Polyoxygenated coumarins. Oxonium ylides en route to polyoxa- macrocyclic coumarins

Tetrahedron

Volumn 55, Issue 21, 1999, Pages 6577-6584

  Cenini, Sergio ^a   Cravotto, Giancarlo ^b   Giovenzana, Giovanni B ^c   Palmisano, Giovanni ^d   Tollari, Stefano ^a  

^a CNR   (Italy)

^b UNIVERSITY OF TURIN   (Italy)

^c Istituto di Coltivazioni Arborcc   (Italy)

^d Dipartimento di Scienze Mediche   (Italy)

Author keywords

Carbene Ylides; Coumarins; Crown Ethers; Diazo Compounds

Indexed keywords

2,3,5,6,8,9,11,12 OCTAHYDRO [1,4,10]TRIOXACYCLOPENTADECINOL[2,3 C]BENZOPYRAN 14 ONE; BENZOPYRAN DERIVATIVE; COUMARIN DERIVATIVE; CROWN ETHER DERIVATIVE; ETHER DERIVATIVE; MACROCYCLIC COMPOUND; RHODIUM TETRAACETATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; DECOMPOSITION; OLIGOMERIZATION; OXYGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0033591191     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00291-4     Document Type: Article

References (29)

1. Silberad, O.; Roy, C.J. J.Chem.Soc. 1906, 89, 179.
2. a) Doyle, M.P., McKervey, M.A.; Ye T. In "Modern Catalytic Methods for Organic Synthesis with Diazo Compounds", John Wiley & Sons: New York, 1997;
3. b) Taber, D.F. Comprehensive Organic Synthesis; Pattenden, G. Ed.; Pergamon Press: Oxford, 1991, Vol. 3;
4. c) Doyle, M.P. In "Homogeneous Transition-Metal Catalysis in Organic Chemistry", Moser, W.R; Slocum, D.W., Eds.; ACS Advanced Chemistry Series, No. 230, American Chemical Society: Washington, 1992, Ch. 30;
5. d) Padwa, A.; Austin, D.J. Angew.Chem.Int.Ed.Engl. 1994, 33, 1797;
6. e) Ye, T.; McKervey, M.A. Chem.Rev. 1994, 94, 1091;
7. f) Doyle, M.P. Chem.Rev. 1986, 86, 547;
8. g) Doyle, M.P. "Transition-Metal Carbene Complexes: Diazo-Decomposition, Ylide and Insertion" in "Comprehensive Organometallic Chemistry, II"; Abel, E.W.; Stone, F.G.A.; Wilkinson, G., Eds.; Pergamon Press, Oxford, 1995; Vol. 12.
9. Huebneck, C.F.; Ink, K.P. J.Am.Chem.Soc. 1945, 67, 97.
10. Taber, D.F.; You, K.; Song, Y. J.Org.Chem. 1995, 60, 1093.
11. Cenini, S.; Giovenzana G.B.; Mattavelli, V.; Palmisano, G.; Tollari, S. unpublished results.
12. 2O catalysis have been reported. See, John, D.I. "6-Diazopenicillanate Chemistry and Some Aspects of Penam Rearrangements" in "Recent Advances in the Chemistry of β-Lactam Antibiotics"; Brown, A.G.; Roberts, S.M., Eds.; The Royal Society of Chemistry: London, 1985.
13. Roelens, S. J.Am.Chem.Soc. 1990, 112, 58.
14. Frimer, A.A.; Marks, V.; Gilinsky-Sharon, P.; Aljadeff, G.; Gottlieb, H.E. J.Org.Chem. 1995, 60, 4510.
15. a) Pirrung, M.C.; Zhang, J.; Lackey, K.; Sternbach, D.D.; Brown, T. J.Org.Chem. 1995, 60, 2112;
16. b) Pirrung, M.C.; Zhang, J.; McPhail, A.T. J.Org.Chem. 1991, 56, 6269.
17. Pine S.H. Org. React. 1970, 18, 403.
18. The intramolecular reaction would be endo-trig, a class disfavoured according to Baldwin's rules (Baldwin, J.E. J.Chem.Soc., Chen.Commun. 1976, 734).
19. a) Ito, K.; Yoshitake, M.; Katsuki, T. Heterocycles 1996, 42, 305; Chem.Lett. 1995, 1027; Tetrahedron 1996, 42, 3905;
20. a) Ito, K.; Yoshitake, M.; Katsuki, T. Heterocycles 1996, 42, 305; Chem.Lett. 1995, 1027; Tetrahedron 1996, 42, 3905;
21. a) Ito, K.; Yoshitake, M.; Katsuki, T. Heterocycles 1996, 42, 305; Chem.Lett. 1995, 1027; Tetrahedron 1996, 42, 3905;
22. b) Doyle, M.P.; Ene, D.G.; Forbes, D.C.; Todrow, J.S. Tetrahedron Lett. 1997, 38, 4367.
23. a) Appendino, G.; Cravotto, G.; Toma, L.; Annunziata, R.; Palmisano, G. J.Org.Chem. 1994, 59, 5556;
24. b) Annunziata, R.; Raimondi, L.; Appendino, G.; Cravotto, G.; Palmisano, G. Gazz.Chim.Ital. 1995, 125, 465;
25. c) .; Appendino, G.; Cravotto, G.; Palmisano, G., Annunziata, R. Synth.Commun. 1996, 26, 33-59.
26. Lin, Y.-S.; Jiang, S.-Y.; Huang, T.-C; Lin, S.-J.; Chow, Y.L. J.Org.Chem. 1998, 63, 3364.
27. Three-component coupling reactions of photogenerated carbenes with cyclic ethers and a nucleophile have been reported (Oku, A.; Kimura, K.; Ohwaki, S. Acta Chem.Scand. 1993, 47, 391).
28. Cunningham, P.D.; Geraghty, N.W.A.; McArdle, P.J.; Murphy, P.V.; O'Sullivan, T.J. J.Chem.Soc., Perkin I 1997, 1.
29. Diazacrown ethers substituted with functionalised coumarins and their photophysical properties have been reported, see: Bourjon, J.; Pouget, J.; Valeur, B. J.Phys.Chem. 1993, 97, 4552.