Single Crystal X-ray Study of 6-Phenyl-4-( p -tolyl)pyridin-2(1 H )-one
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TRUCTURE OF ORGANIC COMPOUNDS
Single Crystal X-ray Study of 6-Phenyl-4-(p-tolyl)pyridin-2(1H)-one1 Rajni Khajuriaa, Suresh Sharmab, Kamal K. Kapoora,*, and Vivek K. Guptab,** aDepartment bX-ray
of Chemistry, University of Jammu, Jammu and Kashmir, 180006 India Crystallography Laboratory, Department of Physics and Electronics,University of Jammu, Jammu and Kashmir, 180006 India *e-mail: [email protected] **e-mail: [email protected] Received June 28, 2016
Abstract—The title compound 6-phenyl-4-(p-tolyl)pyridin-2(1H)-one was synthesized via one-pot, three component reaction of (E)-1-phenyl-3-(p-tolyl)-2-propen-1-one, ethyl 2-nitroacetate and ammonium acetate in refluxing ethanol, as a shiny green crystalline solid in 83% yield. Its structure was characterized by spectral studies and unambiguously corroborated by X-ray diffraction crystallography. The crystals of title compound are monoclinic, sp. gr. P21/n, a = 11.8346(7) Å, b = 13.4413(9) Å, c = 17.7626(10) Å, β = 99.479(5)°, and Z = 8. All the rings in molecule of the title compound are planar. Hydrogen interactions play significant role in stabilizing the crystal structure and the supramolecular aggregate of molecules is facilitated by strong N–H···O and C–H···O type of hydrogen interactions. DOI: 10.1134/S1063774517070227
INTRODUCTION Pyridin-2(1H)-ones represent a “privileged” class of six-membered aza heterocyclic compounds, having significant interest in current medicinal chemistry and emerge in many biologically active natural products, therapeutics and synthetic compounds [1, 2]. Due to the dual properties of an aromatic ring and an amide, pyridin-2(1H)-ones show many useful interactions with biological molecules. Pyridin-2(1H)-ones display a variety of interesting biological properties including anti-cancer [3], cardiotonic [4], cardiovascular [5], anti-viral [6], anti-hypertensive [7], antianaphylactic [8], anti-allergenic [9], anti-inflammatory [10], anti-oxidant [11], and anti-microbial [12] ones. Pyridin-2(1H)-ones have also been used as lead compounds for the preparation of several drugs such as selective anti-cancer agents [13], anti-viral agents [14], potent anti-hepatitis B [15], subtype selective GABA receptor agonists [16], MEK-1 inhibitors [17], receptor tyrosine kinase c-Kit inhibitors [18], anaplastic lymphoma kinase inhibitors [19], pim-1 kinase inhibitors and inhibitors of amyloid-β peptide aggregation, an important character in amyloid formation in Alzheimer’s disease [20]. Owing to the significance of pyridin-2(1H)-ones as bioactive molecules, we reported an expedient metal/base-free, one-pot method of preparation of pyridin-2(1H)-one core 1 The article is published in the original.
bearing 4,6-diarylpyridin-2(1H)-ones [21]. In this paper, we report the structural elucidation of the title compound 6-phenyl-4-(p-tolyl)pyridin-2(1H)-one (I) by X-ray crystallographic study along with other analytical and spectral data. EXPERIMENTAL Synthesis. In an oven-dried round bottomed flask, a mixture of (E)-1-phenyl-3-(p-tolyl)-2-propen-1one
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