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路易斯酸催化2-吲哚甲醇与炔丙醇的(3+2)环化反应以合成环戊并[ ]吲哚

Lewis-Acid-Catalyzed (3+2) Annulation of 2-Indolylmethanols with Propargylic Alcohols to Access Cyclopenta[]indoles.

作者信息

Wu Teng-Fei, Fu Zhao-Jie, Zhang Yi-Rui, Qiu Zong-Wang, Li Bao Qiong, Chen Shao-Shuai, Pan Han-Peng, Ma Ai-Jun, Zhang Xiang-Zhi

机构信息

Guangdong Provincial Key Laboratory of Large Animal Models for Biomedicine, School of Pharmacy and Food Engineering, Wuyi University, Jiangmen 529020, China.

出版信息

Molecules. 2024 Mar 12;29(6):1251. doi: 10.3390/molecules29061251.

Abstract

Herein, a Sc(OTf)-catalyzed (3+2) annulation of 2-indolylmethanols with propargylic alcohols is reported. The reaction proceeds via a Friedel-Crafts-type allenylation/5-exo-annulation cascade. In the reaction, 2-indolylmethanol is used as a three-carbon synthon, and propargyl alcohol is used as a two-carbon synthon. This method provides a direct and high-yield pathway for synthetically useful cyclopenta[]indoles. In general, the method features easily accessible substrates with broad scope and generality, the formation of multiple bonds with high efficiency, and easy scale-up.

摘要

本文报道了一种由三氟甲磺酸钪催化的2-吲哚甲醇与炔丙醇的(3+2)环化反应。该反应通过傅克型烯丙基化/5-外环化串联反应进行。在反应中,2-吲哚甲醇用作三碳合成子,炔丙醇用作二碳合成子。该方法为合成有用的环戊[ ]吲哚提供了一条直接且高产率的途径。一般来说,该方法的特点是底物易于获得,适用范围广且具有通用性,能高效形成多个化学键,并且易于放大规模。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9304/10974089/f0155459e5c8/molecules-29-01251-g001.jpg

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