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Synthesis and Reactions of Some Novel Triazolo‐, Azolo‐, Tetrazolo‐Pyridopyrimidine and Their Nucleoside Derivatives
Author(s) -
AbuZied Kh. M.,
ElGazzar A. B. A.,
Hassan N. A.
Publication year - 2008
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200800031
Subject(s) - chemistry , pyrimidine , formic acid , acetic anhydride , nucleoside , acetic acid , pyridine , nitrous acid , medicinal chemistry , organic chemistry , stereochemistry , catalysis
Pyridopyrimidine reacted with aromatic aldehydes afforded the arylhydrazone 2a,b which could be cyclized into the pyrido[2,3‐ d ][1,2,4]triazolo[4,3‐ a ]pyrimidine 3a,b , with formic acid, and carbon disulphide to give pyrido[2,3‐ d ][1,2,4]traizolo[4,3‐ a ]pyrimidine 4, 5. Reaction of 1 with nitrous acid afforded tetrazolo[1,5‐ a ]pyrido[2,3‐ d ]pyrimidine 6 , which was reduced by zinc dust to give 2‐amino‐pyrido‐[2,3‐ d ]pyrimidine 7. Finally the reaction of 2‐hydrazino 1 with D‐xylose or D‐glucose afforded the acyclic N‐nucleoside 8, 11 which were converted into tetra/penta O ‐acetate acyclic C ‐nucleoside 9, 12 in acetic anhydride/pyridine. De‐acetylation of compounds 9, 12 afforded C ‐nucleosides 10, 13.