Russian Journal of Organic Chemistry

, Volume 52, Issue 6, pp 834–837 | Cite as

Functionalization of methyl 3-acetyl-5-[(methoxycarbonyl)amino]-2-methyl-1H-indole-1-carboxylate

  • A. V. Velikorodov
  • V. A. Ionova
  • E. A. Shustova
  • N. N. Stepkina


Oxidative heterocyclization of methyl 3-{1-[2-(carbamoylhydrazinylidene)]ethyl}-2-methyl-5-[(methoxycarbonyl)amino]-1H-indole-1-carboxylate by the action of selenium dioxide in acetic acid and heating of the corresponding thiosemicarbazone in boiling acetic anhydride gave 1,2,3-selenadiazole and 2,3-dihydro-1,3,4-thiadiazole derivatives, respectively. Methyl 3-acetyl-2-methyl-5-[(methoxycarbonyl)amino]-1H-indole-1-carboxylate reacted with selenium dioxide in dioxane–water (30: 1) at 80‒90°C to form methyl 5-[(methoxycarbonyl)amino]-2-methyl-3-(2-oxoacetyl)-1H-indole-1-carboxylate whose condensation with o-phenylenediamine afforded methyl 2-methyl-5-[(methoxycarbonyl)amino]-3-(quinoxalin-2-yl)-1H-indole-1-carboxylate.


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  1. 1.
    Velikorodov, A.V. and Mochalin, V.B., Russ. J. Org. Chem., 1998, vol. 34, p. 1490.Google Scholar
  2. 2.
    Velikorodov, A.V., Kuanchalieva, A.K., and Titova, A.K., Russ. J. Org. Chem., 2010, vol. 46, p. 1060.CrossRefGoogle Scholar
  3. 3.
    Arsenyan, P., Pudova, O., and Lukevics, E., Tetrahedron Lett., 2002, vol. 43, p. 4817.CrossRefGoogle Scholar
  4. 4.
    Arsenyan, P., Oberte, K., Pudova, O., and Lukevics, E., Chem. Heterocycl. Compd., 2002, vol. 38, p. 1437.CrossRefGoogle Scholar
  5. 5.
    Regitz, M. and Krill, S., Phosphorus, Sulfur Silicon Relat. Elem., 1996, vol. 99, p. 15.Google Scholar
  6. 6.
    Lalezari, I. and Shafiee, A., J. Org. Chem., 1971, vol. 36, p. 2836.CrossRefGoogle Scholar
  7. 7.
    Lalezari, I., Shafiee, A., and Yalpani, M., J. Org. Chem., 1973, vol. 38, p. 338.CrossRefGoogle Scholar
  8. 8.
    Saravanan, S., Nithya, A., and Muthusubramanian, S., J. Heterocycl. Chem., 2006, vol. 43, p. 149.CrossRefGoogle Scholar
  9. 9.
    Riley, H.A. and Gray, A.R., Organic Syntheses, Blatt, A.H., Ed., New York: Wiley, 1943, collect. vol. 2, p. 509.Google Scholar
  10. 10.
    Lokhande, P.D., Waghmare, S.R., Gaikwad, H., and Hankare, P.P., Indian J. Chem., Sect. B, 2013, vol. 52, p. 300.Google Scholar
  11. 11.
    Floyd, M.B., Du, M.T., Fabio, P.F., Jacob, L.A., and Johnson, B.D., J. Org. Chem., 1985, vol. 50, p. 5022.CrossRefGoogle Scholar
  12. 12.
    Rimaz, M. and Mousavi, H., Turk. J. Chem., 2013, vol. 37, p. 252.Google Scholar
  13. 13.
    Anaraki-Ardakani, H., Noei, M., Carbalaei-Harofteh, M., and Zomorodbaksh, S., Eur. J. Chem., 2012, vol. 9, p. 2239.Google Scholar
  14. 14.
    Eftekhari-Sis, B. and Vahdati-Khajeh, S., Curr. Chem. Lett., 2013, vol. 2, p. 85.CrossRefGoogle Scholar
  15. 15.
    Petrova, O.N., Zamigailo, L.L., Ostras, K.S, Shishkina, S.V., Shishkin, O.V., Borisov, A.V., Musatov, V.I., Shirobokova, M.G., and Lipson, V.V., Chem. Heterocycl. Compd., 2015, vol. 51, p. 310.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • A. V. Velikorodov
    • 1
  • V. A. Ionova
    • 1
  • E. A. Shustova
    • 1
  • N. N. Stepkina
    • 1
  1. 1.Astrakhan State UniversityAstrakhanRussia

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