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Beyond a Protecting Reagent: DMAP-Catalyzed Cyclization of Boc-Anhydride with 2-Alkenylanilines

Ya-Nan Huang, Yin-Long Li, Jian Li and Jun Deng*

*School of Pharmaceutical Science and Technology, Key Laboratory for Modern Drug Delivery & High-Efficiency, Tianjin University, Tianjin, 300072 P. R. China, Email: jdengtju.edu.cn

Y.-N. Huang, Y.-L. Li, J. Li, J. Deng, J. Org. Chem., 2016, 81, 4645-4653.

DOI: 10.1021/acs.joc.6b00519 (free Supporting Information)


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Abstract

A rapid synthesis of quinolines from 2-alkenylanilines involves an unexpected DMAP-catalyzed cyclization of 2-alkenylanilines with di-tert-butyl dicarbonate providing a series of tert-butyl quinolin-2-yl carbonates with various functional groups in good yields under mild conditions. Furthermore, the tert-butyl quinolin-2-yl carbonate can be easily converted into corresponding quinolinones and 2-(pseudo)haloquinolines.

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Key Words

2-Quinolones, Quinolines


ID: J42-Y2016