PIFA-Mediated oxidative cyclization of 1-aroyl-N-arylcyclopropane-1-carboxamides and their application in the synthesis of pyrrolo[3,2-c]quinolinones

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出版日 2016-12-13

DOI 10.1039/C6QO00598E

インパクトファクター 5.281

著者

Xiaolong Gao, Zhonglian Li, Guisheng Zhang, Nana Ma, Qingfeng Liu, Tongxin Liu

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要旨

An efficient ring-closing reaction was developed for the synthesis of spirocyclopropane quinolinediones from 2,2-disubstituted 2-benzoylacetamides in the presence of [bis-(trifluoroacetoxy)iodo]benzene (PIFA). This reaction proceeds at room temperature in the absence of a metal catalyst to provide spirocyclopropane quinolinediones in good to excellent yields. Furthermore, these compounds were readily converted to the corresponding pyrrolo[3,2-c]quinolinones to provide tricyclic ring structures similar to those found in the natural products martinellic acid and martinelline via an intermolecular amine ring-opening cyclization reaction.

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Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

PIFA-Mediated oxidative cyclization of 1-aroyl-N-arylcyclopropane-1-carboxamides and their application in the synthesis of pyrrolo[3,2-c]quinolinones

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