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一锅法通过 CH2 挤出反应区域选择性合成喹喔啉。

One-Pot Regiospecific Synthesis of Quinoxalines via a CH2-Extrusion Reaction.

机构信息

Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences, Huaqiao University & Engineering Research Center of Molecular Medicine, Ministry of Education , Xiamen 361021, China.

出版信息

Org Lett. 2016 Mar 18;18(6):1378-81. doi: 10.1021/acs.orglett.6b00309. Epub 2016 Feb 29.

DOI:10.1021/acs.orglett.6b00309
PMID:26925522
Abstract

A convenient "one-pot" regiospecific synthesis of substituted quinoxalines from o-phenylenediamines and ynones under metal-free conditions has been developed. An intermolecular Michael addition reaction, a dehydration condensation, and a base-promoted C-α-CH2-extrusion were involved in this procedure, which features high regioselectivity, efficiency, and environmental friendliness. Various quinoxalines were provided in up to 95% yield for 33 examples.

摘要

一种方便的“一锅法”在无金属条件下，由邻苯二胺和炔酮合成取代喹喔啉的方法被开发出来。该方法涉及分子间的迈克尔加成反应、脱水缩合以及碱促进的 C-α-CH2 消除反应，具有高区域选择性、高效率和环境友好性。在 33 个实例中，各种喹喔啉的产率高达 95%。

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