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The Synthesis of 3,5‐Diamino‐1,2,4‐oxadiazoles. 1st Communication
Author(s) -
Tilley Jefferson W.,
Ramuz Henri
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630411
Subject(s) - chemistry , guanidine , amino acid , hydroxylamine , nucleophile , hydroxylamine hydrochloride , medicinal chemistry , stereochemistry , organic chemistry , catalysis , biochemistry
Reaction of the 1‐substituted‐3‐cyano‐isothioureas 6 with hydroxylamine gave mixtures of the 5‐amino‐3‐substituted‐amino‐1,2,4‐oxadiazoles 1 and the isomeric 3‐amino‐5‐substituted‐amino‐1,2,4‐oxadiazoles 8 in which 1 usually predominated. The structural assignment of these products is discussed. In a second method, the 2‐hydroxy‐1‐methyl‐1‐phenyl‐guanidine 15 was converted to the corresponding 3‐disubstituted‐amino‐5‐trichloromethyl‐1,2,4‐oxadiazole 16 , a precursor to the 5‐amino derivatives 17 by nucleophilic displacement of the trichloromethyl group.