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Paper | Regular issue | Vol 36, No. 12, 1993, pp.2805-2810
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6524
C-Nucleosides. 23. Synthesis of Enaminone Glycoside and 4-(β-D-Ribofuranosyl)quinoline-2-carboxamide from Furanone Glycoside

Isamu Maeba,* Yasutaka Ito, Masakazu Wakimura, and Chihiro Ito

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku, Nagoya 468-8503, Japan

Abstract

Furanone glycoside (1) was treated with aniline to yield 3-anilino-5-hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)furan-2(5H)-one (2). Reaction of 2 with trifluoroacetic acid afforded enaminone glycoside (3), whereas treatment of 2 with hydrochloric acid in methanol brought about the ring formation to furnish methyl 4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)quinoline-2-carboxylate (6) together with methyl 2-anilino-4-(3,5-di-O-benzoyl-1,4-anhydro-2-deoxy-D-erythropent-1-enofuranosyl)-4-oxobutanoate (4) and methyl 2-anilino-4-(5-benzoyloxymethylfuran-2-yl)-4-oxobutanoate (5) in yields of 12%, 12%, and 7%, respectively. The quinoline ester (6) reacted with aq. ammonia in methanol to produce quinolinecarboxamide C-nucleoside (7).