Diels-Alder reactions of benzo[b]furan-4,5-diones and benzo[b]furan-4,7- diones

Heterocycles

Volumn 50, Issue 2, 1999, Pages 1137-1156

  Nebois, Pascal ^a   Fillion, Houda ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE;

BROMINATION; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTALLIZATION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 0033117368     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/rev-98-sr(h)7     Document Type: Review

References (70)

1. For references on natural sources and biological activities, see: (a) H. M. Chang, K. P. Cheng, T. F. Choang, H. F. Chow, K. Y. Chui, P. M. Hon, F. W. L. Tan, Y. Yang, Z. P. Zhong, C. M. Lee, H. L. Sham, C. F. Chan, Y. X. Cui, and H. N. C. Wong, J. Org. Chem., 1990, 55, 3537;
2. (b) J. Lee and J. K. Snyder, J. Org. Chem., 1990, 55, 4995.
3. As examples of natural sources, see: (a) H. Kakisawa, T. Hayashi, and T. Yamazaki, Tetrahedron Lett., 1969, 301;
4. (b) K. Inoue, C.-C. Chen, H. Inouye, and K. Kuriyama, J. Chem. Soc., Perkin Trans. I, 1981, 2764;
5. (c) K. Inoue, H. Inouye, and C.-C. Chen, Phytochemistry, 1981, 20, 2271;
6. (d) M. Madhusudana Rao and D. G. I. Kingston, J. Nat. Prod., 1982, 45, 600;
7. (e) M. Girard, D. Kindack, B. A. Dawson, J.-C. Ethier, D. V. C. Awang, and A. H. Gentry, J. Nat. Prod., 1988, 51, 1023;
8. (f) H. Wagner, B. Kreher, H. Lotter, M. O. Hamburger, and G. A. Cordell, Helv. Chim. Acta, 1989, 72, 659;
9. (g) C. E. Heltzel, A. A. L. Gunatilaka, T. E. Glass, D. G. I. Kingston, G. Hoffmann, and R. K. Johnson, J. Nat. Prod., 1993, 56, 1500;
10. (h) S. Ueda, T. Umemura, K. Dohguchi, T. Matsuzaki, H. Tokuda, H. Nishino, and A. Iwashima, Phytochemistry, 1994, 36, 323.
11. (a) R. H. Thomson, J. Org. Chem., 1951, 16, 1082;
12. (b) J.W. Mc Leod and R. H. Thomson, J. Org. Chem., 1960, 25, 36.
13. P. Nebois, O. Cherkaoui, L. Benameur, and H. Fillion, Tetrahedron, 1994, 50, 8457.
14. J. Lee, J. Tang, and J. K. Snyder, Tetrahedron Lett., 1987, 28, 3427.
15. J. Lee and J. K. Snyder, J. Am. Chem. Soc., 1989, 111, 1522.
16. For a survey of sonochemical Diels-Alder reactions, see: P. Nebois, Z. Bouaziz, H. Fillion, L. Moeini, M. J. Aurell Piquer, J.-L. Luche, A. Riera, A. Moyano, and M. A. Pericas, Ultrasonics Sonochemistry, 1996, 3, 7.
17. M. Haiza, J. Lee, and J. K. Snyder, J. Org. Chem., 1990, 55, 5008.
18. J. Lee, J.-H. Li, S. Oya, and J. K. Snyder, J. Org. Chem., 1992, 57, 5301.
19. The synthetic usefulness of α,β-unsaturated N, N-dimethylhydrazones was established by:
20. (a) B. Serckx-Poncin, A.-M. Hesbain-Frisque, and L. Ghosez, Tetrahedron Lett., 1982, 23, 3261;
21. (b) K. T. Potts, D. Bhattacharjee, and E. B. Walsh, J. Chem. Soc., Chem. Commun., 1984, 114;
22. (c) L. Ghosez, B. Serckx-Poncin, M. Rivera, P. Bayard, F. Sainte, A. Demoulin, A.-M. Frisque-Hesbain, A. Mockel, L. Munoz, and C. Bernard-Henriet, Lect. Heterocycl. Chem., 1985, 8, 69;
23. (d) K. T. Potts, E. B. Walsh, and D. Bhattacharjee, J. Org. Chem., 1987, 52, 2285;
24. (e) M. Chigr, H. Fillion, and A. Rougny, Tetrahedron Lett., 1988, 29, 5913;
25. (f) C. Gesto, E. De La Cuesta, and C. Avendano, Tetrahedron, 1989, 45, 4477;
26. (g) A. M. Echavarren, J. Org. Chem., 1990, 55, 4255;
27. (h) H. Lee and W. K. Anderson, Tetrahedron Lett., 1990, 31, 4405;
28. (i) P. Nebois, R. Barret, and H. Fillion, Tetrahedron Lett., 1990, 31, 2569;
29. (j) P. Nebois and H. Pillion, Tetrahedron Lett., 1991. 32, 1307;
30. (k) J. A. Valderrama, H. Pessoa-Mahana, and R. Tapia, J. Heterocycl. Chem., 1992, 29, 1177;
31. (l) Y. Kitahara and A. Kubo, Heterocycles, 1992, 34, 1089;
32. (m) P. Nebois, H. Fillion, L. Benameur, B. Fenet, and J.-L. Luche, Tetrahedron, 1993, 49, 9767;
33. (n) R. Tapia, J. A. Valderrema, and C. Quintanar, Heterocycles, 1994, 38, 1797;
34. (o) Y. Kitahara, F. Tamura, and A. Kubo, Chem. Pharm. Bull., 1994, 42, 1363;
35. (p) M. Villacampa, J. M. Perez, C. Avendano, and J. C. Menendez, Tetrahedron, 1994, 50, 10047;
36. (q) J. M. Perez, C. Avendano, and J. C. Menendez, Tetrahedron, 1995, 51, 6573;
37. (r) L. M. Diaz-Guerra, B. Ocana, J. M. Perez, C. Avendano, M. Espada, J. C. Menendez, T. Ramos, M. A. Ruiz, and J. M. Pingarron, Bull. Soc. Chim. Belg., 1995, 104, 683;
38. (s) R. A. Tapia, C. Quintanar, and J. A. Valderrama, Heterocycles, 1996, 43, 447;
39. (t) M. Mar Blanco, M. A. Alonso, C. Avendano, and J. C. Menendez, Tetrahedron, 1996, 52, 5933;
40. (u) C. Tödter and H. Lackner, Liebigs Ann. Chem., 1996, 1385;
41. (v) J. M. Perez, P. Lopez-Alvarado, M. A. Alonso, C. Avendano, and J. C. Menendez, Tetrahedron Lett., 1996, 37, 6955;
42. (w) J. M. Cuerva and A. M. Echavarren, Synlett, 1997, 173;
43. (x) J. A. Valderrama, M. Spate, and M. F. Gonzalez, Heterocyclic Commun., 1997, 3, 23;
44. (y) M. Del Mar Blanco, C. Avendano, and J. C. Menendez, Tetrahedron, 1997, 53, 11465;
45. (z) R. Barret, N. Roue, and H. Fillion, Chem. Pharm. Bull., 1998, 46, 548.
46. As examples of natural sources of maturinone, see: (a) J. Correa and J. Romo, Tetrahedron, 1966, 22, 685;
47. (b) K. C. Joshi, P. Singh, and G. Singh, Ind. J. Chem., 1976, 14B, 637;
48. (c) K. Naya, Y. Miyoshi, H. Mori, K. Takai, and M. Nakanishi, Chem. Lett., 1976, 73;
49. (d) N. A. El-Emary, T. Takemoto, and G. Kusano, Planta Med., 1980, 38, 161;
50. (e) P. Torres, B. Mancheno, R. Chinchilla, M. C. Asensi, and M. Grande, Planta Med., 1988, 54, 257;
51. (f) S. Abdo, M. De Bernardi, G. Marinoni, G. Mellerio, S. Samaniego, G. Vidari, and P. Vita Finzi, Phytochemistry, 1992, 31, 3937.
52. (a) H. Kakisawa, Y. Inouye, and J. Romo, Tetrahedron Lett., 1969, 1929;
53. (b) Y. Inouye, Y. Uchida, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1977, 50, 961.
54. M. Aso, A. Ojida, G. Yang, O.-J. Cha, E. Osawa, and K. Kanematsu, J. Org. Chem., 1993, 58, 3960.
55. F. Bohlmann, H.-J. Forster, and C.-H. Fischer, Liebigs Ann. Chem., 1976, 1487.
56. K. Yamakawa and T. Satoh, Chem. Pharm. Bull., 1977, 25, 2535.
57. A. Ojida, F. Tanoue, and K. Kanematsu, J. Org. Chem., 1994, 59, 5970.
58. Y. Inouye and H. Kakisawa, Bull. Chem. Soc. Jpn., 1969, 42, 3318.
59. O. Cherkaoui, P. Nebois, H. Fillion, M. Domard, and B. Fenet, Tetrahedron, 1996, 52, 9499.
60. For examples on Diels-Alder reactions with halogenated quinones, see: (a) F. Bracher, Liebigs Ann. Chem., 1989, 87;
61. (b) J. R. Grunwell, A. Karipides, C. T. Wigal, S. W. Heinzman, J. Parlow, J. A. Surso, L. Clayton, F. J. Fleitz, M. Daffner, and J. E. Stevens, J. Org. Chem., 1991, 56, 91;
62. (c) E. Gomez-Bengoa and A. M. Echavarren, J. Org. Chem., 1991, 56, 3497;
63. (d) B. Bouammali, F. Pautet, H. Fillion, and M. Soufiaoui, Tetrahedron, 1993, 49, 3125;
64. (e) J. K. Zjawiony, A. R. Srivastava, C. D. Hufford, and A. M. Clark, Heterocycles, 1994, 39, 779;
65. (f) S. Levesque and P. Brassard, Heterocycles, 1994, 38, 2205;
66. (g) K. Krohn and K. Khanbabaee, Liebigs Ann. Chem., 1994, 1109;
67. (h) L. Chaker, F. Pautet, and H. Fillion, Heterocycles, 1995, 41, 1169;
68. (i) A. Poumaroux, Z. Bouaziz, M. Domard, and H. Fillion, Heterocycles, 1997, 45, 585;
69. (j) J. M. Perez, C. Avendano, and J. C. Menendez, Tetrahedron Lett., 1997, 38, 4717.
70. O. Cherkaoui, P. Nebois, and H. Fillion, Chem. Pharm. Bull., 1997, 45, 457.