A Highly Efficient Strategy for One-Pot and Pseudo-Six-Component Synthesis of Hexahydroquinolines

Parvin Mohammadikia; Sorour Ramezanpour; Pezhman Shiri; Wim Dehaen; Linde Achten

doi:10.1021/acsomega.3c06264

A Highly Efficient Strategy for One-Pot and Pseudo-Six-Component Synthesis of Hexahydroquinolines

ACS Omega. 2024 Jan 17;9(4):4466-4473. doi: 10.1021/acsomega.3c06264. eCollection 2024 Jan 30.

Authors

Parvin Mohammadikia¹, Sorour Ramezanpour¹, Pezhman Shiri¹, Wim Dehaen², Linde Achten²

Affiliations

¹ Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran 19697, Iran.
² Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Leuven 3000, Belgium.

Abstract

In this study, a homogeneous acid-catalyzed reaction of a series of benzaldehydes, benzylamines, and Meldrum's acid was presented, allowing the novel one-pot and multicomponent synthesis of hexahydroquinolines with high stereoselectivity. The current strategy has advantages including high regioselectivity, good efficiency, reasonable diversity, utilization of an inexpensive and safe catalyst, and easy purification of products by simple recrystallization. The current reaction utilizes 2 equiv of Meldrum's acid, 3 equiv of benzaldehyde derivatives, and one equiv of amine derivatives to yield (4'S,5'S,7'S)-1'-benzyl-2,2-dimethyl-4',5',7'-triphenyl-3',4',7',8'-tetrahydro-1'H-spiro[[1,3]dioxane-5,6'-quinoline]-2',4,6(5'H)-trione derivatives.