Synthesis and characterization of some nitrogen heterocycles from D- galactose derivatives

The tetrazoles 5-(6'-acetamido-6'-deoxy-1',2':3',4'-di-O-isopropylidene- D-glycero-α-D-galactohexopyranos-6'-yl)tetrazole (1) and 5-(6'-acetamido-6'- deoxy-1',2':3',4'-di-O-isopropylidene-L-glycero-α-D-galactohexopyranos-6'- yl)-t...

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Detalles Bibliográficos
Autores principales:	Faraco, A.A.G., Prado, M.A.F., D'Accorso, N.B., Alves, R.J., De Souza Filho, J.D., Prado, R.F.
Formato:	JOUR
Materias:	galactose heterocyclic compound article chemical analysis chemical reaction drug structure drug synthesis nuclear magnetic resonance spectroscopy structure analysis
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_0022152X_v36_n5_p1129_Faraco
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

Descripción
Sumario:	The tetrazoles 5-(6'-acetamido-6'-deoxy-1',2':3',4'-di-O-isopropylidene- D-glycero-α-D-galactohexopyranos-6'-yl)tetrazole (1) and 5-(6'-acetamido-6'- deoxy-1',2':3',4'-di-O-isopropylidene-L-glycero-α-D-galactohexopyranos-6'- yl)-tetrazole (2) were synthesized by the 1,3-dipolar cycloaddition reaction of the epimeric α-acetamidonitriles 5 and 6, respectively, with sodium azide. Reaction of tetrazole 1 with acetic anhydride in the presence of pyridine afforded the N-acetyl-1,3,4-oxadiazole derivative 3 and the N- acetylacetamido-1,3,4-oxadiazole derivative 7. The N-acetylacetamido-1,3,4- oxadiazole derivative (8) was isolated when the tetrazole 2 was allowed to react under the same conditions. The physical and spectroscopic data of the five new compounds 1, 2, 3, 7 and 8 are presented.