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Divergent Synthesis of Functionalized Quinolines from Aniline and Two Distinct Amino Acids

Jia-Chen Xiang, Zi-Xuan Wang, Yan Cheng, Shi-Qing Xia, Miao Wang, Bo-Cheng Tang, Yan-Dong Wu and An-Xin Wu*

*Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Hubei, Wuhan 430079, P. R. China, Email: chwuaxmail.ccnu.edu.cn

J.-C. Xiang, Z.-X. Wang, Y. Cheng, S.-Q. Xia, M. Wang, B.-C. Tang, Y.-D. Wu, A.-X. Wu, J. Org. Chem., 2017, 82, 9210-9216.

DOI: 10.1021/acs.joc.7b01501 (free Supporting Information)



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Abstract

A practicable quinoline synthesis from aniline and two amino acids provides a wide range of quinolines with high efficiency and diversity including pharmaceutical derivatives, photochemical active compounds, and challenging scaffolds. Mechanistic studies revealed that I2 promotes decarboxylation, oxidative deamination, and selective formation of new C-N and C-C bonds.

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proposed mechanism



Key Words

quinolines, multicomponent reactions, iodine, DMSO


ID: J42-Y2017