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Synfacts 2005(3): 0289-0289  
DOI: 10.1055/s-2005-916142
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of 2-Substituted 3-Acylindoles

Contributor(s): Victor Snieckus, Farhad Nowrouzi
A. Arcadi, S. Cacchi*, G. Fabrizi, F. Marinelli, L. M. Parisi
Università di L’Aquila, and Università degli Studi La Sapienza, Rome, Italy
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

The palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes to afford 2-substituted 3-alkynylindoles in satisfactory to high yields is reported. The sequential hydroamination-Sonogashira-type coupling involves the use of 1-halo-1-alkynes which have not been used in indole coupling chemistry previously. Interesting N-unprotected 3-alkynyl indoles, with some functional group variation were prepared which, by chemoselective hydration, lead to 3-acyl indoles.