Synfacts 2009(4): 0376-0376  
DOI: 10.1055/s-0028-1087891
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Multicomponent Synthesis of Benzothiazepinones

Contributor(s): Victor Snieckus, Johnathan Board
S.-J. Tu*, X.-D. Cao, W.-J. Hao, X.-H. Zhang, S. Yan, S.-S. Wu, Z.-G. Han, F. Shi
Xuzhou Normal University, Jiangsu, P. R. of China
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Publikationsverlauf

Publikationsdatum:
23. März 2009 (online)

Significance

Reported is an efficient three-component synthesis of benzo[e][1,4]thiazepin-2-(1H,3H,5H)-ones in water under microwave irradiation. A plausible mechanism is proposed which involves initial electrophilic ortho-substitution by the aromatic aldehyde, followed by reaction with mercaptoacetic acid. Certain substrates (deactivated aldehydes bearing EWGs) generated thiazolidinone products; results which are rationalized by initial reaction of the aromatic aldehyde and the aniline to form an imine, which then undergoes ­reaction with mercaptoacetic acid. The formation of thiazolidinones was also achieved by the use of aprotic solvents. A detailed investigation to support the proposed mechanism would ensure the full utility of this work.