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The synthetic utility of heteroaromatic azido compounds. Part VII. Preparation of some 2‐ and 4‐substituted thieno[3,2‐ d ]pyrimidines
Author(s) -
Westerlund Christer
Publication year - 1980
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.5570170827
Subject(s) - chemistry , bromine , nucleophile , bond cleavage , medicinal chemistry , nitrogen , alkaline hydrolysis , stereochemistry , combinatorial chemistry , organic chemistry , hydrolysis , catalysis
Abstract Synthetically useful scission reactions of some 1 H ‐1,2,3‐triazolo[1,5‐ a ]thieno[3,2‐ d ]pyrimidines have been studied. The net result of these reactions is an elimination of nitrogen, and a 1,1‐addition of the cleaving agent, forming 2‐substituted thieno[3,2‐ d ]pyrimidines. The mechanism of the scission is discussed, and a concomitant nucleophilic attack and expulsion of nitrogen is proposed. An unusual reaction between the unsubstituted triazole‐fused parent compound ( 1 ) and bromine in alkaline medium is also reported.