Synthesis of 4-acyl-1H-1,2,3-triazolic nucleosides.
Two simple regiospecific methodologies based on triazolic ring construction in the course of synthesis were applied for the synthesis of 1,2,3triazolic nucleoside analogues. The cycloaddition reactions between diazomalonaldehyde and appropriate glycosylamine derivatives were rather effective, producing the desired nucleosides 11, 17 and 24. Diazotization of enamines 21a and 21b led to the corresponding triazolic ribonucleoside derivatives 22a and 22b, in good yields. Deprotection reaction of 22a, 22b and 24 was easily achieved by Lewis acid catalysis, producing the corresponding ribonucleosides 23a, 23b and 25.
Cunha
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AC
Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, RJ, Brazil.
Pereira
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LO
de Souza
R O
RO
de Souza
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MC
Ferreira
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VF
D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D009705:Nucleosides; D014230:Triazoles