Efficient Synthesis of 3-Arylphthalides†

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

Madhusudhan V. Paradkar, Anup A. Ranade, Madhuri S. Kulkarni, Himanshu M. Godbole and Augustine R. Joseph


Abstract

A convenient method for the synthesis of 3-arylphthalides (3aq) involving condensation of phthalaldehydic acids (1a,b) with aromatic substrates (2ak) in the presence of TFA is described.


References

  1. E. Sing and P. C. Gupta, J. Indian Chem. Soc., 1973, 50, 676 Search PubMed.
  2. N. S. Narasimhan and R. S. Mali, Synthesis, 1975, 797 CrossRef CAS.
  3. J. E. Baldwin and K. W. Bair, Tetrahedron Lett., 1978, 2559 CrossRef CAS.
  4. K. S. Kim, M. W. Spatz and F. Johnson, Tetrahedron Lett., 1979, 331 CrossRef CAS.
  5. W. H. Putersbaugh and C. R. Hauser, J. Org. Chem., 1964, 29, 853 CAS.
  6. Fr. M 5,606, Soc. Des. Usinem Chimiques, Rhone Poulenc (Chem. Abstr., 71, P 49976c) Search PubMed.
  7. (a) V. W. Floutz, J. Org. Chem., 1960, 25, 643 CrossRef CAS; (b) V. W. Floutz, J. Org. Chem., 1961, 26, 2584 CrossRef CAS; (c) R. Al-Hamdany, J. M. Al-Rawi and S. Ibrahim, J. Prakt. Chem., 1987, 126 CAS.
  8. E. S. Jones, W. H. Perkin Jr. and R. Robinson, J. Chem. Soc., 1912, 10, 257 Search PubMed.
  9. M. S. Newman, J. Org. Chem., 1975, 2996 CrossRef CAS; M. S. Newman, V. Sankaran and D. R. Olson, J. Am. Chem. Soc., 1976, 98, 3237 CrossRef CAS.
  10. Org. Synth., 1955, Coll. Vol. III, 737 Search PubMed.
  11. M. S. Newman and W. M. Hung, Org. Prep. Proced. Int., 1972, 4, 227 CAS; L. L. Woods and J. Sapp, J. Org. Chem., 1964, 29, 3445 CAS; 1962, 27, 3703.
  12. S. A. Kulkarni, Ph.D. Thesis, Pune University, 1995.
  13. J. N. Chatterjea, H. C. Jha and A. K. Chattopadhyay, Tetrahedron Lett., 1972, 3409 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.