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A reinvestigation of the cyclodesulfurization of thiosemicarbazides
Author(s) -
Sunder Shyam,
Peet Norton P.,
Barbuch Robert J.
Publication year - 1981
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.5570180823
Subject(s) - chemistry , sequence (biology) , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , biochemistry
A recent report describing the preparation of 2‐(substituted‐amino)‐3,4‐dihydro‐5 H ‐1,3,4‐benzotriazepin‐5‐ones (3), by the cyclodesulfurization of hydrazides prepared from o‐aminobenzoylhydrazine ( 1 ) and isothiocyanates, is erroneus. The products resulting from this reaction sequence are, instead, 2‐(substituted‐amino)‐5‐( o ‐aminophenyl)‐1,3,4‐oxadiazoles ( 4 ). Alternate syntheses of the oxadiazoles led to the correct structural assignments.