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Modified synthesis and structural features of 2-benzylidene-4-nitro-2,5-dihydrothiophene 1,1-dioxides

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Chemistry of Heterocyclic Compounds Aims and scope

A modified procedure for achieving condensation reactions between 3-methyl-4-nitro-2,5-dihydrothiophene 1,1-dioxide and aromatic aldehydes was used to synthesize a broad range of previously unknown 2-benzylidene-4-nitro-2,5-dihydrothiophene 1,1-dioxides – promising substrates for the assembly of fused polycyclic nitrosulfolane derivatives. The structural features of the obtained nitrosulfodienes were established on the basis of IR spectra, 1Н and 13С NMR spectra, two-dimensional 1Н–13С HMQC and 1Н–13С HMBC experiments, quantum-chemical calculations, and X-ray structural analysis.

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References

  1. (a) Halimehjani, A. Z.; Namboothiri, I. N. N.; Hooshmand S. E. RSC Adv. 2014, 4, 31261. (b) Halimehjani, A. Z.; Namboothiri, I. N. N.; Hooshmand, S. E. RSC Adv. 2014, 4, 48022. (c) Halimehjani, A. Z.; Namboothiri, I. N. N.; Hooshmand, S. E. RSC Adv. 2014, 4, 51794.

  2. Brant, M. G.; Wulff, J. E. Org. Lett. 2012, 14, 5876.

    Article  CAS  Google Scholar 

  3. Efremova, I. E.; Lapshina, L. V.; Baichurin, R. I.; Serebryannikova, A. V.; Savelev, I. I. Russ. J. Gen. Chem. 2020, 90, 1369. [Zh. Obshch. Khim. 2020, 90, 1153.]

  4. Berestovitskaya, V. M.; Efremova, I. E.; Lapshina, L. V.; Serebryannikova, A. V.; Gurzhiy, V. V.; Abzianidze, V. V. Mendeleev Commun. 2015, 25, 191.

    Article  CAS  Google Scholar 

  5. Efremova, I. E.; Serebryannikova, A. V.; Lapshina, L. V.; Gurzhiy, V. V.; Berestovitskaya, V. M. Russ. J. Gen. Chem. 2016, 86, 622. [Zh. Obshch. Khim. 2016, 86, 481.]

  6. Efremova, I. E.; Serebryannikova, A. V.; Belyakov, A. V.; Lapshina, L. V. Russ. J. Gen. Chem. 2019, 89, 536. [Zh. Obshch. Khim. 2019, 89, 468.]

  7. Efremova, I. E.; Serebryannikova, A. V.; Lapshina, L. V.; Gurzhiy, V. V.; Ryabin, A. E. Chem. Heterocycl. Compd. 2019, 55, 902. [Khim. Geterotsikl. Soedin. 2019, 55, 902.]

  8. Efremova, I. E.; Serebryannikova, A. V.; Lapshina, L. V.; Savelev, I. I. Russ. J. Gen. Chem. 2020, 90, 2522. [Zh. Obshch. Khim. 2020, 90, 1958.]

  9. Berestovitskaya, V. M.; Efremova, I. E.; Serebryannikova, A. V.; Lapshina, L. V.; Gurzhiy, V. V. Chem. Heterocycl. Compd. 2018, 54, 76. [Khim. Geterotsikl. Soedin. 2018, 54, 76.]

  10. Berestovitskaya, V. M.; Selivanova, M. V.; Vakulenko, M. I.; Efremova, I. E.; Berkova, G. A. Russ. J. Org. Chem. 2009, 45, 1814. [Zh. Org. Khim. 2009, 45, 1818.]

  11. Korotchenko, V. N.; Nenajdenko, V. G.; Balenkova, E. S.; Shastin, A. V. Russ. Chem. Rev. 2004, 73, 957. [Usp. Khim. 2004, 73, 1039.]

  12. Perekalin, V. V.; Lipina, E. S.; Berestovitskaya, V. M.; Efremov, D. A. Nitroalkenes. Conjugated Nitro Сompounds; New York; London: Willey & Sons, 1994.

    Google Scholar 

  13. Vasil'eva, M. V.; Berestovitskaya, V. M.; Berkova, G. A.; Pozdnyakov, V. P. J. Org. Chem. USSR 1986, 22, 379. [Zh. Org. Khim. 1986, 22, 428.]

  14. Bortnikov, S. V.; Efremova, I. E.; Berestovitskaya, V. M. Chem. Heterocycl. Compd. 2001, 37, 775. [Khim. Geterotsikl. Soedin. 2001, 840.]

  15. Lapshina, L. V.; Serebryannikova, A. V.; Efremova, I. E.;Perkhunova, A. D.; Bortnikov, S. V.; Berestovitskaya, V. M. Russ. J. Gen. Chem. 2014, 84, 1519. [Zh. Obshch. Khim. 2014, 84, 1293.]

  16. van Beurden, K.; de Koning, S.; Molendijk, D.; van Schijndel, J. Green Chem. Lett. Rev. 2020, 13, 349.

    Article  Google Scholar 

  17. Berestovitskaya, V. M. Russ. J. Gen. Chem. 2000, 70, 1419. [Zh. Obshch. Khim. 2000, 70, 1512.]

  18. CrysAlisPro, Version 1.171.38.46; Rigaku Oxford Diffraction, 2015.

  19. Sheldrick, G. M. Acta Crystallogr., Sect. A: Struct. Chem.2015, A71, 3.

  20. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem.2015, C71, 3.

  21. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

  22. 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. V.; 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.; Ranasinghe, D.; 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. J.; Heyd, J. J.; Brothers, E. N.; Kudin, K. N.; Staroverov, V. N.; Keith, T. A.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; 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 16, Revision C.01; Gaussian, Inc.: Wallingford, 2019.

  23. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.

    Article  CAS  Google Scholar 

  24. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104.

    Article  Google Scholar 

  25. McLean, A.D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, 48 Moyka River Embankment, Saint Petersburg, 191186, Russia

    Igor I. Savelev & Irina E. Efremova

  2. S. M. Kirov Military Medical Academy, 6 Akademika Lebedeva St, Saint Petersburg, 194044, Russia

    Lidiya V. Lapshina

  3. Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg, 199034, Russia

    Vladislav V. Gurzhiy

  4. Saint Petersburg State Institute of Technology (Technical University), 26 Moskovskii Ave, Saint Petersburg, 190013, Russia

    Alexander V. Belyakov

Authors
  1. Igor I. Savelev
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  2. Irina E. Efremova
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  3. Lidiya V. Lapshina
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  4. Vladislav V. Gurzhiy
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  5. Alexander V. Belyakov
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Correspondence to Irina E. Efremova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(7/8), 861–865

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Savelev, I.I., Efremova, I.E., Lapshina, L.V. et al. Modified synthesis and structural features of 2-benzylidene-4-nitro-2,5-dihydrothiophene 1,1-dioxides. Chem Heterocycl Comp 57, 861–865 (2021). https://doi.org/10.1007/s10593-021-02992-6

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  • DOI: https://doi.org/10.1007/s10593-021-02992-6

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