Aniline assisted dimerization of phenylalanines: convenient synthesis of 2-aroyl-3-arylquinoline in an I2-DMSO system

Jin-Tian Ma; Ting Chen; Xiang-Long Chen; You Zhou; Zhi-Cheng Yu; Shi-Yi Zhuang; Yan-Dong Wu; Jia-Chen Xiang; An-Xin Wu

doi:10.1039/D2OB02283D

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Aniline assisted dimerization of phenylalanines: convenient synthesis of 2-aroyl-3-arylquinoline in an I₂-DMSO system†

Jin-Tian Ma,^a Ting Chen,^a Xiang-Long Chen,^a You Zhou,^a Zhi-Cheng Yu,^a Shi-Yi Zhuang,^a Yan-Dong Wu,^a Jia-Chen Xiang

*^b and An-Xin Wu

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China
E-mail: chwuax@mail.ccnu.edu.cn

^b School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China
E-mail: xiangjiachen@seu.edu.cn

Abstract

We herein report an efficient synthesis of 2-aroyl-3-arylquinolines from phenylalanines and anilines. The mechanism involves I₂-mediated Strecker degradation enabled catabolism and reconstruction of amino acids and a cascade aniline-assisted annulation. Both DMSO and water act as oxygen sources in this convenient protocol.

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Article information

DOI: https://doi.org/10.1039/D2OB02283D
Article type: Communication
Submitted: 19 Dec 2022
Accepted: 14 Feb 2023
First published: 15 Feb 2023

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Org. Biomol. Chem., 2023,21, 2091-2095

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Aniline assisted dimerization of phenylalanines: convenient synthesis of 2-aroyl-3-arylquinoline in an I₂-DMSO system

J. Ma, T. Chen, X. Chen, Y. Zhou, Z. Yu, S. Zhuang, Y. Wu, J. Xiang and A. Wu, Org. Biomol. Chem., 2023, 21, 2091 DOI: 10.1039/D2OB02283D

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Organic & Biomolecular Chemistry