Synthesis of Nitrogen Heterocycles from Methyl alfa- and beta-D-glucopyranosides

CAPANEMA PEDROSA, MARÍA TERESA; BRONDI ALVES, ROSEMEIRE; FONTES PRADO, MARÍA A.; DIAZ DE SOUZA FILHO, JOSÉ; ALVES, RICARDO JOSÉ; D'ACCORSO NORMA BEATRIZ

JOURNAL OF CARBOHYDRATE CHEMISTRY

Marcel Dekker

Lugar: New York; Año: 2003 vol. 22 p. 433 - 442

0732-8303

Eight nitrogen heterocycles, mono and disubstituted tetrazoles and oxadiazoles, were synthesized from methyl D-glucopyranoside anomers. The monosubstituted tetrazoles resulted from the reaction of 6-cyanoglucopyranoside derivatives with sodium azide. By alkylation of the monosubstituted tetrazoles, the 1,5 and 2,5 disubstituted tetrazoles were obtained. The monosubstituted tetrazoles were reacted with acetic anhydride to give the oxadiazoles.