AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
The aldehyde 2 prepared from [5-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-methylfuran-3-yl]methanol (1) was converted to E,Z-oximes 3, 4 and imine derivative 5 by the reaction with hydroxylamine and pyridin-2-yl amine, respectively. The Knoevenagel reaction with malonic acid afforded exclusively the 3-substituted acrylic acid 6 while corresponding Hantzsch 1,4-dihydropyridines 7 and 8 were obtained by the reaction of aldehyde 2 with ethyl acetoacetate or acetylacetone and ammonia. 3,5-Dicyano-1,4-dihydropyridine derivative 9 was isolated only in forms of hydrates after the reaction of aldehyde 2 with 3-aminocrotonitrile. 1,4-Dihydropyridines 7 and 9 were aromatized to corresponding pyridines 10 and 11. Isoxazoles 12, 13 and isoxazolines 14, 15 were prepared by 1,3-cycloaddition of appropriate dienophiles to a nitrile oxide generated from aldoximes 3, 4. Ferricyanide oxidation of 1-{[5-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-methylfuran-3-yl]methyl}pyridinium chloride (17a), -3-methylpyridinium chloride (19a) and the corresponding isoquinolinium chloride 21a gave optically active pyridin-2(1H)-ones 22, 23 and 2H-isoquinolone derivative 24 while the procedure with 2-methylpyridinium salt 18a and 4-methylpyridinium salt 20a led to complex mixtures of products. Reaction of 2,4,6-triphenylpyrylium perchlorate with furanoid amine 26 afforded a mixture of major 2,4,6-triphenylpyridine, minor pyridinium perchlorate 25 and primary alcohol 1. The absolute configuration of the studied compounds has been confirmed by X-ray analysis of the Schiff base 5.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
3-Hydroxymethyl-5-(2,3-O-isopropylidene-β-D-erythro-furanosyl)-2-methylfuran (2) prepared from 3-ethoxycarbonyl derivative 1 was converted to 3-chloromethyl-5-(2,3-O-isopropylidene-β-D-erythro-furanosyl)-2-methylfuran (3). Compound 3 reacted with cytosine, adenine, 6-chloropurine, 6-mercaptopurine, and nicotinamide to corresponding optically active heterocyclic derivatives 5-10 and 14. The 6-chloro derivative 9 was converted to 6-alkoxy derivatives 11 and 12 by the reaction with methanol or ethanol, respectively, in the presence of diazabicyclooctane. Dithionite reduction of quaternary chloride 14 gave 1,4-dihydropyridine derivative 15 capable to transform ethyl phenylglyoxylate to optically active ethyl mandelate.
