Oxidative oxy-cyclization of 2-alkynylbenzamide enabled by TBAB/Oxone: switchable synthesis of isocoumarin-1-imines and isobenzofuran-1-imine

文献情報

出版日 2019-04-01

DOI 10.1039/C9OB00320G

インパクトファクター 3.876

著者

Guanyinsheng Qiu, Hongwei Zhou, Jin-Biao Liu

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要旨

A TBAB-catalyzed oxidative 6-endo-dig oxy-cyclization of 2-alkynylbenzamide is described herein for the synthesis of isocoumarin-1-imines. The transformation proceeds regioselectively and provides the final products with high efficiency and a broad reaction scope. Interestingly, an array of isobenzofuran-1-imines is also achieved under standard conditions when N-phenyl 2-trimethylsilylethynylbenzamides are used as substrates. Mechanism studies show that 3-bromomethenisobenzofuran-1-imine is a pivotal intermediate, which goes through C–O bond migration and debromination to offer the final isocoumarin-1-imines.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Oxidative oxy-cyclization of 2-alkynylbenzamide enabled by TBAB/Oxone: switchable synthesis of isocoumarin-1-imines and isobenzofuran-1-imine

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Organic & Biomolecular Chemistry

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