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a b s t r a c t Three ionic liquids, [BMIM][BF 4 ] doped with 60 mol % of LiCl ([BMIM][BF 4 ]-LiCl), N,N,N,N-tetramethylguanidinium trifluoroacetate (TMGT), and N,N,N,N-tetramethylguanidinium triflate (TMGT f ) were found useful as catalyst solvents for controlled 3-indolylation of isatins. Our investigation revealed that the reaction between isatin and indoles in [BMIM] [BF 4 ]-LiCl or TMGT f media stops at the step of addition of the two components providing 3-indolyl-3-hydroxyindolin-2-ones while the ionic liquid TMGT runs the reaction further through accompanying Friedel-Crafts substitution to afford symmetrical 3,3-di(indol-3-yl)indolin-2-ones. To take advantage of the difference between the effects of these ionic liquids on the reaction progress, we planned a two-step protocol for the efficient synthesis of unsymmetrical 3,3-di(indol-3-yl)indolin-2-ones.

NH 2 CN MW N N NH 2 R + R-C(OEt) 3 + AcNH 4 5-7 minA facile and rapid synthesis of the title compounds via one-pot reaction of 2-aminobenzonitrile, orthoesters and ammonium acetate under solvent-free and microwave condition is described.

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