Functionalization of Ethyl 6-Amino-4-(4-chlorophenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate: Facile Synthesis of a New Series of Pyrano[2,3-d]pyrimidine Derivatives

Herein, synthesis of a new series of pyrano[2,3- d ]pyrimidine scaffolds is presented. Ethyl 6-amino-4-(4-chlorophenyl)-5-cyano-2-methyl-4 H -pyran-3-carboxylate has been reacted with formamide, formic acid, urea, thiourea, semicarbazide, and thiosemicarbazide to give six new pyrano[2,3- d ]pyrimidi...

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Bibliographic Details
Published in:Russian journal of general chemistry 2021-07, Vol.91 (7), p.1403-1408
Main Authors: El-Sayed, H. A., Said, S. A., El-Hamid, A. Abd, Mohamed, A. S. A., Amr, A. E., Morsy, H. A.
Format: Article
Language:English
Subjects:
Acylation
Aniline
Carbon disulfide
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Formic acid
Medical laboratories
Morpholine
Organic acids
Piperidine
Pyrimidines
Substitution reactions
Synthesis
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Summary:Herein, synthesis of a new series of pyrano[2,3- d ]pyrimidine scaffolds is presented. Ethyl 6-amino-4-(4-chlorophenyl)-5-cyano-2-methyl-4 H -pyran-3-carboxylate has been reacted with formamide, formic acid, urea, thiourea, semicarbazide, and thiosemicarbazide to give six new pyrano[2,3- d ]pyrimidine derivatives in moderate to high yields (48–78%). Acylation and intramolecular cyclization of pyran with carbon disulfide, ethyl cyanoacetate, acetic anhydride, or chloroacetyl chloride has resulted in formation of the corresponding desired bicyclic pyrimidine derivatives. The chloromethyl derivative was subjected to nucleophilic substitution by its reaction with morpholine, piperidine or aniline resulting in the corresponding 2-substituted pyrimidine derivatives in good yields.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363221070203