S. Pekcan, H. Heimgartner
Nov 2, 1988
Citations
0
Influential Citations
26
Citations
Journal
Helvetica Chimica Acta
Abstract
N-(1,3-Thiazol-5(4H)-ylidene)amines via 1,3-Dipolar Cycloaddition of Azides and 1,3-Thiazol-5(4H)-thiones Organic azides 5 and 4,4-dimethyl-2-phenyl-1,3-thiazol-5(4H)-thione (2) in toluene at 90° react to give the corresponding N-(1,3-thiazol-5(4H)-ylidene)amines (= 1,3-thiazol-5(4H)-imines) 6 in good yield (Table). A reaction mechanism for the formation of these scarcely investigated thiazole derivatives is formulated in Scheme 3: 1,3-Dipolar azide cycloaddition onto the CS group of 2 leads to the 1:1 adduct C. Successive elimination of N2 and S yields 6, probably via an intermediate thiaziridine E.