Synthesis of Fused Carbazoles by Gold-Catalyzed Tricyclization of Conjugated Diynes via Rearrangement of an N-Propargyl Group

被引：41

作者：

Taguchi, Masamitsu ^{[1
]}

Tokimizu, Yusuke ^{[1
]}

Oishi, Shinya ^{[1
]}

Fujii, Nobutaka ^{[1
]}

Ohno, Hiroaki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

基金：

日本学术振兴会;

关键词：

CLAISEN-TYPE REARRANGEMENT; C-N; CASCADE CYCLIZATION; DOMINO REACTION; ALKYNES; INDOLES; ETHERS; CYCLOISOMERIZATION; HETEROCYCLES; DERIVATIVES;

D O I：

10.1021/acs.orglett.5b03254

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various N-propargylanilines bearing a conjugated diyne moiety at the 2-position were converted to tetracyclic fused carbazoles by treatment with a homogeneous gold(I) catalyst. This cascade reaction proceeds through indole formation with concomitant rearrangement of the N-propargyl group, intramolecular nucleophilic addition toward the resulting allene moiety, and subsequent hydroalkenylation. This transformation enables a one-pot synthesis of fused carbazoles from readily accessible substrates with 100% atom economy.

引用

页码：6250 / 6253

页数：4

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