TY - JOUR
T1 - Microwave-assisted 1,3-dipolar cycloaddition reactions of vinylic glycosides with aryl azides - unexpected synthesis of triazoles and acetyl group migration
AU - Barros, Maria Teresa
AU - Andrade, Marta Morais Saraiva de
PY - 2009/1/1
Y1 - 2009/1/1
N2 - The synthesis of sugar-derived triazolines was attempted under microwave irradiation, by 1,3-dipolar cycloaddition to azides. However, due to the "push-pull" nature of the dipolarophile, we have obtained triazoles by elimination of the sugar unit, which then has one free hydroxyl group at a selective carbon position. The triazoles obtained are important precursors of anticonvulsive drugs. Furthermore, we have observed that under microwave irradiation of 300W it is possible to promote acetyl group migration to a free hydroxyl group within the carbohydrate moiety.
AB - The synthesis of sugar-derived triazolines was attempted under microwave irradiation, by 1,3-dipolar cycloaddition to azides. However, due to the "push-pull" nature of the dipolarophile, we have obtained triazoles by elimination of the sugar unit, which then has one free hydroxyl group at a selective carbon position. The triazoles obtained are important precursors of anticonvulsive drugs. Furthermore, we have observed that under microwave irradiation of 300W it is possible to promote acetyl group migration to a free hydroxyl group within the carbohydrate moiety.
KW - Microwave 1
KW - 3-dipolar cycloaddition azides triazoles acetyl group migration substituted benzyl azides anticonvulsant agents derivatives spectroscopy irradiation products
M3 - Article
SN - 1424-6376
VL - 11
SP - 299
EP - 306
JO - Arkivoc
JF - Arkivoc
IS - NA
ER -