Synthesis, Characterization and 1, 3-Dipolar Cycloaddition of Novel Sugar-Derived Nitrones with N-Arylmaleimides

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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)

[ref1] Tufariello J., In 1,3- Dipolar Cycloaddition Chemistry, John Wiley & Sons: New York., 9 (1984)

[ref2] 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)

[ref3] Bloch R., Addition of organomatallic reagents to C=N bonds: reactivity and selectivity, Chem. Rev, 98, 1407–1438, (1998)

[ref4] 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)

[ref5] Ross S.A., Gulve E.A and Wang M., Chemistry and biochemistry of type two diabetes, M. Chem. Rev, 104, 1255–1282 (2004)

[ref6] Torssell K.B.G., Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH: Weinheim, (1988)

[ref7] Frederickson M., optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkene: application inorganic synthesis, Tetrahedron, 53, 403-425 (1997)

[ref8] 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)

[ref9] 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)

[ref10] 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)

[ref11] 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)

[ref12] Vasella A., Stereoselectivity and Regioselectivity of 1,3-dipolar Cycloaddition chiral N- (Alkoxyalkyl)-nitrone, Helv. Chim. Acta, 60, 1273 (1977)

[ref13] Huber R., Knierzinger A., Obrecht J.P and Vasella A., Nuclophilic additions to N- glycosylnitrone. Asymmetric synthesis of -aminophosphonic acids, Helv. Chim, 681730(1985)

[ref14] Panfil I and Chmielewskj M., Cycloaddition of nitrones and -unsaturated sugar lactones, Tetrahedron, 20, 4713 (1985)

[ref15] 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)