A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2391-2392

  Yavari, Issa ^a   Hekmat Shoar, Rahim ^a   Zonouzi, Afsaneh ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN DERIVATIVE; PHENOL DERIVATIVE; PHOSPHINE DERIVATIVE; PHOSPHONIUM DERIVATIVE;

ARTICLE; CARCINOGENICITY; CHEMICAL REACTION; PROTON TRANSPORT; SYNTHESIS;

EID: 0032537144     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00206-8     Document Type: Article

References (13)

1. 1. Murray, D. H., Mondez, J. and Brown, S. A. The Natural Coumarins: Occurrence, Chemistry and Biochemistry, Wiley, 1982, New York.
2. 2. Hurvey, R. G., Corts, C. Ananthanarayan, T. P. and Schmolka, S. J. Org. Chem., 1988, 53, 3936.
3. 3. Ziegler, T., Mohler, H. and Effenberger, F. Chem. Ber., 1987, 120, 373.
4. 4. Kadis, S., Ciegler, A. and Ajl, S. Microb. Toxins, 1972, 7, Chapter 1.
5. 5. Ellis, G. P. and West, G. B. Prog. Med Chem., 1974, 10, 109.
6. 6. Wells, P. and Morrison, H. J. Am. Chem. Soc., 1975, 97, 154
7. 7. Although, this work is not the first to have prepared coumarins from the reaction of a phenol with DMAD (Davies, S. G., Mobbs, B. E. and Goodwin, C. J. J. Chem. Soc. Perkin Trans, 1, 1987, 2597.), the yields are superior and the use of a vinyltriphenylphosphonium salt is unprecedented. We did not observe any of the corresponding chromone derivatives from these reactions by nucleophilic attack on the vinyltriphenylphosphonium salt via the phenolate oxygen itself. Thus, the present method appears to be selective for coumarins.
8. 8. Cobridge, D. E. C. "Phosphorus, An Outline of the Chemistry, Biochemistry and Uses", 5th ed. Elsevier, 1995, Amsterdam.
9. 9. Johnson, A. W. and Tebby, J, C. J. Chem. Soc., 1961, 2126. Caesar, J. C., Griffiths, D. V., Griffiths, P. A. and Tebby, J. C. J. Chem. Soc. Perkin Trans. 1, 1989, 2425.
10. 9. Johnson, A. W. and Tebby, J, C. J. Chem. Soc., 1961, 2126. Caesar, J. C., Griffiths, D. V., Griffiths, P. A. and Tebby, J. C. J. Chem. Soc. Perkin Trans. 1, 1989, 2425.
11. 2 (6 ml) at -5°C over 10 min. The reaction mixture was then refluxed for 120 hr. The solvent was removed under reduced pressure and the solid mass was purified by recrystalization from ethanol (95%).
12. 13C NMR, MS, IR) are in good agreement with the proposed structures.
13. 12. Sethna, S. and Phadke, R. Org. React. (N. Y.), 1953, 7, 1.