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Synfacts 2011(5): 0475-0475
DOI: 10.1055/s-0030-1259848
DOI: 10.1055/s-0030-1259848
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Thienopyrroles and Benzothienoquinolines via Palladium-Catalyzed Domino Reactions
G. A. Salman, M. Hussain, V. Iaroshenko, A. Villinger, P. Langer*
Universität Rostock and Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Germany
Further Information
Publication History
Publication Date:
15 April 2011 (online)
Significance
Reported is a synthesis of thieno-pyrroles and benzothienoquinolines from the reaction of 2-alkynylthiophenes and 2-alkynylbenzothiophenes, respectively, with anilines. The reactions proceed in a proposed domino C-N coupling-hydroamination and C-N coupling-annulation sequence, respectively. The latter reaction appears to be the first of its type to be reported. The substrate scope was well studied and the yields of products are generally good. Additionally, three 2-alkynylbenzothiophenes (R4 or R5 = NO2, CN, CO2Me) were converted into benzothienopyrroles in good yields. When R4 and/or R5 = EDG, such as OMe, mixtures of benzothienopyrroles and -quinolines ensued.