Bismuth(III) Triflate Catalyzed Condensation of Isatin with Indoles and Pyrroles­: A Facile Synthesis of 3,3-Diindolyl- and 3,3-Dipyrrolyl Oxindoles

Jhillu S. Yadav; Basireddy V. SubbaReddy; Kamakolanu Uma Gayathri; Syeda Meraj; Attaluri R. Prasad

doi:10.1055/s-2006-950373

SHORTPAPER

Bismuth(III) Triflate Catalyzed Condensation of Isatin with Indoles and Pyrroles: A Facile Synthesis of 3,3-Diindolyl- and 3,3-Dipyrrolyl Oxindoles

Jhillu S. Yadav*, Basireddy V. SubbaReddy, Kamakolanu Uma Gayathri, Syeda Meraj, Attaluri R. Prasad
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: 91(40)7160387; e-Mail: yadavpub@iict.res.in;

Abstract

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Abstract

Indoles and pyrroles undergo a rapid condensation with isatin in the presence of 2 mol% of Bi(OTf)₃, under mild reaction conditions, to afford the corresponding 3,3-di(3-indolyl)- and 3,3-di(2-pyrroryl)oxindoles in excellent yields and high regioselectivity. This method is ideal for the direct introduction of indoles and pyrroles onto an isatin moiety at the 3-position.

Keywords

bismuth - Bi(OTf)₃ - oxindoles - 3,3-diindolyl oxindoles - 3,3-dipyrrolyl oxindoles

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Bismuth(III) Triflate Catalyzed Condensation of Isatin with Indoles and Pyrroles­: A Facile Synthesis of 3,3-Diindolyl- and 3,3-Dipyrrolyl Oxindoles

Bismuth(III) Triflate Catalyzed Condensation of Isatin with Indoles and Pyrroles: A Facile Synthesis of 3,3-Diindolyl- and 3,3-Dipyrrolyl Oxindoles