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DOI: 10.1039/A703747C (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 425-430

Isomerisation of benzopyran-2-imines in [2H6]dimethyl sulfoxide

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Conor N. O’Callaghan, T. Brian H. McMurry and John E. O’Brien

Abstract

When 2-imino-2H-benzopyran-3-carboxamide 1 (X = H) is dissolved in [2H6]dimethyl sulfoxide, NMR spectra show that a mixture of 1 and the isomeric 2-cyano-3-(2-hydroxyphenyl)prop-2-ene-1-carboxamide 3 (X = H) is present. Other benzopyran-2-imines behave similarly; the degree of isomerisation varies considerably, depending on the nature and position of the substituents present.

References

  1. G. P. Schiemenz, Chem. Ber., 1962, 95, 483 CAS.
  2. C. N. O'Callaghan, J. Chem. Soc., Perkin Trans. 1, 1980, 1335 RSC.
  3. G. Satzinger, H. Barth, J. Hartenstein, M. Herrmann, E. Fritschi and I. D. Schnett, 1985, Ger. Pat. DE 3,335,472 (Chem. Abstr., 1985, 103, 104 997) Search PubMed.
  4. G. E. H. Elgemeie and A. H. H. Elghandour, Bull. Chem. Soc., Jpn., 1990, 63, 1230 CAS.
  5. C. N. O'Callaghan and M. L. Conalty, Proc. Roy. Irish Acad., 1979, 79B, 87 Search PubMed.
  6. G. Satzinger, H. Barth, J. Hartenstein, M. Herrmann, E. Fritschi and I. D. Schnett, 1985, Ger. Pat. DE 3,335,473 (Chem. Abstr., 1985, 103, 123 504) Search PubMed.
  7. T. R. Burke, B. Lim, V. E. Marquez, Z.-H. Li, J. B. Bolen, I. Stefanova and I. D. Horak, J. Med. Chem., 1993, 36, 425 CrossRef CAS.
  8. (a) T. Shiraishi, T. Domoto, Y. Shimada, N. Imai, H. Kondo, I. Katsumi, T. Hidaka and K. Watanabe, Jpn. Pat., 1987, 6239558 (Chem. Abstr., 1987, 107, 58 668t) Search PubMed; (b) A. Gazit, P. Yaish, C. Gilon and A. Levitzki, J. Med. Chem., 1989, 32, 2344 CrossRef CAS; (c) A. Gazit, H. App, G. McMahon, J. Chen, A. Levitzki and F. D. Bohmer, J. Med. Chem., 1996, 39, 2170 CrossRef CAS.
  9. R. H. Curtis, J. N. E. Day and L. G. Kimmins, J. Chem. Soc., 1923, 123, 3131(cf. also T. Zsolnai, Biochem. Pharmacol., 1965, 14, 1325) Search PubMed.
  10. C. N. O'Callaghan, T. B. H. McMurry and C. J. Cardin, J. Chem. Res., 1990, (S), 132; (M), 0901 Search PubMed.
  11. H. Cho, T. Iwashita, M. Hamaguchi and Y. Oyama, Chem. Pharm. Bull., 1991, 39, 3341 CAS.
  12. M. Mesilaakso, Magn. Reson. Chem., 1996, 34, 989 CrossRef CAS.
  13. D. Prajapati, K. C. Lekhok, J. S. Sandhu and A. C. Ghosh, J. Chem. Soc., Perkin Trans. 1, 1996, 959 RSC.
  14. G. Sunagawa and H. Nakao, Chem. Pharm. Bull., 1965, 13, 443 CAS.
  15. C. N. O'Callaghan, Proc. Roy. Irish Acad., 1977, 77B, 533 Search PubMed.
  16. P. Czerney and H. Hartmann, J. Prakt. Chem., 1981, 323, 691 CAS.
  17. G. Satzinger and P. Stoss, Ger. Pat., 1979, 2,801,353 (Chem. Abstr., 1979, 91, 193 183) Search PubMed.
  18. H. Yasuda and H. Midorikawa, Bull. Chem. Soc. Jpn., 1966, 39, 1754 CAS.
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