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SYNTHESIS, CHARACTERIZATION, THERMAL, X-RAY, AND DFT ANALYSES OF 6-TERT-BUTYL 3-ETHYL  2-[(3-METHOXY/5-BROMO)-2-HYDROXY AND (3-NITRO/3-METHOXY)BENZYLIDENEAMINO]-4,5-DIHYDROTHIENO[2,3-C]PYRIDINE-3,6(7H)-DICARBOXYLATE

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Abstract

In this work, 6-tert-butyl 3-ethyl 2-amino-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate is synthesized from starting tert-butyl 4-oxopiperidine-1-carboxylate, ethyl cyanomalonate, and sulfur, and then, coupled with same aromatic aldehyde affords the corresponding Schiff base compounds. These compounds (2a–d) are characterized using FTIR, 1H and 13C NMR spectroscopic methods. The crystal and molecular structure of (E)-6-tert-butyl 3-ethyl 2-((2-hydroxy-3-methoxybenzylidene)amino)-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate (2a) is characterized by the X-ray crystallographic analysis. Compound 2a crystallizes in the monoclinic space group P21/c. The molecular and crystal structure is stabilized by two O–H⋯N and O–H⋯O intramolecular hydrogen bonds (O⋯N and O⋯O are 2.598(5) Å and 2.990(5) Å, respectively; O–H⋯N = 147° and O–H⋯O = 134°). According to DFT, compound 2d also shows the intramolecular hydrogen bonding, while there is no this type of interaction in compound 2b and 2c.

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REFERENCES

  1. R. W. Sabnis, D. W. Rangnekar, and N. D. Sonawane. J. Heterocycl. Chem., 1999, 36, 333.

  2. G. G. Mohamed, M. M. Omar, and A. M. M. Hindy. Spectrochim. Acta, Part A: Mol. Biomol. Spectrosc., 2005, 62, 1140.

    Article  CAS  PubMed  Google Scholar 

  3. S. Kathiresan, S. Mugesh, J. Annaraj, and M. Murugan. New J. Chem., 2017, 41, 1267.

    Article  CAS  Google Scholar 

  4. A. S. Abu-Surrah, M. Kettunen, M. Leskela, and Y. Z. Al-Abed. Anorg. Allg. Chem., 2008, 634, 2655.

    Article  CAS  Google Scholar 

  5. D. R. Allen, A. Bolt, G. A. Chapman, R. L. Knight, J. W. G. Meissner, D. A. Owen, and R. J. Watson. Bioorg. Med. Chem. Lett., 2007, 17, 697.

    Article  CAS  Google Scholar 

  6. X. Hu and T. J. Maimone. J. Am. Chem. Soc., 2014, 136, 5287.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. L. G. Kapitsa, E. V. Suslov, G. V. Teplov, D. V. Korchagina, N. L. Komarova, K. P. Volcho, T. A. Voronina, A. I. Shevela, and N. F. Salakhutdinov. J. Pharm. Chem., 2012, 46, 263.

    Article  CAS  Google Scholar 

  8. K. Singh, M. S. Barwa, and P. Tyagi. Eur. J. Med. Chem., 2006, 41, 147.

    Article  CAS  PubMed  Google Scholar 

  9. S. N. Pandeya, D. Sriram, G. Nath, and E. D. Clercq. Eur. J. Pharm. Sci., 1999, 9, 25.

  10. P. K. Panchal, H. M. Parekh, and P. B. Pansuriya. J. Enzyme Inhib. Med. Chem., 2006, 21, 203.

    Article  CAS  PubMed  Google Scholar 

  11. S. M. Borisov, R. Saf, R. Fischer, and I. Klimant. Inorg. Chem., 2013, 52, 1206.

    Article  CAS  PubMed  Google Scholar 

  12. J. Chai, Y. Wu, B. Yang, and B. Liu. J. Mater. Chem., C, 2018, 6, 4057.

    Article  CAS  Google Scholar 

  13. M. Yan, T. Li, and Z. Yang. Inorg. Chem. Commun., 2011, 3, 463.

  14. X. Tang, J. Han, Y. Wang, L. Ni, X. Bao, L. Wang, and W. Zhang. Spectrochim. Acta, Part. A: Mol. Biomol. Spectrosc., 2017, 173, 721.

    Article  CAS  PubMed  Google Scholar 

  15. C. Pan, K. Wang, S. Ji, H. Wang, Z. Li, H. He, and Y. Huo. RSC Adv., 2017, 7, 36007.

    Article  CAS  Google Scholar 

  16. V. Nishal, D. Singh, A. Kumar, V. Tanwar, I. Singh, R. Srivastava, and P. S. Kadyan. J. Org. Semicond., 2014, 2, 15.

    Article  CAS  Google Scholar 

  17. J. H. Jia, X. M. Tao, Y. J. Li, and W. J. Sheng. Chem. Phys. Lett., 2011, 524, 114.

  18. W. A. Zoubi and Y. G. Ko. Appl. Organomet. Chem., 2017, 31, 3574.

    Article  CAS  Google Scholar 

  19. A. W. Jeevadason, K. K. Murugavel, and M. A. Neelakantan. Renewable Sustainable Energy Rev., 2014, 36, 220.

    Article  CAS  Google Scholar 

  20. J. Zhang, L. Xu, and W. Y. Wong. Coord. Chem. Rev., 2018, 355, 180.

    Article  CAS  Google Scholar 

  21. M. Sedighipoor, A. H. Kianfar, G. Mohammadnezhad, H. Gorls, and W. Plass. Inorg. Chim. Acta, 2018, 476, 20.

    Article  CAS  Google Scholar 

  22. N. Raman, R. Jeyamurugan, R. Senthilkumar, B. Rajkapoor, and S. G. Franzblau. Eur. J. Med. Chem., 2010, 45, 5438.

    Article  CAS  PubMed  Google Scholar 

  23. M. Mesbah, T. Douadi, F. Sahli, S. Issaadi, S. Boukazoula, and S. Chafaa. J. Mol. Struct., 2018, 1151, 41.

    Article  CAS  Google Scholar 

  24. M. Mohamadi, S. Y. Ebrahimipour, M. Torkzadeh-Mahani, S. Foro, and A. Akbari. RSC Adv., 2015, 5, 101063.

    Article  CAS  Google Scholar 

  25. M. Z. Ghdhayeb, R. A. Haque, S. Budagumpi, M. B. Khadeer Ahamed, and A. M. S. A. Majid. Inorg. Chem. Commun., 2017, 75, 41.

    Article  CAS  Google Scholar 

  26. N. P. Peet, S. Sunder, R. J. Barbuch, and A. P. Vinogradoff. J. Heterocycl. Chem., 1986, 23, 129–134.

    Article  CAS  Google Scholar 

  27. APEX2, SAINT and SADABS. Bruker AXS: Madison, Wisconsin, USA, 2012.

  28. G. M. Sheldrick. SHELXS97. Univ. of Göttingen: Germany:, 1997.

  29. G. M. Sheldrick. SHELXL97. Univ. of Göttingen: Germany:, 1997.

  30. C. K. Johnson. ORTEP, Report ORNL-3794. Oak Ridge National Laboratory: Tenessee, USA, 1965.

  31. M. Nardelli. J Appl. Crystallogr., 1995, 28, 659.

    Article  CAS  Google Scholar 

  32. A. L Spek. PLATON. University of Utrecht: The Netherlands, 2003.

  33. P. Walters, M. Stahl. Babel, Version 1.1. Tucson, AZ: Department of Chemistry, University of Arizona, 1994.

  34. D. Roy, K. Todd, M. John. GaussView, Version 5. Shawnee Mission, KS: Semichem, 2009.

  35. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox. Gaussian 09, Revision C.01. Gaussian: Wallingford, CT, 2010.

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Funding

The authors acknowledge the Aksaray University Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State of Planning Organization). The numerical calculations reported in this paper were fully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Hitit University, Corum, Turkey

    N. Çolak

  2. Department of Physics, Faculty of Arts and Sciences, Hitit University, Corum, Turkey

    A. Karayel

  3. Department of Food Processing, Technical Science Vocational School, Muş Alparslan University, Muş, Turkey

    K. Buldurun

  4. Department of Chemistry, Faculty of Arts and Sciences, Muş Alparslan University, Muş, Turkey

    N. Turan

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  1. N. Çolak
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  2. A. Karayel
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Correspondence to N. Çolak.

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Çolak, N., Karayel, A., Buldurun, K. et al. SYNTHESIS, CHARACTERIZATION, THERMAL, X-RAY, AND DFT ANALYSES OF 6-TERT-BUTYL 3-ETHYL  2-[(3-METHOXY/5-BROMO)-2-HYDROXY AND (3-NITRO/3-METHOXY)BENZYLIDENEAMINO]-4,5-DIHYDROTHIENO[2,3-C]PYRIDINE-3,6(7H)-DICARBOXYLATE. J Struct Chem 62, 37–46 (2021). https://doi.org/10.1134/S0022476621010054

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