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Pt(IV)-Catalyzed Hydroamination Triggered Cyclization: A Strategy to Fused Pyrrolo[1,2-a]quinoxalines, Indolo[1,2-a]quinoxalines, and Indolo[3,2-c]quinolines

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posted on 2010-05-21, 00:00 authored by Nitin T. Patil, Rahul D. Kavthe, Valmik S. Shinde, Balasubramanian Sridhar
A PtCl4-catalyzed hydroamination-triggered cyclization strategy to access biologically interesting N-containing heterocycles such as pyrrolo[1,2-a]quinoxalines, indolo[1,2-a]quinoxalines, and indolo[3,2-c]quinolines is described. The reaction makes use of aminoaromatics such as 1-(2-aminophenyl)pyrroles, N-(2-aminophenyl)indoles, 2-(2-aminophenyl)indoles, and alkynes having a tethered hydroxyl group. Mechanistically, the reaction is very appealing since it involves multiple catalytic cycles catalyzed by a single metal catalyst PtCl4. We observed a remarkable enhancement of the rate when reactions were run under microwave-assisted conditions.