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Some Features of the Reactions of 3-Nitro-6-phenylhexa-3,5-dien-2-one with Thiophenols

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Abstract

The reaction of 3-nitro-6-phenylhexa-3,5-diene-2-one with 4-methyl- and 4-chlorothiophenols yields 1,4- and 1,6-addition products at conjugated dienone system. By the example of the 1,4-addition adduct of 4-methylthiophenol, its conversion in solution to the 1,6-addition product was shown. 4-Methyl-3-nitro-2-styryl-2,3-dihydrobenzo[b][1,4]thiazepine was synthesized by reacting 3-nitro-6-phenylhexa-3,5-dien-2-one with o-aminothiophenol.

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REFERENCES

  1. Csákÿ, A.G., de la Herrána, G., and Murcia, M.C., Chem. Soc. Rev., 2010, vol. 39, no. 11, p. 4080. https://doi.org/10.1039/B924486G

    Article  PubMed  Google Scholar 

  2. Silva, E.M.P. and Silva, A.M.S., Synthesis, 2012, vol. 44, no. 20, p. 3109. https://doi.org/10.1055/s-0032-1316778

    Article  CAS  Google Scholar 

  3. Kowalczyk, R. and Boratyński, P.J., Adv. Synth. Catal., 2016, vol. 358, no. 8, p. 1289. https://doi.org/10.1002/adsc.201501138

    Article  CAS  Google Scholar 

  4. Shaw, S. and White, J.D., Synthesis, 2016, vol. 48, no. 17, p. 2768. https://doi.org/10.1055/s-0035-1562103

    Article  CAS  Google Scholar 

  5. Kaberdin, R.V., Potkin, V.I., and Zapol’skii, V.A., Russ. Chem. Rev., 1997, vol. 66, no. 10, p. 827. https://doi.org/10.1070/RC1997v066n10ABEH000310

    Article  Google Scholar 

  6. Ballini, R., Araújo, N., Gil, M.V., Román, E., and Serrano, J.A., Chem. Rev., 2013, vol. 113, no. 5, p. 3493. https://doi.org/10.1021/cr2002195

    Article  CAS  PubMed  Google Scholar 

  7. Peng, J. and Du, D.-M., Eur. J. Org. Chem., 2012, no. 21, p. 4042. https://doi.org/10.1002/ejoc.201200382

    Article  CAS  Google Scholar 

  8. Bianchi, L., Giorgi, G., Maccagno, M., Petrillo, G., Scapolla, C., and Tavani, C., Tetrahedron Lett., 2012, vol. 53, no. 7, p. 752. https://doi.org/10.1016/j.tetlet.2011.11.137

    Article  CAS  Google Scholar 

  9. Muruganantham, R. and Namboothiri, I., J. Org. Chem., 2010, vol. 75, no. 5, p. 2197. https://doi.org/10.1021/jo902595e

    Article  CAS  PubMed  Google Scholar 

  10. He, T. and Wu, X.-Y., Synth. Commun., 2012, vol. 42, no. 5, p. 667. https://doi.org/10.1080/00397911.2010.529227

    Article  CAS  Google Scholar 

  11. Vamisetti, G.B., Chowdhury, R., Kumar, M., and Ghosh, S.K., Org. Lett., 2016, vol. 18, no. 9, p. 1964. https://doi.org/10.1021/acs.orglett.6b00460

    Article  CAS  PubMed  Google Scholar 

  12. Shi, D., Xie, Y., Zhou, H., Xia, C., and Huang, H., Angew. Chem. Int. Ed., 2012, vol. 51, no. 5, p. 1248. https://doi.org/10.1002/anie.201107495

    Article  CAS  Google Scholar 

  13. Tsakos, M., Elsegood, M.R.J., and Kokotos, C.G., Chem. Commun., 2013, vol. 49, no. 22, p. 2219. https://doi.org/10.1039/C3CC39165E

    Article  CAS  Google Scholar 

  14. Ayyagari, N., Jose, D., Mobin, S.M., and Namboothiri, I.N.N., Tetrahedron Lett., 2011, vol. 52, no. 2, p. 258. https://doi.org/10.1016/j.tetlet.2010.11.017

    Article  CAS  Google Scholar 

  15. Biswas, S., Dagar, A., Srivastava, A., and Samanta, S., Eur. J. Org. Chem., 2015, no. 20, p. 4493. https://doi.org/10.1002/ejoc.201500470

    Article  CAS  Google Scholar 

  16. Tissot, M. and Alexakis, A., Chem. Eur. J., 2013, vol. 19, no. 34, p. 11352. https://doi.org/10.1002/chem.201300538

    Article  CAS  PubMed  Google Scholar 

  17. Vil’davskaya, A.I., Rall’, K.B., and Petrov, A.A., J. Org. Chem. USSR, 1967, vol. 3, no. 3, p. 418.

    Google Scholar 

  18. Bloom, A.A. and Mellor, J.M., Tetrahedron Lett., 1986, vol. 27, no. 7, p. 873. https://doi.org/10.1016/S0040-4039(00)84124-6

    Article  CAS  Google Scholar 

  19. Bloom, A.J. and Mellor, J.M., J. Chem. Soc. Perkin Trans. 1, 1987, no. 12, p. 2737. https://doi.org/10.1039/p19870002737

    Article  Google Scholar 

  20. Kowalczyk, R., Nowak, A.E., and Skarzewski, J., Tetrahedron Asym., 2013, vol. 24, no. 8, p. 505. https://doi.org/10.1016/j.tetasy.2013.03.007

    Article  CAS  Google Scholar 

  21. Yang, W. and Du, D.-M., Org. Biomol. Chem., 2012, vol. 10, no. 34, p. 6876. https://doi.org/10.1039/C2OB26068A

    Article  CAS  PubMed  Google Scholar 

  22. Wu, L., Wang, Y., Song, H., Tang, L., Zhou, Z., and Tang, C., Adv. Synth. Cat., 2013, vol. 355, no. 6, p. 1053. https://doi.org/10.1002/adsc.201300086

    Article  CAS  Google Scholar 

  23. Baichurin, R.I., Alizada, L.M., Aboskalova, N.I., and Makarenko, S.V., Russ. J. Gen. Chem., 2018, vol. 88, no. 1, p. 36. https://doi.org/10.1134/S1070363218010061

    Article  CAS  Google Scholar 

  24. Baichurin, R.I., Aboskalova, N.I., Alizada, L.M., Berestov, I.V., and Berestovitskaya, V.M., Russ. J. Org. Chem., 2016, vol. 52, no. 6, p. 818. https://doi.org/10.1134/S1070428016060099

    Article  CAS  Google Scholar 

  25. Baichurin, R.I., Baichurina, L.V., Aboskalova, N.I., Trukhin, E.V., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2014, vol. 84, no. 7, p. 1277. https://doi.org/10.1134/S1070363214070056

    Article  CAS  Google Scholar 

  26. Baichurin, R.I., Aboskalova, N.I., and Berestovitskaya, V.M., Russ. J. Org. Chem., 2010, vol. 46, no. 10, p. 1590. https://doi.org/10.1134/S1070428010100295

    Article  CAS  Google Scholar 

  27. Berestovitskaya, V.M., Baichurin, R.I., Aboskalova, N.I., Lysenko, K.A., and Anan’ev, I.V., Russ. J. Gen. Chem., 2011, vol. 81, no. 6, p. 1163. https://doi.org/10.1134/S1070363211060156

    Article  CAS  Google Scholar 

  28. Berestovitskaya, V.M., Baichurin, R.I., Aboskalova, N.I., and Gurzhiy, V.V., Mendeleev Commun., 2014, vol. 24, no. 6, p. 380. https://doi.org/10.1016/j.mencom.2014.11.025

    Article  CAS  Google Scholar 

  29. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2012.

  30. Chaffman, M. and Brogden, R.N., Drugs, 1985, vol. 29, no. 5, p. 387. https://doi.org/10.2165/00003495-198529050-00001

    Article  CAS  PubMed  Google Scholar 

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Funding

This work was financially supported by the Russian Foundation for Basic Research (project no. 18-33-01017).

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Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, 191186, St. Petersburg, Russia

    R. I. Baichurin, V. D. Sergeev, N. I. Aboskalova & S. V. Makarenko

  2. Kirov Military Medical Academy, 194044, St. Petersburg, Russia

    L. V. Baichurina

Authors
  1. R. I. Baichurin
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  2. V. D. Sergeev
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  3. N. I. Aboskalova
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  4. L. V. Baichurina
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  5. S. V. Makarenko
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Correspondence to S. V. Makarenko.

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Baichurin, R.I., Sergeev, V.D., Aboskalova, N.I. et al. Some Features of the Reactions of 3-Nitro-6-phenylhexa-3,5-dien-2-one with Thiophenols. Russ J Gen Chem 90, 769–772 (2020). https://doi.org/10.1134/S1070363220050011

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