title: Divergent regioselective synthesis of 2,5,6,7-tetrahydro-1H-1,4-diazepin-2-ones and 5H-1,4-benzodiazepines.
abstract: A novel and simple one-pot synthesis of 3-substituted 2,5,6,7-tetrahydro-1H-1,4-diazepin-2-ones from 1,2-diaza-1,3-dienes (DDs) and N-unsubstituted aliphatic 1,3-diamines is described. Here we also report a procedure to selectively obtain alkyl 5H-1,4-benzodiazepine-3-carboxylates from the DDs and 2-aminobenzylamine. Both processes occur by means of sequential 1,4-conjugated addition followed by regioselective 7-exo cyclization. The behavior of N-methyl- and N,N'-dimethyl-1,3-diaminopropanes toward the DDs furnished pyrazol-3-ones and bis-α-aminohydrazones, respectively.
authors: Istituto di Chimica Organica, Università degli Studi di Urbino Carlo Bo, Via I Maggetti 24, 61029 Urbino, Italy.
authors: Orazio A
authors: OA
authors: Attanasi
authors: Lucia
authors: L
authors: De Crescentini
authors: Gianfranco
authors: G
authors: Favi
authors: Fabio
authors: F
authors: Mantellini
authors: Simona
authors: S
authors: Nicolini
mesh_terms: D000473:Alkanes / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry; D001569:Benzodiazepines / Q000032:analysis / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002855:Chromatography, Thin Layer; D003500:Cyclization; D003959:Diamines / Q000032:analysis / Q000138:chemical synthesis*; D055808:Drug Discovery; D006801:Humans; D006835:Hydrazones / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D010455:Peptides / Q000737:chemistry; D011619:Psychotropic Drugs / Q000032:analysis / Q000138:chemical synthesis*; D047069:Pyrazolones / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D001372:Aza Compounds; D002264:Carboxylic Acids; D003959:Diamines; D006835:Hydrazones; D010455:Peptides; D011619:Psychotropic Drugs; D047069:Pyrazolones; D001569:Benzodiazepines