Gold-catalyzed reactions of 2-alkynyl-phenylamines with alpha,beta-enones.
[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.
Alfonsi
Maria
M
Dipartimento di Chimica, Ingegneria Chimica e Materiali, Facoltà di Scienze, Università di L'Aquila, Via Vetoio, 67010 Capitol (AQ), Italy.
Arcadi
Antonio
A
Aschi
Massimiliano
M
Bianchi
Gabriele
G
Marinelli
Fabio
F
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
D000480:Alkynes; D000814:Aniline Compounds; D007659:Ketones; D006046:Gold