Nazarov cyclization of 1, 4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1, 4′-quinoline]s. Issue 13 (15th January 2016)

• Record Type: Journal Article
• Authors: Wang, Zhiming; Xu, Xingzhu; Gu, Zhanshou; Feng, Wei; Qian, Houjun; Li, Zhengyi; Sun, Xiaoqiang; Kwon, Ohyun
• Is Part Of: Chemical communications. Volume 52:Issue 13(2016)
• Page Start: 2811
• Page End: 2814
• Publication Date: 2016-01-15
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c5cc08596a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The first Lewis acid-catalyzed intramolecular interrupted Nazarov cyclization of 1, 4-pentadien-3-ols is described. 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.