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Reaction of 3-trimethylsilylprop-2-ynal with α-hydroxyamino oximes

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Abstract

3-Trimethylsilylprop-2-ynal reacted with aliphatic α-hydroxyamino oximes in a chemoselective fashion at the aldehyde group to give hitherto unknown open-chain 3-trimethylsilylprop-2-yn-1-ylideneamine oxides. The possibility for intramolecular hydrogen bonding with participation of OH, C≡C, and N→O groups in the products was studied by IR spectroscopy.

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References

  1. Adams, J.P. and Box, D.S., J. Chem. Soc., Perkin Trans. 1, 1999, p. 749; Rigolet, S. and Melot, J.M., J. Chem. Soc., Perkin Trans. 1, 2000, p. 1095; Bowman, W.R., Davies, R.V., Slawin, M.Z., Sohal, G.S., Titaman, R.B., and Wilkins, D.J., J. Chem. Soc., Perkin Trans. 1, 1997, p. 15; Shirahase, M., Kanemasa, Sh., and Oderaotoshi, Y., Org. Lett., 2004, vol. 6, p. 675.

    Article  Google Scholar 

  2. Kanemasa, Sh., Ueno, N., and Shirahase, M., Tetrahedron Lett., 2002, vol. 43, p. 657; Malamidou-Xenikaki, E., Stampelos, X.N., Coutouli-Argyropoulou, E., Cardin, C.J., Teixeira, S., and Kavounis, C.A., J. Chem. Soc., Perkin Trans. 1, 1997, p. 949; Burdisso, M., Gandolfi, R., and Grunanger, P., Tetrahedron, 1989, vol. 45, p. 5579.

    Article  CAS  Google Scholar 

  3. Tamura, O., Shiro, T., Toyao, A., and Ishibashi, H., Chem. Commun., 2003, p. 2678; Vleggaar, R., Ackerman, L.G.J., and Steyn, P.S., J. Chem. Soc., Perkin Trans. 1, 1992, p. 3095.

  4. Young, I.S., Williams, J.L., and Kerr, M.A., Org. Lett., 2005, vol. 7, p. 953.

    Article  PubMed  CAS  Google Scholar 

  5. Philips, J.W. and Clough-Helfman, C., Med. Sci. Res., 1990, vol. 18, p. 403; Thomas, C.E., Carney, J.M., Bernotas, R.C., Hay, D.A., and Carr, A.A., Ann. N.Y. Acad. Sci., 1994, vol. 234, p. 243.

    Google Scholar 

  6. Iesce, M.R., Cermola, F., and Guitto, A., Synthesis, 1998, p. 333.

  7. Klyatskaya, S.V., Tret’yakov, E.V., and Vasilevskii, S.E., Izv. Ross. Akad. Nauk, Ser. Khim., 2002, p. 122.

  8. Medvedeva, A.S., Russ. J. Org. Chem., 1996, vol. 32, p. 272.

    Google Scholar 

  9. Volodarsky, L.V. and Tikhonov, A.Ya., Synthesis, 1986, p. 704; Dulepova, N.V., Mazhukin, D.G., Tikhonov, A.Ya., and Volodarskii, L.B., Khim. Geterotsikl. Soedin., 1986, p. 1060.

  10. Yavari, I. and Ramazani, A., Synth. Commun., 1997, vol. 27, p. 1449.

    CAS  Google Scholar 

  11. Short, K.M. and Ziegler, C.B., Jr., Tetrahedron Lett., 1993, vol. 34, p. 75.

    Article  CAS  Google Scholar 

  12. Keiko, N.A., Funtikova, E.A., Larina, L.I., Sarapulova, G.I., Mazhukin, D.G., Rybalova, T.V., and Tikhonov, A.Ya., Russ. J. Org. Chem., 2005, vol. 41, p. 1421.

    Article  CAS  Google Scholar 

  13. Egorochkin, A.N. and Khorshev, S.Ya., Usp. Khim., 1980, vol. 49, p. 1687.

    CAS  Google Scholar 

  14. Demina, M., Velikanov, A., Medvedeva, A., Larina, L., and Voronkov, M., J. Organomet. Chem., 1998, vol. 553, p. 129; Medvedeva, A.S., Demina, M.M., Novopashin, P.S., Sarapulova, G.I., and Afonin, A.V., Mendeleev Commun., 2002, p. 110.

    Article  CAS  Google Scholar 

  15. Medvedeva, A.S., Andreev, M.V., Safronova, L.P., Sarapulova, G.I., Pavlov, D.V., and Afonin, A.V., Russ. J. Org. Chem., 2002, vol. 38, p. 10.

    Article  CAS  Google Scholar 

  16. Medvedeva, A.S., Mareev, A.V., Borisova, A.I., and Afonin, A.V., Arkivoc, 2003, part (xiii), p. 157.

  17. Matsuo, J., Shibata, T., Kitagawa, H., and Mukayama, T., Arkivoc, 2001, part (x), p. 58.

  18. Philp, D. and Robinson, J.M.A., J. Chem. Soc., Perkin Trans. 2, 1998, p. 1643; Calhodra, M.J., Chem. Commun., 2000, p. 801.

    Google Scholar 

  19. Demina, M.M., Medvedeva, A.S., Protsuk, N.I., and Vyazankin, N.S., Zh. Obshch. Khim., 1978, vol. 48, p. 1563.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    M. M. Demina, P. S. Novopashin, G. I. Sarapulova, A. V. Afonin & A. S. Medvedeva

  2. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    A. Ya. Tikhonov

Authors
  1. M. M. Demina
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  2. P. S. Novopashin
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  3. G. I. Sarapulova
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  4. A. V. Afonin
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  5. A. Ya. Tikhonov
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  6. A. S. Medvedeva
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Additional information

Original Russian Text © M.M. Demina, P.S. Novopashin, G.I. Sarapulova, A.V. Afonin, A.Ya. Tikhonov, A.S. Medvedeva, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 4, pp. 510–513.

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Demina, M.M., Novopashin, P.S., Sarapulova, G.I. et al. Reaction of 3-trimethylsilylprop-2-ynal with α-hydroxyamino oximes. Russ J Org Chem 43, 507–510 (2007). https://doi.org/10.1134/S1070428007040033

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  • DOI: https://doi.org/10.1134/S1070428007040033

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