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Synthesis of a pyrrolo annulated pyrido[2,3‐ D ]pyrimidine as a potential nonclassical antifolate
Author(s) -
Gangjee Aleem,
Patel Jasmin,
Lin FuTyan
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250563
Subject(s) - chemistry , tricyclic , pyrimidine , pyrrolidine , yield (engineering) , stereochemistry , lactam , ether , ring (chemistry) , antifolate , derivative (finance) , annulation , organic chemistry , catalysis , materials science , antimetabolite , toxicity , metallurgy , economics , financial economics
Cyclocondensation of 2,4,6‐triaminopyrimidine ( 4 ) with ethyl N ‐benzyl‐4‐oxo‐3‐pyrrolidine carboxylate ( 5 ) in diphenyl ether regiospecifically afforded a new tricyclic, angular 1,3,8‐trisubstituted pyrrolo[3′,4′:4,5]‐pyrido[2,3‐ d ]pyrimidine‐6‐one 1 in excellent yield. The ketoester 5 was prepared by a literature method. Compound 1 in addition to being a new heterocyclic system is an important key precursor to a variety of classical and nonclassical tricyclic, 5‐deaza analogues of the folate cofactor 5,10‐methylenetetrahydrofolate 3 .