AlCl3-PROMOTED CYCLIZATION OF β-KETO DERIVATIVES WITH IN SITU GENERATED ENAMINES UNDER SOLVENT-FREE HIGH SPEED BALL MILLING: AN EFFICIENT ONE-POT ACCESS TO POLYSUBSTITUTED 1,4-DIHYDROPYRIDINES

被引:3
作者
Zeng, Ji-Chao [1 ]
Yu, Fei [1 ]
Asiri, Abdullah M. [2 ]
Marwani, Hadi M. [2 ]
Zhang, Ze [1 ]
机构
[1] Anhui Polytech Univ, Sch Biol & Chem Engn, Wuhu 241000, Peoples R China
[2] King Abdulaziz Univ, Fac Sci, Chem Dept, Jeddah 21589, Saudi Arabia
关键词
1,4-Dihydropyridine; High Speed Ball Milling (HSBM); Solvent-Free Reaction; Cyclization Reaction; Enamine; SUBSTITUTED 1,4-DIHYDROPYRIDINES; POLYHYDROQUINOLINE DERIVATIVES; 1,3-DICARBONYL COMPOUNDS; 3-COMPONENT CYCLIZATION; ORGANIC-SYNTHESIS; DIHYDROPYRIDINES; CHEMISTRY; ALDEHYDES; ACID; TETRAHYDROPYRIDINES;
D O I
10.3987/COM-17-13801
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under high speed ball milling (HSBM), a simple method for efficient synthesis of structurally diverse polysubstituted 1,4-dihydropyridines is developed via AlCl3-promoted Robinson-like cyclization of beta-keto derivatives with in situ generated enamines. This one-pot protocol exhibits the advantages of high chemoselectivity, short reaction time, good functional group tolerance, mild reaction condition and easy work-up.
引用
收藏
页码:2054 / 2064
页数:11
相关论文
共 40 条
[31]   A new protocol to synthesize 1,4-dihydropyridines by using 3,4,5-trifluorobenzeneboronic acid as a catalyst in ionic liquid:: synthesis of novel 4-(3-carboxyl-1H-pyrazol-4-yl)-1,4-dihydropyridines [J].
Sridhar, R ;
Perumal, PT .
TETRAHEDRON, 2005, 61 (09) :2465-2470
[32]   Ball milling in organic synthesis: solutions and challenges [J].
Stolle, Achim ;
Szuppa, Tony ;
Leonhardt, Silke E. S. ;
Ondruschka, Bernd .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2317-2329
[33]   Selective Synthesis of Fused 1,4-and 1,2-Dihydropyridines by Domino Reactions of Arylamines, Acetylenedicarboxylate, Aldehydes, and Cyclic 1,3-Diketones [J].
Sun, Jing ;
Sun, Yan ;
Gao, Hong ;
Yan, Chao-Guo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (34) :6952-6956
[34]   Synthesis of 3,4-Dihydropyridin-2(1H)-ones and 3,4-Dihydro-2H-pyrans via Four-Component Reactions of Aromatic Aldehydes, Cyclic 1,3-Carbonyls, Arylamines, and Dimethyl Acetylenedicarboxylate [J].
Sun, Jing ;
Xia, Er-Yan ;
Wu, Qun ;
Yan, Chao-Guo .
ACS COMBINATORIAL SCIENCE, 2011, 13 (04) :421-426
[35]   Recent advances in new multicomponent synthesis of structurally diversified 1,4-dihydropyridines [J].
Wan, Jie-Ping ;
Liu, Yunyun .
RSC ADVANCES, 2012, 2 (26) :9763-9777
[36]   Mechanochemical organic synthesis [J].
Wang, Guan-Wu .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (18) :7668-7700
[37]   Facile Yb(OTf)3 promoted one-pot synthesis of polyhydroquinoline derivatives through Hantzsch reaction [J].
Wang, LM ;
Sheng, J ;
Zhang, L ;
Han, JW ;
Fan, ZY ;
Tian, H ;
Qian, CT .
TETRAHEDRON, 2005, 61 (06) :1539-1543
[38]   Progress in coenzyme NADH model compounds and asymmetric reduction of benzoylformate [J].
Wang, Nai-Xing ;
Zhao, Jia .
SYNLETT, 2007, (18) :2785-2791
[39]   AlCl3-catalyzed [3+3] cycloaddition of chalcones and β-enamine ketones (esters): a highly efficient access to multisubstituted cyclohexa-1,3-dienamines [J].
Xing, Meng-Ming ;
Xu, Hui ;
Hou, Li-Fen ;
Gao, Jian-Rong ;
Li, Yu-Jin .
RSC ADVANCES, 2016, 6 (13) :10943-10948
[40]   Efficient and clean aldol condensation catalyzed by sodium carbonate in water [J].
Zhang, Z ;
Dong, YW ;
Wang, GW .
CHEMISTRY LETTERS, 2003, 32 (10) :966-967