Mohammadikia Parvin, Ramezanpour Sorour, Shiri Pezhman, Dehaen Wim, Achten Linde
Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran 19697, Iran.
Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Leuven 3000, Belgium.
ACS Omega. 2024 Jan 17;9(4):4466-4473. doi: 10.1021/acsomega.3c06264. eCollection 2024 Jan 30.
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'-spiro[[1,3]dioxane-5,6'-quinoline]-2',4,6(5')-trione derivatives.
在本研究中，展示了一系列苯甲醛、苄胺和丙二酸亚异丙酯的均相酸催化反应，可实现具有高立体选择性的新型六氢喹啉一锅多组分合成。当前策略具有区域选择性高、效率良好、多样性合理、使用廉价安全的催化剂以及通过简单重结晶易于纯化产物等优点。当前反应使用2当量的丙二酸亚异丙酯、3当量的苯甲醛衍生物和1当量的胺衍生物，以生成(4'S,5'S,7'S)-1'-苄基-2,2-二甲基-4',5',7'-三苯基-3',4',7',8'-四氢-1'-螺[[1,3]二氧六环-5,6'-喹啉]-2',4,6(5')-三酮衍生物。
