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Synthesis of 2‐substituted‐5‐rnethylthiazolo[ 3,2‐b ] ‐1,2,4‐lriazoles and acylatcd 3‐amino‐2‐imino‐4‐methyl‐2‐thiazolines
Author(s) -
Pilgram Kurt,
Pollard G. E.
Publication year - 1976
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.5570130615
Subject(s) - chemistry , thiazoline , ethyl formate , ring (chemistry) , carbon disulfide , cyanogen bromide , bromide , medicinal chemistry , trifluoroacetic acid , acetic acid , benzoic acid , organic chemistry , biochemistry , peptide sequence , gene
3‐Amino‐2‐imino‐4‐mcthyl‐2‐thiazoline, 1, underwent ring closure with ethyl formate, cyanogen bromide and carbon disulfide, giving moderate yields of 2‐substituted‐5‐methylthiazolo[ 3,2‐b ]‐1,2,4‐triazoles, II. Reaction of I‐HCl with acid anhydrides (acetic, propionie, trifluoroacetic) resulted in the formation of the corresponding II compounds, whereas other anhydrides (benzoic, perfluoropropionic, perfluorobutyric) gave high yields of 3‐aeylamido‐2‐acylimido‐4‐melhyl‐2‐thiazolines. With acid chlorides and I‐HCl, in the presence of trielhylamine, mixtures of 2‐acyl‐irnino‐3‐aniino‐4‐methyl‐2‐thiazolines and 2‐aeylimino‐3‐(diacylamido)‐4‐methyl‐2‐thiazolines are formed. Spectral characteristics are reported.