J. L. Kelley, E. W. McLean, Ronda Davis
Sep 1, 1990
Citations
0
Influential Citations
4
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
6-[[(Hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-imidazo[4,5-b]pyridin-2-amine (1), an aza analogue of enviroxime, was synthesized in eight steps from 6-hydroxynicotinic acid (2). Acid 2 was nitrated, chlorinated with phosphorus pentachloride, and subjected to Friedel-Crafts aroylation to give 6-chloro-5-nitro-3-pyridyl phenyl ketone (5). Amination of 5 was followed by reduction of the nitro group and condensation with ethoxycarbonylisothiocyanate to give 6-benzyl-2-ethoxycarbonylamino-1H-imidazo[4,5-d]pyridine (8). The ethoxycarbonyl moiety of 8 was cleaved, N-1 was isopropylsulfonylated, and the carbonyl moiety was condensed with hydroxylamine to give 1. Compound 1 was inactive against rhinovirus 1B and poliovirus type 1.