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N ‐(1,3‐Thiazol‐5(4 H )‐yliden)amine aus 1,3‐dipolaren Cycloadditionen von Aziden mit 1,3‐Thiazol‐5(4 H )‐thionen
Author(s) -
Pekcan Sare,
Heimgartner Heinz
Publication year - 1988
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.19880710713
Subject(s) - chemistry , thiazole , cycloaddition , medicinal chemistry , adduct , yield (engineering) , amine gas treating , toluene , azide , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
N ‐(1,3‐Thiazol‐5(4 H )‐ylidene)amines via 1,3‐Dipolar Cycloaddition of Azides and 1,3‐Thiazol‐5(4 H )‐thiones Organic azides 5 and 4,4‐dimethyl‐2‐phenyl‐1,3‐thiazol‐5(4 H )‐thione ( 2 ) in toluene at 90° react to give the corresponding N ‐(1,3‐thiazol‐5(4 H )‐ylidene)amines (= 1,3‐thiazol‐5(4 H )‐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 N 2 and S yields 6 , probably via an intermediate thiaziridine E .