A novel protocol for the synthesis of furo[2,3-b]benzofurans and dihydrofuro[2,3-b]benzofurans

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

Mukund G. Kulkarni and Ravindra M. Rasne


Abstract

A Wittig olefination–Claisen rearrangement approach has been successfully applied to develop a novel protocol for the synthesis of the dihydrofuro[2,3-b]benzofuran and furo[2,3-b]benzofuran ring systems.


References

  1. W. F. Busby and G. N. Wogan, Chemical Carcinog., ACS Monogr., 1984, 182, 945 Search PubMed.
  2. J. V. J. Rodricks, Agric. Food Chem., 1969, 17, 457 Search PubMed.
  3. H. E. Zaugg, V. Papendick and R. J. Michaels, J. Am. Chem. Soc., 1964, 86, 1399 CrossRef CAS; J. A. Knight, J. C. Roberts and P. Roffey, J. Chem. Soc. (C), 1966, 1308 RSC; P. Kuser, E. F. Frauenfelder and C. H. Eugster, Helv. Chim. Acta, 1971, 54, 969 CAS; D. T. Conner and M. Strandtmann, J. Org. Chem., 1973, 38, 3874 CrossRef; N. E. Pawlowski, D. J. Jones and R. O. Sinnhuber, Tetrahedron Lett., 1974, 14, 1321 CrossRef; S. D. Joshi and R. N. Usgaonkar, Ind. J. Chem., 1982, 21B, 399 Search PubMed; M. E. Alonso, P. Jano and M. I. Hernandez, J. Org. Chem., 1983, 48, 3047 CrossRef CAS; E. Wenkert, M. E. Alonso, B. L. Buckwalter and E. L. Sanchez, J. Am. Chem. Soc., 1983, 105, 2021 CrossRef CAS; A. C. Jain, A. K. Mathur and O. D. Tyagi, Indian J. Chem., 1985, 24B, 549 Search PubMed; G. A. Kraus, J. O. Nagy and J. DeLano, Tetrahedron, 1985, 41, 2337 CrossRef CAS; Y. Shizuri, K. Nakamura and S. Yamamura, J. Chem. Soc., Chem. Commun., 1985, 530 RSC; B. B. Snider and R. A. H. F. Hui, J. Org. Chem., 1985, 50, 5167 CrossRef CAS; C. P. Gorst-Allman and P. S. Steyn, J. Chem. Soc., Perkin Trans. 1, 1987, 163 RSC; S. Wolff and H. M. R. Hoffmann, Synthesis, 1988, 760 CrossRef CAS; J. M. Mellor and S. Mohammed, Tetrahedron Lett., 1991, 32, 7107 CrossRef CAS; B. Schmidt and H. M. R. Hoffmann, Tetrahedron, 1991, 47, 9357 CrossRef CAS; U. Albrecht, R. Wartchow and H. M. R. Hoffmann, Angew. Chem., 1992, 104, 903 CAS; Angew. Chem., Int. Ed. Engl., 1992, 31, 910 Search PubMed; M. C. Pirrung and J. Zhang, Tetrahedron Lett., 1992, 33, 5987 Search PubMed; A. Mitra, S. Biswas and V. R. Venkateswaran, J. Org. Chem., 1993, 58, 7913 CrossRef CAS; H. Rapport and E. R. Civitello, J. Org. Chem., 1994, 59, 3775 CrossRef; C. W. Holzapfel and D. B. G. Williams, Tetrahedron, 1995, 51, 8555 CrossRef CAS.
  4. M. G. Kulkarni, D. S. Pendharkar and R. M. Rasne, Tetrahedron Lett., 1997, 38, 1459 CrossRef CAS.
  5. M. G. Kulkarni and D. S. Pendharkar, Tetrahedron, 1997, 53, 3167 CrossRef CAS.
  6. M. G. Kulkarni and D. S. Pendharkar, J. Chem. Soc., Perkin Trans. 1, 1997, 21, 3127 RSC.
  7. M. G. Kulkarni and R. M. Rasne, Synthesis, 1997, 1420 CrossRef CAS.
  8. All the compounds gave satisfactory analytical data.
  9. J. Bujans, F. Sánchez-baeza and A. Messeguer, Tetrahedron, 1994, 50, 7597 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.