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The synthetic utility of heteroaromatic azido compounds. Part VI. Preparation of some 1 H ‐1,2,3‐triazolo[1,5‐ a ]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.5570170826
Subject(s) - chemistry , methylene , decarboxylation , acetal , intramolecular force , derivative (finance) , intramolecular reaction , condensation , ethyl cyanoacetate , medicinal chemistry , bicyclic molecule , stereochemistry , combinatorial chemistry , organic chemistry , malononitrile , catalysis , physics , financial economics , economics , thermodynamics
Some 1,2,3‐triazolo[1,5‐ a ]thieno[3,2‐ d ]pyrimidines have been prepared by the reaction of active methylene nitriles with 3‐azido‐2‐substituted thiophenes. Thus, for example the 3‐carboxy derivative 5 was prepared by condensation of 3‐azido‐2‐formylthiophene dimethyl acetal ( 1 ) with ethyl cyanoacetate, followed by intramolecular cyclization. Decarboxylation of 5 led to the unsubstituted parent compound 6 . The structure of the triazole‐fused compounds is discussed.