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- Title
Nucleosid-Synthesen in der Imidazolreihe.
- Authors
Wyss, Pierre C.; Fischer, Ulf
- Abstract
Synthesis of Imidazole Nucleosides The acid-catalyzed fusion of dimethyl imidazole-4,5-dicarboxylate ( 7) with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose ( 6) provided dimethyl 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4,5-dicarboxylate ( 11) as the major product together with some β-anomer ( 13). The β-anomer ( 11) was obtained as the only product when the trimethylsilyl derivative ( 9) of 7 was condensed with 6 in the presence of stannic chloride. Nucleoside 11 was treated with ammonia, and various primary amines to provide 1-β-D-ribofuranosylimidazole-4, 5-dicarbox-amide ( 5) and N, N'-disubstitued dicarboxamides ( 18-26) respectively. The synthesis of 1-β-( 33) and 1-β-D-arabinofuranosylimidazole-4,5-dicarboxamide ( 34), is also described. The conformation of 5, as studied by 1H-and 13C-NMR.-spectroscopy, was shown to be very similar to that of adenosine. The oxidation of the 2′,3′-O′-isopropylidene derivative ( 15) of 5 with potassium permanganate or chromic oxide, followed by deprotection, or the direct oxidation of 5 with oxygen in the presence of platinum catalyst, led to the corresponding 5′-carboxylic acid 36. This was further converted into esters ( 37 and 38) and amides ( 39-42). Treatment of some nucleosides with fuming nitric acid in oleum at - 30° yielded the nitric acid esters 43-51. Beside the nitration of their sugar residues, one of the imidazolecarboxamide functions in nucleosides 46-51 and both N-methyl-carboxamide functions in 44 were nitrated. Finally, reaction of the N, N'-dimethyl-N, N'-dinitrodicarboxamide 44 with alkyl- und aralkylamines, afforded the N, N'-dialkyl-and N, N'-diaralkyldicarboxamides 52-56.
- Publication
Helvetica Chimica Acta, 1978, Vol 61, Issue 8, p3149
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19780610843