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Unexpected Annulation between 2-Aminobenzyl Alcohols and Benzaldehydes in the Presence of DMSO: Regioselective Synthesis of Substituted Quinolines

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

*College of Chemistry and Chemical Engineering, Advanced Catalytic Engineering Research Center, Hunan University, Changsha 410082, China, Email:,

T. Yang, Z.-w. Nie, M.-d. Su, H. Li, W.-p. Luo, Q. Liu, C.-C. Guo, J. Org. Chem., 2021, 86, 15232-15241.

DOI: 10.1021/acs.joc.1c01850


An annulation between 2-aminobenzyl alcohols, benzaldehydes, and DMSO provides quinolines. Interestingly, introducing substituent groups to the α-position of sulfoxides resulted in the interchange of the positions between benzaldehydes and sulfoxides in the product quinolines.

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proposed mechanism

Key Words

quinolines, oxygen, multicomponent reactions

ID: J42-Y2021