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Gold‐Catalyzed C‐3‐Alkylation of 7‐Azaindoles Through Michael‐Type Addition to α,β‐Enones
Author(s) -
Alfonsi Maria,
Arcadi Antonio,
Bianchi Gabriele,
Marinelli Fabio,
Nardini Antonella
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500998
Subject(s) - chemistry , alkylation , regioselectivity , catalysis , conjugate , medicinal chemistry , aryl , michael reaction , addition reaction , organic chemistry , mathematical analysis , alkyl , mathematics
The Au III ‐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‐substituted7‐azaindoles through an aza‐Michael‐type reaction. Incontrast, 6‐substituted 7‐azaindoles underwent regioselective C ‐3‐alkylation through a Na[AuCl 4 ] · 2H 2 O‐catalyzed conjugate addition‐type reaction. Analogously, the Na[AuCl 4 ] · 2H 2 O‐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[AuCl 4 ] · 2H 2 O‐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, 69451 Weinheim, Germany, 2006)