902134-83-2Relevant articles and documents
Gold-catalyzed C-3-alkylation of 7-azaindoles through Michael-type addition to α,β-enones
Alfonsi, Maria,Arcadi, Antonio,Bianchi, Gabriele,Marinelli, Fabio,Nardini, Antonella
, p. 2393 - 2402 (2007/10/03)
The AuIII-catalyzed reactions of 7-azaindole derivatives with α,β-enones are described. Factors that can direct the C-3-versus N-1-alkylation reaction on the 7-azaindole nucleus are explored. The Au III-catalyzed reaction of 7-azaindole with β-unsubstituted α,β-enones afforded 1-substituted 7-azaindoles through an aza-Michael-type reaction. In contrast, 6-substituted 7-azaindoles underwent regioselective C-3-alkylation through a Na[AuCl4]·2H 2O-catalyzed conjugate addition-type reaction. Analogously, the Na[AuCl4]·2H2O-catalyzed reaction of 7-azaindole derivatives with β-aryl-substituted α,β-enones gave 3-substituted 7-azaindoles in moderate-to-satisfactory yields. Moreover, the Na[AuCl4]·2H2O-catalyzed reaction of 1-substituted 7-azaindoles with α,β-enones allowed an easy entry to 1,3-disubstituted 7-azaindoles in moderate-to-high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.