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

被引：32

作者：

Abe, Takumi ^{[1
]}

Shimizu, Haruka ^{[1
]}

Takada, Shiori ^{[1
]}

Tanaka, Takahiro ^{[1
]}

Yoshikawa, Mai ^{[1
]}

Yamada, Koji ^{[1
]}

机构：

[1] Hlth Sci Univ Hokkaido, Fac Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 06期

关键词：

SPONGE KIRKPATRICKIA-VARIALOSA; INDOLE ALKALOIDS; VARIOLIN-B; DERIVATIVES; CASCADE; HINCKDENTINE; ACTIVATION; INHIBITOR; CHEMISTRY; REAGENTS;

D O I：

10.1021/acs.orglett.8b00332

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel cascade reaction of indole-2,3-epoxide equivalents with gamma-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.

引用

页码：1589 / 1592

页数：4

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