Premium
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
Abstract 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.