Nazarov Cyclization of 1,4-pentadien-3-ols: Preparation of Cyclopenta[b]indoles and Spiro[indene-1,4'-quinoline]s

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2016 Jan 16

PMID 26771024

Citations 2

Authors

Zhiming Wang

Xingzhu Xu

Zhanshou Gu

Wei Feng

Houjun Qian

Zhengyi Li

Xiaoqiang Sun

Ohyun Kwon

Affiliations

Soon will be listed here.

Abstract

The first Lewis acid-catalyzed intramolecular interrupted Nazarov cyclization of 1,4-pentadien-3-ols is described. Using FeBr3 as the catalyst, a series of new substituted cyclopenta[b]indoles was prepared-through a sequence of Nazarov cyclization, nucleophilic amination, and isomerization-with good yields and high diastereo- and regioselectivities. A similar catalytic process was also developed for the synthesis of structurally interesting spiro[indene-1,4'-quinoline]s.

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