Convenient synthesis of 2-substituted indoles from 2-ethynylanilines with tetrabutylammonium fluoride

Akito Yasuhara; Yuichi Kanamori; Masashi Kancko; Atsushi Numata; Yoshinori Kondo; Takao Sakamoto

doi:10.1039/a808842j

Convenient synthesis of 2-substituted indoles from 2-ethynylanilines with tetrabutylammonium fluoride

Akito Yasuhara, Yuichi Kanamori, Masashi Kancko, Atsushi Numata, Yoshinori Kondo, Takao Sakamoto

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

127 Citations (Scopus)

Abstract

The cyclization reaction of various 2-ethynylanilines, which were easily synthesized from 2-haloanilines by the palladium-catalyzed reaction with terminal alkynes, with tetrabutylammonium fluoride (TBAF) to yield 2-substituted indoles proceeded at refluxing or room temperature in THF in excellent yields without affecting the bromo, chloro, cyano, ethoxycarbonyl, and ethynyl groups.

Original language	English
Pages (from-to)	529-534
Number of pages	6
Journal	Journal of the Chemical Society - Perkin Transactions 1
Issue number	4
DOIs	https://doi.org/10.1039/a808842j
Publication status	Published - 1999

ASJC Scopus subject areas

Chemistry(all)

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abstract = "The cyclization reaction of various 2-ethynylanilines, which were easily synthesized from 2-haloanilines by the palladium-catalyzed reaction with terminal alkynes, with tetrabutylammonium fluoride (TBAF) to yield 2-substituted indoles proceeded at refluxing or room temperature in THF in excellent yields without affecting the bromo, chloro, cyano, ethoxycarbonyl, and ethynyl groups.",

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T1 - Convenient synthesis of 2-substituted indoles from 2-ethynylanilines with tetrabutylammonium fluoride

AU - Yasuhara, Akito

AU - Kanamori, Yuichi

AU - Kancko, Masashi

AU - Numata, Atsushi

AU - Kondo, Yoshinori

AU - Sakamoto, Takao

PY - 1999

Y1 - 1999

N2 - The cyclization reaction of various 2-ethynylanilines, which were easily synthesized from 2-haloanilines by the palladium-catalyzed reaction with terminal alkynes, with tetrabutylammonium fluoride (TBAF) to yield 2-substituted indoles proceeded at refluxing or room temperature in THF in excellent yields without affecting the bromo, chloro, cyano, ethoxycarbonyl, and ethynyl groups.

AB - The cyclization reaction of various 2-ethynylanilines, which were easily synthesized from 2-haloanilines by the palladium-catalyzed reaction with terminal alkynes, with tetrabutylammonium fluoride (TBAF) to yield 2-substituted indoles proceeded at refluxing or room temperature in THF in excellent yields without affecting the bromo, chloro, cyano, ethoxycarbonyl, and ethynyl groups.

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Convenient synthesis of 2-substituted indoles from 2-ethynylanilines with tetrabutylammonium fluoride

Abstract

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