A novel acylative ring cleavage of benzothieno[3,2-b]pyran-4-ols: application to the synthesis of dibenzothiophenes and fused-ring derivatives

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Christopher D. Gabbutt, John D. Hepworth, B. Mark Heron and Jean-Luc Thomas


Abstract

The benzothienopyranols 3, readily available from the ketone 1, are transformed to the carbamates 5 on treatment with N,N-dimethylcarbamoyl chloride, subsequent thermal electrocyclisation provides access to dibenzothiophene derivatives 6 and 11–13.


References

  1. R. K. Russell and J. B. Press, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 2, p. 679 Search PubMed.
  2. J. Larsen and K. Bechgaard, Acta Chem. Scand., 1996, 50, 71 77.
  3. C. Bianchini and A. Meli, Synlett, 1997, 643 CAS.
  4. (a) L. H. Klemm, Adv. Heterocycl. Chem., 1982, 32, 127 CAS; (b) Y. Shiraishi, Y. Taki, T. Hirani and I. Komasawa, Chem. Commun., 1998, 2601 RSC.
  5. J. Ashby and C. C. Cook, Adv. Heterocycl. Chem., 1974, 16, 181 CAS; J. Nakayama, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol.2, p.607 Search PubMed.
  6. S. J. Collier and R. C. Storr, Prog. Heterocycl. Chem., 1998, 10, 25 Search PubMed.
  7. K. Buggle, Ú. N. Ghógaín, M. Nangle and P. MacManus, J. Chem. Soc., Perkin Trans. 1, 1983, 1427 RSC; P. M. Jackson and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1990, 681 RSC; P. M. Jackson, C. J. Moody and P. Shah, J. Chem. Soc., Perkin Trans. 1, 1990, 2909 RSC.
  8. Y. Tominaga and R. N. Castle, J. Heterocycl. Chem., 1996, 33, 523 CAS and references cited therein.
  9. J. C. Jutz, Top. Curr. Chem., 1979, 73, 125; C. Jutz, R.-M. Wagner and H.-G. Löbering, Angew. Chem., Int. Ed. Engl., 1974, 13, 737 CrossRef.
  10. L. S. Liebeskind and J. Wang, J. Org. Chem., 1993, 58, 3550 CrossRef CAS.
  11. S. Smiles and E. W. McClelland, J. Chem. Soc., 1921, 119, 1810 Search PubMed.
  12. For a review see, H. McNab, in Comprehensive Organic Functional Group Transformations, ed. A. R. Katritzky, O. Meth-Cohn and C. W. Rees, Pergamon, Oxford, 1995, vol. 1, p. 771 Search PubMed.
  13. I. J. Turchi, J. B. Press, J. J. McNally, M. P. Bonner and K. L. Sorgi, J. Org. Chem., 1993, 58, 4629 CrossRef CAS.
  14. M. L. Tedjamulia, Y. Tominaga, R. N. Castle and M. L. Lee, J. Heterocycl. Chem., 1983, 20, 1485 CAS.
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