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Oxitranyl-Β-aminovinyl ketones. 2. Synthesis of 3(2H)-furanones

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Abstract

The reaction of oxiranyl-Β-dimethylaminovinyl ketones with secondary amines, hydrochloric, and hydrobromic acids leads to the formation of the corresponding 2-aminomethyl- and 2-halomethyl-3-(2H)-furanones.

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Literature Cited

  1. G. Z. Stasevich, O. N. Bubel', I. G. Tishchenko, and M. V. Kudrevatikh, Khim. Geterotsikl. Soedin., No. 8, 1028 (1987).

    Google Scholar 

  2. A. S. Martin, J. Rovirosa, O. Munoz, M. H. M. Chen, R. D. Gunerathe, and J. Clardy, Tetrahedron Lett., 24, 4063 (1983).

    Google Scholar 

  3. R. M. Carman, F. N. Lahey, and J. K. MacLeod, Aust. J. Chem., 20, 1957 (1967).

    Google Scholar 

  4. S. M. Kupchan, C. W. Sigel, M. J. Matz, C. J. Gilmore, and R. F. Bryan, J. Am. Chem. Soc., 98, 2295 (1976).

    Google Scholar 

  5. P. W. Le Quesne, M. D. Menachery, M. P. Pastore, C. J. Kelly, T. F. Brennan, K. D. Onan, R. F. Raffauf, and C. M. Weeks, J. Org. Chem., 47, 1519 (1982).

    Google Scholar 

  6. W. Parker, R. A. Raphael, and D. I. Wilkinson, J. Chem. Soc., No. 11, 3871 (1958).

    Google Scholar 

  7. F. N. Lahey and J. K. MacLeod, Aust. J. Chem., 26, 1943 (1967).

    Google Scholar 

  8. P. G. Baraldi, A. Barco, S. Benetti, M. Guarneri, S. Manfredini, G. P. Pollini, and D. Simoni, Tetrahedron Lett., 26, 5319 (1985).

    Google Scholar 

  9. R. F. W. Jackson and R. A. Raphael, J. Chem. Soc., Perkin Trans. 1, No. 3, 535 (1984).

    Google Scholar 

  10. G. Casnatti and A. Ricca, Tetrahedron Lett., No. 4, 327 (1967).

    Google Scholar 

  11. D. P. Curran and D. H. Singleton, Tetrahedron Lett., 24, 2079 (1983).

    Google Scholar 

  12. I. G. Tishchenko, V. M. Yazychenko, N. M. Pasechnik, and P. M. Malashko, Izv. Akad. Nauk Beloruss. SSR, Ser. Khim., No. 6, 103 (1969).

    Google Scholar 

  13. E. S. Balenkova and M. A. Gorokhova, Zh. Org. Khim., 13, 1625 (1977).

    Google Scholar 

  14. I. G. Tishchenko, I. F. Revinskii, V. G. Grinkevich, and V. P. Suboch, Vest. Beloruss. Gos. Univ., Ser. 2, No. 1, 28 (1978).

    Google Scholar 

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For Communication 1, see [1].

Translated from Khimiii Geterotsiklicheskikh Soedinenii, No. 12, pp. 1600–1603, December, 1988.

Original article submitted May 20, 1987.

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Stasevich, G.Z., Bubel', O.N., Tishchenko, I.G. et al. Oxitranyl-Β-aminovinyl ketones. 2. Synthesis of 3(2H)-furanones. Chem Heterocycl Compd 24, 1321–1324 (1988). https://doi.org/10.1007/BF00486669

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  • DOI: https://doi.org/10.1007/BF00486669

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