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Cyanation and sulfonylation of 5‐substituted tetrazoles. imidoyl azides
Author(s) -
Subba Rao O.,
Lwowski Walter
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.5570170136
Subject(s) - chemistry , cyanation , tetrazole , ring (chemistry) , cyanogen bromide , bromide , medicinal chemistry , azide , acylation , hydrazine (antidepressant) , nitrile , combinatorial chemistry , organic chemistry , catalysis , biochemistry , chromatography , peptide sequence , gene
Reaction of 5‐methoxy‐ and 5‐ethoxytetrazole with methanesulfonyl chloride and cyanogen bromide was found to occur in the 1‐position of the tetrazole. This is in marked contrast to other acylations of 5‐substituted tetrazoles, where high yields of the 2‐acyl derivatives are reported for dozens of examples and a variety of acylating agents. The 1‐methanesulfonyl‐ and 1‐cyano‐5‐alkoxytetrazoles ring‐open spontaneously to the corresponding imidoyl azides, which are conveniently prepared by this method.