Synthesis, Crystal Structure, and DFT Study of a New Compound 6-(2-Fluorophenyl)-N-( p -Tolyl)Imidazo[1,2-A]Pyridine-2-C
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SYNTHESIS, CRYSTAL STRUCTURE, AND DFT STUDY OF A NEW COMPOUND 6-(2-FLUOROPHENYL)N-(p-TOLYL)IMIDAZO[1,2-A]PYRIDINE-2-CARBOXAMIDE* Y. Qin1,2**, D. Long1,2, X. Zhu1,2, Z. Zhou1,2, H. Chai3, and C. Zhao1,2,4
6-(2-Fluorophenyl)-N-(p-tolyl)imidazo[1,2-a]pyridine-2-carboxamide is an organic intermediate having both functions of azabicyclo and amide groups. In this paper, the title compound is obtained by the ring closure reaction, the Suzuki reaction, the hydrolysis and amidation reactions. The structure of the compound is confirmed by FT-IR, 1H NMR, 13C NMR spectroscopy, and MS. At the same time, a single crystal of the title compound is measured by X-ray diffraction and subjected to crystallographic and conformational analyses. The molecular structure is further calculated using density functional theory (DFT) and compared with the X-ray diffraction value. The results of the conformation analysis indicate that the molecular structure optimized by DFT is consistent with the crystal structure determined by single crystal X-ray diffraction. In addition, the molecular electrostatic potential and frontier molecular orbitals of the title compound are further investigated using DFT, revealing some physicochemical properties of the compound. DOI: 10.1134/S0022476619120072 Keywords: imidazopyridine, synthesis, X-ray diffraction, DFT.
INTRODUCTION Nitrogen-containing heterocyclic compounds are an important class of biologically active compounds with a potential pharmaceutical and commercial value [1-5]. In particular, imidazopyridine nitrogen-containing fused heterocyclic compounds and their derivatives, due to specific antitumor, antiviral, calming hypnosis, anti-inflammatory, antiulcer physiological activities and structural similarities with indole and azaindole, have become a research hotspot of organic and pharmaceutical chemists [6-7]. Amide compounds have a wide range of biological activities and are often used in pesticides and pharmaceuticals such as insecticides, herbicides, sterilization, and antiviral [8-10]. For example, Sonidegib is a Hedgehog signaling pathway inhibitor for the treatment of locally advanced basal cell carcinoma (BCC) in adult patients [11]. Imidazopyridine amides have the dual characteristics of azabicyclo and amide group, being important intermediates in the medicine, pesticide, and organic chemical industry, which have attracted the interest of researchers [12-14].
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School of Pharmaceutical Sciences, Guizhou University, Guiyang, P. R. China; **[email protected]. 2Guizhou Engineering Laboratory for Synthetic Drugs, Guiyang, P. R. China. 3Department of Pharmacy, Guiyang College of Traditional Chinese Medicine, Guiyang, P. R. China. 4Key Laboratory of Guizhou for Fermentation Engineering and Biomedicine, Guiyang, P. R. China. Original article submitted April 12, 2019; revised July 17, 2019; accepted July 18, 2019. * Supplementary materials are available for this article at doi 10.1134/S0022476619120072 and are accessible for authorized users. 0022-4766/19/6012-1917 © 2019 by Pleiades Publishing,
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