Metal-Free Synthesis of Pyrrolo[1,2-a]quinoxalines Mediated by TEMPO Oxoammonium Salts

Heng-rui Huo; Xiang-Ying Tang; Yue-fa Gong

doi:10.1055/s-0037-1610131

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(14): 2727-2740
DOI: 10.1055/s-0037-1610131

paper

Metal-Free Synthesis of Pyrrolo[1,2-a]quinoxalines Mediated by TEMPO Oxoammonium Salts

Heng-rui Huo

School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, P. R. of China eMail: gongyf@mail.hust.edu.cn eMail: xytang@hust.edu.cn

,

Xiang-Ying Tang*

School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, P. R. of China eMail: gongyf@mail.hust.edu.cn eMail: xytang@hust.edu.cn

,

Yue-fa Gong *

School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, P. R. of China eMail: gongyf@mail.hust.edu.cn eMail: xytang@hust.edu.cn

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Abstract

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Abstract

We herein describe a novel TEMPO oxoammonium salt initiated Pictet–Spengler reaction of imines, generated in situ from carbonyl compounds and pyrrole- or indole-containing substrates, to afford 4,5-dihydropyrrolo[1,2-a]quinoxalines or 5,6-dihydroindolo[1,2-a]quinoxalines in good to excellent yields. Moreover, a one-pot synthesis of a biologically important quinoxaline is achieved via a cyclization–dehydrogenation process using one equivalent of the oxoammonium salt.

Key words

TEMPO oxoammonium salts - Pictet–Spengler reaction - imines - dihydroquinoxalines - quinoxalines

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