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
id todo:paper_0022152X_v36_n5_p1129_Faraco
record_format dspace
spelling todo:paper_0022152X_v36_n5_p1129_Faraco2023-10-03T14:27:44Z Synthesis and characterization of some nitrogen heterocycles from D- galactose derivatives Faraco, A.A.G. Prado, M.A.F. D'Accorso, N.B. Alves, R.J. De Souza Filho, J.D. Prado, R.F. galactose heterocyclic compound article chemical analysis chemical reaction drug structure drug synthesis nuclear magnetic resonance spectroscopy structure analysis 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. Fil:D'Accorso, N.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0022152X_v36_n5_p1129_Faraco
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic galactose
heterocyclic compound
article
chemical analysis
chemical reaction
drug structure
drug synthesis
nuclear magnetic resonance spectroscopy
structure analysis
spellingShingle galactose
heterocyclic compound
article
chemical analysis
chemical reaction
drug structure
drug synthesis
nuclear magnetic resonance spectroscopy
structure analysis
Faraco, A.A.G.
Prado, M.A.F.
D'Accorso, N.B.
Alves, R.J.
De Souza Filho, J.D.
Prado, R.F.
Synthesis and characterization of some nitrogen heterocycles from D- galactose derivatives
topic_facet galactose
heterocyclic compound
article
chemical analysis
chemical reaction
drug structure
drug synthesis
nuclear magnetic resonance spectroscopy
structure analysis
description 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.
format JOUR
author Faraco, A.A.G.
Prado, M.A.F.
D'Accorso, N.B.
Alves, R.J.
De Souza Filho, J.D.
Prado, R.F.
author_facet Faraco, A.A.G.
Prado, M.A.F.
D'Accorso, N.B.
Alves, R.J.
De Souza Filho, J.D.
Prado, R.F.
author_sort Faraco, A.A.G.
title Synthesis and characterization of some nitrogen heterocycles from D- galactose derivatives
title_short Synthesis and characterization of some nitrogen heterocycles from D- galactose derivatives
title_full Synthesis and characterization of some nitrogen heterocycles from D- galactose derivatives
title_fullStr Synthesis and characterization of some nitrogen heterocycles from D- galactose derivatives
title_full_unstemmed Synthesis and characterization of some nitrogen heterocycles from D- galactose derivatives
title_sort synthesis and characterization of some nitrogen heterocycles from d- galactose derivatives
url http://hdl.handle.net/20.500.12110/paper_0022152X_v36_n5_p1129_Faraco
work_keys_str_mv AT faracoaag synthesisandcharacterizationofsomenitrogenheterocyclesfromdgalactosederivatives
AT pradomaf synthesisandcharacterizationofsomenitrogenheterocyclesfromdgalactosederivatives
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AT alvesrj synthesisandcharacterizationofsomenitrogenheterocyclesfromdgalactosederivatives
AT desouzafilhojd synthesisandcharacterizationofsomenitrogenheterocyclesfromdgalactosederivatives
AT pradorf synthesisandcharacterizationofsomenitrogenheterocyclesfromdgalactosederivatives
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