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Additionsreaktion von 1,3‐Thiazol‐5(4 H )‐thionen und inaminen; Bildung von Thioamiden und Thioketonen
Author(s) -
Jenny Christjohannes,
Heimgartner Heinz
Publication year - 1986
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.19860690121
Subject(s) - chemistry , thiazole , medicinal chemistry , ring (chemistry) , toluene , cycloaddition , stereochemistry , organic chemistry , catalysis
Addition Reaction of 1,3‐Thiazole‐5(4 H )‐thiones and Ynamines; Formation of Thioamides and Thioketones Ynamines and 1,3‐thiazole‐5(4 H )‐thiones of type 1 undergo an addition reaction on heating in toluene yielding mainly α,β‐unsaturated 2‐(4,5‐dihydro‐1,3‐thiazol‐5‐yliden)thioamides of type 7 ( Scheme 2 and Table ). In some cases, 1‐diethylamino‐1‐(4,5‐dihydro‐1,3‐thiazol‐5‐yliden)‐2‐alkanethiones 8 have been isolated as minor products. In analogy to other reactions of ynamines with CO and CS bonds, a [2 + 2] cycloaddition to thiete intermediates, followed by an electrocyclic ring opening is suggested as reaction mechanism.