title: Syntheses of imidazo-, oxa-, and thiazepine ring systems via ring-opening of aziridines/Cu-catalyzed C-N/C-C bond formation.
abstract: A simple and unpredicted synthetic pathway toward racemic and scalemic tetrahydrodibenzoimidazoazepines has been invented serendipitously proceeding through an S(N)2-type ring-opening of N-activated aziridines with 2-bromobenzylamine followed by a hitherto unprecedented cascade cyclization reaction sequence comprising a Cu-catalyzed cross dehydrogenation C-N coupling and an Ullmann C-C bond formation reaction. The tetrahydrobenzoxazepine and the tetrahydrobenzothiazepine derivatives have also been synthesized via the ring-opening of aziridines with 2-bromobenzyl alcohols and -mercaptan, respectively, followed by Cu-catalyzed N-arylation reaction.
authors: Department of Chemistry, Indian Institute of Technology , Kanpur, Uttar Pradesh 208016, India.
authors: Manas K
authors: MK
authors: Ghorai
authors: Ashis Kumar
authors: AK
authors: Sahoo
authors: Aditya
authors: A
authors: Bhattacharyya
mesh_terms: D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D013841:Thiazepines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001381:Azepines; D001388:Aziridines; D013841:Thiazepines; D003300:Copper