1,4 - 戊二烯 - 3 - 醇的纳扎罗夫环化反应：环戊并[b]吲哚和螺[茚 - 1,4'-喹啉]的制备
Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4'-quinoline]s.
作者信息
Wang Zhiming, Xu Xingzhu, Gu Zhanshou, Feng Wei, Qian Houjun, Li Zhengyi, Sun Xiaoqiang, Kwon Ohyun
机构信息
Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.
Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569, USA.
出版信息
Chem Commun (Camb). 2016 Feb 14;52(13):2811-4. doi: 10.1039/c5cc08596a.
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.
摘要
首次描述了1,4-戊二烯-3-醇的首例路易斯酸催化的分子内间断纳扎罗夫环化反应。以FeBr₃为催化剂，通过纳扎罗夫环化、亲核胺化和异构化序列，制备了一系列新的取代环戊并[b]吲哚，产率良好，具有高非对映选择性和区域选择性。还开发了一种类似的催化过程用于合成结构有趣的螺[茚-1,4'-喹啉]。
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