Gold-Catalyzed C-3-Alkylation of 7-Azaindoles Through Michael-Type Addition to α,β-Enones

Alfonsi, M.; Arcadi, A.; Bianchi, G.; Marinelli, Fabio; Nardini, A.

doi:10.1002/ejoc.200500998

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The Au-III-catalyzed reactions of 7-azaindole derivatives with alpha,beta-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 P-unsubstituted alpha,beta-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]center dot 2H(2)O-catalyzed conjugate addition-type reaction. Analogously, the Na[AuCl4]center dot 2H(2)O-catalyzed reaction of 7-azaindole derivatives with beta-aryl-substituted alpha,beta-enones gave 3-substituted 7-azaindoles in moderate-to-satisfactory yields. Moreover, the Na [AuCl4]center dot 2H(2)O-catalyzed reaction of 1-substituted 7-azaindoles with alpha,beta-enones allowed an easy entry to 1,3-disubstituted 7-azaindoles in moderate-to-high yields.

Titolo:	Gold-Catalyzed C-3-Alkylation of 7-Azaindoles Through Michael-Type Addition to α,β-Enones
Autori:	M. ALFONSI ARCADI, Antonio G. BIANCHI MARINELLI, Fabio A. NARDINI mostra contributor esterni nascondi contributor esterni
Data di pubblicazione:	2006
Rivista:	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Abstract:	The Au-III-catalyzed reactions of 7-azaindole derivatives with alpha,beta-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 P-unsubstituted alpha,beta-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]center dot 2H(2)O-catalyzed conjugate addition-type reaction. Analogously, the Na[AuCl4]center dot 2H(2)O-catalyzed reaction of 7-azaindole derivatives with beta-aryl-substituted alpha,beta-enones gave 3-substituted 7-azaindoles in moderate-to-satisfactory yields. Moreover, the Na [AuCl4]center dot 2H(2)O-catalyzed reaction of 1-substituted 7-azaindoles with alpha,beta-enones allowed an easy entry to 1,3-disubstituted 7-azaindoles in moderate-to-high yields.
Handle:	http://hdl.handle.net/11697/9033
Appare nelle tipologie:	1.1 Articolo in rivista

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