title: Facile synthesis of fully substituted dihydro-β-carbolines via Brønsted acid promoted cascade reactions of α-indolyl propargylic alcohols with nitrones.
abstract: A straightforward synthesis of fully substituted β-carbolines via Brønsted acid promoted cyclizations of α-indolyl propargylic alcohols with nitrones is described. The use of nitrones bearing alkenyl or electron-rich aryl groups as the R(4) substituent dramatically switches the reaction pathway to afford tetrasubstituted alkenes and amines, which is assumed to proceed through a rearrangement reaction involving N-O bond cleavage and 1,2-migration of the R(4) group to an adjacent nitrogen atom.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, People's Republic of China.
authors.forename: Lu
authors.initials: L
authors.lastname: Wang
authors.forename: Xin
authors.initials: X
authors.lastname: Xie
authors.forename: Yuanhong
authors.initials: Y
authors.lastname: Liu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D009584:Nitrogen; D009589:Nitrogen Oxides / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*
chemical_list: D000480:Alkynes; D002243:Carbolines; D009589:Nitrogen Oxides; D020005:Propanols; C015388:nitrones; C028255:propargyl alcohol; D009584:Nitrogen