Simple and New Protocol for the Synthesis of Novel (z)-3-Arylidenebenzothiazepin-4-ones Using Baylis–Hillman Derivatives

Abstract

A simple synthesis of novel (Z)-3-arylidene-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-ones from bromo compounds derived from Baylis–Hillman adducts involving selective S-alkylation followed by a lactum formation has been described.

Keywords:

• 2-Amino thiophenol
• Baylis–Hillman reaction
• benzothiazepinones
• diltiazem
• thiazesim
• p-toluenesulfonic acid

ACKNOWLEDGMENTS

We thank Department of Science & Technology (New Delhi) for the financial support under the fast track scheme. We thank Department of Science & Technology-Fund for Improvement of Science & Technology Infrastructure in Higher Educational Institutions for the funding program at the Department of Organic Chemistry, University of Madras, Chennai.

Notes

^a All the products gave satisfactory IR, ¹H NMR (300 MHz), ¹³C NMR (75 MHz), and mass spectral data and elemental analyses.

^b Yields of the pure product (6a–k) obtained after column chromatography.