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DOI: 10.1055/s-0028-1087891
Multicomponent Synthesis of Benzothiazepinones
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
Publication History
Publication Date:
23 March 2009 (online)
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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.