We recently published a synthesis of homodimeric indirubins that proceeded through an indoxyl intermediate. This intermediate was generated using Mo(CO)<sub>6 </sub>in the presence of peroxide followed by careful control of temperature to bias the reaction towards indirubin and not indigo. A series of substrates were evaluated and will serve as a template for further elaboration, mainly the synthesis of heterodimeric systems by utilizing isatin as a trapping agent for indoxyl. A series of indoles and isatins were reacted using 2% Mo(CO)<sub>6</sub>, 1 equivalent of indoxyl acetate at 60°C for 48 hours to serve as a comparative measure for general reactivity of this method. While many examples proceeded to only form the desired heterodimeric indirubin, the homodimeric indirubin and indigo products were observed in some cases in small amounts. Additional optimization was performed on each system that didn’t solely form indirubin under the parent reaction conditions. Trends in reactivity will be discussed for this general and convenient synthesis of indirubins. Potential applications for the indirubins include potential as kinase inhibitors as well as novel supramolecular behavior.

Molybdenum-initiated synthesis of heterodimeric indirubins using an isatin trap

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