The Hantzsch synthesis has been used for the preparation of the 1,4-Dihydropyridines compounds with different pharmacophore groups. The use of a designed glycosylated compound in Hantzsch synthesis would lead to a novel Dihydropyridines C-Glycosylated compound. We used the 6-methoxy-2, 2-dimethyltetrahydrofuro [3, 4-d] [1, 3] dioxole-4-carbaldehyde as a glycosylated-based aldehydes. The 4-(3,4-Dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxy-lic acid 3-ethyl ester 5-methyl ester was synthesized. The structure of compounds was determined by NMR spectroscopy, FTIR and mass spectroscopy methods. We synthesized this 1,4-Dihydropyridines compound by ionic liquid under ultrasound irradiation as a green chemistry synthesis.
References
[1]
Sridharan, V., Perumal, P.T., Avendano, C. and Menendez, J.C. (2007) A New Three-Component Domino Synthesis of 1,4-Dihydropyridines. Tetrahedron, 63, 4407-4413. https://doi.org/10.1016/j.tet.2007.03.092
[2]
Kumar, A. and Maurya, R.A. (2003) Organocatalysed Three-Component Domino Synthesis of 1,4-Dihydropyridines under Solvent Free Conditions. Tetrahedron, 64, 3477-3482. https://doi.org/10.1016/j.tet.2008.02.022
[3]
Tewari, N., Dwivedi, N. and Tripathi, R.P. (2004) Tetrabutylammonium Hydrogen Sulfate Catalyzed Eco-Friendly and Efficient Synthesis of Glycosyl 1,4-Dihydropyridines. Tetrahedron Letters, 45, 9011-9014. https://doi.org/10.1016/j.tetlet.2004.10.057
[4]
Sabitha, G., Kumar Reddy, G.S.K., Reddy, Ch.S. and Yadav, J.S. (2003) A Novel TMSI-Mediated Synthesis of Hantzsch 1,4-Dihydropyridines at Ambient Temperature. Tetrahedron Letters, 44, 4129-4131.
https://doi.org/10.1016/S0040-4039(03)00813-X
[5]
Moreau, J., Duboc, A., Hubert, C., Hurvois, J.P. and Renaud, J.L. (2007) Metal-Free Brønsted Acids Catalyzed Synthesis of Functional 1,4-Dihydropyridines. Tetrahedron Letters, 48, 8647-8650. https://doi.org/10.1016/j.tetlet.2007.10.040
[6]
Barton, D.H.R., Gero, S.D., Quiclet-Sire, B. and Samadi, M. (1994) Stereocontrolled Radical Reactions in Carbohydrate and Nucleoside Chemistry. Tetrahedron Asymmetry, 5, 2123-2136. https://doi.org/10.1016/S0957-4166(00)86288-6
[7]
Dondoni, A., Massi, A. and Minghini, E. (2002) Dihydropyridine C-Glycoconjugates by Hantzsch Cyclocondensation. Synthesis of a C(6)-Glycosylated Nifedipine Analogue. Helvetica Chimia Acta, 85, 3331-3348.
https://doi.org/10.1002/1522-2675(200210)85:10<3331::AID-HLCA3331>3.0.CO;2-X
[8]
Dondoni, A. and Massi, A. (2003) Decoration of Dihydropyrimidine and Dihydropyridine Scaffolds with Sugars via Biginelli and Hantzsch Multicomponent Reactions: An Efficient Entry to a Collection of Artificial Nucleosides. Molecular Diversity, 6, 261-270. https://doi.org/10.1023/B:MODI.0000006806.91483.a3
[9]
Dondoni, A., Massi, A., Sabbatini, S. and Bertolasi, V. (2002) Three-Component Biginelli Cyclocondensation Reaction Using C-Glycosylated Substrates. Preparation of a Collection of Dihydropyrimidinone Glycoconjugates and the Synthesis of C-Glycosylated Monastrol Analogues. Journal of Organic Chemistry, 67, 6979-6994.
https://doi.org/10.1021/jo0202076
[10]
Datar, P.A. and Auti, P.B. (2016) Design and Synthesis of Novel 4-Substituted 1,4-Dihydropyridine Derivatives as Hypotensive Agents. Journal of Saudi Chemical Society, 20, 510-516. https://doi.org/10.1016/j.jscs.2012.08.003
[11]
Wang, S.X., Li, Z.Y., Zhang, J.C. and Li, J.T. (2008) The Solvent-Free Synthesis of 1,4-Dihydropyridines under Ultrasound Irradiation without Catalyst. Ultrasonic Sonochemistry, 15, 677-680. https://doi.org/10.1016/j.ultsonch.2008.02.009
[12]
Sridhar, R. and Perumal, P.T. (2005) 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 Tetrahedron, 61, 2465-2470.
[13]
Legeay, J.C., Eynde, J.J.V. and Bazureau, J.P. (2005) Ionic Liquid Phase Technology Supported the Three Component Synthesis of Hantzsch 1,4-Dihydropyridines and Biginelli 3,4-Dihydropyrimidin-2(1H)-ones under Microwave Dielectric Heating. Tetrahedron, 61, 12386-12397. https://doi.org/10.1016/j.tet.2005.09.118
[14]
Kumar, J.A., Shridhar, G., Ladage, S. and Ravishankard, L. (2016) Synthesis of 1,4-Dihydropyridine Esters Using Low-Melting Sugar Mixtures as Green Solvents. Synthethic Commnucation, 9, 438.