Russian Journal of Organic Chemistry

, Volume 51, Issue 8, pp 1101–1110 | Cite as

Heterocumulenes reactions with organometallic reagents XXIII. Quantum-chemical study of structural transformations of (propargylsulfanyl)-substituted 2-Aza-1,3,5-triene treated with potassium tert-butoxide

Article

Abstract

Quantum-chemical B3LYP/6-31G(d,p) method was applied to the investigation of the formation of 4,5-dihydro-3H-azepine and/or 4,5-dihydro-1,3-thiazole structures from (propargylsulfanyl)-substituted 2-aza-1,3,5-triene at treatment with potassium tert-butoxide. According to the calculation the formation of 4,5-dihydro-1,3-thiazole ring prevailed.

Keywords

Thiazole Propargyl Sulfanyl Thiazole Ring Ketimine 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Shagun, V.A. and Nedolya, N.A., Russ. J. Org. Chem., 2015, vol. 51, p. 504.CrossRefGoogle Scholar
  2. 2.
    Nedolya, N.A., Novel Chemistry Based on Isothiocyanates and Polar Organometallics, Ph.D Thesis of Utrecht University. The Netherlands: Utrecht, 1999.Google Scholar
  3. 3.
    Brandsma, L., Nedolya, N.A., Tarasova, O.A., and Trofimov, B.A., Chem. Heterocycl. Compd., 2000, vol. 36, p. 1241.CrossRefGoogle Scholar
  4. 4.
    Brandsma, L. and Nedolya, N.A., Synthesis, 2004, p. 735.Google Scholar
  5. 5.
    Brandsma, L., Nedolya, N.A., Verkruijsse, H.D., Owen, N.L., Li, Du, and Trofimov, B.A., Tetrahedron Lett., 1997, vol. 38, p. 6905.CrossRefGoogle Scholar
  6. 6.
    Nedolya, N.A., Brandsma, L., Tarasova, O.A., Albanov, A.I., and Trofimov, B.A., Russ. J. Org. Chem., 2011, vol. 47, p. 659.CrossRefGoogle Scholar
  7. 7.
    Nedolya, N.A., Dmitrieva, L.L., Albanov, A.I., Klyba, L.V., Tarasova, O.A., and Ushakov, I.A., Russ. J. Org. Chem., 2006, vol. 42, p. 465.CrossRefGoogle Scholar
  8. 8.
    Nedolya, N.A., Tarasova, O.A., Volostnykh, O.G., Albanov, A.I., and Trofimov, B.A., J. Organometal. Chem., 2011, vol. 696, p. 3359.CrossRefGoogle Scholar
  9. 9.
    Nedolya, N.A., Tarasova, O.A., Albanov, A.I., Volostnykh, O.G., Brandsma, L., and Trofimov, B.A., Mendeleev Commun., 2008, vol. 18, p. 164.CrossRefGoogle Scholar
  10. 10.
    Nedolya, N.A., Tarasova, O.A., Volostnykh, O.G., and Albanov, A.I., Chem. Heterocycl. Compd., 2008, vol. 44, p. 1113.CrossRefGoogle Scholar
  11. 11.
    Nedolya, N.A., Tarasova, O.A., Albanov, A.I., Klyba, L.V., and Trofimov, B.A., Russ. J. Gen. Chem., 2009, vol. 79, p. 1041.CrossRefGoogle Scholar
  12. 12.
    Nedolya, N.A., Volostnykh, O.G., Tarasova, O.A., Albanov, A.I., and Trofimov, B.A., Russ. Chem. Bull., 2011, vol. 60, p. 2617.CrossRefGoogle Scholar
  13. 13.
    Nedolya, N.A., Tarasova, O.A., Volostnykh, O.G., Albanov, A.I., Klyba, L.V., and Trofimov, B.A., Synthesis, 2011, p. 2192.Google Scholar
  14. 14.
    Nedolya, N.A. and Trofimov, B.A., Chem. Heterocycl. Compd., 2013, vol. 49, p. 152.CrossRefGoogle Scholar
  15. 15.
    Nedolya, N.A., Tarasova, O.A., and Volostnykh, O.G., Strukturnaya reorganizatsiya azatrienovykh system v azepiny, LAP Lambert Academic Publishing, 2014.Google Scholar
  16. 16.
    Tarasova, O.A., Nedolya, N.A., Volostnykh, O.G., and Trofimov, B.A., Khimiya geterotsiklicheskikh soedinenii. Sovremennye aspekty, Kartsev, V.G., Ed., Moscow: MBFNP, 2014, vol. 2.Google Scholar
  17. 17.
    Nedolya, N.A. and Trofimov, B.A., Khimiya geterotsiklicheskikh soedinenii. Sovremennye aspekty, Kartsev, V.G., Ed., Moscow: MBFNP, 2014, vol. 1.Google Scholar
  18. 18.
    Nedolya, N.A., Tarasova, O.A., Albanov, A.I., and Trofimov, B.A., Russ. J. Org. Chem., 2013, vol. 49, p. 1491.CrossRefGoogle Scholar
  19. 19.
    Nedolya, N.A., Tarasova, O.A., Albanov, A.I., and Trofimov, B.A., Tetrahedron Lett., 2014, vol. 55, p. 2495.CrossRefGoogle Scholar
  20. 20.
    Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648.CrossRefGoogle Scholar
  21. 21.
    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Gaussian 09, Revision A.01, Gaussian, Inc., Wallingford, 2009.Google Scholar
  22. 22.
    Peng, C. and Schlegal, H.B., Israel J. Chem., 1993, vol. 33, p. 449.CrossRefGoogle Scholar
  23. 23.
    De Meijere, A., Faber, D., Heinecke, U., Walsh, R., Müller, T., and Apeloig, Y., Eur. J. Org. Chem., 2001, p. 663.Google Scholar
  24. 24.
    Kakkar, R. and Padhi, B.S., Ind. J. Chem., 1999, vol. 38B, p. 1262.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2015

Authors and Affiliations

  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian BranchRussian Academy of SciencesIrkutskRussia

Personalised recommendations