One-pot construction of 3,3′-bisindolylmethanes through Bartoli indole synthesis

Takumi Abe; Shuuhei Nakamura; Reiko Yanada; Tominari Choshi; Satoshi Hibino; Minoru Ishikura

doi:10.1021/ol401486s

One-pot construction of 3,3′-bisindolylmethanes through Bartoli indole synthesis

Takumi Abe, Shuuhei Nakamura, Reiko Yanada, Tominari Choshi, Satoshi Hibino, Minoru Ishikura

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

70 Citations (Scopus)

Abstract

A one-pot approach to 3,3′-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3′-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH ₄Cl.

Original language	English
Pages (from-to)	3622-3625
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	14
DOIs	https://doi.org/10.1021/ol401486s
Publication status	Published - Jul 19 2013
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A one-pot approach to 3,3′-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3′-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH 4Cl.",

author = "Takumi Abe and Shuuhei Nakamura and Reiko Yanada and Tominari Choshi and Satoshi Hibino and Minoru Ishikura",

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T1 - One-pot construction of 3,3′-bisindolylmethanes through Bartoli indole synthesis

AU - Abe, Takumi

AU - Nakamura, Shuuhei

AU - Yanada, Reiko

AU - Choshi, Tominari

AU - Hibino, Satoshi

AU - Ishikura, Minoru

PY - 2013/7/19

Y1 - 2013/7/19

N2 - A one-pot approach to 3,3′-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3′-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH 4Cl.

AB - A one-pot approach to 3,3′-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3′-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH 4Cl.

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One-pot construction of 3,3′-bisindolylmethanes through Bartoli indole synthesis

Abstract

ASJC Scopus subject areas

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