Acid catalysed rearrangements of 1-hydroxy-2,3,4,4a-tetrahydro-9H-xanthen-9-ones: Synthesis and cycloaddition reactions of 3,4-dihydro-9H-xanthen-9-ones

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 9, 1998, Pages 1547-1553

  Gabbutt, Christopher D ^a   Hepworth, John D ^a   Urquhart, Michael W J ^a   Vazquez De Miguel, Luis M ^b  

^a UNIVERSITY OF CENTRAL LANCASHIRE   (United Kingdom)

^b UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748638440     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a800235e     Document Type: Article

References (34)

1. A. Schonberg, A. Mustafa and G. Aziz, J. Am. Chem. Soc., 1954, 76, 4576.
2. A. Mustafa and M. I. Ali, J. Org. Chem., 1956, 21, 849.
3. R. M. Letcher and T.-Y. Yue, J. Chem. Res. (M), 1992, 2078.
4. G. Aziz, J. Org. Chem., 1962, 27, 1929.
5. H. Marona, Pol. J. Chem., 1979, 53, 1877.
6. A. Quillinan and F. Scheinmann, J. Chem. Soc., Chem. Commun., 1971, 966.
7. I. T. Badejo, R. Karaman, N. W. I. Lee, E. C. Lutz, M. T. Mamanta and J. L. Fry, J. Chem. Soc., Chem. Commun., 1989, 566;
8. R. Karaman, I. T. Badejo and J. L. Fry, J. Am. Chem. Soc., 1989, 111, 6450;
9. I. T. Badejo, R. Karaman and J. L. Fry, J. Org. Chem., 1989, 54, 4591.
10. C. D. Gabbutt and J. D. Hepworth, Tetrahedron Lett., 1985, 1879.
11. C. D. Gabbutt, J. D. Hepworth, M. W. J. Urquhart and L. M. Vazquez de Miguel, J. Chem. Soc., Perkin Trans. 1, 1997, 1819.
12. S. Klutchko, M. von Strandtman and J. R. Shavel, US Patent, 1975, 3 862 141.
13. F. Eiden and W. Luft, Arch. Pharm. (Weinheim), 1973, 307, 634.
14. F. M. Dean and S. Murray, J. Chem. Soc., Perkin Trans. 1, 1975, 1706;
15. F. M. Dean, K. M. Hindley, S. Murray and W. Taylor, J. Chem. Soc., Perkin Trans. 1, 1976, 2444.
16. J. F. W. McOmie, M. L. Watts and D. E. West, Tetrahedron, 1969, 24, 2289.
17. P. E. Eaton and R. H. Mueller, J. Am. Chem. Soc., 1972, 94, 1014;
18. F. Camps, O. Colomina, J. Coll and A. Messeguer, Tetrahedron, 1982, 38, 2955.
19. V. A. Mironov, A. D. Fedorovich and A. A. Akhrem, Izv. Akad. Nauk. SSSR, Ser. Khim., 1973, 2036.
20. A. J. Fatiadi, Synthesis, 1986, 249.
21. H. Kwart and K. King, Chem. Rev., 1968, 68, 415;
22. R. W. Sweger and A. W. Czarnik, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 5, p. 551.
23. W. Fischer, Helv. Chim. Acta, 1991, 74, 1119.
24. G. W. Rewcastle and W. A. Denny, Synthesis, 1985, 220.
25. C. J. Moody, Adv. Heterocycl. Chem., 1982, 30, 1;
26. S. Radl, Adv. Heterocycl. Chem., 1996, 67, 119.
27. L. A. Paquette and R. T. Taylor, Tetrahedron Lett., 1976, 2745;
28. H. M. Sirat, E. J. Thomas and N. D. Tyrrell, J. Chem. Soc., Chem. Commun., 1979, 36;
29. L. A. Paquette and R. F. Doehner Jr., J. Org. Chem., 1980, 45, 5105.
30. M. Christi and M. Lechner, Chem. Ber., 1982, 115, 1.
31. M. P. Johnson and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1985, 71.
32. D. D. Perrin and W. L. F. Armarego, in Purification of Laboratory Chemicals, 3rd edn., Pergamon Press, Oxford, 1988.
33. W. C. Still, M. Khan and A. Mitra, J. Org. Chem., 1978, 43, 2923.
34. Aldrich Catalogue Handbook of Fine Chemicals, 1996-1997, p. 1574.