Dehydrogenation by iodine-dimethylsulfoxide system: A general route to susbtituted chromones and thiochromones

Heterocyclic Communications

Volumn 3, Issue 3, 1997, Pages 223-229

  Patonay, Tamás ^a   Cavaleiro, José A S ^b   Lévai, Albert ^a   Silva, Artur M S ^b  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2742589493     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (46)

1. For monographs and reviews see: (a) K. Böhm, Die Flavonoide: Eine Übersicht über ihre Physiologie, Pharmakodynamik und therapeutische Verwendung, Cantor, Aulendorf, 1967 (b) N.S. Parmar and M.N. Ghosh, Indian J. Pharmacol. 12, 213 (1980) (c) B. Havsteen, Biochem. Pharmacol. 32, 1141 (1983) - M. Gábor, The Pharmacology of Benzopyrȧn derivatives and related Compounds, Akadémiai Kiadó, Budapest, 1988
2. For monographs and reviews see: (a) K. Böhm, Die Flavonoide: Eine Übersicht über ihre Physiologie, Pharmakodynamik und therapeutische Verwendung, Cantor, Aulendorf, 1967 (b) N.S. Parmar and M.N. Ghosh, Indian J. Pharmacol. 12, 213 (1980) (c) B. Havsteen, Biochem. Pharmacol. 32, 1141 (1983) - M. Gábor, The Pharmacology of Benzopyrȧn derivatives and related Compounds, Akadémiai Kiadó, Budapest, 1988
3. For monographs and reviews see: (a) K. Böhm, Die Flavonoide: Eine Übersicht über ihre Physiologie, Pharmakodynamik und therapeutische Verwendung, Cantor, Aulendorf, 1967 (b) N.S. Parmar and M.N. Ghosh, Indian J. Pharmacol. 12, 213 (1980) (c) B. Havsteen, Biochem. Pharmacol. 32, 1141 (1983) - M. Gábor, The Pharmacology of Benzopyrȧn derivatives and related Compounds, Akadémiai Kiadó, Budapest, 1988
4. For monographs and reviews see: (a) K. Böhm, Die Flavonoide: Eine Übersicht über ihre Physiologie, Pharmakodynamik und therapeutische Verwendung, Cantor, Aulendorf, 1967 (b) N.S. Parmar and M.N. Ghosh, Indian J. Pharmacol. 12, 213 (1980) (c) B. Havsteen, Biochem. Pharmacol. 32, 1141 (1983) - M. Gábor, The Pharmacology of Benzopyrȧn derivatives and related Compounds, Akadémiai Kiadó, Budapest, 1988
5. (a) M.C. Bibby, Br. J. Cancer 63, 3 (1991)
6. (b) D. Dauzonne and L. Martinez, Tetrahedron Lett. 36, 1845 (1995)
7. (c) N. De Meyer, A. Haemers, L. Mishra, H.-K. Pandey, L.A.C. Pieters, D.A Vanden Berghe and A.J. Vlietinck, J. Med. Chem. 34, 736 (1991)
8. (d) R.I. Brinkworth, M.J. Stoermer and D.P. Fairlie, Bichem. Biophys. Res. Commun. 188, 631 (1992)
9. (e) R. Tang, K Chen, M. Cosentino and K.-H. Lee, Biomed. Chem. Lett. 4, 455 (1994)
10. (f) M. Cushman, D. Nagarathnam, D.L. Burg and R.L. Geahlen, J. Med. Chem. 34, 798 (1991)
11. (g) M. Cushman, H. Zhu, R.L. Geahlen and A.J. Kraker, J. Med. Chem. 37, 3353 (1994)
12. For details see: (a) T.A. Geissman (Ed.), The Chemistry of Flavonoid Compounds, Pergamon, Oxford, 1962 (b) J.B. Harborne, T.J. Mabry and H. Mabry (Eds.), The Flavonoids, Chapman & Hall, London, 1975 (c) G.P. Ellis (Ed.), Chromenes, Chromanones and Chromones, Wiley, New York, 1977 (d) T. Patonay, D. Molnár and Z. Murányi, Bull. Soc. Chim. Fr. 132, 233 (1995)
13. For details see: (a) T.A. Geissman (Ed.), The Chemistry of Flavonoid Compounds, Pergamon, Oxford, 1962 (b) J.B. Harborne, T.J. Mabry and H. Mabry (Eds.), The Flavonoids, Chapman & Hall, London, 1975 (c) G.P. Ellis (Ed.), Chromenes, Chromanones and Chromones, Wiley, New York, 1977 (d) T. Patonay, D. Molnár and Z. Murányi, Bull. Soc. Chim. Fr. 132, 233 (1995)
14. For details see: (a) T.A. Geissman (Ed.), The Chemistry of Flavonoid Compounds, Pergamon, Oxford, 1962 (b) J.B. Harborne, T.J. Mabry and H. Mabry (Eds.), The Flavonoids, Chapman & Hall, London, 1975 (c) G.P. Ellis (Ed.), Chromenes, Chromanones and Chromones, Wiley, New York, 1977 (d) T. Patonay, D. Molnár and Z. Murányi, Bull. Soc. Chim. Fr. 132, 233 (1995)
15. For details see: (a) T.A. Geissman (Ed.), The Chemistry of Flavonoid Compounds, Pergamon, Oxford, 1962 (b) J.B. Harborne, T.J. Mabry and H. Mabry (Eds.), The Flavonoids, Chapman & Hall, London, 1975 (c) G.P. Ellis (Ed.), Chromenes, Chromanones and Chromones, Wiley, New York, 1977 (d) T. Patonay, D. Molnár and Z. Murányi, Bull. Soc. Chim. Fr. 132, 233 (1995)
16. (a) A.G. Doshi, P.A. Soni and B.J. Ghiya, Indian J. Chem. 25B, 759 (1986)
17. (b) J.A.S. Cavaleiro, J. Elguero, M.L. Jimeno and A.M.S. Silva, Chem. Lett. 445 (1991)
18. (a) J.K. Makrandi and Seema, Indian J. Chem. 30B, 788 (1991)
19. (b) W.A. Price, A.M.S. Silva and J.A.S. Cavaleiro, Heterocycles 36, 2601 (1993)
20. (c) A.M.S. Silva, D.C.G.A. Pinto and J.A.S. Cavaleiro, Tetrahedron Lett. 35, 5899 (1994)
21. (d) D.C.G.A. Pinto, A.M.S. Silva and J.A.S. Cavaleiro, Tetrahedron Lett. 35, 9459 (1994)
22. (a) W. Fatma, J. Iqbal, H. Ismail, K. Ishratullah, W.A. Shaida and W. Rahman, Chem. Ind. (London) 315 (1979)
23. (b) N. Hans and S.K. Grover, Synth. Commun. 23, 1021 (1993)
24. (a) T. Thorstenson and J. Songstad, Acta Chem. Scand. 32A, 133 (1978)
25. (b) K. Maartman-Moe, K. Sanderud and J. Songstad, Acta Chem. Scand. 36B, 211 (1982)
26. (c) S. Oae, N. Yamada, K. Fujimori and O. Kikuchi, Bull. Chem. Soc. Jpn. 56, 248 (1983)
27. (a) T. Durst, in Comprehensive Organic Chemistry, Vol. 3, D.H.R. Barton and W.D. Ollis (Eds.), Pergamon, Oxford, 1979, 121
28. (b) A.J. Mancuso and D. Swern, Synthesis 165 (1981)
29. 2 (Hlg = Cl, Br, I) reagents see: (a) E.J. Corey and U. Kim, Tetrahedron Lett. 919 (1973) (b) P.A. Zoretic, J. Org. Chem. 40, 1867 (1975) (c) T.V. Lee, in Comprehensive Organic Synthesis, Vol. 7, B.M. Trost and I. Fleming, I. (Eds.), Pergamon, Oxford, 1991, 291 (d) R.M. Munavu, J. Org. Chem. 45, 3341 (1980) (e) M. Mikolajczyk and M. Luczak, Synthesis 114 (1975)
30. 2 (Hlg = Cl, Br, I) reagents see: (a) E.J. Corey and U. Kim, Tetrahedron Lett. 919 (1973) (b) P.A. Zoretic, J. Org. Chem. 40, 1867 (1975) (c) T.V. Lee, in Comprehensive Organic Synthesis, Vol. 7, B.M. Trost and I. Fleming, I. (Eds.), Pergamon, Oxford, 1991, 291 (d) R.M. Munavu, J. Org. Chem. 45, 3341 (1980) (e) M. Mikolajczyk and M. Luczak, Synthesis 114 (1975)
31. 2 (Hlg = Cl, Br, I) reagents see: (a) E.J. Corey and U. Kim, Tetrahedron Lett. 919 (1973) (b) P.A. Zoretic, J. Org. Chem. 40, 1867 (1975) (c) T.V. Lee, in Comprehensive Organic Synthesis, Vol. 7, B.M. Trost and I. Fleming, I. (Eds.), Pergamon, Oxford, 1991, 291 (d) R.M. Munavu, J. Org. Chem. 45, 3341 (1980) (e) M. Mikolajczyk and M. Luczak, Synthesis 114 (1975)
32. 2 (Hlg = Cl, Br, I) reagents see: (a) E.J. Corey and U. Kim, Tetrahedron Lett. 919 (1973) (b) P.A. Zoretic, J. Org. Chem. 40, 1867 (1975) (c) T.V. Lee, in Comprehensive Organic Synthesis, Vol. 7, B.M. Trost and I. Fleming, I. (Eds.), Pergamon, Oxford, 1991, 291 (d) R.M. Munavu, J. Org. Chem. 45, 3341 (1980) (e) M. Mikolajczyk and M. Luczak, Synthesis 114 (1975)
33. 2 (Hlg = Cl, Br, I) reagents see: (a) E.J. Corey and U. Kim, Tetrahedron Lett. 919 (1973) (b) P.A. Zoretic, J. Org. Chem. 40, 1867 (1975) (c) T.V. Lee, in Comprehensive Organic Synthesis, Vol. 7, B.M. Trost and I. Fleming, I. (Eds.), Pergamon, Oxford, 1991, 291 (d) R.M. Munavu, J. Org. Chem. 45, 3341 (1980) (e) M. Mikolajczyk and M. Luczak, Synthesis 114 (1975)
34. C.T. Chang, F.C. Chen, T.S. Chen, K.K. Hsu, T. Ueng and M. Hung, J. Chem. Soc. 3414 (1961)
35. K. Auwers and L. Anschütz, Ber. 54, 1543 (1921)
36. G. Litkei, T. Patonay, R. Bognár, V.P. Khilya, A. Aitmambetov and F. Babichev, Pharmazie 39, 741 (1984)
37. T. Patonay, G. Litkei, E. Péli, V.P. Khilya and A. Aitmambetov, Pharmazie 42, 662 (1987)
38. T. Patonay, R. Bognár and G. Litkei, Tetrahedron 40, 2555 (1984)
39. P. Da Re, A. Colleoni, L. Verlicchi, Ann. Chim. (Rome) 48, 762 (1958); Chem. Abstr. 53, 21924h (1959)
40. P. Da Re, A. Colleoni, L. Verlicchi, Ann. Chim. (Rome) 48, 762 (1958); Chem. Abstr. 53, 21924h (1959)
41. F.C. Chen, T.S. Chen and T. Ueng, J. Chinese Chem. Soc. (Taiwan) 9, 308 (1962); Chem. Abstr. 60, 10639a (1964)
42. F.C. Chen, T.S. Chen and T. Ueng, J. Chinese Chem. Soc. (Taiwan) 9, 308 (1962); Chem. Abstr. 60, 10639a (1964)
43. S. Grossmann and. S. Kostanecki, Ber. 33, 2516 (1900)
44. A.T.M. Dunne, J.E. Gowan, K. Keane, B.M. O'Kelly, D. O'Sullivan, M.M. Roche, P.M. Ryan and T.S. Wheeler, J. Chem. Soc. 1252 (1950)
45. T. Patonay, G. Litkei and R. Bognár, Tetrahedron 40, 3425 (1984)
46. F. Amdt, Ber. 58, 1612 (1925)