Intramolecular Anionic Friedel-Crafts Equivalents. A General Regiospecific Route to Substituted and Naturally Occurring Xanthen-9-ones

Synlett

Volumn 1997, Issue 9, 1997, Pages 1081-1083

  Familoni, O B ^a   Ionica, Ileana ^a   Bower, Justin F ^a   Snieckus, Victor ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002276097     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1533     Document Type: Article

References (42)

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6. Formally this reaction is related to the Parham cyclization which, however, requires initiation by RLi-mediated metal-halogen exchange: Parham, W. E.; Bradsher, C. K. Acc. Chem. Res. 1982, 15, 300.
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23. Reviews: Dean, F. M. in ApSimon, J. Total Synth. Nat. Prod. 1973, 1, 534; and Afzal, M.; Al-Hassan, J. M. Heterocycles 1980, 14, 1173; For a new approach to xanthones, see: Sun, L.; Liebeskind, L. S. Tetrahedron Lett. 1997, 38, 3663.
24. Reviews: Dean, F. M. in ApSimon, J. Total Synth. Nat. Prod. 1973, 1, 534; and Afzal, M.; Al-Hassan, J. M. Heterocycles 1980, 14, 1173; For a new approach to xanthones, see: Sun, L.; Liebeskind, L. S. Tetrahedron Lett. 1997, 38, 3663.
25. Diaryl ether carboxamides were prepared by the Ullmann (Moroz, A. A.; Shvartsberg, M. S. Russ. Chem. Rev. 1974, 43, 679; and Lindsay, J. Tetrahedron 1984, 40, 1433) protocol using a) traditional (Bacon, G. R.; Steward, O. J. J. Chem. Soc. 1965, 4953) or b) improved Soula, G. Ligenheld, L. Rhone-Poulenc Industries S. A. FR. Demande 2456727, EP21868A1, 12 Dec. 1980, 33; Chem. Abstr. CA95: 97356t) procedures.
26. Diaryl ether carboxamides were prepared by the Ullmann (Moroz, A. A.; Shvartsberg, M. S. Russ. Chem. Rev. 1974, 43, 679; and Lindsay, J. Tetrahedron 1984, 40, 1433) protocol using a) traditional (Bacon, G. R.; Steward, O. J. J. Chem. Soc. 1965, 4953) or b) improved Soula, G. Ligenheld, L. Rhone-Poulenc Industries S. A. FR. Demande 2456727, EP21868A1, 12 Dec. 1980, 33; Chem. Abstr. CA95: 97356t) procedures.
27. Diaryl ether carboxamides were prepared by the Ullmann (Moroz, A. A.; Shvartsberg, M. S. Russ. Chem. Rev. 1974, 43, 679; and Lindsay, J. Tetrahedron 1984, 40, 1433) protocol using a) traditional (Bacon, G. R.; Steward, O. J. J. Chem. Soc. 1965, 4953) or b) improved Soula, G. Ligenheld, L. Rhone-Poulenc Industries S. A. FR. Demande 2456727, EP21868A1, 12 Dec. 1980, 33; Chem. Abstr. CA95: 97356t) procedures.
28. Diaryl ether carboxamides were prepared by the Ullmann (Moroz, A. A.; Shvartsberg, M. S. Russ. Chem. Rev. 1974, 43, 679; and Lindsay, J. Tetrahedron 1984, 40, 1433) protocol using a) traditional (Bacon, G. R.; Steward, O. J. J. Chem. Soc. 1965, 4953) or b) improved Soula, G. Ligenheld, L. Rhone-Poulenc Industries S. A. FR. Demande 2456727, EP21868A1, 12 Dec. 1980, 33; Chem. Abstr. CA95: 97356t) procedures.
29. a) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837;
30. b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
31. 2, 3 and for X=NR systems: Moreau, P.; Gray, M.; Briggs L. E.; MacNeil, S.; Snieckus, V. unpublished results.
32. a) de Oliveira, G. G.; Mesquita, A. A. L.; Gottlieb, O. R.; Magalhaes, M. T. An. Acad. Brasil. Cienc. 1966, 38, 421; Chem. Abstr. 1967, 67, 108528a;
33. a) de Oliveira, G. G.; Mesquita, A. A. L.; Gottlieb, O. R.; Magalhaes, M. T. An. Acad. Brasil. Cienc. 1966, 38, 421; Chem. Abstr. 1967, 67, 108528a;
34. b) Rocha, L.; Marston, A.; Auxiliadora, M.; Kaplan, C.; Stoeckli-Evans, H.; Thull, U.; Testa, B.; Hostettmann, K.; Phytochemistry 1994, 36, 1381;
35. c) Locksley, H. D.; Quillinan, A. J.; Scheinmann, F. J. Chem. Soc. (C) 1971, 3804 (0.3% overall yield for 14).
36. Dean, F. M.; Goodchild, J.; Houghton, L. E.; Martin, J. A.; Morton, R. B.; Parton, B.; Price, A. W.; Somvichien, N. Tetrahedron Lett. 1966, 4153.
37. da Silva, A. J.; Lopes, C. C.; Lopes, R. S. C.; Chauder, B.; Snieckus, V. submitted for publication.
38. The isomeric compound i was also isolated in 2% yield. (Matrix Presented)
39. 6
40. 2 (31%)
41. 2 (31%)
42. 5: C, 70.16; H, 6.47; found C, 70.03; H, 6.23.