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Synthesis and Addition Reactions of 1,3‐Thiazole‐5(4 H )‐thione Oxides
Author(s) -
Shi Junxing,
Tromm Peter,
Heimgartner Heinz
Publication year - 1994
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.19940770806
Subject(s) - chemistry , thiazole , reagent , medicinal chemistry , organolithium compounds , grignard reagent , organic chemistry , ion , deprotonation
1,3‐Thiazole‐5(4 H )‐thione oxides 2 were prepared by oxidation of the corresponding 1,3‐thiazole‐5(4 H )‐thiones 1 with m ‐chloroperbenzoic acid ( Table 1 ). Addition reactions of 2 with organolithium and Grignard reagents yielded 4,5‐dihydro‐4,4‐dimethyl‐1,3‐thiazol‐5‐yl methyl sulfoxides of type 4 via thiophilic attack ( Table 2 ). Whereas the reaction with the organolithium compounds proceeded with fair‐to‐excellent yields, the Grignard reagents reacted only very sluggishly. The sulfoxides 4 could also be prepared via oxidation of 4,5‐dihydro‐4,4‐dimethyl‐5‐(methylthio)‐1,3‐thiazoles of type 3 with m ‐chloroperbenzoic acid, together with the corresponding sulfones 5 ( Scheme 1 ).