320591-44-4Relevant academic research and scientific papers
Novel ring transformation of 5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)isoxazole-4-carbaldehyde with 1,2-diaminobenzenes to 3-cyano-1,5-benzodiazepine C-nucleosides
Nishimura, Natsu,Hisamitsu, Haruna,Sugiura, Michiharu,Maeba, Isamu
, p. 681 - 686 (2000)
Syntheses of 3-cyano-7- and 8-substituted-4-(β-D-ribofuranosyl)-1H-1,5-benzodiazepines were reported. Treatment of isoxazole carbaldehyde with 1,2-diamino-4-nitrobenzene in chloroform gave a Schiff's base, 4-(2-amino-5-nitrophenyl)iminomethyl-5-(2,3,5-tri-O-benzoyl-β-D-ribofuran osyl)isoxazole in 82% yield with no trace of the other regioisomer. The cyclocondensation of the resulting Schiff's base in benzene containing trifluoroacetic acid (TFA) gave 3-cyano-8-nitro-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1H-1,5-benzodia zepine in 49% yield. The same reaction of isoxazole carbaldeyde with 1,2-diamino-4-methoxy- and 4-chlorobenzenes afforded the corresponding Schiff's bases. Extending the reaction time for Schiff's base gave the corresponding cyanobenzodiazepines in good yields. Debenzoylation of the compounds with sodium methoxide produced deprotected C-nucleosides. (C) 2000 Elsevier Science Ltd.
