Synthesis of fused aromatic [1,3]dioxoles from 2-hydroxymethylphenols

Synlett

Volumn , Issue 12, 1997, Pages 1395-1396

  Gesson, Jean Pierre ^a   Mondon, Martine ^a   Pokrovska, Natacha ^a  

^a UNIVERSITÉ DE POITIERS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344100344     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1037     Document Type: Article

References (29)

1. (a) Podophyllotoxin: Hartwell, J.L.; Schrecker, A.W. Fortschr. Chem. Org. Naturst. 1958, 15, 83.
2. (b) Liriodenine: Gupta, Y.P.; Ind. J. Chem. 1983, 22B, 429.
3. 3: Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Heterocycles 1996, 42, 359.
4. 3: Klix, R.C.; Cain, M.H.; Bhatia, A.V. Tetrahedron Lett. 1995, 36, 6413.
5. 2, CsF: Kobayashi, K.; Kanno, Y.; Seko, S.; Suginome, H. J. Chem. Soc. Perkin Trans. I 1992, 3111.
6. 3: Zelle, R.E.; McClellan, W.J. Tetrahedron Lett. 1991, 22, 2461.
7. (a) Sako, M., Ohara, S.; Hirota, K.; Maki, Y. J. Chem. Soc. Perkin Trans. I 1990, 3339.
8. (b) Chioccara, F.; Di Gennaro, P.; La Monica, G.; Sebastiano, R.; Rindone, B. Tetrahedron 1991, 47, 4429.
9. (c) Yoshizawa, I.; Tamura, M.; Kimura, M. Chem. Pharm. Bull. 1972, 20, 1842.
10. (d) Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1982, 23, 1577.
11. (a) Brennemann A.R.; Kaufman, S. Biochem. Biophys. Res. Commun. 1964, 17, 177.
12. (b) Klibanov, A.M.; Berman, Z.; Alberti, B.N. J. Am. Chem. Soc. 1981, 103, 6263.
13. (a) Guzman, J.A.; Mendoza, V.; Garcia, E.; Garibay, C.F.; Olivares, L.Z.; Maldonado, L.A. Synth. Commun. 1995, 14, 2121.
14. (b) Kabalka, G.W.; Reddy, N.K.; Narayana, C. Tetrahedron Lett. 1992, 33, 865.
15. (a) Adler, E.; Brasen, S.; Miyake, H. Acta Chem. Scand. 1971, 25, 2055.
16. (b) Becker, H.D.; Bremholt, T.; Adler, E. Tetrahedron Lett. 1972, 4205.
17. Becker, H.D.; Bremholt, Tetrahedron Lett. 1973, 197.
18. See also: Kasturi, T.R.; Jayaram, S.K.; Sattigeri, J.A.; Pragnacharyulu, P.V.P.; Row, T.N.G.; Renuka, K.; Venkatesan, K.; Begum, N.S.; Munirathinam, N. Tetrahedron 1993, 49, 7145.
19. Cacioli, P.; Reiss, J.A. Aust. J. Chem. 1984, 37, 2525.
20. 3) 5.96 (s, 2H), 6.67 (d, 1H, J=7 HZ), 6.94 (dd, 1H, J=7 and 2 Hz), 6.96 (broad s, 1H).
21. 4) and concentrated. Products were purified or separated by flash chromatography.
22. Tius, M.A.; Reddy, N.K. Synth. Commun. 1994, 24, 859.
23. 3); 6.13 (s, 2H), 7.17(d, 1H, J=8.8 Hz), 7.30 (t, 1H, J=7.3 Hz), 7.38 (d, 1H, J=8.8 Hz), 7.42 (t, 1H, J=7.3 Hz), 7.78 (t, 2H, J=7.3 Hz).
24. 3); 3.12 (d, 1H, J=8 Hz), 3.38 (d, 1H, J=8 Hz), 6.33 (d, 1H, J=10 Hz), 7.25 (m, 1H), 7.39 (m,3H), 7.59 (d, 1H, J=10 Hz).
25. 3); 0.22 (s, 6H), 1.04 (s, 9H), 6.09 (s, 2H), 7.12 (d, 1H, J=8.8 Hz), 7.38 (t, 1H, J=8 Hz), 7.50 (t, 1H, J=8 Hz). 7.60 (d, 1H, J=8.8 Hz), 7.76 (d, 1H, J=8 Hz), 8.18 (d, 1H, J=8 Hz).
26. Nagata, W.; Okada, K.; Aoki, T. Synthesis 1979, 365.
27. 3); 1.72 (m, 4H), 2.63 (m,4H), 4.84 (s, 2H), 6.63 (d,1H, J=8 Hz), 6.87 (d, 1H, J=8 Hz)
28. Andretti, G.D; Böhmer, V.; Jordon, J.G; Tabatabai, M.; Ugozzoli, F.; Vogt, W.; Wolff, A. J. Org. Chem. 1993, 58, 4023.
29. 3);1.76 (m, 4H), 2.68 (m, 4H), 5.90 (s, 2H), 6.54 and 6.61 (ABq, 2H, J=8 Hz).