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Org Lett. 2016 May 20;18(10):2499-502. doi: 10.1021/acs.orglett.6b01090. Epub 2016 May 5.

Synthesis of Carbazolequinones by Formal [3 + 2] Cycloaddition of Arynes and 2-Aminoquinones.

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1
School of Pharmaceutical Sciences and Innovative Drug Research Centre, Chongqing University , 55 Daxuecheng South Road, Shapingba, Chongqing 401331, P. R. China.

Abstract

A formal cycloaddition reaction for the synthesis of biologically and pharmaceutically important carbazolequinones via the annulation of aminoquinones with arynes has been developed. This practical and metal-free cascade reaction proceeds through successive C-C/C-N bond formations. Moreover, this novel method has been utilized for the concise synthesis of bioactive murrayaquinone A and koeniginequinone B and their analogues.

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