L-proline-catalyzed synthesis of highly functionalized multisubstituted 1,4-dihydropyridines.
Highly functionalized multisubstituted 1,4-dihydropyridines 5 have been concisely synthesized in moderate to good yields via L-proline-catalyzed one-pot multicomponent reactions (MCRs) of alkynoates or alkynones 1, amines 2, beta-dicarbonyl compounds 3 and aldehydes 4 under mild conditions. The MCR process involves hydroamination/Knoevenagel condensation/Michael-type addition/intramolecular cyclization processes and leads to the formation of 1,4-dihydropyridines 5. The molecular structure of 5ckaa was confirmed by single-crystal X-ray diffraction. This method is energy saving and environmentally friendly, providing easy access to diverse multisubstituted polyfunctional 1,4-dihydropyridines.
Jiang
Huanfeng
H
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P.R. of China. jianghf@scut.edu.cn
Mai
Ronghuan
R
Cao
Hua
H
Zhu
Qiuhua
Q
Liu
Xiaohang
X
D002384:Catalysis; D018360:Crystallography, X-Ray; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
D004095:Dihydropyridines; C038806:1,4-dihydropyridine; D011392:Proline