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Pt(IV)催化的氢胺化引发环化:一种构建稠合吡咯并[1,2-a]喹喔啉、吲哚并[1,2-a]喹喔啉和吲哚并[3,2-c]喹啉的策略。

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.

机构信息

Organic Chemistry Division II, Indian Institute of ChemicalTechnology, Hyderabad 500 607, India.

出版信息

J Org Chem. 2010 May 21;75(10):3371-80. doi: 10.1021/jo100373w.

Abstract

A PtCl(4)-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 PtCl(4). We observed a remarkable enhancement of the rate when reactions were run under microwave-assisted conditions.

摘要

描述了一种 PtCl(4)催化的氨化引发环化策略,用于构建具有生物活性的含氮杂环化合物,如吡咯并[1,2-a]喹喔啉、吲哚并[1,2-a]喹喔啉和吲哚并[3,2-c]喹啉。该反应利用氨基芳烃如 1-(2-氨基苯基)吡咯、N-(2-氨基苯基)吲哚、2-(2-氨基苯基)吲哚和带有连接羟基的炔烃作为底物。该反应具有吸引力的是,它涉及到由单个金属催化剂 PtCl(4)催化的多个催化循环。我们观察到在微波辅助条件下反应时,速率有显著提高。

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