The review is devoted to the transformation of oxazoles (including those with cationoid and mesoionic structures) into compounds of the pyrrole series.
Similar content being viewed by others
References
J. A. Joule and K. Mills, Heterocyclic Chemistry, 5th ed., Wiley (2010), 689 p.
D. C. Palmer (editor), Oxazoles: Synthesis, Reactions, and Spectroscopy (Chemistry of Heterocyclic Compounds), Vol. 60, Part A, Wiley, New York (2003).
D. C. Palmer (editor), Oxazoles: Synthesis, Reactions, and Spectroscopy (Chemistry of Heterocyclic Compounds), Vol. 60, Part B.Wiley, New York (2004).
H. Kubota, T. Moriya, and K. Matsumoto, Chem. Pharm. Bull., 38, 570 (1990).
J. Cornforth, in: R. Elderfield (editor), Heterocyclic Compounds [Russian translation], Vol. 5, Izd-vo inostr. lit., Moscow (1961), p. 242.
G. Ya. Kondrat’eva, Russ. Chem. Bull. Int. Ed. [English translation], 8, 457 (1959).
S. V. Stepanova, S. D. L’vova, B. S. Elyanov, and V. L. Gunar, Khim.-Farm. Zh.,11, No. 6, 92 (1977).
G. Sandford, I. Wilson, and C. M. Timperley, J. Fluorine Chem., 125, 1425 (2004).
K. Fukushima, Y. Q. Lu, and T. Ibata, Bull. Chem. Soc. Jpn., 69, 3289 (1996).
H. Bayer, H. Gotthardt, and R. Huisgen, Chem. Ber., 103, 2356 (1970).
W. Steglich, P. Gruber, Y.-U. Heininger, and F. Kneidl, Chem. Ber., 104, 3816 (1971).
W. Tian, Y. Luo, Y. Chen, and A. Yu, J. Chem. Soc., Chem. Commun., 101 (1993).
F. Clerici, M. L. Gelmi, and P. Trimarco, Tetrahedron, 54, 5763 (1998).
I. J. Turchi (editor), Oxazoles (Chemistry of Heterocyclic Compounds), Vol. 45, Wiley, New York (1986).
D. Clerin, B. Meyer, J. Fleury, and H. Fritz, Tetrahedron, 32, 1055 (1976).
K. Potts, S. Chen, and J. Szmuszkovicz, J. Org. Chem., 42, 2525 (1977).
E. Tighineanu and D. Raileanu, Rev. Roum. Chim., 37, N 11–12, 1307 (1992).
Z.-G. M. Kazhkenov, A. A. Bush, and E. V. Babaev, Molecules, 10, 1109 (2005).
A. A. Bush, Author’s Abstract of Candidate’s Thesis, Moscow (2006).
V. B. Rybakov, A. A. Bush, S. I. Troyanov, E. V. Babaev, and E. Kemnitz, Acta Cryst., Sect. E, 63, o3620 (2007).
W. E. McEwen, I. C. W. Huang, C. P. C. Marin, F. McCarty, E. M. Segnini, C. M. Zepp III, and J. L. Lubinkowski, J. Org. Chem., 47, 3098 (1982).
A. W. Bridge, M. B. Hursthouse, C. W. Lehmann, D. J. Lythgoe, and C. G. Newton, J. Chem. Soc, Perkin Trans. 1, 1839 (1993).
A. Hassner, B. Fischer, J. Org. Chem., 57, 3070 (1992).
E. V. Babaev, S. V. Bozhenko, and D. A. Maiboroda, Izv. Akad. Nauk, Ser. Khim., 11, 2298 (1995).
E. V. Babaev, Khim. Geterotsikl. Soedin., 962 (1993). [Chem. Heterocycl. Compd., 29, 818 (1993).]
E. Vedejs and J. W. Grissom, J. Am. Chem. Soc., 110, 3238 (1988).
A. S. Fisyuk and M. A. Voroncova, Khim. Geterotsikl. Soedin., 979 (1997). [Chem. Heterocycl. Compd., 33, 857 (1997).]
E. V. Babaev and S. V. Bozhenko, Khim. Geterotsikl. Soedin., 141 (1997). [Chem. Heterocycl. Compd., 33, 125 (1997).]
E. V. Babaev, A. V. Efimov, V. B. Rybakov, and S. G. Zhukov, Khim. Geterotsikl. Soedin., 401 (2000). [Chem. Heterocycl. Compd., 36, 339 (2000).]
V. F. Lipnitskii and O. P. Shvaika, Khim. Geterotsikl. Soedin., 1689 (1988). [Chem. Heterocycl. Compd., 24, 1398 (1988).]
A. Padwa, U. Chiacchio, and M. K. Venkatramanan, J. Chem. Soc, Chem. Commun., 1108 (1985).
E. Vedejs and J. W. Grissom, J. Am. Chem. Soc., 108, 6433 (1986).
A. Hassner and B. Fischer, Tetrahedron Lett., 31, No. 49, 7213 (1990).
E. V. Babaev, Obzorn. Zh. po Khim., 1, No. 2, 168 (2011).
E. Vedejs and S. L. Dax, Tetrahedron Lett., 30, 2627 (1989).
E. Vedejs and D. W. Piotrowski, J. Org. Chem., 58, 1341 (1993).
E. Vedejs, D. W. Piotrowski, and F. C. Tucci, J. Org. Chem., 65, 5498 (2000).
E. V. Babaev, V. L. Alifanov, and A. V. Efimov, Izv. Akad. Nauk, Ser. Khim., 4, 837 (2008).
E. V. Babaev and A. V. Efimov, Khim. Geterotsikl. Soedin., 998 (1997). [Chem. Heterocycl. Compd., 33, 875 (1997).]
E. V. Babaev, A. V. Efimov, D. A. Maiboroda, and K. Jug, Eur. J. Org. Chem., 193 (1998).
E. V Babaev, J. Heterocycl. Chem., 37, 519 (2000).
E. V. Babaev, A. A. Tsisevich, D. V. Al’bov, V. B. Rybakov, and A. A. Aslanov, Izv. Akad. Nauk, Ser. Khim., 1, 253 (2005).
P. Tielmann and C. Hoenke, Tetrahedron Lett., 47, 261 (2006).
E. V. Babaev, A. V. Efimov, A. A. Tsisevich, A. A. Nevskaya, and V. B. Rybakov, Mendeleev Commun., 17, 130 (2007).
O. S. Mazina, V. B. Rybakov, S. I. Troyanov, E. V. Babaev, and L. A. Aslanov, Kristallografiya, 50, No. 1, 68 (2005).
D. V. Albov, V. B. Rybakov, E. V Babaev, and L. A. Aslanov, Acta Cryst, Sect. E, 60, 2313 (2004).
E. V. Babaev, A. A. Nevskaya, I. V. Dlinnykh, and V. B. Rybakov, Khim. Geterotsikl. Soedin., 110 (2009). [Chem. Heterocycl. Compd., 45, 93 (2009).]
E. V. Babaev and V. L. Alifanov, Izv. Akad. Nauk, Ser. Khim., 8, 1611 (2008).
E. V Babaev, D. E. Lushnikov, and N. S. Zefirov, J. Amer. Chem. Soc., 115, 2416 (1993).
E. V. Babaev and N. S. Zefirov, Khim. Geterotsikl. Soedin., 808 (1992). [Chem. Heterocycl. Compd., 28, 671 (1992).]
E. V. Babaev, in: O. A. Attanasi, D. Spinelli (editors), Targets in Heterocyclic Systems - Chemistry and Properties, Societa Chimica Italiana, Rome (1997), p. 105.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 64-77, January, 2012.
Rights and permissions
About this article
Cite this article
Babaev, E.V. Pyrroles from oxazoles. Chem Heterocycl Comp 48, 59–72 (2012). https://doi.org/10.1007/s10593-012-0970-x
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-012-0970-x