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Synfacts 2011(3): 0255-0255
DOI: 10.1055/s-0030-1259574
DOI: 10.1055/s-0030-1259574
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Domino Approach to 1-Aminoindoles from 2-Halophenylacetylenes
N. Halland*, M. Nazaré, J. Alonso, O. R’kyek, A. Lindenschmidt*
Sanofi-Aventis Deutschland GmbH, Frankfurt am Main, Germany
Further Information
Publication History
Publication Date:
16 February 2011 (online)
Significance
Reported is the synthesis of 1-aminoindoles 3 via a palladium-catalyzed domino C-N coupling-5-endo-dig cyclization strategy. The reaction is equally tolerant of EDGs and EWGs on the haloarene (R¹). Additionally, both alkyl and aryl acetylenes (R²) were shown to participate efficiently in the reaction, although slightly lower yields were obtained with alkyl substituents. A wide range of both electron-rich and -poor hydrazines, including N-amino heterocycles, were shown to give the aminoindole products in excellent yields.