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铜催化氮杂环稠合苯并咪唑和1,2,4-苯并噻二嗪1,1-二氧化物衍生物的多米诺合成

Copper-catalyzed domino synthesis of nitrogen heterocycle-fused benzoimidazole and 1,2,4-benzothiadiazine 1,1-dioxide derivatives.

作者信息

Yang Daoshan, An Baojuan, Wei Wei, Tian Laijin, Huang Ben, Wang Hua

机构信息

The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University , Qufu 273165, Shandong China.

出版信息

ACS Comb Sci. 2015 Feb 9;17(2):113-9. doi: 10.1021/co500125n. Epub 2015 Jan 16.

DOI:10.1021/co500125n
PMID:25549532
Abstract

A convenient copper-catalyzed domino method for the synthesis of nitrogen heterocycle-fused benzoimidazole and 1,2,4-benzothiadiazine 1,1-dioxides has been developed using readily available 2-bromo-N-phenylbenzenesulfonamides and benzimidazole derivatives as the starting materials. The domino process comprises an Ullmann-type N-arylation and intramolecular C-H amination. The inexpensive and efficient copper-catalyzed method should provide a new and useful strategy for for constructing novel, biologically interesting heterocycles containing benzoimidazole and 1,2,4-benzothiadiazine 1,1-dioxide motifs.

摘要

已开发出一种便捷的铜催化多米诺方法,以易于获得的2-溴-N-苯基苯磺酰胺和苯并咪唑衍生物为起始原料,用于合成氮杂环稠合的苯并咪唑和1,2,4-苯并噻二嗪1,1-二氧化物。该多米诺过程包括乌尔曼型N-芳基化和分子内C-H胺化。这种廉价且高效的铜催化方法应为构建含有苯并咪唑和1,2,4-苯并噻二嗪1,1-二氧化物基序的新型、具有生物学意义的杂环提供一种新的有用策略。

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