title: 1,2- and 1,4-additions of 2-alkynylcyclohexadienimines with aromatic amines to access 4-amino-N-arylindoles and -azepinoindoles.
abstract: 2-Alkynylcyclohexadienimines, derived from the oxidation of 2-alkynylanilines, react with aromatic amines leading to N-arylindoles with a 4-amino substitution. The reaction was metal-controlled, and Bi(OTf)(3) proved to be the best catalyst. The resulting 4-amino N-arylindoles could be converted to azepino[4,3,2-cd]indoles through condensation with aldehydes.
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.
authors.forename: Li
authors.initials: L
authors.lastname: Zhang
authors.forename: Zhiming
authors.initials: Z
authors.lastname: Li
authors.forename: Renhua
authors.initials: R
authors.lastname: Fan
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000447:Aldehydes; D000480:Alkynes; D000588:Amines; D007211:Indoles