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

✍ Scribed by André Augusto Gomes Faraco; José Dias De Souza Filho; Maria Auxiliadôra Fontes Prado; Ricardo José Alves; Renata Fontes Prado; Norma Beatriz D'Accorso

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
312 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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‐galacto‐hexopyranos‐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.

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