Synthesis of oxazolidinones through ring-opening and annulation of vinylene carbonate with 2-pyrrolyl/indolylanilines under Rh(III) catalysis

Fang-Peng Hu; Xue-Guo Zhang; Meng Wang; He-Song Wang; Guo-Sheng Huang

doi:10.1039/d1cc05059a

Synthesis of oxazolidinones through ring-opening and annulation of vinylene carbonate with 2-pyrrolyl/indolylanilines under Rh(III) catalysis

Chem Commun (Camb). 2021 Nov 11;57(90):11980-11983. doi: 10.1039/d1cc05059a.

Authors

Fang-Peng Hu¹, Xue-Guo Zhang², Meng Wang¹, He-Song Wang¹, Guo-Sheng Huang¹

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, Department of Chemistry, Lanzhou University, Lanzhou 730000, China. hgs@lzu.edu.cn.
² Department of Materials Science and Engineering, Liaocheng University, Liaocheng 252059, P. R. China.

PMID: 34709263
DOI: 10.1039/d1cc05059a

Abstract

Herein, we have developed a rhodium-catalyzed C-H functionalization and subsequent intramolecular ring-opening/cyclization of vinylene carbonate with 2-pyrrolyl/indolylanilines, which leads to oxazolidinones in moderate to good yields. In this transformation, vinylene carbonate only eliminates one oxygen atom rather than -CO₃ or CO₂. Furthermore, some control experiments are conducted to elucidate the reaction mechanism.