A Green Aerobic Oxidative Synthesis of Pyrrolo[1,2-a]quinoxalines from Simple Alcohols without Metals and Additives

被引：44

作者：

Li, Jixing ^{[1
,2
]}

Zhang, Jinlong ^{[1
]}

Yang, Huameng ^{[1
]}

Gao, Zeng ^{[1
,2
]}

Jiang, Gaoxi ^{[1
]}

机构：

[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 01期

关键词：

ONE-POT SYNTHESIS; IN-VITRO; BIOLOGICAL EVALUATION; POTENTIAL INHIBITORS; EFFICIENT SYNTHESIS; DERIVATIVES; IDENTIFICATION;

D O I：

10.1021/acs.joc.6b02501

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical and concise protocol for the efficient preparation of pyrrolo[1,2-a]quinoxalines through a cascade of alcohol oxidation/imine formation/intramolecular cyclization/oxidative dehydrogenation has been established. A series of substituted pyrrolo[1,2-a]quinoxaline derivatives were constructed readily in yields of 53-93% from the cheap primary alcohols by using dioxygen as the terminal oxidant. Remarkably, the fact that no extra metals and additives were necessary makes this unprecedented aerobic oxidation process highly step- and atom-economical. The usefulness of this transformation was further demonstrated with the gram-scale synthesis of compound 3aa under standard conditions.

引用

页码：765 / 769

页数：5

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