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

Abstract

The acid catalysed rearrangement of 1-hydroxy-2,3,4,4a-tetrahydro-9H-xanthen-9-ones can give 1-alkoxy- or 1-alkylidene-1,2,3,4-tetrahydro-9H-xanthen-9-ones and/or 3,4-dihydro-9H-xanthen-9-ones depending on the conditions employed. The last compounds undergo facile Diels–Alder cycloaddition reactions.

References

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; R. Karaman, I. T. Badejo and J. L. Fry, J. Am. Chem. Soc., 1989, 111, 6450; I. T. Badejo, R. Karaman and J. L. Fry, J. Org. Chem., 1989, 54, 4591.
8. C. D. Gabbutt and J. D. Hepworth, Tetrahedron Lett., 1985, 1879.
9. C. D. Gabbutt, J. D. Hepworth, M. W. J. Urquhart and L. M. Vazquez de Miguel, J. Chem. Soc., Perkin Trans. 1, 1997, 1819.
10. S. Klutchko, M. von Strandtman and J. R. Shavel, US Patent, 1975, 3 862 141.
11. F. Eiden and W. Luft, Arch. Pharm. (Weinheim), 1973, 307, 634.
12. F. M. Dean and S. Murray, J. Chem. Soc., Perkin Trans. 1, 1975, 1706; F. M. Dean, K. M. Hindley, S. Murray and W. Taylor, J. Chem. Soc., Perkin Trans. 1, 1976, 2444.
13. J. F. W. McOmie, M. L. Watts and D. E. West, Tetrahedron, 1969, 24, 2289.
14. P. E. Eaton and R. H. Mueller, J. Am. Chem. Soc., 1972, 94, 1014; F. Camps, O. Colomina, J. Coll and A. Messeguer, Tetrahedron, 1982, 38, 2955.
15. V. A. Mironov, A. D. Fedorovich and A. A. Akhrem, Izv. Akad. Nauk. SSSR, Ser. Khim., 1973, 2036.
16. A. J. Fatiadi, Synthesis, 1986, 249.
17. H. Kwart and K. King, Chem. Rev., 1968, 68, 415; 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.
18. W. Fischer, Helv. Chim. Acta, 1991, 74, 1119.
19. G. W. Rewcastle and W. A. Denny, Synthesis, 1985, 220.
20. C. J. Moody, Adv. Heterocycl. Chem., 1982, 30, 1; S. Radl, Adv. Heterocycl. Chem., 1996, 67, 119.
21. L. A. Paquette and R. T. Taylor, Tetrahedron Lett., 1976, 2745; H. M. Sirat, E. J. Thomas and N. D. Tyrrell, J. Chem. Soc., Chem. Commun., 1979, 36; L. A. Paquette and R. F. Doehner Jr., J. Org. Chem., 1980, 45, 5105.
22. M. Christl and M. Lechner, Chem. Ber., 1982, 115, 1.
23. M. P. Johnson and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1985, 71.
24. D. D. Perrin and W. L. F. Armarego, in Purification of Laboratory Chemicals, 3rd edn., Pergamon Press, Oxford, 1988.
25. W. C. Still, M. Khan and A. Mitra, J. Org. Chem., 1978, 43, 2923.
26. Aldrich Catalogue Handbook of Fine Chemicals, 1996–1997, p. 1574.