Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4'-quinoline]s

Chemical Communications : Chem Comm
Zhiming WangOhyun Kwon

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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Citations

Apr 27, 2017·Organic & Biomolecular Chemistry·Yuyang ZhaoZhiming Wang
Jun 10, 2017·Chemistry : a European Journal·Luisa LempenauerGilles Lemière
Mar 3, 2018·Angewandte Chemie·Julia KaufmannEdgar Haak
Sep 30, 2017·Organic & Biomolecular Chemistry·Maxim G VinogradovSergei G Zlotin
Mar 29, 2019·Angewandte Chemie·Bo XuFayang G Qiu
Sep 4, 2020·The Journal of Organic Chemistry·Nicolai A AksenovMichael Rubin

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