View PDF Version
 
DOI: 10.1039/A906965H (Paper) Reference Section for: Chem. Commun., 1999, 2371-2372

Pyridine ring formation through the photoreaction of arenecarbothioamides with diene-conjugated carbonyl compounds†

(Note: The full text of this document is currently only available in the PDF Version )

Kazuaki Oda, Rikiji Nakagami, Naozumi Nishizono and Minoru Machida

Abstract

Irradiation of arenecarbothioamides with hexa-2,4-dienal in benzene solution gives 2-arylpyridines in moderate yields.

References

  1. K. Oda, M. Sakai, K. Ohno and M. Machida, Heterocycles, 1999, 50, 277 CAS.
  2. F. S. Yates, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon, Oxford, 1984, vol. 2, p. 511 Search PubMed.
  3. H. Bönnemann and W. Brijoux, in Advance in Heterocyclic Chemistry, ed. A. R. Katritzky, Academic Press, San Diego, 1990, vol. 48, p. 177 Search PubMed.
  4. P. Ribereau and G. Queguiner, Can. J. Chem., 1983, 61, 334 CAS; R. A. Jones and P. U. Civcir, Tetrahedron, 1997, 34, 11 529 CrossRef.
  5. T. Kambara, K. Koshida, N. Sato, I. Kuwajima, K. Kubota and T. Yamamoto, Chem. Lett., 1992, 583.
  6. K. V. Rao, K. Biemann and R. B. Woodward, J. Am. Chem. Soc., 1963, 85, 2532 CrossRef CAS.
  7. T. Meyer, Acc. Chem. Res., 1989, 22, 163 CrossRef CAS.
  8. K. Oda and M. Machida, J. Chem. Soc., Chem. Commun., 1994, 1477 RSC; K. Oda, H. Tsujita, K. Ohno and M. Machida, J. Chem. Soc., Perkin Trans. 1, 1995, 2931 RSC; K. Oda, R. Hiratsuka and M. Machida, Heterocycles, 1996, 43, 463 CAS; K. Oda, M. Sakai and M. Machida, Chem. Pharm. Bull., 1997, 45, 584 CAS; K. Oda, M. Sakai, H. Tsujita and M. Machida, Synth. Commun., 1997, 27, 1183 CAS.
  9. K. Oda, H. Tsujita, M. Sakai and M. Machida, Chem. Pharm. Bull., 1998, 46, 1522 CAS.
  10. To avoid formation of the photodimer of 2, the molar ratio of 1a and 2 was varied. As a result, the yield of 3a increased to 32% using a ratio of 2:1.
  11. C. J. Pouchert and J. R. Campbell, in The Aldrich Library of NMR Spectra, Aldrich Chemical Company, Wisconsin, 1974, vol. 9. Search PubMed.
  12. M. Tingoli, M. Tiecco, L. Testaferri, R. Andrenacci and R. Balducci, J. Org. Chem., 1993, 58, 6097 CrossRef CAS.
  13. G. R. Newkome and D. L. Fishel, J. Org. Chem., 1972, 37, 1329 CrossRef CAS.
  14. E. C. Constable, R. P. G. Henney and D. A. Tocher, J. Chem. Soc., Dalton Trans., 1992, 2467 RSC.
  15. J. R. Brooks, D. N. Harcourt and R. D. Waigh, J. Chem. Soc., Perkin Trans. 1, 1973, 2588 RSC.
  16. 8-Methylbicyclo[4.2.0.]octa-1(6),2,4-7-one 9 was derived from 6 by intramolecular photocyclization: S. V. Kessar, A. K. S. Mankotia, J. C. Scaiano, M. Barra, J. Gebicki and K. Huben, J. Am. Chem. Soc., 1996, 118, 4361 Search PubMed.
  17. J. Becher, Synthesis, 1980, 589 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.