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通过自由基途径将喹啉和异喹啉引入叔酰胺的非活化α-C-H 键。

Introduction of Quinolines and Isoquinolines onto Nonactivated α-C-H Bond of Tertiary Amides through a Radical Pathway.

机构信息

Graduate School of Science and ‡Molecular Chirality Research Center, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.

出版信息

J Org Chem. 2017 Jan 6;82(1):170-178. doi: 10.1021/acs.joc.6b02303. Epub 2016 Dec 15.

DOI:10.1021/acs.joc.6b02303
PMID:27976909
Abstract

Treatment of quinolines and isoquinolines with benzoyl peroxide in tertiary amides, such as N,N-dimethylacetamide, N,N-dimethylpropionamide, and N-acetylpyrrolidine, etc., under irradiation with a Hg lamp in the temperature range of 35 °C to 40 °C gave C-C-bonded quinolines and isoquinolines bearing amide groups with high regioselectivity in good to moderate yields, respectively, under transition-metal-free conditions.

摘要

在 35°C 至 40°C 的温度范围内,用汞灯照射,在三酰胺(如 N,N-二甲基乙酰胺、N,N-二甲基丙酰胺和 N-乙酰基吡咯烷等)中用过氧化苯甲酰处理喹啉和异喹啉,可以在无过渡金属条件下,以良好至中等收率、高度区域选择性地得到 C-C 键合的带有酰胺基团的喹啉和异喹啉。

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