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Synthesis and characterization of some nitrogen heterocycles from d‐galactose derivatives
Author(s) -
Faraco André Augusto Gomes,
De Souza Filho José Dias,
Prado Maria Auxiliadôra Fontes,
Alves Ricardo José,
Prado Renata Fontes,
D'Accorso Norma Beatriz
Publication year - 1999
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570360503
Subject(s) - tetrazole , chemistry , oxadiazole , sodium azide , cycloaddition , derivative (finance) , acetic anhydride , pyridine , sodium ethoxide , medicinal chemistry , pyrimidine , 1,3 dipolar cycloaddition , organic chemistry , stereochemistry , ethanol , financial economics , economics , catalysis
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.