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1-chloroacetyloxindole(isatin) in reactions with some N-nucleophiles. Unexpetedly easy cleavage of chloroacetyl group

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Abstract

Reactions of 1-chloroacetyloxindole and 1-chloroacetylisatin with some secondary amines, Girard’s reagent T and thiourea were studied. All investigated reactions proceeded via cleavage of the acyl group to form 3-substituted isatin or oxindole derivatives.

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References

  1. Dreifuss, A.A., Bastos-Pereira, A.L., Avila, T.V., Soley, B. de S., Rivero, A.J., Aguilar, J.L., and Acco, A., J. Ethnopharmacol., 2010, vol. 130, p. 127. DOI: 10.1016/j.jep.2010.04.029.

    Article  Google Scholar 

  2. Garcia Gimenez, D., Garcia Prado, E., Saenz Rodriguez, T., Fernandez Arche, A., and De La Puerta, R., Planta Med., 2010, vol. 76, p. 133. DOI: 10.1055/s-0029-1186048.

    Article  Google Scholar 

  3. Bishop, J.M., Science, 1987, vol. 235, p. 305. DOI: 10.1126/science.3541204.

    Article  CAS  Google Scholar 

  4. Guan, H., Laird, A.D., Blake, R.A., Tang, C., and Liang, C., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 187. DOI: 10.1016/j.bmcl.2003.09.069.

    Article  CAS  Google Scholar 

  5. Kang, T.H., Murakami, Y., Matsumoto, K., Takayama, H., Kitajima, M., Aimi, N., and Watanabe, H., Eur. J. Pharmacol., 2002, vol. 455, p. 27. DOI: 10.1016/S0014-2999(02)02581-5.

    Article  CAS  Google Scholar 

  6. Swensen, A.M., Herrington, J., Bugianesi, R.M., Dai, G., Haedo, R.J., Ratliff, K.S., Smith, M.M., Warren, V.A., Arneric, S.P., Eduljee, C., Parker, D., Snutch, T.P., Hoyt, S.B., London, C., Duffy, J.L., Kaczorowski, G.J., and McManus, O.B., Mol. Pharmacol., 2012, vol. 81, p. 488. DOI: 10.1124/mol.111.075226.

    Article  CAS  Google Scholar 

  7. Whatmore, J.L., Swann, E., Barraja, P., Newsome, J.J., Bunderson, M., Beall, H.D., Tooke, J.E., and Moody, C.J., Angiogenesis, 2002, vol. 5, p. 45. DOI: 10.1023/A:1021528628524.

    Article  CAS  Google Scholar 

  8. Peddibhotla, S., Curr. Bioactive Compd., 2009, vol. 5, p. 20. DOI: 10.2174/157340709787580900.

    Article  CAS  Google Scholar 

  9. Abbadie, C., McManus, O.B., Sun, S.Y., Bugianesi, R.M., Dai, G., Haedo, R.J., Herrington, J.B., Kaczorowski, G.J., Smith, M.M., Swensen, A.M., Warren, V.A., Williams, B., Arneric, S.P., Eduljee, C., Snutch, T.P., Tringham, E.W., Jochnowitz, N., Liang, A., Euan MacIntyre, D., McGowan, E., Mistry, S., White, V.V., Hoyt, S.B., London, C., Lyons, K.A., Bunting, P.B., Volksdorf, S., and Duffy, J.L., J. Pharmacol. Exp. Ther., 2010, vol. 334, p. 545. DOI: 10.1124/jpet.110.166363.

    Article  CAS  Google Scholar 

  10. Ziarani, Gh.M., Gholamzadeh, P., Lashgari, N., and Hajiabbasi, P., Arkivoc, 2013, vol. i, p.470.

    Google Scholar 

  11. Bogdanov, A.V., Musin, L.I., and Mironov, V.F., Arkivoc, 2015, vol. vi, p. 362. DOI: 10.3998/ark.5550190.p009.090.

    Google Scholar 

  12. Bogdanov, A.V., Kutuzova, T.A., and Mironov, V.F., Russ. J. Org. Chem., 2015, vol. 51, no. 9, p. 1349. DOI: 10.1134/S1070428015090249.

    Article  CAS  Google Scholar 

  13. Kaur, N. and Kishore, D., Synth. Commun., 2014, vol. 44, p. 2789. DOI: 10.1080/00397911.2013.815215.

    Article  CAS  Google Scholar 

  14. Singh, A., Sirohi, R., Shastri, S., and Kishore, D., Indian J. Chem. (B), 2003, vol. 42, p. 3124.

    Google Scholar 

  15. Taher, A.T. and Mohammed, L.W., Arch. Pharm. Res., 2013, vol. 36, p. 684. DOI: 10.1007/s12272-013-0081-y.

    Article  CAS  Google Scholar 

  16. Kaur, N., Tyagi, R., Srivastava, M., and Kishore, D., J. Heterocycl. Chem., 2014, vol. 51, p. E50, DOI: 10.1002/jhet.1841.

    Article  CAS  Google Scholar 

  17. Huntress, E.H. and Bornstein, J., J. Am. Chem. Soc., 1949, vol. 71, p. 745. DOI: 10.1021/ja01170a510.

    Article  CAS  Google Scholar 

  18. Ismail, M.M., Kamel, M.M., Mohamed, L.W., and Faggal, S.I., Molecules, 2012, vol. 17, p. 4811. DOI: 10.3390/molecules17054811.

    Article  CAS  Google Scholar 

  19. Abdel Rahman, R.M., El Gendy, Z., and Mahmoud, M.B., Indian J. Chem. (B), 1990, vol. 29, p.352.

    Google Scholar 

  20. Jones, G., Org. Reactions, 2011, vol. 15, p. 204. DOI: 10.1002/0471264180.or015.02.

    Article  Google Scholar 

  21. Marvel, C.S. and Hiers, G.S., Org. Synth., 1941, vol. 1, p.327.

    Google Scholar 

  22. Holzer, W. and Gyorgydeak, Z., J. Heterocycl. Chem., 1996, vol. 33, p. 675. DOI: 10.1002/jhet.5570330326.

    Article  CAS  Google Scholar 

  23. Spencer, J., Chowdhry, B.Z., Hamid, S., Mendham, A.P., Male, L., Coles, S.J., and Hursthouse, M.B., Acta Crystallogr. (C), 2010, vol. 66, p. o71. DOI: 10.1107/S0108270109054134.

    CAS  Google Scholar 

  24. Sheldrick, G.M., SADABS, 1997, Bruker AXS Inc., Madison, WI-53719, USA.

    Google Scholar 

  25. Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, p. 112. DOI: 10.1107/S0108767307043930.

    Article  CAS  Google Scholar 

  26. Farrugia, L.J., J. Appl. Crystallogr., 1999, vol. 32, p. 837. DOI: 10.1107/S0021889899006020.

    Article  CAS  Google Scholar 

  27. APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A, Bruker Advansed X-ray Solutions, BrukerAXS Inc., Madison, Wisconsin, USA, 2006.

  28. Farrugia, L.J., J. Appl. Crystallogr., 1997, vol. 30, p. 565. DOI: 10.1107/S0021889897003117.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Akademika Arbuzova 8, Kazan, Tatarstan, 420088, Russia

    A. V. Bogdanov, T. A. Kutuzova, D. B. Krivolapov, A. B. Dobrynin & V. F. Mironov

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  1. A. V. Bogdanov
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  2. T. A. Kutuzova
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  3. D. B. Krivolapov
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  4. A. B. Dobrynin
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  5. V. F. Mironov
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Correspondence to A. V. Bogdanov.

Additional information

Original Russian Text © A.V. Bogdanov, T.A. Kutuzova, D.B. Krivolapov, A.B. Dobrynin, V.F. Mironov, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 3, pp. 396–400.

To the 100th Anniversary of A.N. Pudovik

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Bogdanov, A.V., Kutuzova, T.A., Krivolapov, D.B. et al. 1-chloroacetyloxindole(isatin) in reactions with some N-nucleophiles. Unexpetedly easy cleavage of chloroacetyl group. Russ J Gen Chem 86, 539–543 (2016). https://doi.org/10.1134/S1070363216030087

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  • DOI: https://doi.org/10.1134/S1070363216030087

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