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An unexpected aminolysis in the synthesis of 5‐substituted 3‐(1 H ‐tetrazol‐5‐yl)pyrazolo[1, 5‐ a ]quinazolines
Author(s) -
Peet Norton P.
Publication year - 1989
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.5570260335
Subject(s) - chemistry , hydrazoic acid , sodium azide , tetrazole , aminolysis , ammonia , medicinal chemistry , organic chemistry , catalysis
A synthetic route to 5‐substituted 3‐(1 H ‐tetrazol‐5‐yl)pyrazolo[1, 5‐ a ]quinazolines is described. An unexpected displacement of a 4‐morpholinyl group from the 5‐position of this system occurred during tetrazole formation by the ammonia produced by in situ generation of hydrazoic acid from ammonium chloride and sodium azide.