Abstract
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, lH 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.
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04 September 2020
In the original article there was a mistake in the information of the corresponding author. The correct spelling of the names of the authors and their order is: Y.��M. Qin1,2, D. Long1,2, X. Zhu1,2, Z.��X. Zhou1,2, H.��F. Chai3(saieho@126.com), and C.��S. Zhao1,2,4(chunshenzhao@163.com).
References
X. H. Ji and J. F. Lu. Chin. J. Synth. Chem., 2019, 27, 41–45.
A. S. Hassan, D. M. Masoud, F. M. Sroor, and A. A. Askar. Med. Chem. Res., 2017, 26, 2909–2919.
M. Zhao, H. Ren, J. Chang, D. Zhang, Y. Yang, Y. He, C. Qi, and H. Zhang. Euro. J. Med. Chem., 2016, 119, 183–196.
W. M. Al-Adiwish, M. I. M. Tahir, A. Siti-Noor-Adnalizawati, S. F. Hashim, N. Ibrahim, and W. A. Yaacob. Euro. J. Med. Chem., 2013, 64, 464–476.
L. F. S. P. Azeredo, J. P. Coutinho, and V. A. P. Jabor. Euro. J. Med. Chem., 2017, 126, 72–83.
K. Paul, V. Luxami, R. Goel. Curr. Top. Med. Chem., 2016, 16, 3590–3616.
J. C. Liu and Q. Y. Chen. Prog. Chem., 2010, 22, 631–638.
X. Wang, C. H. Tang, R. Tan, X. T. Wu, M. He, and S. Y. Wang. Fine Chem. Intermed., 2016, 46, 1–14.
I. M. Nanni, A. Pirondi, D. Mancini, G. Stammler, R. Gold, and I. Ferri. Pest Manag. Sci, 2016, 72, 1537–1539.
Y. Hong, H. Dai, L. Y. Ye, S. L. Zhong, X. F. Cao, Y. J. Shi, C. J. Li, J. Shi, and L. Shi. Chin. J. Org. Chem., 2017, 37, 3006–3012.
E. Ramelyte, V. C. Amann, and R. Dummer. Expert Opin. Pharmaco., 2016, 17, 1963–1968.
S. X. Luo, X. J. Chen, H. W. Zhu, X. Y. Zhang, and G. Wei. Chem. Bull., 2014, 77, 1098–1102.
A. Rajput and R. Mukherjee. Coord. Chem. Rev., 2013, 257, 350–368.
C. Y. Shi, C. H. Ge, and Q. T. Liu. Chin. J. Inorg. Chem., 2010, 26, 1323–1332.
J. S. Zhao, P. Jin, N. Xi, and D. D. Wei. Chin. J. Struct. Chem., 2017, 36, 937–942.
W. Y. Lin, F. Yang, A. N. Duan, W. W. You, and P. L. Zhao. Chin. J. Struct. Chem., 2018, 37, 1557–1562.
G. M. Sheldrick. SHELXS-2014/7. Program for Solution of Crystal Structures. University of Gongen: Gongen, Germany, 2014.
G. M. Sheldrick. SHELXL-2014/7. Program for Refinement of Crystal Structures. University of Gongen: Gongen, Germany, 2014.
M. Frisch, G. Tracks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, and G. Petersson. Gaussian 09, Revision C.01, Gaussian, Wallingford, 2010.
A. Frish, A. B. Nielsen, and A. J. Holder. Gauss View User Manual, Gaussian Inc., Pittsburg, PA, 2011.
Y. Y. Liu, K. Z. Lv, Y. Li, Q. L. Nan, and J. Y. Xu. Chin. J. Struct. Chem., 2019, 38, 171–186.
B. J. Deppmeier, A. J. Driessen, T. S. Hehre, W. J. Hehre, J. A. Johnson, P. E. Klunzinger, J. M. Leonard, I. N. Pham, W. J. Pietro, and J. Yu. Spartan'08, Wavefunction Inc., Irvine, CA, 2009.
H. H. Brintzinger, M. H. Prosenc, F. Schaper, A. Weeber, and U. Wieser. J. Mol. Struct., 1999, 485-485, 409–419.
N. Huang, C. Kalyanaraman, K. Bernacki, and M. P. Jacobson. Phys. Chem. Chem. Phys., 2006, 8, 5166–5177.
Funding
This work was supported by the Major Social Development Project (SY20143054), the Science and Technology Program of Guizhou province ([2017] 1049) and the Science and Technology Cooperation Program of Guizhou province (LH20167442). The theoretical calculations were conducted on the ScGrid and Deepcomp7000 the Supercomputing Center, Computer Network Information Center of Chinese Academy of Sciences.
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The authors declare that they have no conflict of interests.
Text © The Author(s), 2019, published in Zhurnal Strukturnoi Khimii, 2019, Vol. 60, No. 12, pp. 2002-2009.
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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
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Qin, Y., Long, D., Zhu, X. et al. Synthesis, Crystal Structure, and DFT Study of a New Compound 6-(2-Fluorophenyl)-N-(p-Tolyl)Imidazo[1,2-A]Pyridine-2-Carboxamide. J Struct Chem 60, 1917–1924 (2019). https://doi.org/10.1134/S0022476619120072
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DOI: https://doi.org/10.1134/S0022476619120072