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: fqiangliu
qq.com, ccguohnu.edu.cn
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
Abstract
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.
see article for more examples
proposed mechanism
Key Words
quinolines, oxygen, multicomponent reactions
ID: J42-Y2021
