Synthesis of ribonucleosides of 4(5)‐cyano‐5(4)‐methylimidazole and related 4‐substituted‐5‐methylimidazole ribosides | Zendy

Andrés J. Ignacio | Zendy; GarcíaLopez M. Teresa | Zendy

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Synthesis of ribonucleosides of 4(5)‐cyano‐5(4)‐methylimidazole and related 4‐substituted‐5‐methylimidazole ribosides

Author(s) -

Andrés J. Ignacio,

GarcíaLopez M. Teresa

Publication year - 1986

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.5570230308

Subject(s) - chemistry , ammonia , hydroxylamine , hydrochloride , hydroxylamine hydrochloride , cyanide , salt (chemistry) , ammonium , medicinal chemistry , nucleoside , ammonium chloride , catalytic hydrogenation , chloride , potassium , derivative (finance) , nitrile , catalysis , organic chemistry , stereochemistry , financial economics , economics

4‐Cyano‐1‐(2,3,5‐tri‐ O ‐acetyl‐β‐D‐ribofuranosyl)‐5‐methylimidazole ( 4 ) and its corresponding 5‐cyano‐4‐methyl substituted isomer ( 5 ) have been obtained by ribosylation of 4(5)‐cyano‐5(4)‐methylimidazole ( 3 ) via the mercuric cyanide method or by ribosylation of the trimethylsilyl derivative of 3 . Treatment of 4 with methanolic ammonia, ammonium chloride in liquid ammonia and potassium hydrosulfide provided 4‐cyano‐1‐β‐D‐ribofuranosyl‐5‐methylimidazole ( 6 ), 1‐β‐D‐ribofuranosyl‐5‐methylimidazole‐4‐carboxamide ( 2 ) and 1‐β‐D‐ribofuranosyl‐5‐methylimidazole‐4‐thiocarboxamide ( 11 ) respectively. Reaction of 6 with hydroxylamine afforded the corresponding 4‐carboxamidoxime substituted nucleoside ( 13 ) which on catalytic reduction in the presence of ammonium chloride, was transformed into 1‐β‐D‐ribofuranosyl‐5‐methylimidazole‐4‐carboxamidine ( 14 ) as hydrochloride salt.

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