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[3+1+1+1] Annulation to the Pyridine Structure in Quinoline Molecules Based on DMSO as a Nonadjacent Dual-Methine Synthon: Simple Synthesis of 3-Arylquinolines from Arylaldehydes, Arylamines, and DMSO

Tonglin Yang, Hui Li, Zhiwen Nie, Miao-dong Su, Wei-ping Luo, Qiang Liu* and Can-Cheng Guo

*College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China, Email:,

T. Yang, H. Li, Z. Nie, M.-d. Su, W.-p. Luo, Q. Liu, C.-C. Guo, J. Org. Chem., 2022, 87, 2797-2808.

DOI: 10.1021/acs.joc.1c02708

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A [3+1+1+1] annulation of arylamines, arylaldehydes and dimethyl sulfoxide (DMSO) provides 3-arylquinolines in very good yields. In this annulation, arylamines provide two carbon atoms and one nitrogen atom, arylaldehydes furnish one carbon atom, and DMSO provides two nonadjacent methines (=CH-).

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proposed mechanism

Key Words

quinolines, potassium peroxydisulfate, multicomponent reactions

ID: J42-Y2022