Synthesis of azocino[5,4-b]indoles via gold-catalyzed intramolecular alkyne hydroarylation

Vsevolod A. Peshkov; Olga P. Pereshivko; Erik V.Van Der Eycken

doi:10.1002/adsc.201200305

Synthesis of azocino[5,4-b]indoles via gold-catalyzed intramolecular alkyne hydroarylation

Vsevolod A. Peshkov, Olga P. Pereshivko, Erik V.Van Der Eycken

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

63 Citations (Scopus)

Abstract

An efficient procedure for the synthesis of the azocinoACHTUNGTRENUNG[5,4- b]indole framework is presented, relying on a cationic gold-catalyzed intramolecular alkyne hydroarylation of propargylic amides derived from various tryptamines and 3-substituted 2- propynoic acids. The triphenylphosphinegold(I) chloride/silver(I) triflate catalytic system was found to be superior to our previously described mercury( II) triflate catalyst, and hence the substrate scope of the process was significantly expanded.

Original language	English
Pages (from-to)	2841-2848
Number of pages	8
Journal	Advanced Synthesis and Catalysis
Volume	354
Issue number	14-15
DOIs	https://doi.org/10.1002/adsc.201200305
Publication status	Published - Oct 8 2012
Externally published	Yes

Keywords

C-C coupling
Cyclization
Gold catalysis
Medium-ring compounds
Nitrogen heterocycles

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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title = "Synthesis of azocino[5,4-b]indoles via gold-catalyzed intramolecular alkyne hydroarylation",

abstract = "An efficient procedure for the synthesis of the azocinoACHTUNGTRENUNG[5,4- b]indole framework is presented, relying on a cationic gold-catalyzed intramolecular alkyne hydroarylation of propargylic amides derived from various tryptamines and 3-substituted 2- propynoic acids. The triphenylphosphinegold(I) chloride/silver(I) triflate catalytic system was found to be superior to our previously described mercury( II) triflate catalyst, and hence the substrate scope of the process was significantly expanded.",

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AU - Peshkov, Vsevolod A.

AU - Pereshivko, Olga P.

AU - Der Eycken, Erik V.Van

PY - 2012/10/8

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AB - An efficient procedure for the synthesis of the azocinoACHTUNGTRENUNG[5,4- b]indole framework is presented, relying on a cationic gold-catalyzed intramolecular alkyne hydroarylation of propargylic amides derived from various tryptamines and 3-substituted 2- propynoic acids. The triphenylphosphinegold(I) chloride/silver(I) triflate catalytic system was found to be superior to our previously described mercury( II) triflate catalyst, and hence the substrate scope of the process was significantly expanded.

KW - C-C coupling

KW - Cyclization

KW - Gold catalysis

KW - Medium-ring compounds

KW - Nitrogen heterocycles

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