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Versatile three-component synthesis of 2′-amino-1,2-dihydrospiro[(3H)-indole-3,4′-(4′H)-pyran]-2-ones

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Abstract

A versatile method for the synthesis of 2′-amino-1,2-dihydrospiro[(3H)-indole-3,4′-(4′H)-pyran]-2-ones has been suggested consisting in the three-component reaction of isatins, cyanoacetic acid derivatives, and α-methylenecarbonyl compounds (β-dicarbonyl compounds, activated phenols, and OH-substituted heterocycles) in ethanol in the presence of triethylamine as a catalyst. The reaction proceeds selectively to form spiro[(3H)-indole-3,4′-(4′H)-pyrans].

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References

  1. C. Wiener, C. H. Schroeder, B. D. West, K. P. Link, J. Org. Chem., 1962, 27, 3086.

    Article  CAS  Google Scholar 

  2. J. L. Marco, C. Rhos, A. G. Garcia, M. Villarroya, M. C. Carreiras, C. Martins, A. Eleuterio, A. Morreale, M. Orozco, F. J. Luque, Bioorg. Med. Chem., 2004, 12, 2199.

    Article  CAS  Google Scholar 

  3. W. Kemnitzer, J. Drewe, S. Jiang, H. Zhang, Y. Wang, J. Zhao, S. Jia, J. Herich, D. Labreque, R. Storer, K. Meerovitch, D. Bouffard, R. Rej, R. Denis, C. Blais, S. Lamothe, G. Attardo, H. Gourdeau, B. Tseng, S. Kasibhatla, S. X. Cai, J. Med. Chem., 2004, 47, 6299.

    Article  CAS  Google Scholar 

  4. M. A. Al-Haiza, M. S. Mostafa, M. Y. El-Kady, Molecules, 2003, 8, 275.

    Article  CAS  Google Scholar 

  5. H. Junek, H. Aigner, Chem. Ber., 1973, 106, 914.

    Article  CAS  Google Scholar 

  6. Yu. A. Sharanin, Zh. Org. Khim., 1980, 16, 2188 [J. Org. Chem. USSR, 1980, 16, 1866 (Engl. Transl.)].

    CAS  Google Scholar 

  7. S. Marchalin, D. Ilavsky, J. Kovac, M. Bruncko, Collect. Czech. Chem. Commun., 1990, 55, 718.

    Article  CAS  Google Scholar 

  8. A. M. Shestopalov, Yu. M. Emel′yanova, V. N. Nesterov, Izv. Akad. Nauk, Ser. Khim., 2003, 1103 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1164].

    Google Scholar 

  9. A. M. Shestopalov, Yu. M. Emel′yanova, V. N. Nesterov, Izv. Akad. Nauk, Ser. Khim., 2002, 2079 [Russ. Chem. Bull., Int. Ed., 2002, 51, 2238].

  10. G. V. Klokol, S. G. Krivokolysko, V. D. Dyachenko, V. P. Litvinov, Khim. Geterotsikl. Soedin., 1999, 1363 [Chem. Heterocycl. Comp., 1999, 35, 1183 (Engl. Transl.)].

    Google Scholar 

  11. P. V. Pasternak, B. B. Averkiev, M. Yu. Antipin, A. S. Peregudov, N. D. Chkanikov, J. Fluorine Chem., 2004, 125, 1853.

    Article  CAS  Google Scholar 

  12. A. M. Shestopalov, Yu. M. Emeliyanova, A. A. Shestopalov, L. A. Rodinovskaya, Z. I. Niazimbetova, D. H. Evans, Org. Lett., 2002, 4, 423.

    Article  CAS  Google Scholar 

  13. A. M. Shestopalov, Yu. M. Emeliyanova, A. A. Shestopalov, L. A. Rodinovskaya, Z. I. Niazimbetova, D. H. Evans, Tetrahedron, 2003, 59, 7491.

    Article  CAS  Google Scholar 

  14. A. M. Shestopalov, A. A. Shestopalov, L. A. Rodinovskaya, Synthesis, 2008, 1.

  15. A. M. Shestopalov, S. G. Zlotin, A. A. Shestopalov, V. Yu. Mortikov, L. A. Rodinovskaya, Izv. Akad. Nauk, Ser. Khim., 2004, 546 [Russ. Chem. Bull., Int. Ed., 2004, 53, 573].

    Google Scholar 

  16. A. A. Shestopalov, L. A. Rodinovskaya, A. M. Shestopalov, V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2004, 690 [Russ. Chem. Bull., Int. Ed., 2004, 53, 724].

    Google Scholar 

  17. K. Higashiyama, H. Otomasu, Chem. Pharm. Bull., 1980, 28, 648.

    CAS  Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. Yu. Mortikov, Yu. M. Litvinov, A. A. Shestopalov, L. A. Rodinovskaya & A. M. Shestopalov

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  1. V. Yu. Mortikov
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  2. Yu. M. Litvinov
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  3. A. A. Shestopalov
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  4. L. A. Rodinovskaya
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  5. A. M. Shestopalov
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Corresponding author

Correspondence to A. M. Shestopalov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2326–2332, November, 2008.

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Mortikov, V.Y., Litvinov, Y.M., Shestopalov, A.A. et al. Versatile three-component synthesis of 2′-amino-1,2-dihydrospiro[(3H)-indole-3,4′-(4′H)-pyran]-2-ones. Russ Chem Bull 57, 2373–2380 (2008). https://doi.org/10.1007/s11172-008-0338-7

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  • DOI: https://doi.org/10.1007/s11172-008-0338-7

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