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Lewis Acids Catalyzed Annulations of Ynamides with Acyl Chlorides for Constructing 4-Amino-2-naphthol Derivatives and 3-Aminocyclobutenones

Cheng Peng, Jingyi Zhang, Jian Xue, Siqi Li, Xiao-Na Wang*, Junbiao Chang*

*School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, P. R. China, Email: wangxnzzu.edu.cn, changjunbiaozzu.edu.cn

C. Qian, K. Liu, S.-W. Tao, F.-L. Zhang, Y.-M. Zhu, S.-L. Yang, J. Org. Chem., 2018, 83, 9201-9209.

DOI: 10.1021/acs.joc.8b01255 (free Supporting Information)


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Abstract

A one-pot synthesis of 4-amino-2-naphthol derivatives is accomplished via a ZnI2-catalyzed tandem Friedel-Crafts reaction sequence. While in the presence of Pd(0) catalyst, a [2 + 2] cycloaddition reaction of ynamides with monosubstituted ketenes provides 3-aminocyclobutenones, which were subsequently converted to 3-amino-1-naphthols.

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Key Words

cyclobutenones


ID: J42-Y2018