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1,3-Dipolar cycloaddition of (E)-4-(4-chlorophenyl)-2-oxobut-3-enic acid to 2-oxindole azomethine ylides

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Chemistry of Heterocyclic Compounds Aims and scope

The α-keto carboxylic acid motif has been embedded to the novel spirooxindolepyrrolizidines via a three-component 1,3-dipolar cycloaddition of 2-oxindole azomethine ylides generated in situ from isatin and proline with (E)-4-(4-chlorophenyl)-2-oxo-but-3-enoic acid as dipolarophile. The stereochemistry of cycloaddition was confirmed by NMR spectra data as well as with the calculations of the geometrical structures of all possible conformers and charge distribution in the reacting systems by means of M06-2X /cc-pVTZ basis set in the Gaussian 09 program.

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References

  1. Wu, G.; Ouyang, L.; Liu, J.; Zeng, S.; Huang, W.; Han, B.; Wu, F.; He, G.; Xiang, M. Mol. Diversity 2013, 17, 271.

    Article  CAS  Google Scholar 

  2. Pavlovska, T. L.; Redkin, R. G.; Lipson, V. V.; Atamanuk, D. V. Mol. Diversity 2016, 20, 299.

    Article  CAS  Google Scholar 

  3. Ye, N.; Chen, H.; Wold, E. A.; Shi, P.-Y.; Zhou, J. ACS Infect. Dis. 2016, 2, 382.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Wu, J. S.; Zhang, X.; Zhang, Y. L.; Xie, J. W. Org Biomol. Chem. 2015, 13, 4967.

    Article  CAS  PubMed  Google Scholar 

  5. Wu, L.; Liu, Y.; Li, Y. Molecules 2018, 23, 2330.

    Article  CAS  PubMed Central  Google Scholar 

  6. Rouatbi, F.; Askri, M.; Nana, F.; Kirsch, G.; Sriram, D.; Yogeeswari, P. Tetrahedron Lett. 2016 , 57, 163.

    Article  CAS  Google Scholar 

  7. Taghizadeh, M. J.; Javidan, A.; Keshipour, S. Chem. Heterocycl. Compd. 2015, 51, 467. [Khim. Geterotsikl. Soed. 2015, 51, 467.]

  8. Fokas, D.; Ryan, W. J.; Casebier, D. S.; Coffen, D. L. Tetrahedron Lett. 1998, 39, 2235.

    Article  CAS  Google Scholar 

  9. El-Ahl, A.-A. S. Heteroat. Chem. 2002, 13, 324.

    Article  CAS  Google Scholar 

  10. Hazra, A.; Paira, P.; Sahu Kr, B.; Naskar S.; Saha Pr.; Paira R.; Mondal Sh.; Maity A.; Luger P.; Weber M.; Mondal N. B.; Banerjee S. Tetrahedron Lett. 2010, 51, 1585.

  11. Babu, S. R.; Raghunathan, R. Tetrahedron Lett. 2008, 49, 4618.

    Article  CAS  Google Scholar 

  12. Dandia, A.; Jain, A. K.; Bhati, D. S. Tetrahedron Lett. 2011, 52, 5333.

    Article  CAS  Google Scholar 

  13. Ponnala, S.; Kumar, R.; Maulik, P. R.; Sahu, D. P. J. Heterocycl. Chem. 2006, 43, 1635.

    Article  CAS  Google Scholar 

  14. Shvets, A.; Kurbatov, S. V. Chem. Heterocycl. Compd. 2009, 45, 866. [Khim. Geterotsikl. Soedin. 2009, 1087.]

  15. Poornachandran, M.; Raghunathan, R. Synth. Commun. 2007, 37, 2507.

    Article  CAS  Google Scholar 

  16. Grigg, R. Bull. Soc. Chim. Belges. 1984, 93, 593.

    Article  CAS  Google Scholar 

  17. Faraji, L.; Arvinnezhad, H.; Alikami, N.; Jadidi, K. Lett. Org. Chem. 2010, 7, 472.

    Article  CAS  Google Scholar 

  18. Pavlovskaya, T. L.; Yaremenko, F. G.; Lipson, V. V.; Shishkina, S. V.; Shishkin, O. V.; Musatov, V. I.; Karpenko, A. S. Beilstein J. Org. Chem. 2014, 10, 117.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215.

    Article  CAS  Google Scholar 

  20. Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. J. J. Chem. Phys. 1992, 6796.

  21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Li, X.; Caricato, M.; Marenich, A.; Bloino, J.; Janesko, B. G.; Gomperts, R.; Mennucci, B.; Hratchian, H. P.; Ortiz, J. V.; Izmaylov, A. F.; Sonnenberg, J. L.; Williams-Young, D.; Ding, F.; Lipparini, F.; Egidi, F.; Goings, J.; Peng, B.; Petrone, A.; Henderson, T.; Zakrzewski, V. G.; Gao, J.; Rega, N.; Zheng, G.; Liang, W.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Throssell, K.; Montgomery, J. A. Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Millam, J. M.; Klene, M.; Adamo, C.; Cammi, R.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Farkas, O.; Foresman, J. B.; Fox, D. J. Gaussian 09, Revision B.01; Gaussian, Inc.: Wallingford, 2010.

    Google Scholar 

  22. Weinhold, F. In Encyclopedia of Computational Chemistry; Schleyer, P. V. R.; Allinger, N. L.; Clark, T.; Gasteiger, P. A.; Kollman, J.; Schaefer, H. F., III; Schreiner, P. R., Eds.; John Wiley & Sons: Chichester, 1998, p. 1792.

    Google Scholar 

  23. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO 5.0 ; Theoretical Chemistry Institute, University of Wisconsin: Madison, 2001.

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Authors thank National Academy of Sciences of Ukraine for financial support in the frame of the projects “Creation of modern bases for obtaining and analyzing substances and components of materials for pharmaceutical purposes” (0119U100727) and “Investigation of structural features of nitrogen-containing heterocycles with potential biological activity” (0119U100716).

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Authors and Affiliations

  1. SSI “Institute for Single Crystals”, National Academy of Sciences of Ukraine, 60 Nauky Ave, Kharkiv, 61074, Ukraine

    Tetiana L. Pavlovska, Victoria V. Lipson, Svetlana V. Shishkina & Vladimir I. Musatov

  2. Antidiabetic Drug Laboratory, SI “V. Ya. Danilevsky Institute for Endocrine Pathology Problems”, Academy of Medical Sciences of Ukraine, 10 Alchevskih St, Kharkiv, 61002, Ukraine

    Victoria V. Lipson

  3. Chemistry Department, V. N. Karazin Kharkiv National University, 4 Svobody Sq, Kharkiv, 61022, Ukraine

    Tetiana L. Pavlovska, Victoria V. Lipson & Svetlana V. Shishkina

  4. Enamine Ltd, 23 Chervonotkatska St, Kyiv, 01003, Ukraine

    Alexander V. Borisov

  5. A.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, 86 Lustdorfska Road, Odessa, 65080, Ukraine

    Alexander V. Mazepa

Authors
  1. Tetiana L. Pavlovska
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  2. Victoria V. Lipson
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  3. Svetlana V. Shishkina
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  4. Vladimir I. Musatov
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  5. Alexander V. Borisov
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  6. Alexander V. Mazepa
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Correspondence to Tetiana L. Pavlovska.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 679–683

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Pavlovska, T.L., Lipson, V.V., Shishkina, S.V. et al. 1,3-Dipolar cycloaddition of (E)-4-(4-chlorophenyl)-2-oxobut-3-enic acid to 2-oxindole azomethine ylides. Chem Heterocycl Comp 55, 679–683 (2019). https://doi.org/10.1007/s10593-019-02517-2

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  • DOI: https://doi.org/10.1007/s10593-019-02517-2

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