RT Conference Proceedings
T1 Intramolecular [3+2] cycloaddition of azido-unsaturated esters derived of monosaccharides
A1 Pino-González, María Soledad
A1 Romero-Carrasco, Antonio
A1 Calvo-Losada, Saturnino
A1 Quirante-Sánchez, José Joaquín
K1 Química orgánica
AB Iminosugars have been shown to be very potent inhibitors of glycosidases and glycolsyltransferases. Due to their ability to resemble the transition states of the sugarsinvolved in these processes, a variety of monocyclic and bicyclic iminosugars have beensynthesized or isolated from natural sourcesover the years. As part of our ongoing workon the preparation of glycosidase inhibitors, we developed stereoselective methods forsynthesizing iminosugars from 2,3-epoxyamides obtained from monosaccharides.Now, we are interested in the syntheses of novel bicyclic triazoles, by intramolecular cycloaddition, due to the possibility of combining azido group and unsaturated esters in the same molecule. The triazole system is broadly considered in syntheses of bioactive products and the option of fused iminosugar with triazole has been evaluated.Firstly, we started with a less complex azido derivative 2a to continue with azido compounds2b obtained from our 2,3-epoxyamides 3, by regioselective introduction of an azido group. The fused triazolines 4a were formed by heating of2a. Aromatization of 4a afforded byciclic triazoles. There are several possibilities in the cyclization process depending on the reaction conditions and products 5,6 and 7can be formed. Moreover, we conducted a theoretical DFT based study of the cycloaddition to value the probability of formation of the triazoline 4a and subsequent aroma tization to triazole 1,versus elimination to the unsaturated ester 5
YR 2013
FD 2013-11-05
LK http://hdl.handle.net/10630/6323
UL http://hdl.handle.net/10630/6323
LA eng
NO Universidad de Málaga. Campus de Excelencia Internacional Andalucía Tech
DS RIUMA. Repositorio Institucional de la Universidad de Málaga
RD 23 ene 2026