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Pharmaceuticals 2012, 5(6), 591-612; doi:10.3390/ph5060591
Article

a-Anilinoketones, Esters and Amides: A Chemical Study

1,2,*  and 1
1 Department of Medicinal Chemistry and Pharmacognosy, Faculty of Pharmacy, Jordan University of Science and Technology, Irbid 22110, Jordan 2 Pharmaceutical Sciences Department, College of Pharmacy, King Saud bin Abdulaziz University for Health Sciences, Riyadh 11426, Saudi Arabia
* Author to whom correspondence should be addressed.
Received: 14 May 2012 / Revised: 28 May 2012 / Accepted: 29 May 2012 / Published: 5 June 2012
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Abstract

A group of a-anilinoketones, 2-aminoalcohols, a-anilinoesters and a-anilinoamides were successfully synthesized and characterized by NMR spectroscopy and mass spectrometry. The yields were, in general, moderate to good (up to 75.4%), except for the a-anilinoesters (16.9–35.6%). The a-halocarbonyl starting materials showed different chemical reactivities. a-Haloketones and a-chloroacetates afforded monoalkylation, while small a-chloroamides afforded dialkylation. Finally, NMR spectroscopy revealed interesting structural features about the 2-aminoalcohols and diphenylamides.
Keywords: a-anilinoketones; 2-anilinoalcohols; a-anilinoesters; a-haloketones; intramolecular hydrogen bond a-anilinoketones; 2-anilinoalcohols; a-anilinoesters; a-haloketones; intramolecular hydrogen bond
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Qandil, A.M.; Fakhouri, L.I. a-Anilinoketones, Esters and Amides: A Chemical Study. Pharmaceuticals 2012, 5, 591-612.

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