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

Xian-Xing Shang; Huu-Manh Vu; Xu-Qin Li

doi:10.1055/s-0036-1590933

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(02): 377-383
DOI: 10.1055/s-0036-1590933

paper

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

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Abstract

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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.

Key words

benzoxazinones - hypervalent iodine - indoles - oxidation - water-assisted

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Referenzen

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