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Paper | Regular issue | Vol 34, No. 3, 1992, pp.569-574
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5946
C-Nucleosides. 17. A Synthesis of 2-Substituted 7-(β-D-Ribofuranosyl)pyrrolo[2,1-f]-1,2,4-triazines. A New Type of "Purine Like" C-Nucleoside

Masanori Hayashi, Akemi Araki, and Isamu Maeba*

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

Abstract

A versatile intermediate pyranulose glycoside (1) for C-nucleoside synthesis was treated with semicarbazides (3a) and (3b) to give the corresponding semicarbazones (4a) and (4b) in good yield. Treatment of 4a with concentrated hydrochloric acid in dioxane yielded 1-ureido-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrole-2-carboxaldehyde (5), which on heating in acetic acid gave 2-oxo-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f]-1,2,4-triazine (6a). Compond (4b) was treated by the same procedure to give 2-thioxo-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f]-1,2,4-triazine (7a) and 3-hydroxymethyl-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyridazine (8). The removal of the sugar protecting groups in 6a and 7a afforded the deprotected C-nucleosides (6b) and (7b).