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Synthesis of pyrrole N-derivatives from oxazolidines

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Abstract

Transformations of oxazolidine derivatives synthesized from industrially produced amino alcohols, aldehydes, and ketones under basic or acidic catalysis lead to the formation of N-alkyl- and N-(hydroxyalkyl)-substituted pyrroles in 19-81% yields.

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References

  1. Gossauer, A., Die Chemie der Pyrrole, Berlin: Springer-Verlag, 1974; Jones R.A. and Bean, G.P., The Chemistry of Pyrroles, New York: Academic Press, 1977; Trofimov, B.A., The Chemistry of Heterocyclic Compounds. Part 2, Jones, R.A., New York: Wiley, 1992, vol. 48, p. 131; Trofimov, B.A., Mikhaleva, A.I., Schmidt, E.Yu., Sobenina, L.N., Adv. Heterocycl. Chem. 2010, vol. 99, p. 209; Baumann, M., Baxendale, I.R., Ley, S.V. and Nikbin, N. Beilst., 2011, vol. 7, p. 442; Trofimov, B.A., Mikhaleva, A.I., Shmidt, E.Yu., and Sobenina, L.N., Khimiya pirola. Novye stranitsy (Chemistry of Pyrrole. New Trends), Novosibirsk: Nauka, 2012; Song, S., Ko, S.-J., Shin, H., Jin, Y., Kim, I., Kim, J.Y., and Suh, H., Sol. Energy Mater. Sol. Cell, 2013, vol. 112, p. 120; Ates, M., Mater. Sci. Eng. C, 2013, vol. 33, no. 4, p. 1853.

    Book  Google Scholar 

  2. Ono, N., Heterocycles, 2008, vol. 75, p. 243; Estevez, V., Villacampa, M., and Menendez, J.C., Chem. Soc. Rev., 2010, vol. 39, p. 4402; Bergman, J. and Janosik, T., Mod. Heterocycl. Chem. Sh. 4, Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA, 2011, p. 269; Sakhuja, R., Panda, S. S., and Bajaj, K., Curr. Org. Chem. 2012, vol. 16, p. 789.

    Article  CAS  Google Scholar 

  3. Kukharev B.F., Stankevich V.K., and Kukhareva V.A., Chem. Heterocycl. Comp, 1986, no. 4, p. 440.

    Google Scholar 

  4. Kukharev, B.F., Russ. Chem. Bull., 1997, vol. 46, p. 1482.

    Article  CAS  Google Scholar 

  5. Woodward, R.B., Wendler, N.L., and Brutschu, F.J., J. Am. Chem. Soc. 1945, vol. 67, p. 1425.

    Article  CAS  Google Scholar 

  6. Kukharev, B.F., Stankevich, V.K., and Kukhareva, V.A., Khim. Geterotsikl. Soedin., 1984, vol. 5, p. 700.

    Google Scholar 

  7. Piloty, O. and Hirsch, P., Lieb. Ann. Chem., 1913, vol. 395, p. 63.

    Article  CAS  Google Scholar 

  8. Kukharev, B.F. and Atavin, A.S., Zh. Org. Khim., 1974, vol. 10, p. 670.

    CAS  Google Scholar 

  9. Bergman, E.D., Chem. Rev., 1953, vol. 53, p. 309.

    Article  Google Scholar 

  10. Cope, A.C. and Hancock, E.M., J. Am. Chem. Soc. 1944, vol. 66, p. 1453; Bergmann, E.D., Gil-Av, E., and Pinchas, S., J. Am. Chem. Soc., 1953, vol. 75, p. 358; Neelakantan, L., J. Org. Chem., 1971, vol. 36, p. 2256; Saavedra, J.E., J. Org. Chem., 1985, vol. 50, p. 2379.

    Article  CAS  Google Scholar 

  11. Amarnath, V., Amarnath, K., Amarnath, K., Davies, S., and Roberts, L., J. Chem. Res. Toxicol., 2004, vol. 17, no. 3, p. 410.

    Article  CAS  Google Scholar 

  12. Malinovskii, M.S., Okisi olefinov i ikh proizvodnye (Olefin Oxides, and Their Derivatives), Moscow: GKhI, 1961, p. 263.

    Google Scholar 

  13. Cope, A.C. and Hancock, E.M., J. Am. Chem. Soc., 1942, vol. 64, p. 1503.

    Article  CAS  Google Scholar 

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Correspondence to E. Kh. Sadykov.

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Original English Text © E.Kh. Sadykov, V.K. Stankevich, N.A. Lobanova, G.R. Klimenko, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 2, pp. 226–231.

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Sadykov, E.K., Stankevich, V.K., Lobanova, N.A. et al. Synthesis of pyrrole N-derivatives from oxazolidines. Russ J Org Chem 50, 219–224 (2014). https://doi.org/10.1134/S1070428014020134

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  • DOI: https://doi.org/10.1134/S1070428014020134

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