title: Synthesis of 6-substituted 6-nitroperhydro-1,4-diazepines via novel tandem retro-Henry and Mannich/Michael reactions.
abstract: N,N'-Dibenzyl-6-hydroxymethyl-6-nitroperhydro-1,4-diazepine was converted into a nitronate via retro-Henry reaction, followed by either Michael reaction with several acrylic derivatives or Mannich reaction with different amines, thus leading to 6-substituted 6-nitroperhydro-1,4-diazepines. The tandem retro-Henry/Mannich reaction was also carried out using benzylamine as base, solvent, and reagent at the same time. Selective hydrogenation of the nitro group and complete hydrogenolysis were also successfully achieved.
authors.affiliation: Dipartimento di Scienze e Innovazione Tecnologica, Università del Piemonte Orientale A. Avogadro, Viale T. Michel 11, 15121 Alessandria, Italy.
authors.forename: Jonathan
authors.initials: J
authors.lastname: Martinelli
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Gugliotta
authors.forename: Lorenzo
authors.initials: L
authors.lastname: Tei
mesh_terms: D001381:Azepines / Q000138:chemical synthesis*; D006865:Hydrogenation; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*
chemical_list: D001381:Azepines; D009574:Nitro Compounds