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Paper | Regular issue | Vol 34, No. 5, 1992, pp.955-964
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5966
C-Nucleosides. 19. Synthesis of 7- and 8-Substituted 4-[1-(β-D-Ribofuranosyl)oxo]-1,3-dihydro-2H-1,5-benzodiazepin-2-one

Yasutaka Ito, Masakazu Wakimura, C. Ito, and Isamu Maeba*

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

Abstract

The synthesis of 7- and 8-substituted 4-[1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)oxo]-1,3-dihydro-2H-1,5-benzodiazepin-2-one from furanone glycoside (1) is described. Treatment of 1,2-diamino-4-substituted benzenes (2a-c) with 1 gave a mixture of 7- and 8-substituted 4-[1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)oxo]-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one (3a-d). Dehydrogenation of 3a-d with DDQ and a trace of PTSA afforded 7- and 8-substituted 4-[1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)oxo]-1,3-dihydro-2H-1,5-benzodiazepin-2-ones (4a-f). The position of the substituent in compounds (4a-f) was confirmed by 1H- 13C long-range COSY and NOE experiments with the corresponding N1-methyl derivatives (5a-c). Deprotection of compounds (4a-e) with methanolic sodium hydroxide afforded 4g-k.