Iodine-mediated oxythiolation of o-vinylanilides with disulfides for the synthesis of benzoxazines.

Yu Yang,Zhiyong Wang,Liyan Liu,Kuiliang Li,Qi Sun,Zhenggen Zha

doi:10.1039/d2ra01078j

Abstract

An efficient iodine-mediated oxythiolation of o-vinylanilides with disulfides was developed. By virtue of this method, a series of thio-tethered benzoxazine derivatives were synthesized in good to excellent yields. The reaction features high yields, is metal-free, and has a wide substrate scope.

Highlights

An efficient iodine-mediated oxythiolation of o-vinylanilides with disulfides was developed
Benzo [d][1,3]oxazine, an essential heterocyclic skeleton which is widely found in natural products and biological active molecule,[6–10] could be synthesized by the intramolecular cyclization of N-(2-(1-phenylvinyl)phenyl)-benzamides (Scheme 1).[11–23]
In the 1980s, Capozzi and co-workers synthesized methylthiobenzo[d][1,3]oxazine with this strategy for the rst time, using Me3S3SbCl6 as the methylthiolating agent (Scheme 1a).[19]. This was the only way to generate this kind of compound for the three decades

Summary

Introduction

An efficient iodine-mediated oxythiolation of o-vinylanilides with disulfides was developed. Yu Yang,‡ab Liyan Liu,‡b Kuiliang Li,b Zhenggen Zha, and Zhiyong Wang *b b Qi Sun*b In view of the importance of sulfur-containing compounds,[24–31] it is still highly desirable to develop a simple and efficient method to build thio-tethered compounds with good reaction compatibility under mild conditions.

Results

Conclusion