title: Scandium pentafluorobenzoate-catalyzed unexpected cascade reaction of 2-aminobenzaldehydes with primary amines: a process for the preparation of ring-fused aminals.
abstract: An unexpected cascade reaction of 2-aminobenzaldehydes with arylamines catalyzed by scandium pentafluorobenzoate [Sc(Pfb)3] was reported as a facile strategy for the efficient synthesis of a novel class of polycyclic ring-fused aminals N-substituted-6,7,11b,13-tetrahydro-6,12-[1,2]benzenoquinazolino[3,4-a]quinazolin-13-amines 1. Under similar conditions, a series of the analogues of Tröger's base, 13-substituted-5,6,11,12-tetrahydro-6,12-epiminodibenzo[b,f][1,5]diazocines 2 were obtained when the arylamines were replaced by methanamines. A possible mechanism for the formation of 1 and 2 was proposed.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, P. R. China.
authors.forename: Dan
authors.initials: D
authors.lastname: Mao
authors.forename: Jun
authors.initials: J
authors.lastname: Tang
authors.forename: Wenbo
authors.initials: W
authors.lastname: Wang
authors.forename: Shengying
authors.initials: S
authors.lastname: Wu
authors.forename: Xin
authors.initials: X
authors.lastname: Liu
authors.forename: Jianjun
authors.initials: J
authors.lastname: Yu
authors.forename: Limin
authors.initials: L
authors.lastname: Wang
mesh_terms: D000588:Amines / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012538:Scandium / Q000737:chemistry*
chemical_list: D000588:Amines; D001547:Benzaldehydes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D009942:Organometallic Compounds; C000062:2-aminobenzaldehyde; D012538:Scandium