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Amino acids in the synthesis of heterocyclic compounds. Transformations of thiazolones into imidazole derivatives
Author(s) -
Copar Anton,
Stanovnik Branko,
Tisler Miha
Publication year - 1992
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.5570290128
Subject(s) - chemistry , acetic anhydride , sodium methoxide , imidazole , dichloromethane , methanol , hydrazide , methyl iodide , organic chemistry , acetic acid , hydrazine (antidepressant) , sodium iodide , ammonium thiocyanate , iodide , medicinal chemistry , hydrogen peroxide , catalysis , chromatography , solvent
Abstract 5(4 H )‐Thiazolone derivative 4 , obtained from N ‐dithiocarbobenzoxyglycine ( 1 ) and N,N ‐dimethyl‐ N ′‐heteroarylformamidines 3 in acetic anhydride, was rearranged with sodium methoxide in methanol followed by acidification with acetic acid into imidazole‐4‐carboxylic acid derivatives 5, 6 and 7 . These were further converted with methyl iodide into methylthio derivatives 8 , with hydrogen peroxide into the corresponding disulphide 9 , with hydrazine and amines into hydrazide 10 and amides 11 . In the reactions of 4a and 6a with amines in the presence of dichloromethane symetrically disubstituted methanes 14–18 were formed.