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Paper | Regular issue | Vol 32, No. 10, 1991, pp.1955-1960
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5824
C-Nucleosides. 16. A Synthesis of 1,5-Benzodiazepin-2-one Homo-C-nucleoside through Condensation of 1,2-Diaminobenzene with 5-Hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)furan-2(5H)-one

Yasutaka Ito, Chihiro Ito, and Isamu Maeba*

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

Abstract

The novel ring transformation of 5-hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)furan-2(5H)-one (1) with 1,2-diaminobenzene to 1,5-benzodiazepin-2-one is described. Treatment of 1 with 1,2-diaminobenzene followed by dehydrgenation with 2,3-dichloro-5,5-dicyano-p-benzoquinone (DDQ) and p-toluenesulfonic acid afforded 4-[1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-oxo]-1,3-dihydro-2H,-1,5-benzodiazepin-2-one (2) as the major product. A possible mechanism for this reaction is proposed. The removal of the sugar protecting groups in 2 afforded the deprotected homo-C-nucleoside (5).