51. Part 7: Synthesis of Some New 1,5-Benzodiazepines Fused with Different Heterocyclic Moieties
- Author
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H. Abdel-Ghany, Ahmed Khodairy, Ahmed M. El-Sayed, and H. Salah
- Subjects
Inorganic Chemistry ,Carbon disulfide ,chemistry.chemical_compound ,Acetic anhydride ,chemistry ,Intramolecular force ,Organic Chemistry ,Ring (chemistry) ,Biochemistry ,Medicinal chemistry - Abstract
3-cyano-1,11-dihydro-4,5-diphenyl-2-thioxopyrido[2,3-b](1,5)benzodiazepine 2 and 3-(2′-cyano-1′-phenyl-2′-ethanethiocarboxamide)-4-phenyl-1(H)(1,5)benzodiazepin2-one 3 were prepared via the reaction of 1,3-dihydro-4-phenyl-(1,5)benzodiazepin-2-one 1 with benzylidenecyanothioacetamide. Compound 2 was treated with halo compounds to give the corresponding S-alkylated compounds 4 a−c, which underwent as intramolecular ring closure to thieno[3,2.5,6]pyrido[2,3-b](1,5)benzodiazepines 5 a−c under PTC conditions. One-pot syntheis of compounds 5 a−c was achieved via the reaction of compound 2 with the appropriate halo compound under PTC conditions. Compound 1 and 1-ethyl-4-phenyl-(1,5)benzodiazepin-2-one 9 were treated with carbon disulfide or phenylisothiocyanate and active nitriles to afford 4-thioxothiopyrano[4,3-b](1,5)benzodiazepines 8 and 10–14. Treatment of compound 10 with phenylisothiocyanate or acetic anhydride yielded oxazino-and pyrimido[4,5-b]thiopyrano-[4′,3′-b′](1,5)benzodiazepine 15 and 17. The rea...
- Published
- 2007
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