title: Gold-catalyzed reactions of 2-alkynyl-phenylamines with alpha,beta-enones.
abstract: [reaction: see text] The gold-catalyzed reaction of 2-alkynyl-phenylamines with alpha,beta-enones represents a new general one-pot entry into C-3-alkyl-indoles by sequential reactions. Gold-catalyzed sequential cyclization/alkylation, N-alkylation/cyclization, or N-alkylation/cyclization/alkylation reactions leading to different indoles can be directed by changing the 2-alkynyl-phenylamine 1/alpha,beta-enone 3 ratio and the reaction temperature. Unusual gold-catalyzed rearrangement reaction of indoles are observed at 140 degrees C. New gold-catalyzed formation of propargyl-alkyl ether under mild conditions and the hydration reaction of N-acetyl-2-ethynyl-phenylamine are reported.
authors.affiliation: Dipartimento di Chimica, Ingegneria Chimica e Materiali, Facoltà di Scienze, Università di L'Aquila, Via Vetoio, 67010 Capitol (AQ), Italy.
authors.forename: Maria
authors.initials: M
authors.lastname: Alfonsi
authors.forename: Antonio
authors.initials: A
authors.lastname: Arcadi
authors.forename: Massimiliano
authors.initials: M
authors.lastname: Aschi
authors.forename: Gabriele
authors.initials: G
authors.lastname: Bianchi
authors.forename: Fabio
authors.initials: F
authors.lastname: Marinelli
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000480:Alkynes; D000814:Aniline Compounds; D007659:Ketones; D006046:Gold