alexa The Behavior of 3-Anilinoenone and N-Phenyl Cinnamamide toward Carbon Nucleophiles: Spectroscopy and X-Ray Studies Reveal Interesting New Synthesis Routes to Nicotinonitriles and Tetrahydropyridine-3- Carbonitrile| Abstract

ISSN: 2161-0401

Organic Chemistry: Current Research

  • Research Article   
  • Organic Chem Curr Res 2013, Vol 3(1): 123
  • DOI: 10.4172/2161-0401.1000123

The Behavior of 3-Anilinoenone and N-Phenyl Cinnamamide toward Carbon Nucleophiles: Spectroscopy and X-Ray Studies Reveal Interesting New Synthesis Routes to Nicotinonitriles and Tetrahydropyridine-3- Carbonitrile

Al-Omran F* and El-Khair A
Department of Chemistry, Faculty of Science, Kuwait University, P.O. Box 12613, Safat 13060, Kuwait
*Corresponding Author : Al-Omran F, Department of Chemistry, Faculty of Science, Kuwait University, P.O. Box 12613, Safat 13060, Kuwait, Tel: (965) 2498 5205, Email: [email protected]

Received Date: Sep 12, 2013 / Accepted Date: Dec 26, 2013 / Published Date: Jan 03, 2014

Abstract

The reactions of 3-anilinoenones with active methylene nitrile either in acid or base media were investigated. Reasonable mechanisms to account for the formation of the nicotinonitrile, ethyl nicotinate, nicotinic acid and dienamide derivatives were suggested. A one-pot multicomponent reactions (MCRs) of enaminone, aniline and either malononitrile or ethyl cyanoacetate in acid or base media afforded 1,3,5-triacycl benzene derivative. Treatment of N-phenyl cinnamamide with malononitrile in refluxing sodium ethoxide lead to tetrahydropyridine derivative. The structures of the synthesized compounds were elucidated by elemental analyses, X-ray and a variety of spectroscopic methods, including proton and carbon nuclear magnetic resonance spectroscopy (1H-NMR and 13C-NMR), correlation spectroscopy (COSY), heteronuclear single quantum coherence spectroscopy (HSQC), and mass spectrometry (MS).

Citation: Al-Omran F, El-Khair A (2014) The Behavior of 3-Anilinoenone and N-Phenyl Cinnamamide toward Carbon Nucleophiles: Spectroscopy and X-Ray Studies Reveal Interesting New Synthesis Routes to Nicotinonitriles and Tetrahydropyridine-3-Carbonitrile. Organic Chem Curr Res 3: 123. Doi: 10.4172/2161-0401.1000123

Copyright: © 2014 Al-Omran F, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

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