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

被引:0
作者
Mohammadikia, Parvin [2 ]
Ramezanpour, Sorour [2 ]
Shiri, Pezhman [2 ]
Dehaen, Wim [1 ]
Achten, Linde [1 ]
机构
[1] Katholieke Univ Leuven, Dept Chem, Mol Design & Synth, B-3000 Leuven, Belgium
[2] KN Toosi Univ Technol, Dept Chem, Tehran 19697, Iran
来源
ACS OMEGA | 2024年 / 9卷 / 04期
关键词
DERIVATIVES; ACID;
D O I
10.1021/acsomega.3c06264
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:4466 / 4473
页数:8
相关论文
共 42 条
[1]   One-Pot Multicomponent Coupling Reaction of Catechols, Benzyl Alcohols/Benzyl Methyl Ethers, and Ammonium Acetate toward Synthesis of Benzoxazoles [J].
Aboonajmi, Jasem ;
Panahi, Farhad ;
Sharghi, Hashem .
ACS OMEGA, 2021, 6 (34) :22395-22399
[2]   Materials Functionalization with Multicomponent Reactions: State of the Art [J].
Afshari, Ronak ;
Shaabani, Ahmad .
ACS COMBINATORIAL SCIENCE, 2018, 20 (09) :499-528
[3]   Facile synthesis of indole heterocyclic compounds based micellar nano anti-cancer drugs [J].
Ali, Imran ;
Mukhtar, Sofi Danish ;
Hsieh, Ming Fa ;
Alothman, Zeid A. ;
Alwarthan, Abdulrahman .
RSC ADVANCES, 2018, 8 (66) :37905-37914
[4]   Efficient one pot and chemoselective synthesis of functionalized 3-bromo-4,5-dihydroisoxazole derivatives &ITvia &IT1,3-dipolar cycloaddition reactions of nitrile oxides [J].
Alizadeh, Abdolali ;
Roosta, Atefeh ;
Rezaiyehrad, Reza ;
Halvagar, Mohammadreza .
TETRAHEDRON, 2017, 73 (48) :6706-6711
[5]   The application of isatin-based multicomponent-reactions in the quest for new bioactive and druglike molecules [J].
Brandao, Pedro ;
Marques, Carolina ;
Burke, Anthony J. ;
Pineiro, Marta .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2021, 211
[6]   The Pummerer reaction: Methodology and strategy for the synthesis of heterocyclic compounds [J].
Bur, SK ;
Padwa, A .
CHEMICAL REVIEWS, 2004, 104 (05) :2401-2432
[7]   Michael addition approach for the synthesis of novel spiro compounds and 2-substituted malonic acid derivatives from Meldrum's acid [J].
Chande, MS ;
Khanwelkar, RR .
TETRAHEDRON LETTERS, 2005, 46 (45) :7787-7792
[8]   A Multicomponent Protocol for the Synthesis of Highly Functionalized γ-Lactam Derivatives and Their Applications as Antiproliferative Agents [J].
del Corte, Xabier ;
Lopez-Frances, Adrian ;
Maestro, Aitor ;
Villate-Beitia, Ilia ;
Sainz-Ramos, Myriam ;
Martinez de Marigorta, Edorta ;
Pedraz, Jose Luis ;
Palacios, Francisco ;
Vicario, Javier .
PHARMACEUTICALS, 2021, 14 (08)
[9]   Cu/base co-catalyzed [3+3] cycloaddition for the synthesis of highly functionalized 4-fluoropyridines [J].
Dong, Jinhuan ;
Feng, Wanzhong ;
Wang, Lei ;
Li, Mei ;
Chen, Zhe ;
Xu, Xianxiu .
CHEMICAL COMMUNICATIONS, 2021, 57 (94) :12635-12638
[10]   AgI-Catalyzed Reaction of Enol Diazoacetates and Imino Ethers: Synthesis of Highly Functionalized Pyrroles [J].
Dong, Kuiyong ;
Humeidi, Ahmad ;
Griffith, Wendell ;
Arman, Hadi ;
Xu, Xinfang ;
Doyle, Michael P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (24) :13394-13400