Double "open and Shut" Transformation of γ-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds

Takumi Abe; Haruka Shimizu; Shiori Takada; Takahiro Tanaka; Mai Yoshikawa; Koji Yamada

doi:10.1021/acs.orglett.8b00332

Double "open and Shut" Transformation of γ-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds

Takumi Abe, Haruka Shimizu, Shiori Takada, Takahiro Tanaka, Mai Yoshikawa, Koji Yamada

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

15 Citations (Scopus)

Abstract

A novel cascade reaction of indole-2,3-epoxide equivalents with γ-carbolines by utilizing a double "open and shut" transformation to access multiheterocyclic compounds containing both isotryptamines and pyrimido[1,6-a]indoles has been developed. This strategy utilizes the in situ formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Mannich/retro-Mannich/cyclization cascade sequences.

Original language	English
Pages (from-to)	1589-1592
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.8b00332
Publication status	Published - Mar 16 2018
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b00332

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abstract = "A novel cascade reaction of indole-2,3-epoxide equivalents with γ-carbolines by utilizing a double {"}open and shut{"} transformation to access multiheterocyclic compounds containing both isotryptamines and pyrimido[1,6-a]indoles has been developed. This strategy utilizes the in situ formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Mannich/retro-Mannich/cyclization cascade sequences.",

author = "Takumi Abe and Haruka Shimizu and Shiori Takada and Takahiro Tanaka and Mai Yoshikawa and Koji Yamada",

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AU - Abe, Takumi

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AU - Takada, Shiori

AU - Tanaka, Takahiro

AU - Yoshikawa, Mai

AU - Yamada, Koji

N1 - Funding Information: This work was financially supported by JSPS KAKENHI Grant No. 16K18849 (T.A.) through a Grant-in-Aid for Young Scientists (B). Publisher Copyright: © 2018 American Chemical Society.

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AB - A novel cascade reaction of indole-2,3-epoxide equivalents with γ-carbolines by utilizing a double "open and shut" transformation to access multiheterocyclic compounds containing both isotryptamines and pyrimido[1,6-a]indoles has been developed. This strategy utilizes the in situ formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Mannich/retro-Mannich/cyclization cascade sequences.

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Double "open and Shut" Transformation of γ-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds

Abstract

ASJC Scopus subject areas

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