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Journal articles on the topic '3-d]pyrimidines synthesis'

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Published: 4 June 2021

Last updated: 1 February 2022

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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

Sirakanyan, Spinelli, Geronikaki, Hakobyan, Sahakyan, Arabyan, Zakaryan, et al. "Synthesis, Antitumor Activity, and Docking Analysis of New Pyrido[3’,2’:4,5]furo(thieno)[3,2-d]pyrimidin-8-amines." Molecules 24, no. 21 (October 31, 2019): 3952. http://dx.doi.org/10.3390/molecules24213952.

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Continuing our research in the field of new heterocyclic compounds, herein we report on the synthesis and antitumor activity of new amino derivatives of pyrido[3’,2’:4,5](furo)thieno[3,2-d]pyrimidines as well as of two new heterocyclic systems: furo[2–e]imidazo[1,2-c]pyrimidine and furo[2,3-e]pyrimido[1,2-c]pyrimidine. Thus, by refluxing the 8-chloro derivatives of pyrido[3’,2’:4,5]thieno(furo)[3,2-d]pyrimidines with various amines, the relevant pyrido[3’,2’:4,5]thieno(furo)[3,2-d]pyrimidin-8-amines were obtained. Further, the cyclization of some amines under the action of phosphorus oxychloride led to the formation of new heterorings: imidazo[1,2-c]pyrimidine and pyrimido[1,2-c]pyrimidine. The possible antitumor activity of the newly synthesized compounds was evaluated in vitro. The biological tests evidenced that some of them showed pronounced antitumor activity. A study of the structure–activity relationships revealed that the compound activity depended mostly on the nature of the amine fragments. A docking analysis was also performed for the most active compounds.

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5

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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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

El-Bahaie, S., and M. G. Assy. "Synthesis of 2-Arylthiopyrano[2, 3-d]Pyrimidines and Thieno[2, 3-D]Pyrimidines." Journal of the Chinese Chemical Society 37, no. 5 (October 1990): 497–500. http://dx.doi.org/10.1002/jccs.199000068.

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8

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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9

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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10

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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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

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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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

Abdel-Hafez, Shams H., Ragaa A. Ahmed, Mohamed A. Abdel-Azim, and Khairy M. Hassan. "Selenium containing Heterocycles: Part 1. Synthesis of Some New Substituted Pyrido[3′,2′:4,5]selenolo[3,2-d]pyrimidines and Related Fused Tetracyclic Systems." Journal of Chemical Research 2007, no. 10 (October 2007): 580–84. http://dx.doi.org/10.3184/030823407x25506.

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New series of selenolo[2,3- b]pyridine, pyrido[3′,2′:4,5]selenolo[3,2- d]pyrimidine, 7,8-dihydro-2,4-dimethylpyrrolo [1,2- a]pyrido[3′,2′:4,5]selenolo[3,2- d]pyrimidin-10(6 H)-one and 7,9-dimethylpyrido[3′,2′:4,5]selenolo[3,2- d][1,2,4] triazolo[4,3- c]pyrimidine derivatives were synthesised from 3-cyano-4,6-dimethylpyridine-2(1 H)-selenone (1). Spectroscopic (IR, 1H, MS) of the newly synthesised compounds are reported.

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15

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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16

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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17

Salaheldin, Abdellatif M. "Enaminonitriles in Heterocyclic Synthesis: Novel Synthesis of 3-Aminopyrroles and Pyrrolo[3,2-d]pyrimidine Derivatives." Zeitschrift für Naturforschung B 63, no. 5 (May 1, 2008): 564–70. http://dx.doi.org/10.1515/znb-2008-0514.

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Several new 3-aminopyrrole derivatives have been synthesized from 3-substituted amino-2-phenylacrylonitriles using Thorpe-Ziegler cyclization. These substituted pyrroles are readily converted into 5H-pyrrolo[3,2-d]pyrimidines (9-deazapurines).

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18

Shurrab, Nabil Kh, Hussein Alhendawi, and Manar A. Kerrit. "Synthesis of New 3,7,9-Trisubstituted Pyrazolo[4,3-e][1,2,4]Triazolo[4,3-c] Pyrimidines Acyclo C-Nucleosides via Oxidative Cyclisation." Journal of Chemical Research 42, no. 12 (December 2018): 601–3. http://dx.doi.org/10.3184/174751918x15414291150879.

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Condensation of 4-hydrazino-1,3-diphenylpyrazolo[3,4-d]-pyrimidine with the aldohexoses, namely, D-glucose, D-galactose, D-mannose and the aldopentoses, D-arabinose, D-xylose and D-ribose, by heating in an aqueous ethanol in the presence of a catalytic amount of HCl, gave the respective aldehydo-sugar hydrazones. Oxidative cyclisation of such hydrazones by stirring with iron(III) chloride in ethanol at room temperature afforded the expected acyclo C-nucleosides 3-substituted-7,9-diphenylpyrazolo[4,3-e][1,2,4]triazolo[4,3-c]-pyrimidines. The structures of the cyclised sugar hydrazones were confirmed by their elemental analyses and spectral data.

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19

BISTRYAKOVA, I. D., N. M. SMIRNOVA, and T. S. SAFONOVA. "ChemInform Abstract: Pyrido(2,3-d)pyrimidines. Part 8. Synthesis of Pyrrolo(2′,3′:4,5) pyrido(2,3-d)pyrimidines." ChemInform 25, no. 15 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199415204.

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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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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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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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Nagahara, Katsuhiko, Jack D. Anderson, Ganesh D. Kini, N. Kent Dalley, Steven B. Larson, Donald F. Smee, Ai Jin, Brahma S. Sharma, and Weldon B. Jolley. "Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-.beta.-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents." Journal of Medicinal Chemistry 33, no. 1 (January 1990): 407–15. http://dx.doi.org/10.1021/jm00163a064.

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Vaghasia, S. J., and V. H. Shah. "Microwave assisted synthesis and antimicrobial activity of some novel pyrimidine derivatives." Journal of the Serbian Chemical Society 72, no. 2 (2007): 109–17. http://dx.doi.org/10.2298/jsc0702109v.

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The synthesis of thiazolo[5,4-d]pyrimidines can be achieved from different 5- thiazolidinones, 2-butyl-1H-imidazole-5-carbaldehyde and thiourea using microwave irradiation within 5 min. The structures of the products were supported by FTIR, PMR and mass spectral data. The in vitro antimicrobial activity of the synthesized thiazolo[5,4-d]pyrimidines 1a-j, having substituents at the 1- and 3-positions, were determined by the cup-plate method against several standard strains chosen to define the spectrum and potency of the new compounds. The antimicrobial activities of the thiazolo[5,4-d]pyrimidines 1a-j are compared with those of known chosen standard drugs, viz. ampicillin, chloramphenicol, ciprofloxacin, norfloxacin and griseofulvin. .

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25

Urleb, UroŠ, Branko Stanovnik, and Miha Tišler. "The synthesis and transformations of 2-ethoxycarbonyl-3-isothiocyanatopyridine. Pyrido[3,2-d]pyrimidines and some azolopyrido[3,2-d]pyrimidines." Journal of Heterocyclic Chemistry 27, no. 2 (February 1990): 407–12. http://dx.doi.org/10.1002/jhet.5570270256.

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Urleb, Uroš, Branko Stanovnik, and Miha Tišler. "The synthesis and transformations of 3-ethoxycarbonyl-2-isothiocyanatopyridine. Pyrido[2,3-d]pyrimidines and some azolopyrido[2,3-d]pyrimidines." Journal of Heterocyclic Chemistry 27, no. 3 (March 1990): 643–46. http://dx.doi.org/10.1002/jhet.5570270331.

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Artyomov, Vasilii A., Lyudmila A. Rodinovskaya, Anatolii M. Shestopalov, and Victor P. Litvinov. "Synthesis of 2,4-Diaminopyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines." Mendeleev Communications 3, no. 4 (January 1993): 149–51. http://dx.doi.org/10.1070/mc1993v003n04abeh000262.

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Trichili, Sihem, Myriam Kammoun, Hamida Turki-Guermazi, Souhir Abid, and Houcine Ammar. "Synthesis of New 3-Carboxamidine Iminocoumarins and Benzopyrano[2,3-d]pyrimidines." Synthetic Communications 45, no. 8 (January 29, 2015): 958–66. http://dx.doi.org/10.1080/00397911.2014.997365.

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29

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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SAKAMOTO, T., C. SATOH, Y. KONDO, and H. YAMANAKA. "ChemInform Abstract: Condensed Heteroaromatic Ring Systems. Part 21. Synthesis of Pyrrolo(2, 3-d)pyrimidines and Pyrrolo(3,2-d)pyrimidines." ChemInform 24, no. 25 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199325185.

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31

Sirakanyan, Samuel N., Victor G. Kartsev, Athina Geronikaki, Domenico Spinelli, Anthi Petrou, Elmira K. Hakobyan, Jasmina Glamoclij, Manija Ivanov, Marina Sokovic, and Anush A. Hovakimyan. "Synthesis and Evaluation of Antimicrobial Activity and Molecular Dock - ing of New N-1,3-thiazol-2-ylacetamides of Condensed Pyrido[3',2':4,5] furo(thieno)[3,2-d]pyrimidines." Current Topics in Medicinal Chemistry 20, no. 24 (November 2, 2020): 2192–209. http://dx.doi.org/10.2174/1568026620666200628145308.

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Background: From the literature it is known that many derivatives of fused thienopyrimidines and furopyrimidines possess broad spectrum of biological activity. Objectives: The current studies describe the synthesis and evaluation of antimicrobial activity of some new N-1,3-thiazol-2-ylacetamides of pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines. Methods: By cyclocondensation of ethyl 1-aminofuro(thieno)[2,3-b]pyridine-2-carboxylates 1with formamide were converted to the pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidin-7(8)-ones 2.Alkylation of compound 2 with 2-chloro-N-1,3-thiazol-2-ylacetamide led to the aimed N-1,3-thiazol-2-ylaceta-mides of pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines 3. Starting from compound 2 the relevant S-alkylated derivatives of pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines 6 were also synthesized. Results: All the compounds showed antibacterial activity to non-resistant strains. Compounds 3a-3m showed antibacterial activity with MIC/MBC at 0.08-2.31 mg/mL/0.11-3.75 mg/mL .The two most active compounds, 3j and 6b, appeared to be more active towards MRSA than the reference drugs. Half of the tested compounds appeared to be equipotent/more potent than ketoconazole and more potent than bifonazole. The docking analysis provided useful information about the interactions occurring between the tested compounds and the different enzymes. Conclusion: Gram-negative and Gram-positive bacteria and fungi showed different response towards tested compounds, indicating that different substituents may lead to different modes of action or that the metabolism of some bacteria/fungi was better able to overcome the effect of the compounds or adapt to it.

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32

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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33

Balalaie, Saeed, Hamed Esmaeilabadi, Saber Mehrparvar, Frank Rominger, Fatima Hamdan, and Hamid Bijanzadeh. "Synthesis of Functionalized Dihydropyrido[2,3-d]pyrimidines in Aqueous Medium." SynOpen 02, no. 01 (January 2018): 0001–5. http://dx.doi.org/10.1055/s-0036-1591869.

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Synthesis of functionalized 2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one from a cascade reaction between 3-formylchromone, malononitrile, diammonium hydrogen phosphate, and aromatic aldehydes in aqueous media is described.

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34

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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35

AHLUWALIA, V. K., and A. DAHIYA. "ChemInform Abstract: Synthesis of Pyrazolo(3′,4′:5,6)pyrido(2,3-d)pyrimidines." ChemInform 28, no. 6 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199706150.

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36

Muzychka, L. V., E. V. Verves, I. O. Yaremchuk, and O. B. Smolii. "Synthesis of pyrrolo[2,3-d]pyrimidines with 3-amino-2-hydroxypropyl substituents." Chemistry of Heterocyclic Compounds 48, no. 3 (June 2012): 481–87. http://dx.doi.org/10.1007/s10593-012-1019-x.

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37

Aliabiev, S., I. Ivanov, A. Ilyin, D. Kravchenko, and A. Ivachtchenko. "Synthesis of Novel 5,6,7-Substituted 3-Phenyl-6,7-Dihydroisoxazolo[4,5-d]Pyrimidines." Letters in Organic Chemistry 4, no. 3 (April 1, 2007): 203–11. http://dx.doi.org/10.2174/157017807780737318.

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38

Bystryakova, I. D., N. M. Smirnova, and T. S. Safonova. "Pyrido[2,3-d]dipyrimidines 8. Synthesis of pyrrolo(2?,3??4,5)pyrido[2,3-d]pyrimidines." Chemistry of Heterocyclic Compounds 29, no. 6 (June 1993): 687–90. http://dx.doi.org/10.1007/bf00531548.

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39

Abbas, Safinaz E.-S., Riham F. George, Eman M. Samir, Mostafa MA Aref, and Hatem A. Abdel-Aziz. "Synthesis and anticancer activity of some pyrido[2,3-d]pyrimidine derivatives as apoptosis inducers and cyclin-dependent kinase inhibitors." Future Medicinal Chemistry 11, no. 18 (September 2019): 2395–414. http://dx.doi.org/10.4155/fmc-2019-0050.

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Aim: Due to emergence of resistance to available anticancer agents, there is a need to search for new cytotoxic agents. Methods: Pyrido[2,3- d]pyrimidines (4–6) and their tricyclic derivatives (7–13) were prepared and screened for their cytotoxicity against breast MCF-7, prostate PC-3 and lung A-549 cancer cell lines as well as normal fibroblasts WI-38. Results: The most active compounds were 6b, 6e and 8d compared with doxorubicin. Moreover, compounds 6b and 8d induced apoptosis in PC-3 and MCF-7, respectively via activation of CASP3 (in PC-3 only), Bax, p53 and down regulation of Bcl2 in addition to CDK4/6 inhibition. Conclusion: Pyrido[2,3- d]pyrimidine represents an important core for discovery of new potent cytotoxic agents acting on the cell cycle via apoptosis induction through either intrinsic or extrinsic pathways.

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40

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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41

Hussein, Abdel Haleem Mostafa, Essam Abdel Raheem Eshak, and Fathi Aly Abu-Shanab. "Nitriles in Heterocyclic Synthesis: Synthesis of Pyrido[3’,2’:4,5]Thieno[2,3-d] Pyrimidines Derivative." OALib 02, no. 01 (2015): 1–9. http://dx.doi.org/10.4236/oalib.1101307.

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42

Burova, O. A., I. D. Bystryakova, N. M. Smirnova, and T. S. Safonova. "Pyrido[2,3-d]pyrimidines 3. Synthesis and properties of 7-chloro- and 6-nitro-7-chloropyrido[2,3-d]pyrimidine-2,4,5-triones." Chemistry of Heterocyclic Compounds 27, no. 4 (April 1991): 394–98. http://dx.doi.org/10.1007/bf00480837.

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43

Chernov, Nikita M., Roman V. Shutov, Anastasia E. Potapova, and Igor P. Yakovlev. "Convenient Synthesis of Fluorescent Chromeno[4,3-d]pyrimidines from Electron-Deficient 3-Vinylchromones." Synthesis 52, no. 01 (October 21, 2019): 40–50. http://dx.doi.org/10.1055/s-0039-1690723.

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We report an easy and powerful approach to the synthesis of novel chromeno[4,3-d]pyrimidine-5-acetic acids through ANRORC reaction of electron-deficient 3-vinylchromones and 1,3-N,N-binucleophiles. The reaction proceeds under mild conditions (EtOH, rt) and is applicable to a wide range of substrates. The described compounds show fluorescence in the violet-blue range (390–460 nm) with Stokes shift of 40–80 nm and moderate quantum yield (0.15–0.20). As the electron-withdrawing group is conserved in the form of an acetic acid fragment, these compounds may readily be functionalized or conjugated to a required substrate for (bio)analytical purposes.

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44

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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45

Xiao, Qiang, Jin Liu, Jia-Hui Nie, Ling-Bin Kong, Jun Lin, and Sheng-Jiao Yan. "Silver-catalyzed cascade reactions of 3-cyanochromone with 1,1-enediamines: synthesis of highly functionalized 2-(pyridin-3-yl)-chromeno[2,3-d]pyrimidines." Organic Chemistry Frontiers 7, no. 15 (2020): 2035–39. http://dx.doi.org/10.1039/d0qo00388c.

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A novel protocol for the construction of 2-(pyridin-3-yl)-chromeno[2,3-d]pyrimidines from 3-cyanochromone with 1,1-enediamines via an unprecedented cascade reaction has been developed by simply refluxing the reactants under the catalysis of silver carbonate.

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46

Bakhite, E. A., A. A. Geies, and H. S. El-Kashef. "Synthesis of Novel Pyrrylthieno[2,3-d]Pyrimidines and Related Pyrrolo[1″,2″:1″,6″]Pyrazino[2″,3″:4,5]Thieno[2,3-d]Pyrimidines." Phosphorus, Sulfur, and Silicon and the Related Elements 177, no. 2 (February 1, 2002): 303–23. http://dx.doi.org/10.1080/10426500210243.

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47

Abdel-Mohsen, Shawkat A., and Ahmed A. Geies. "Synthesis of pyrido[2‘,3‘:4,5]thieno[2,3-d]pyrimidines through Friedländer reactions." Journal of Chemical Research 2007, no. 12 (December 1, 2007): 689–92. http://dx.doi.org/10.3184/030823407x269961.

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48

Fazlelahi, Hadi Z., Peyman N. Moghadam, Mehdi M. Baradarani, and John A. Joule. "Synthesis of novel spiro‐fused pyrazolo[4′,3′:5,6]pyrido[2,3‐ d ]pyrimidines." Journal of Heterocyclic Chemistry 57, no. 10 (August 6, 2020): 3673–84. http://dx.doi.org/10.1002/jhet.4087.

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Tichý, Michal, Sabina Smoleń, Tomáš Deingruber, Petr Džubák, Radek Pohl, Lenka Poštová Slavětínská, Marián Hajdúch, and Michal Hocek. "Thienopyrrolo[2, 3-d ]pyrimidines, New Tricyclic Nucleobase Analogues: Synthesis and Biological Activities." ChemistrySelect 3, no. 31 (August 22, 2018): 9144–49. http://dx.doi.org/10.1002/slct.201802190.

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ARTYOMOV, V. A., L. A. RODINOVSKAYA, A. M. SHESTOPALOV, and V. P. LITVINOV. "ChemInform Abstract: Synthesis of 2,4-Diaminopyrido(3′,2′:4,5)thieno(3,2-d)pyrimidines." ChemInform 25, no. 34 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199434174.

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