Synthesis 2018; 50(02): 377-383
DOI: 10.1055/s-0036-1590933
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of 2-Arylbenzoxazinones from 2-Arylindoles with (Diacetoxyiodo)benzene as the Sole Oxidant

Xian-Xing Shang
School of Chemical and Biological Engineering, University of Science and Technology Beijing, 30 Xueyuan Road, Haidian District, Beijing 100083, P. R. of China   Email: lixuqin@ustb.edu.cn
,
Huu-Manh Vu
School of Chemical and Biological Engineering, University of Science and Technology Beijing, 30 Xueyuan Road, Haidian District, Beijing 100083, P. R. of China   Email: lixuqin@ustb.edu.cn
,
Xu-Qin Li*
School of Chemical and Biological Engineering, University of Science and Technology Beijing, 30 Xueyuan Road, Haidian District, Beijing 100083, P. R. of China   Email: lixuqin@ustb.edu.cn
› Author Affiliations
This work was supported by grants from the National Standardization Project of Traditional Chinese Medicine (No. ZYBZH-Y-JX-27) and Fundamental Research Funds for the Central Universities (No. FRF-BR-14-002A).
Further Information

Publication History

Received: 12 July 2017

Accepted after revision: 15 September 2017

Publication Date:
19 October 2017 (online)

Abstract

A series of synthetically interesting 2-arylbenzoxazinones was prepared from 2-arylindoles by an efficient oxidative reaction mediated by (diacetoxyiodo)benzene [PhI(OAc)2] and assisted by water. PhI(OAc)2 was used as the sole oxidant and water was a crucial additive. Our preliminary mechanistic investigations suggest that a water-involved, iodine(III)-promoted sequential oxidation of 2-arylindoles, which was terminated by an interesting Grob-type fragmentation of a fused tricyclic precursor, might be the main components of this one-pot transformation.

Supporting Information

 
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