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108. Reactions of Acetoacetates With Electron-deficient Anilines
W. Stadlbauer and N. S. Badgujar, in in Proceedings of ECSOC-11, The Eleventh International Electronic Conference on Synthetic Organic Chemistry, http://www.usc.es/congresos/ecsoc/11/ECSOC11.htm, November 1-30, 2007 (a034); J. A. Seijas, Shu-Kun Lin, M. P. Vázquez Tato (Eds). CD-ROM, edition ISBN 3-3-906980-19-7, Published in 2007 by MDPI, Basel, Switzerland.

The reaction of anilines, having electron-withdrawing substituents such as chloro- or trifluoromethyl groups, with acetoacetates was studied. Using the "watering protocol", acetanilides 3, 7 and 8 were obtained, depending on the substitution pattern. Attempts cyclize them to 2-quinolones failed, in contrast to electron-rich anilides, which gave 2-quinolones 5.

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