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Dehydrogenation of 1-aryl(hetaryl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acids and their esters with dimethyl sulfoxide

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Abstract

Oxidative dehydrogenation of 1-aryl(hetaryl)-1,2,3,4-tetrahydro-9Н-β-carboline-3-carboxylic acids derivatives with dimethyl sulfoxide leads to the formation of 1-aryl(hetaryl)-9Н-β-carbolines. Simultaneously with the dehydrogenation decarboxylation occurs. At the oxidation with dimethyl sulfoxide of methyl 1-aryl (hetaryl)-1,2,3,4-tetrahydro-9Н-β-carboline-3-carboxylicates methyl 1-aryl(hetaryl)-9Н-β-carboline-3-carboxylates formed whose hydrolysis afforded the corresponding 1-aryl(hetaryl)-9Н-β-carboline-3-carboxylic acids.

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References

  1. Pfitzner, K.E. and Moffatt, J.G., J. Am. Chem. Soc., 1963, vol. 85, p. 3027.

    Google Scholar 

  2. Omura, K. and Swern, D., Tetrahedron, 1978, vol. 34, p. 1651.

    Article  CAS  Google Scholar 

  3. Sanz, R., Aguado, R., Pedrosa, M.R., and Arnaiz, F.J., Synthesis, 2002, vol. 7, p. 856.

    Article  Google Scholar 

  4. Le, H.V. and Ganem, B., Org. Lett., 2011, vol. 13, p. 2584.

    Article  CAS  Google Scholar 

  5. Mupparapu, N., Khan, S., Battula, S., Kushwaha, M., Gupta, A.P., Ahmed, Q.N., and Vishwakarma, R.A., Org. Lett., 2014, vol. 16, p. 1152.

    Article  CAS  Google Scholar 

  6. Wu, X., Gao, Q., Liu, S., and Wu, A., Org. Lett., 2014, vol. 16, p. 2888.

    Article  CAS  Google Scholar 

  7. Lomov, D.A., Abramyants, M.G., Astashkina, N.V., Korotkikh, N.I., and Gres’ko, S.V., Russ. J. Org. Chem., 2014, vol. 50, p. 1039.

    Article  CAS  Google Scholar 

  8. Ungemach, F., Soerens, D., Weber, R., DiPierro, M., Campos, O., Mokry, P., Cook, J.M., and Silverton, J.V., J. Am. Chem. Soc., 1980, vol. 102, p. 6976.

    Article  CAS  Google Scholar 

  9. Toth, G., Szantay, J.C., Kalaus, G., Thaler, G., and Snatzke, G., J. Chem. Soc., Perkin. Trans. 2, 1989, p. 1849.

    Google Scholar 

  10. Bailey, P.D. and Hollinshead, S.P., J. Chem. Soc. Chem. Commun., 1985, p. 1575.

    Google Scholar 

  11. Braibanti, A., Dallavalle, F., Leporati, E., and Mori, G., J. Chem. Soc., Dalton Trans., 1973, p. 323.

    Google Scholar 

  12. Organikum, Moscow: Mir, 2008, vol. 2, p. 76.

  13. Organikum, Moscow: Mir, 2008, vol. 2, p. 93.

  14. Soerens, D., Sandrin, J., Ungemach, F., Mokry, P., Wu, G.S., Yamanaka, E., Hutchins, L., DiPierro, M., and Cook, J.M., J. Org. Chem., 1979, vol. 44, p. 535.

    Article  CAS  Google Scholar 

  15. Snyder, H.R., Hansch, C.H., Katz, L., Parmerter, S.M., and Spaeth, E.C., J. Am. Chem. Soc., 1948, vol. 44, p. 219.

    Article  Google Scholar 

  16. Cain, M., Weber, R.W., Guzman, F., Cook, J.M., Barker, A.S., Rice, K.C., Crawley, N.J., Paul, S.M., and Scolnick, P., J. Med. Chem., 1982, vol. 25, p. 1081.

    Article  CAS  Google Scholar 

  17. Cain, M., Campos, O., Guzman, F., and Cook, J.M., J. Am. Chem. Soc., 1983, vol. 105, p. 907.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, ul. R. Luxembourg 70, Donetsk, 83114, Ukraine

    M. G. Abramyants, D. A. Lomov & T. I. Zavyazkina

Authors
  1. M. G. Abramyants
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  2. D. A. Lomov
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  3. T. I. Zavyazkina
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Correspondence to D. A. Lomov.

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Original Russian Text © M.G. Abramyants, D.A. Lomov, T.I. Zavyazkina, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 11, pp. 1617–1621.

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Abramyants, M.G., Lomov, D.A. & Zavyazkina, T.I. Dehydrogenation of 1-aryl(hetaryl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acids and their esters with dimethyl sulfoxide. Russ J Org Chem 52, 1610–1615 (2016). https://doi.org/10.1134/S1070428016110117

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  • DOI: https://doi.org/10.1134/S1070428016110117

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