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Tetrazoles from N ‐(4‐dimethylaminophenyl)nitrones and hydrogen azide
Author(s) -
Moderhack Dietrich
Publication year - 1977
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.5570140509
Subject(s) - chemistry , nitrone , azide , derivative (finance) , hydrogen , medicinal chemistry , polar effect , cycloaddition , organic chemistry , catalysis , financial economics , economics
The reaction of N ‐(4‐dimethylaminophenyl)nitrones, 1 , with hydrogen azide proceeds via three distinct pathways to give a mixture of two tetrazoles, 5 and 9 , and a 2‐azido‐4‐dimethyl‐aminoaniline derivative, 6 . The proportions largely depend on the electron‐withdrawing force resident in the function R attached to nitrone carbon. The formation of 5 constitutes a new synthetic approach to 1,5‐disubstituted tetrazoles.