Synthesis, Characterization and 1, 3-Dipolar Cycloaddition of Novel Sugar-Derived Nitrones with N-Arylmaleimides
Author Affiliations
- 1Department of Chemistry, Yuvaraja’s College, University of Mysore, Mysore, Karnataka, INDIA
- 2Department of Chemistry, College of health medical technology, Baghdad, IRAQ
- 3Department of Chemistry, College of Science and Education University of Aden, YEMEN
Res.J.chem.sci., Volume 4, Issue (3), Pages 60-67, March,18 (2014)
Abstract
The chiral N-D-ribosylnitrones 5-10 have been synthesized in four steps respectively, in the fourth step, D-ribosyloxime (4) condensed with substituted benzaldehyde in cool condition. The heterocyclization of Z- nitrone 6 with substituted N-arylmaleimide by 1,3-dipolar cycloaddition were afforded new heterocyclic system of isoxazolidine derivatives 11-16 and 11'-16' as a mixture of diastereoisomers, the new isoxazolidines 11-16 have been separated purely and characterized by H NMR, mass spectra and elemental analysis.
References
- Tufariello J., In 1,3- Dipolar Cycloaddition Chemistry, John Wiley & Sons: New York., 9 (1984)
- Colacino E., Nun P., Colacino F.M., Martinez J and Lamaty F., Solvent-free synthesis of nitrones in a ball-mill, Tetrahedron, 64, 5569–5576, (2008)
- Bloch R., Addition of organomatallic reagents to C=N bonds: reactivity and selectivity, Chem. Rev, 98, 1407–1438, (1998)
- Chunsheng C., Zhinian L., Jinyan S., Tao L. and Baoyan Z., Synthesis of isoxazolidines by 1,3-dipolar cycloaddition and their bioactivity, Front. Chem. China., 427433 (2006)
- Ross S.A., Gulve E.A and Wang M., Chemistry and biochemistry of type two diabetes, M. Chem. Rev, 104, 1255–1282 (2004)
- Torssell K.B.G., Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH: Weinheim, (1988)
- Frederickson M., optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkene: application inorganic synthesis, Tetrahedron, 53, 403-425 (1997)
- Aftab T., Grigg R., Ladlow M., Sridharan V and Thornton-Pet M., Novel synthesis of fused isoxazolidines via a palladium catalysed allene insertion-intramolecular 1,3- dipolar cycloaddition cascade reaction, Chem. Commun, 16, 1754 (2002)
- Revuelta J., Cicchi S., Goti A and Brandi A., Enantiopure Cyclic Nitrones: a Useful Class of Building Blocks for Asymmetric Syntheses, Synthesis, 485-504 (2007)
- Fu Y., Yuan Zhang H., Hua Liu Y., Feng X., Feng Huang D And Y. Lai Hu., Synthesis of O-glycosyl-aryl nitrones, Chinese Chemical Letters21, 1075–1078 (2010)
- Xiaoliu Li., Takahashi H., Ohtake H and Ikegami S., 1,3-Dipolar cycloaddition of exo- methylenesugars with nitrone: approach to new amino-C-ketosyl disaccharides, Tetrahedron Letters, 454123–4126 (2004)
- Vasella A., Stereoselectivity and Regioselectivity of 1,3-dipolar Cycloaddition chiral N- (Alkoxyalkyl)-nitrone, Helv. Chim. Acta, 60, 1273 (1977)
- Huber R., Knierzinger A., Obrecht J.P and Vasella A., Nuclophilic additions to N- glycosylnitrone. Asymmetric synthesis of -aminophosphonic acids, Helv. Chim, 681730(1985)
- Panfil I and Chmielewskj M., Cycloaddition of nitrones and -unsaturated sugar lactones, Tetrahedron, 20, 4713 (1985)
- Jarošková L., Konopíková M and Fišera L., 1,3-Dipolar cycloaddition of heterocycles. Cycloadditions of nitrones to N-(2,6- dialkylphenyl)maleimidesChem. Papers, 48, 35-39 (1994)