Microwave-Assisted Organic Synthesis of 3-(D-gluco- Pentitol-1-Yl)-1H-1,2,4-Triazole

The condensation of D-glucono- and D-galactono-1,5-lactone and thiocarbohydrazide to give 3-(D-alditol-1-yl)-4-amino-5-mercapto-1,2,4-triazoles 4 and 5 is accelerated by the use of microwave-assisted organic reaction (MAOS). The deamination and dethiolation of compound 4 to give 6 was also accelerat...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2006-01, Vol.25 (3), p.325-335
Main Authors: El Ashry, E. S. H., Awad, L. F., Abdel Hamid, H. M., Atta, A. I.
Format: Article
Language:English
Subjects:
1,2,4-Triazoles
Acyclonucleosides
MAOS
Microwaves
MWI
Seco C-Nucleosides
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:The condensation of D-glucono- and D-galactono-1,5-lactone and thiocarbohydrazide to give 3-(D-alditol-1-yl)-4-amino-5-mercapto-1,2,4-triazoles 4 and 5 is accelerated by the use of microwave-assisted organic reaction (MAOS). The deamination and dethiolation of compound 4 to give 6 was also accelerated by the use of MAOS. Condensation of 4 and 5 with p-nitrobenzaldehyde afforded Schiff bases 8 and 9 , respectively, within 4 min under microwave irradiation (MWI), whereas with ethyl chloroacetate the thioalkylated products 14 and 15 were obtained in 8 min. The structures of the synthesized compounds were confirmed by 1 H NMR, 2D NMR, and mass spectra.
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770500544545