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

a-Anilinoketones, Esters and Amides: A Chemical Study

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 (CC BY 3.0).

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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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