A chemo- and regioselective C6-functionalization of 2,3-disubstituted indoles: highly efficient synthesis of diarylindol-6-ylmethanes

文献情報

出版日 2019-03-12

DOI 10.1039/C9OB00283A

インパクトファクター 3.876

著者

Qiong Wu, Gui-Lin Li, Shuang Yang, Xiao-Qin Shi, Tian-Zi Huang, Xi-Hua Du, Yan Chen

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要旨

An organocatalytic chemo- and regioselective C6-functionalization of 2,3-disubstituted indoles has been established via a reaction with ortho-hydroxybenzyl alcohols, which afforded biologically important diarylindol-6-ylmethanes in overall high yields (up to 99% yield). This protocol not only provides an efficient method for constructing biologically important diarylindol-6-ylmethane frameworks in an atom economical fashion, but also serves as a good example for the direct catalytic C6-functionalization of indoles, which have been rarely investigated. More importantly, the preliminary biological evaluation revealed that this new class of diarylindol-6-ylmethanes exhibited strong cytotoxicity to HeLa cell lines.

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.

A chemo- and regioselective C6-functionalization of 2,3-disubstituted indoles: highly efficient synthesis of diarylindol-6-ylmethanes

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