Enamine Catalytic Annulation of Azonaphthalenes: An Access to Indole Derivatives

Hanhui Zhao; Huijun Yuan; Yanru Zhang; Rongshi Li; Wenjun Li

doi:10.1021/acs.orglett.9b02507

Enamine Catalytic Annulation of Azonaphthalenes: An Access to Indole Derivatives

Hanhui Zhao, Huijun Yuan, Yanru Zhang, Rongshi Li, Wenjun Li

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

13 Scopus citations

Abstract

The secondary-amine mediated [3 + 2] annulation of azonaphthalenes with aldehydes and ketones is described for the first time, which provides an alternative protocol for the synthesis of indole derivatives. It features a cheap and readily available catalyst, a broad scope of reactants, very mild reaction conditions, and high efficiency. Significantly different from the transition-metal-mediated processes, the enamine activation represents the first organic base-catalytic protocol for indole synthesis.

Original language	English (US)
Pages (from-to)	6557-6561
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.9b02507
State	Published - Aug 16 2019
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Enamine Catalytic Annulation of Azonaphthalenes: An Access to Indole Derivatives",

abstract = "The secondary-amine mediated [3 + 2] annulation of azonaphthalenes with aldehydes and ketones is described for the first time, which provides an alternative protocol for the synthesis of indole derivatives. It features a cheap and readily available catalyst, a broad scope of reactants, very mild reaction conditions, and high efficiency. Significantly different from the transition-metal-mediated processes, the enamine activation represents the first organic base-catalytic protocol for indole synthesis.",

author = "Hanhui Zhao and Huijun Yuan and Yanru Zhang and Rongshi Li and Wenjun Li",

note = "Funding Information: The authors acknowledge the financial support from National Natural Science Foundation of China (21502043), the Special Funds of the Taishan Scholar Program of Shandong Province (tsqn201812047), and the Natural Science Foundation of Shandong Province (ZR2017JL011).",

year = "2019",

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doi = "10.1021/acs.orglett.9b02507",

language = "English (US)",

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T1 - Enamine Catalytic Annulation of Azonaphthalenes

T2 - An Access to Indole Derivatives

AU - Zhao, Hanhui

AU - Yuan, Huijun

AU - Zhang, Yanru

AU - Li, Rongshi

AU - Li, Wenjun

N1 - Funding Information: The authors acknowledge the financial support from National Natural Science Foundation of China (21502043), the Special Funds of the Taishan Scholar Program of Shandong Province (tsqn201812047), and the Natural Science Foundation of Shandong Province (ZR2017JL011).

PY - 2019/8/16

Y1 - 2019/8/16

N2 - The secondary-amine mediated [3 + 2] annulation of azonaphthalenes with aldehydes and ketones is described for the first time, which provides an alternative protocol for the synthesis of indole derivatives. It features a cheap and readily available catalyst, a broad scope of reactants, very mild reaction conditions, and high efficiency. Significantly different from the transition-metal-mediated processes, the enamine activation represents the first organic base-catalytic protocol for indole synthesis.

AB - The secondary-amine mediated [3 + 2] annulation of azonaphthalenes with aldehydes and ketones is described for the first time, which provides an alternative protocol for the synthesis of indole derivatives. It features a cheap and readily available catalyst, a broad scope of reactants, very mild reaction conditions, and high efficiency. Significantly different from the transition-metal-mediated processes, the enamine activation represents the first organic base-catalytic protocol for indole synthesis.

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Enamine Catalytic Annulation of Azonaphthalenes: An Access to Indole Derivatives

Abstract

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