Highly Efficient Aluminum Trichloride Catalyzed Michael Addition of Indoles and Pyrroles to Maleimides

Yu-Long An; Zhi-Yu Shao; Jian Cheng; Sheng-Yin Zhao

doi:10.1055/s-0033-1339515

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(19): 2719-2726
DOI: 10.1055/s-0033-1339515

paper

Highly Efficient Aluminum Trichloride Catalyzed Michael Addition of Indoles and Pyrroles to Maleimides

Yu-Long An

Department of Chemistry, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China Fax: +86(21)67792608-805 eMail: syzhao8@dhu.edu.cn

,

Zhi-Yu Shao

Department of Chemistry, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China Fax: +86(21)67792608-805 eMail: syzhao8@dhu.edu.cn

,

Jian Cheng

Department of Chemistry, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China Fax: +86(21)67792608-805 eMail: syzhao8@dhu.edu.cn

,

Sheng-Yin Zhao*

Department of Chemistry, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China Fax: +86(21)67792608-805 eMail: syzhao8@dhu.edu.cn

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Abstract

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Abstract

A highly efficient synthetic strategy for Michael addition of indoles and pyrroles to maleimides has been developed using the Lewis acids zinc chloride or aluminum trichloride as the catalyst. The reactions generated 3-substituted indoles and 2-substituted pyrroles in high yields with excellent regioselectivity in the presence of a catalytic amount of zinc chloride or aluminum trichloride under mild reaction conditions. The method is simple, efficient, and practical.

Key words

Michael addition - indole - pyrrole - maleimide - aluminum trichloride

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