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a-Anilinoketones, Esters and Amides: A Chemical Study
Department of Medicinal Chemistry and Pharmacognosy, Faculty of Pharmacy, Jordan University of Science and Technology, Irbid 22110, Jordan
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; in revised form: 28 May 2012 / Accepted: 29 May 2012 / Published: 5 June 2012
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
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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.
Qandil AM, Fakhouri LI. a-Anilinoketones, Esters and Amides: A Chemical Study. Pharmaceuticals. 2012; 5(6):591-612.
Qandil, Amjad M.; Fakhouri, Lara I. 2012. "a-Anilinoketones, Esters and Amides: A Chemical Study." Pharmaceuticals 5, no. 6: 591-612.