Synthesis of benzo[b][1,4]thiazepines by the reaction of 3‐aryl‐1‐(3‐coumarinyl)propen‐1‐ones with 2‐aminothiophenol

Abstract

3‐(2‐Aryl‐2,3‐dihydro‐benzo[b][1,4]thiazepin‐4‐yl)chromen‐2‐ones (2a, e, f) and (Z)‐3‐(2,3‐dihydro‐2‐arylbenzo[b][1,4]thiazepin‐4(5H)‐ylidene)chroman‐2‐ones (3a‐f) have been synthesized by the reaction of 3‐aryl‐1‐(3‐coumarinyl)propen‐1‐ones (1a‐f) with 2‐aminothiophenol in a hot mixture of toluene and acetic acid. Structures of all new compounds and their complete 1H and 13C assignments were achieved applying different one‐ and two‐dimensional nmr experiments in combination with various spectroscopic techniques.

Friedel-Crafts chemistry. Part 50. Convergent and diversity-oriented constructions of polycyclic quinolines via Friedel-Crafts and Beckmann ring enlargement approaches

“…16 A search for the applied methods for synthesis of medium-sized N,S-heterocyclic systems demonstrated that several established protocols are in practice, and comprehensive reviews of the syntheses and biological activities of various benzo-condensed 1,3-, 1,4-, 1,5-thiazepine and thiazocine regioisomers have been published. [17][18][19][20][21][22][23] Formation of thiazonines and higher ring systems, however, remains unknown. Most of the reported strategies for the synthesis of 1,4-thiazocine and higher ring frameworks are presented in a few select publications.…”