A Pummerer Reaction-Enabled Modular Synthesis of Alkyl Quinoline-3-carboxylates and 3-Arylquinolines from Amino Acids

Jin-Tian Ma, Ting Chen, Bo-Cheng Tang, Xiang-Long Chen, Zhi-Cheng Yu, You Zhou, Shi-Yi Zhuang, Yan-Dong Wu, Jia-Chen Xiang* and An-Xin Wu*

*Southeast University, Nanjing 211189; Central China Normal University, Wuhan 430079, P. R. China, Email: xiangjiachenseu.edu.cn, chwuaxmail.ccnu.edu.cn

J.-T. Ma, T. Chen, B.-C. Tang, X.-L. Chen, Z.-C. Yu, Y. Zhou, S.-Y. Zhuang, Y.-D. Wu, J.-C. Xiang, , J. Org. Chem., 2023, 88, 3714-3723.

DOI: 10.1021/acs.joc.2c03034

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Abstract

An acidic I₂-DMSO system converts readily available aspartates/phenylalanines and anilines into alkyl quinoline-3-carboxylates/3-arylquinolines. While DMSO is activated by HI via a Pummerer reaction, I₂ mediates a Strecker degradation of the the amino acid. A formal [3 + 2 + 1] annulation of these two concurrently generated C1 and C2 synthons with aniline provides the quinoline core.

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proposed mechanism

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Key Words

quinolines, multicomponent reactions

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ID: J42-Y2023