyano-1-(2-methylphenyl)-4,5-diphenyl-1H-pyrrol-2-yl)-acetamides (3b),N-(3-cyano-1-(3-methylphenyl)-4,5-diphenyl-1H-pyrrol-2-yl)-acetamides (3c), 2-amino-1-(4-methoxyphenyl)-4,5-diphenyl-3-tetrazolo-1H-pyrroles (5d),7-(4-methoxyphenyl)-5,6-diphenyl-7H-pyrrolo [2,3-d]pyrimidin-4(3H)-ones (7d), 7-(3-methylphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-thione (9b) andN-(7-(2-methylphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d] pyrimidine)-N-aryl amines (10a)] showed potent antimicrobial activity.

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3

Hossain, M. I., and M. M. H. Bhuiyan. "Synthesis and Antimicrobial Activities of Some New Thieno and Furopyrimidine Derivatives." Journal of Scientific Research 1, no. 2 (April 23, 2009): 317–25. http://dx.doi.org/10.3329/jsr.v1i2.2299.

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Fused pyrimidines, 8,9-dimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 5, 3,8,9-trimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 6, 4-benzylidinehydrazono-5,6 dimethylthieno[2,3-d]pyrimidine 7, 4-[4/-hydroxybenzylidine]hydrazono-5,6-dimethylthi-eno[2,3-d]pyrimidine 8, 4-[4/-tolylidin]hydrazono-5,6-dimethylthieno[2,3-d]pyrimidine 9, 4-[4/-nitrobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 10 and 4-[4/-chlorobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 11 are prepared in good yield by an initial treatment of 2-amino-4,5-dimethylthiophene-3-carbonitrile 1 with formic acid, affording 5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one 2, which is chlorinated with thionyl chloride and then hydrazinated with hydrazine hydrate. Finally hydrazino compound 4 is reacted with formic acid, acetic anhydrate, benzaldehyde, p-hydroxybenzaldehyde, p-toluayldehyde, p-nitrobenzaldehyde and p-chlorobenzaldehyde to give thienotriazolopyrimidines 5-6 and thienopyrimidines 7-11 respectively. All the compounds have been screened for their antimicrobial activity. Keywords: Fused pyrimidines; Hydrazino compound; Thienotriazolopyrmidines; Thienopyrimidines; Antimicrobial activity.© 2009 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved.DOI: 10.3329/jsr.v1i2.2299

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4

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 (March 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. aeruginosa whereas compounds 1-(1,3-benzothiazol-2-yl)-4- (2-chlorophenyl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine (3b), 2-[1-(1,3-benzothiazol-2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin- 4-yl]phenol (3e), 1-(1,3-benzothiazol-2-yl)-4-(3,4-dimethoxyphenyl)- 3-methyl-1H-pyrazolo[3,4-d]pyrimidine (3h), 4-[1-(1,3-benzothiazol-2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyri midin-4-yl]-N,N-dimethylaniline (3j) and 1-(1,3-benzothiazol- 2-yl)-3-methyl-4-[2-phenylvinyl]-1H-pyrazolo[3,4-d]pyrimidine (3k) were found to be active against C. albicans. Some of these synthesized compounds were evaluated for their in vivo acute toxicity, analgesic, anti-inflammatory, and ulcerogenic actions. The tested compound 4-[1-(1,3-benzothiazol- 2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-N, N-dimethylaniline (3j) exhibited maximum analgesic and anti-inflammatory activities. Compounds 1-(1,3-benzothiazol- -2-yl)-3-methyl-4-(3-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidine (3i) and 3j showed a significant gastrointestinal protection compared to the standard drug diclofenac sodium.

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5

Edrees, Mastoura M. "Synthesis of 4-hydrazinopyrazolo[3,4-d]pyrimidines and their Reactions with Carbonyl Compounds." Journal of Chemical Research 37, no. 1 (January 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 reactions of 2-[4,6-bis(benzylsulfanyl)-1 H-pyrazolo[3,4- d]pyrimidin-3-yl]acetonitrile with arylamines gave the respective 4-( N-arylamino)-6-benzylsulfanylpyrazolo[3,4- d]pyrimidine derivatives.

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6

Ahmed, Essam Kh, Mohamed A. Ameen, and Fathy F. Abdel-Latif. "Microwave-Assisted Synthesis of Novel Imidazo- and Pyrimidopyrido[4’,3’:4,5]thieno[2,3-d]pyrimidines." Zeitschrift für Naturforschung B 60, no. 2 (February 1, 2005): 221–26. http://dx.doi.org/10.1515/znb-2005-0216.

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It is reported on the microwave-assisted synthesis of imidazo- and pyrimidopyrido [4’,3’:4,5]thieno[ 2,3-d]pyrimidines from 2-ethoxymethylene-amino-3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]- pyridine-6-carboxylic acid ethyl ester and 4-chloro-pyridothieno[2,3-d]pyrimidine.

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7

Thokchom, Herojit S., Anita D. Nongmeikapam, and Warjeet S. Laitonjam. "Synthesis of fused pyrazolo-, isoxazolo-, pyrimido-, and pyridopyrimidines." Canadian Journal of Chemistry 83, no. 8 (August 1, 2005): 1056–62. http://dx.doi.org/10.1139/v05-054.

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A systematic study of the synthesis of the 5,7-diaryl-4-oxo-pyrazolo[3,4-d]pyrimidin-6-thiones (3), 2-phenyl-5,7-bis(2′-methylphenyl)-4-oxo-pyrazolo[3,4-d]pyrimidin-6-thiones (4b), 2(3H)-3-phenyl-5,7-diaryl-4-oxo-pyrazolo[3,4-d]pyrimidin-6-thiones (5), 5,7-diaryl-4-oxo-isoxazolo[5,4-d]pyrimidin-6-thiones (7), 3,5,7-triaryl-2,3-dihydro-4-oxo-isoxazalo[5,4-d]pyrimidin-6-thiones (8), 2-amino-6,8-diaryl-5-oxo-pyrimido[4,5-d]pyrimidin-7-thiones (9), 3,4-dihydro-2-amino-4-phenyl-6,8-diaryl-5-oxo-pyrimido[4,5-d]pyrimidin-7-thiones (10), 3-cyano-6,8-diaryl-2,5-dioxo-pyrido[2,3-d]pyrimidin-7-thiones (11) from the condensation products 1 and 2, derived from 1,3-diaryl-2-thiobarbituric acids is described.Key words: synthesis, fused, pyrazole, isoxazole, pyrimidines.

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8

Salahuddin, Md, Sunil Kakad, and S. M. Shantakumar. "Synthesis of Some Novel Thieno[2, 3-d] pyrimidines and their Antibacterial Activity." E-Journal of Chemistry 6, no. 3 (2009): 801–8. http://dx.doi.org/10.1155/2009/361282.

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Bromination of intermediate 1-[4-(6, 7-dihydro-5H-cyclopenta [4, 5] thieno[2, 3-d]pyrimidin-4-yl amino) phenyl] ethanone(4)yielded(5). Which upon reaction with different substituted benzothiazoles give a novel series of pyrimidine[6(a-g)]. However reaction of(5)with 4-chloro-2-triflouro acetyl aniline provided(6h). Similarly reaction of(5)with 5-amino tetrazole & 2-amino benzimidazole produced(6i)&(6j)respectively. All the synthesized compounds were tested against bacteria (Gram positive and Gram negative).

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9

Youssif, Shaker, and Fatmah Agili. "One-pot Synthesis of Fused 2-Thiouracils: Pyrimidopyrimidines, Pyridopyrimidines and Imidazolopyrimidines." Zeitschrift für Naturforschung B 63, no. 7 (July 1, 2008): 860–64. http://dx.doi.org/10.1515/znb-2008-0709.

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Several 6-substitued-1-methyl-2,5,7,8-tetrahydro-2-thiopyrimido[4,5-d]pyrimidine-4-ones and ethyl 7-amino-5-aryl-1-methyl-4-oxo-1,2,3,4-tetrahydro-2-thiopyrido[2,3-d]pyrimidines-6-carboxylates were synthesized by treatment of 6-amino-1-methyl-2-thiouracil with primary amines and formalin (40%), and with ethyl 3-aryl-2-cyanoacrylate respectively. 8-Substituted-7-hydroxy-3- methyl-2-thioxanthines were synthesized by the treatment of 6-amino-1-methyl-5-nitroso-2-thiouracil with benzylidene-anilines. Elemental and spectral analyses were performed for the new compounds.

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10

Otero, Iran, Holger Feist, Dirk Michalik, Manfred Michalik, José Quincoces, and 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, no. 11 (November 1, 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-benzimidazolyl-acetonitrile yielded the benz[4,5]imidazo[1,2-a]pyridine-4-carbonitrile (13). Deprotection of 8d in two steps afforded the 2-amino-N-benzyl-5-(methyl 3-deoxy-α-D-altropyranosid-3-yl-methyl)pyrazolo[1,5-a]pyrimidine- 3-carboxamide (10). Compounds 5 and 11d were treated with AcOH/H2O to furnish the 5-(methyl 2-O-benzyl-3-deoxy-α-D-altropyranosid-3-yl-methyl)[1,2,4]triazolo[1,5-a]pyrimidine (6) and the 3-acetyl-1,2-dihydro-1-(4-methoxyphenyl)-6-(methyl 2-O-benzyl-3-deoxy-α-D-altropyranosid-3-ylmethyl)- 4-phenylpyridin-2-one (12), respectively.

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11

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 (September 1, 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-imino-4-(substituted phenyl and/or thienyl)-1,2-dihydropyridine- 3-carbonitrile derivatives 5a-e, 3ʹH-spiro[cyclohexane- 1,2ʹ- thieno[3,2-d]pyrimidin]-3ʹ-yl]phenyl}-2-oxo-4-(substituted phenyl and/or thienyl)-1,2-dihydropyridine-3-carbonitrile derivatives 6a-e, and 4-[(2Z)-3-substituted-arylprop-2-enoyl] phenyl-1ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d]pyrimidine derivatives 7a-e. Cyclocondensation of 7a-e with hydrazine hydrate produced 6ʹ-(4-chlorophenyl)-3ʹ-[4-(5-substituted aryl-4,5-dihydro- 1H-pyrazol-3-yl)phenyl]-1ʹH-spiro[cyclohexane-1,2ʹ-thieno- [3,2-d]pyrimidin]-4ʹ(3ʹH)-ones 8a-e but with hydroxylamine hydrochloride afforded the corresponding isoxazoline derivatives 9a-e. Also, cyclocondensation by thiourea afforded 2-thioxo-1,2- dihydropyrimidin-4-yl)-phenyl-spiro-{cyclohexanethieno[3,2-d] pyrimidin}-4-one derivatives 10a-e. The new compounds were investigated for antimicrobial activity. Compounds 2c, 8b,c, 9b and 10b were the most potent ones against both Gram-negative and Gram-positive bacteria. Compound 8c exhibited higher antifungal activity towards the examined fungi with MIC of 1-2 μmol mL-1 compared to ketoconazole (MIC 2-3 μmol mL-1 ).

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12

Marchalín, Štefan, Františka Pavlíková, and Dušan Ilavský. "Synthesis and spectral properties of pyrrolo[3',4':5,6]-4H-pyrano[2,3-d]pyrimidine derivatives." Collection of Czechoslovak Chemical Communications 54, no. 5 (1989): 1336–45. http://dx.doi.org/10.1135/cccc19891336.

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The starting 2-amino-5-ethoxycarbonyl-6-chloromethyl-4-(2-furyl)-3-cyano-4H-pyran (I) afforded on condensation with triethoxymethane 2-ethoxymethylenamino-4H-pyran II; treatment of the latter with ammonia yielded 2-formamidino-3-cyano-4H-pyran III, which, when heated in dilute ethanol, cyclized to 4-amino-6-ethoxycarbonyl-5-(2-furyl)-7-chloromethyl-4H-pyrano[2,3-d]pyrimidine (IV). Compound IV reacted with alkyl- or arylamines to give substituted 5H,6H,8H-pyrrolo[3',4':5,6]-4H-pyrano[2,3-d]pyrimidines VI, one of which (VIb, R = p-CH3C6H4) was alternatively obtained from 2-formamidino-4H-pyrano derivative III. The structures of new tricyclic heterocycles were corroborated by analysis of the NMR spectral data.

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13

Mahmoud, M. R., A. A. Shalaby, T. A. Gad, and A. A. El-Khamry. "A facile synthesis and heteroannulation of pyrido[2,3-d]pyrimidine and related heterocyclic systems." Journal of Chemical Research 2009, no. 10 (October 2009): 612–15. http://dx.doi.org/10.3184/030823409x12523324765777.

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7-Amino-1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-(3,4,5-trimethoxyphenyl)pyrido[2,3- d]pyrimidine (1) was prepared and reacted with methyl iodide and ethyl chloroacetate to give the S-alkylated products 2 and 3, respectively. The reaction of 1 or 3 with hydrazine hydrate yielded the same 2-hydrazino derivative 4. Treatment of 4 with 2,4-pentanedione, 2-acetylcyclohexanone and ethyl acetoacetate afforded the corresponding pyrazolylpyrido[2,3- d]pyrimidine derivatives (5–7), while phthalic anhydride gave the phthalazinyl compound 8. Ethoxymethylenemalononitrile with the hydrazine 4 formed the fused 1,2,4-triazepine 9, while triazolopyrido[2,3- d]pyrimidines were obtained from the reaction of 4 with benzylidene malononitrile or benzaldehyde (forming 10), acetic acid/anhydride (giving 11), and ethyl chloroformate (giving 12).

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14

Kh. Ahmed, Essam, and Mohamed A. Ameen. "Synthesis of thiopyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]furo[3,2-d]pyrimidines." Chinese Chemical Letters 21, no. 6 (June 2010): 669–73. http://dx.doi.org/10.1016/j.cclet.2009.12.010.

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15

Quinn, RJ, PJ Scammells, CHL Kennard, and G. Smith. "Synthesis of 2-Substituted Pyrazolo[3,4-d]pyrimidines." Australian Journal of Chemistry 44, no. 12 (1991): 1795. http://dx.doi.org/10.1071/ch9911795.

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The reaction of 1-acetyl-2-phenylhydrazine with ethoxymethylenemalononitrile yielded [(4-cyano-1-phenylpyrazol-3-yl)aminomethylene]propanedinitrile. Hydrolysis followed by annulation with methyl isocyanate provided a synthetic route to 2-phenylpyrazolo[3,4-d]pyrimidines.

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16

Loidreau, Yvonnick, Pascal Marchand, Carole Dubouilh-Benard, Marie-Renée Nourrisson, Muriel Duflos, and Thierry Besson. "First synthesis of 4-aminopyrido[2′,3′:4,5]furo[3,2-d]pyrimidines." Tetrahedron Letters 53, no. 8 (February 2012): 944–47. http://dx.doi.org/10.1016/j.tetlet.2011.12.042.

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17

Nasr, Magda N., and Magdy M. Gineinah. "Pyrido [2, 3-d]pyrimidines and Pyrimido[5′, 4′:5, 6]pyrido[2, 3-d]pyrimidines as New Antiviral Agents: Synthesis and Biological Activity." Archiv der Pharmazie 335, no. 6 (August 2002): 289. http://dx.doi.org/10.1002/1521-4184(200208)335:6<289::aid-ardp289>3.0.co;2-z.

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18

Halim, Md E., K. Akhter, SM Ahmed, Md Al Amin Hossain, and UKR Romman. "One pot synthesis of Biginelli 3,4-dihydro-1H-pyrimidin-2-ones and 1,2,3,4-tetrahydro pyrimidines." Bangladesh Journal of Scientific and Industrial Research 55, no. 3 (September 24, 2020): 173–80. http://dx.doi.org/10.3329/bjsir.v55i3.49390.

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A simple and practical route for the Biginelli cyclocondensation reaction using anhydrous ZnCl2 as a catalyst in n-heptane-toluene medium by reaction of substituted benzaldehydes,1a-d (1a=2-ClC6H4-, 1b=2-BrC6H4- and 1c=4-ClC6H4-,1d=2-H3CC6H4-) with 1, 3-dicarbonyl compounds, 2a-b (2a= ethyl acetoacetate and 2b= acetylacetone) and urea or thiourea, 3a-b to give the corresponding Biginelli 3,4-dihydro- 1H-pyrimidin-2-ones and 1,2,3,4-tetrahydro pyrimidines, 4a-d. The structures of the compounds 4a-d were confirmed by their ultraviolet, infrared, 1H NMR, 13C NMR spectra and elemental analyses. Bangladesh J. Sci. Ind. Res.55(3), 173-180, 2020

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19

Ahmed, Essam Kh, and Mohamed A. Ameen. "ChemInform Abstract: Synthesis of Thiopyrano[4′′,3′′:4′,5′]pyrido[3′,2′:4,5]furo[3,2-d]pyrimidines." ChemInform 41, no. 43 (September 30, 2010): no. http://dx.doi.org/10.1002/chin.201043163.

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20

Garaeva, Lydmila D., Irina V. Yartseva, and Stalina Ya Melnik. "Studies on Glycosides of 3, 4, 6-Trisubstituted Pyrazolo-[3, 4-D]Pyrimidines. Synthesis of 2′-Deoxyribonucleosides." Nucleosides and Nucleotides 10, no. 6 (September 1991): 1295–303. http://dx.doi.org/10.1080/07328319108047063.

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21

Nagashree, A. S., K. Kusuma, M. S. Latha, A. S. Sowmyashree, and V. P. Vaidya. "Synthesis and Pharmacological activities of 2-Substituted-3-Hydro/Aryl-3, 4-Dihydro-4-Oxo-Naphtho[2,1-B] Furo [3,2-D] Pyrimidines. (Research Article)." International Journal of Pharmacy and Biological Sciences 11, no. 1 (January 1, 2021): 48–55. http://dx.doi.org/10.21276/ijpbs.2021.11.1.6.

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DAVE, C. G., P. R. SHAH, P. S. PANDYA, and G. K. SHAH. "ChemInform Abstract: Pyridopyrimidines. Part 6. Synthesis and Reactions of 4-Iminopyrido-(2, 3-d)pyrimidines and 3H-2-Thioxopyrido(2,3-d)pyrimidin-4-ones." ChemInform 22, no. 31 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199131209.

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23

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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24

Loidreau, Yvonnick, Pascal Marchand, Carole Dubouilh-Benard, Marie-Renee Nourrisson, Muriel Duflos, and Thierry Besson. "ChemInform Abstract: First Synthesis of 4-Aminopyrido[2′,3′:4,5]furo[3,2-d]pyrimidines." ChemInform 43, no. 24 (May 21, 2012): no. http://dx.doi.org/10.1002/chin.201224171.

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25

TAHA, M. L., H. B. LAZREK, J. L. BARASCUT, and J. L. IMBACH. "ChemInform Abstract: Synthesis of Some 4-Substituted 1-((2-Hydroxyethoxy)methyl)pyrazolo(3, 4-d)pyrimidines." ChemInform 27, no. 34 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199634250.

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26

Kidwai, Mazaahir, and Alkal Mishra. "An expeditious synthesis of 3, 4-dihydro-benzo[2,3-d]pyrimidines using inorganic solid supports." Journal of the Serbian Chemical Society 69, no. 4 (2004): 247–54. http://dx.doi.org/10.2298/jsc0404247k.

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Aseries of novel 5-substituted-8-cyano-4,6,7-triphenyl-3,4-dihydrobenzo [2,3-d]pyrimidines were synthesized by the condensation of 6-substituted-2-amino 1-benzoyl-3-cyano-5-hydroxy-4,5-diphenyl-1,3-cyclohexadiene and formamide using inorganic solid supports under microwaves. Some of the compounds were found to be effective against some fungal and bacterial strains.

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27

Bodige, Srinu, Parameshwar Ravula, Kali Charan Gulipalli, Srinivas Endoori, J. N. Narendra Sharath Chandra, Purna Koteswara Rao Cherukumalli, G. R. Vanaja, and Nareshvarma Seelam. "Design, Synthesis and Biological Evaluation of Novel Urea and Thiourea Bearing thieno[3,2-d]-pyrimidines as PI3 Kinase Inhibitors." Anti-Cancer Agents in Medicinal Chemistry 18, no. 6 (November 12, 2018): 891–902. http://dx.doi.org/10.2174/1871520618666180209151018.

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Background: Phosphatidylinositol-3-kinase α (PI3Kα) is a ubiquitous intracellular enzyme, mainly involved in intracellular signaling pathways, promotes cellular growth, proliferation, and differentiation. Therefore, inhibition of PI3K can be a hotspot in molecular targeted therapy for the treatment of cancer. Methods: The present research work involves molecular docking studies performed to screen derivatives of urea and thiourea bearing thieno [3,2-d]-pyrimidines against the active site of PI3K enzyme using MOE.2008.10. The designed structures (6a-f) and (7a-j) were synthesized by the facile synthetic methods and evaluated for their anticancer activity against HT-29 and MCF-7 cell lines and inhibitory activity against PI3Kα enzyme. Results: Among the tested compounds, 4-(4-(2-(3-(pyrimidin-2-yl)thioureido)ethyl)piperazin-1-yl)thieno[3,2- d]pyrimidine-6-carboxamide (7f) showed the highest anticancer activity against HT-29 and MCF-7 cell lines with IC50 values of 2.18 µM and 4.25 µM, respectively. Further, the same compound also exhibited potent PI3Kα inhibitory activity with IC50 value of 1.26 µM. Conclusion: Docking studies supported the initial pharmacophoric hypothesis and suggested a mode of interaction at the active binding site of PI3Kα, demonstrating that the target compounds were potential inhibitory agents for cancer therapy.

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28

Dabaeva, V. V., A. S. Noravyan, and B. D. Enokyan. "Synthesis of dihydro-10H-pyrano[3?,4?: 5,6]pyrido[3,2:4?,5?]-thieno[3?,2?-d][3,1]oxazines and pyrimidines." Chemistry of Heterocyclic Compounds 31, no. 2 (February 1995): 219–22. http://dx.doi.org/10.1007/bf01169683.

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29

Mkrtchyan, A. P., A. Sh Oganisyan, Art Sh Oganisyan, and A. S. Noravyan. "Derivatives of Condensed Thienopyrimidines. 22. Synthesis of 2-Substituted 4-Thioxopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidines." Chemistry of Heterocyclic Compounds 41, no. 2 (February 2005): 235–37. http://dx.doi.org/10.1007/s10593-005-0133-4.

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30

Suresh, Lingala, Y. Poornachandra, S. Kanakaraju, C. Ganesh Kumar, and G. V. P. Chandramouli. "One-pot three-component domino protocol for the synthesis of novel pyrano[2,3-d]pyrimidines as antimicrobial and anti-biofilm agents." Organic & Biomolecular Chemistry 13, no. 26 (2015): 7294–306. http://dx.doi.org/10.1039/c5ob00693g.

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A simple and facile synthesis of a series of novel pyrano[2,3-d]pyrimidines have been achieved successfullyviaone-pot three-component reaction of 2-amino-7-methyl-5-oxo-4-phenyl-4,5-dihydropyrano[4,3-b]pyran-3-carbonitriles, DMF-DMA and arylamines.

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31

Kurasawa, Yoshihisa, Yumiko Kamigaki, Ho Sik Kim, Rika Futatsukawa, Megumi Kanoh, Mari Okiyama, Atsushi Takada, and Yoshihisa Okamoto. "Synthesis and13C-NMR study of novel pyrazolo[5′,1′:3, 4][1, 2, 4]triazino[5, 6-d]pyrimidines." Journal of Heterocyclic Chemistry 26, no. 3 (May 1989): 853–56. http://dx.doi.org/10.1002/jhet.5570260363.

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32

DABAEVA, V. V., A. S. NORAVYAN, and B. D. ENOKYAN. "ChemInform Abstract: Synthesis of Dihydro-10H-pyrano(3′,4′:5,6)pyrido(3,2:4′′,5′′)thieno(3′′ ,2′′-d) oxazines(3,1) and -pyrimidines." ChemInform 26, no. 38 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199538183.

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33

Ameen, Mohamed A. "Novel Selective 5-HT3 Receptor Ligands: Facile Generation Methods for 2-Amino- and 4-Aminopyrido[4’,3’:4,5]thieno[2,3-d]pyrimidines." Zeitschrift für Naturforschung B 61, no. 10 (October 1, 2006): 1234–38. http://dx.doi.org/10.1515/znb-2006-1008.

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This work reports on the synthesis of new 2-amino- and 4-aminopyridothienopyrimidines, with a view to identify potent and selective ligands for the 5-HT3 receptor, starting from derivatives of 2-aminothiophene-3-carboxylic ester, -3-carboxamide, or 2-amino-3-cyanothiophene.

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34

Ahluwalia, V. K., Rakesh Kumar, Anju Khurana, and Rita Bhatla. "A convenient synthesis of 1,3-diaryl-1,2,3,4,-tetrahydro-5,7,7-trimethyl-4-oxo-2-thioxo-7H-pyrano[ 2 ,3-d ]pyrimidines." Tetrahedron 46, no. 11 (January 1990): 3953–62. http://dx.doi.org/10.1016/s0040-4020(01)90530-7.

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35

Taltavull, Joan, Jordi Serrat, Jordi Gràcia, Amadeu Gavaldà, Míriam Andrés, Mònica Córdoba, Montserrat Miralpeix, et al. "Synthesis and Biological Activity of Pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines as Phosphodiesterase Type 4 Inhibitors." Journal of Medicinal Chemistry 53, no. 19 (October 14, 2010): 6912–22. http://dx.doi.org/10.1021/jm100524j.

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36

Abed, Nosrat Mustafa, Nadia Sobhy Ibrahim, and Mohamed Helmy Elnagdi. "Studies on Heterocyclic Enamines: New Synthesis of Pyrano[2,3-b]pyndine, Pyrano[2,3-d]pyrimidine and Pyrano[2,3-c]pyrazole Derivatives." Zeitschrift für Naturforschung B 41, no. 7 (July 1, 1986): 925–28. http://dx.doi.org/10.1515/znb-1986-0721.

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AbstractA variety of novel pyrano[2,3-d]pyrimidines could be obtained via reaction of ethyl 2-amino- 3-cyano-6-methylpyran-4-carboxylate with a variety of reagents. Evidence for the existance of this pyran derivative as a ring chain tautom er is presented.

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37

Narsaiah, B., A. Sivaprasad, and R. V. Venkataratnam. "Synthesis of novel 2,7-disubstituted-3-amino-9-trifluoromethyl-4-oxo-4H-pyrido-[3',2':4,5]-furo-[3,2-d]-(1,3)-pyrimidines." Journal of Fluorine Chemistry 69, no. 2 (November 1994): 139–43. http://dx.doi.org/10.1016/0022-1139(94)03079-0.

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38

Ahmed, E. Kh, A. M. N. Gohar, and M. A. Ameen. "ChemInform Abstract: Synthesis of New Pyrido[4′,3′:4,5]thieno[2,3-d]-1,2,4-triazolo[3,4-c]pyrimidines and a 5,6-Dihydro-1,2,4-triazolo[4′′,3′′:1′,2′]pyrido[4′,3′:4,5]thieno [2,3-d]pyrimidine Ring System." ChemInform 31, no. 20 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200020129.

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39

Mkrtchyan, A. P., and A. S. Noravyan. "Derivatives of condensed thieno[2,3-d]-pyrimidines. 20. Synthesis of 2-substituted 5,6-dihydro-8H-pyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-ones and 5,6,7,8-tetrahydrobenzo-[b]thieno[2,3-d]pyrimidin-4-ones." Chemistry of Heterocyclic Compounds 42, no. 3 (March 2006): 392–95. http://dx.doi.org/10.1007/s10593-006-0098-y.

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40

Veselovská, Lucia, Radek Pohl, Eva Tloušt′ová, Soňa Gurská, Petr Džubák, Marián Hajdúch, and Michal Hocek. "Pyrido-Fused Deazapurine Bases: Synthesis and Glycosylation of 4-Substituted 9H-Pyrido[2′,3′:4,5]- and Pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidines." ACS Omega 5, no. 40 (October 2, 2020): 26278–86. http://dx.doi.org/10.1021/acsomega.0c04302.

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41

Mkrtchyan, A. P., A. S. Noravyan, and V. M. Petrosyan. "ChemInform Abstract: Derivatives of Condensed Thieno[2,3-d]pyrimidines. Part 15. Synthesis of 2-Substituted 3-Amino-6,6-dimethyl-5,6-dihydro-8H-pyrano[4′,3′:4,5]thieno [2,3-d]pyrimidin-4-ones." ChemInform 33, no. 43 (May 19, 2010): no. http://dx.doi.org/10.1002/chin.200243187.

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42

Blanco, Gerardo, José M. Quintela, and Carlos Peinador. "Synthesis of new heteroaromatic nitrogen ligands: Pyrimido-[4″,5″:4′,5′]-thieno[3′,2′:4,5]thieno[3,2-d]pyrimidines and 1,2,3-triazine[4″,5″:4′,5′]thieno[3′,2′:4,5]thieno[3,2-d]-1,2,3-triazines." Journal of Heterocyclic Chemistry 43, no. 4 (July 2006): 1051–56. http://dx.doi.org/10.1002/jhet.5570430435.

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43

Sirakanyan, S. N., A. A. Ovakimyan, A. S. Noravyan, I. A. Dzhagatspanyan, A. A. Shakhatuni, I. M. Nazaryan, and A. G. Akopyan. "Synthesis and Anticonvulsive Activity of 7-Amino-Substituted Cyclopenta[4′,5′]-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidines." Pharmaceutical Chemistry Journal 47, no. 3 (June 2013): 130–34. http://dx.doi.org/10.1007/s11094-013-0910-9.

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44

Fattahi, Mehri, Abolghasem Davoodnia, Mehdi Pordel, S. Ali Beyramabadi, and Niloofar Tavakoli-Hoseini. "Isolation of intermediates in the synthesis of new 3,4-dihydro-2H-chromeno[2,3-d]pyrimidines." Zeitschrift für Naturforschung B 73, no. 8 (August 28, 2018): 557–63. http://dx.doi.org/10.1515/znb-2018-0042.

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AbstractReaction of N-alkyl-2-imino-2H-chromene-3-carboxamides with dimethyl acetylenedicarboxylate (DMAD) in the presence of sodium carbonate as catalyst in refluxing ethanol gave new tricyclic products identified as methyl 3-alkyl-2-(2-methoxy-2-oxoethyl)-4-oxo-3,4-dihydro-2H-chromeno[2,3-d]pyrimidine-2-carboxylates. In the absence of sodium carbonate, dimethyl 2-((E)-3-(alkylcarbamoyl)-2H-chromen-2-ylideneamino)fumarates were isolated as intermediates. These intermediates could be successfully converted to the same new tricyclic products by heating in ethanol containing sodium carbonate. All new synthetic compounds were characterized on the basis of their FT-IR, 1H and 13C NMR spectra, and microanalytical data. To identify the correct stereoisomer of the intermediates, in one case a 2D nuclear Overhauser effect (2D-NOESY) spectrum together with density functional theory (DFT) calculation at the B3LYP/6-311+G(d,p) level of theory was used.

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45

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 (April 3, 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 pyrazolothienopyrimidine 8. Compound 8 was used as a synthetic precursor to heterocyclic compounds comprised of pyrazole, triazole, triazine, and triazepine derivatives.

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46

Paronikyan, E. G., Sh Sh Dashyan, N. S. Minasyan, and G. M. Stepanyan. "Synthesis of 5,8-Diamino-Substituted Pyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines and Pyrimido[4′,5′:4,5]thieno[2,3-c]isoquinolines." Russian Journal of Organic Chemistry 52, no. 4 (April 2016): 576–81. http://dx.doi.org/10.1134/s1070428016040187.

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47

Solomyannyi, R. N., S. R. Slivchuk, A. N. Vasilenko, E. B. Rusanov, and V. S. Brovarets. "Synthesis of 3-amino-1-benzyl-4-benzenesulfonyl-2-carbonitrilo-1H-pyrrole and preparation of related pyrrolo[3,2-d]pyrimidines." Russian Journal of General Chemistry 82, no. 2 (February 2012): 317–22. http://dx.doi.org/10.1134/s1070363212020235.

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48

Bakhite, E. A., A. G. Al-Sehemi, and Y. Yamada. "Synthesis of novel pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines, pyrido[3″,2″:4′,5′]thieno[3′,2′:4,5]pyrimido[l,6-a]benzimidazoles and related fused systems." Journal of Heterocyclic Chemistry 42, no. 6 (September 2005): 1069–77. http://dx.doi.org/10.1002/jhet.5570420606.

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49

NARSAIAH, B., A. SIVAPRASAD, and R. V. VENKATARATNAM. "ChemInform Abstract: Synthesis of Novel 2,7-Disubstituted-3-amino-9-trifluoromethyl-4-oxo- 4H-pyrido-(3′,2′:4,5)-furo-(3,2-d)-(1,3)-pyrimidines." ChemInform 26, no. 17 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199517159.

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50

Bakhite, Etify A., Abdu E. Abdel-Rahman, and Elham A. Al-Taifi. "Fluorine-Containing Heterocycles: Part I. Synthesis of New 7-(2-thienyl)-9-Trifluoromethylpyrido[3′,2′:4,5]Thieno[3,2-d]Pyrimidines and Related Fused Tetracyclic Systems." Journal of Chemical Research 2005, no. 3 (March 2005): 147–54. http://dx.doi.org/10.3184/0308234054213726.

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3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxamide (3) and 2-carbonitrile analogue 5 were prepared by reaction of 3-cyano-6-(2-thienyl)-4-trifluoromethylpyridine-2(1H)-thione (1) with chloroacetamide or chloroacetonitrile respectively. Heating compound 3 with triethyl orthoformate led to the formation of pyridothienopyrimidinone derivative 6. Reaction of 6 with phosphorus oxychloride produced 4-chloropyrimidine derivative 7 which underwent some nucleophilic displacements upon treatment with thiourea, piperidine, morpholine or hydrazine hydrate to give the target 4-substituted pyridothienopyrimidines 8, 10a, 10b and 11 respectively. Reaction of compound 8 with methyl iodide or ethyl chloroacetate gave compounds 9a,b. The condensation of 3-amino-6-(2-thienyl)-4-trifluoromethyl-thieno[2,3-b]pyridine-2-carbonitrile (5) with triethyl orthoformate led to the formation of methanimidate derivative 21 which upon treatment with hydrazine hydrate gave the target 3-amino-3,4-dihydro-4-imino-7-(2-thienyl)-9-trifluoromethylpyrido[3′,2′:4,5] thieno[3,2-d]pyrimidine (22). The reactions of compounds 11 and 22 with some reagents namely; triethyl orthoformate, acetic anhydride, formic acid, acetic acid, acetylacetone benzaldehyde and/or diethyl malonate were carried out and their products were identified, in most cases as [1,2,4]triazolopyridothienopyrimidines via Dimroth rearrangement.

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