Synthesis of phenanthridines by radical C(aryl)-C(aryl) coupling

Tetrahedron

Volumn 53, Issue 1, 1997, Pages 269-284

  Rosa, Ana M ^a   Lobo, Ana M ^a   Branco, Paula S ^a   Prabhakar, Sundaresan ^a   Pereira, António M D L ^a  

^a UNINOVA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

PHENANTHRIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031060478     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00983-0     Document Type: Article

References (37)

1. a) Giese, B. Radical in Organic Synthesis; Formation of C-C Bonds, Pergamon Press; New York, 1986;
2. b) For a recent review containing copious examples of application of radical chemistry to natural product synthesis, see: Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev., 1991, 91, 1237.
3. a) Narasimhan, N. S.; Aiden, I. S. Tetrahedron Lett., 1988, 29, 2987;
4. b) Togo, H.; Kikuchi, O., Tetrahedron Lett., 1988, 29, 4133;
5. c) Rosa, A. M.; Prabhakar, S.; Lobo, A. M. Tetrahedron Lett., 1990, 31, 1881;
6. d) Motherwell, W. B.; Pennell, A. M. K. J. Chem. Soc., Chem. Commun, 1991, 877.
7. aryl bond formation see: a) Siddiqui, M. A.; Snieckus, V. A. Tetrahedron Lett., 1988, 28, 5463;
8. b) Kessar, S. V.; Pal, D.; Singh, M. Tetrahedron, 1973, 29, 177;
9. c) For the occurrence of dialkoxyphenanthridines such as 6,7-methylenedioxyphenanthridine and its methochloride in nature, see: Suau, R.; Gómez, A. I.; Rico, R. Phytochemistry, 1990, 29, 1710.
10. th FECHEM Conference on Heterocycles in Bio-Organic Chemistry, held in Santiago de Compostela (Spain), on 26-29/9/1993.
11. a) Cushman, M.; Mohan, P.; Smith, E. C. R. J. Med. Chem., 1984, 27, 544;
12. b) Messmer, W. M.; Tin-Wa, M.; Fong, H. H. S.; Bevelle, C.; Farnsworth, N. R.; Abraham, D. J.; Trojanek, J. J. Pharm. Sci., 1972, 61, 1858.
13. For a lengthy synthesis of S (R=OH ; R=OMe), see: Takada, T.; Ohki, S. Chem. Pharm. Bull. (Jpn), 1971, 19, 977.
14. A similar radical, photochemically generated from N-(o-halobenzyl)aniline, has been reported to give, among other products, a low yield (15%) of the 5,6-dihydrophenanthridine: Mizuno, K.; Pac, C.; Sukurai, H. Bull. Chem. Soc. Jpn., 1973, 46, 3316.
15. Firestone, R. A. J. Org. Chem., 1969, 34, 2621.
16. For geometric reasons alkenylaryl radicals incorporating a hetero atom (O or N) in the side chain are expected to afford mainly product of 1,5 cyclisations and this was experimentally observed to be so in the case of oxygen. It is also known that in systems with all carbon framework the kinetically preferred 5-exo cyclisation is retarded by the presence of a substituent at the C atom suffering the radical attack (Beckwith, A. L. J. Tetrahedron, 1981, 37, 3073) and as a consequence the competing 6-endo addition becomes significant or occasionally even exclusive (Padwa, A.; Murphee, S. S.; Yeske, P. E. Tetrahedron Lett., 1990, 31, 2983; Urabe, H. Kuwajima, I. Tetrahedron Lett., 1986, 27, 1355).
17. For geometric reasons alkenylaryl radicals incorporating a hetero atom (O or N) in the side chain are expected to afford mainly product of 1,5 cyclisations and this was experimentally observed to be so in the case of oxygen. It is also known that in systems with all carbon framework the kinetically preferred 5-exo cyclisation is retarded by the presence of a substituent at the C atom suffering the radical attack (Beckwith, A. L. J. Tetrahedron, 1981, 37, 3073) and as a consequence the competing 6-endo addition becomes significant or occasionally even exclusive (Padwa, A.; Murphee, S. S.; Yeske, P. E. Tetrahedron Lett., 1990, 31, 2983; Urabe, H. Kuwajima, I. Tetrahedron Lett., 1986, 27, 1355).
18. For geometric reasons alkenylaryl radicals incorporating a hetero atom (O or N) in the side chain are expected to afford mainly product of 1,5 cyclisations and this was experimentally observed to be so in the case of oxygen. It is also known that in systems with all carbon framework the kinetically preferred 5-exo cyclisation is retarded by the presence of a substituent at the C atom suffering the radical attack (Beckwith, A. L. J. Tetrahedron, 1981, 37, 3073) and as a consequence the competing 6-endo addition becomes significant or occasionally even exclusive (Padwa, A.; Murphee, S. S.; Yeske, P. E. Tetrahedron Lett., 1990, 31, 2983; Urabe, H. Kuwajima, I. Tetrahedron Lett., 1986, 27, 1355).
19. Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans 1, 1986, 1591.
20. The presence of 5,6-dihydrophenanthridines could indeed be detected in all these reactions on the t1c plates. However, they are rapidly oxidised under aerobic conditions.
21. a) Bhacca, N. S.; Johnson, L. F.; Shoolery, J. N. NMR Catalog; Spec. no. 349, Varian Associates, Palo Alto, 1962;
22. b) Blanco, O.; Castedo, L.; Cid, M.; Seijas, J. A.; Vilaverde, C. Heterocycles, 1990, 31, 1077.
23. For a reference to intrusion of reversibility in an intramolecular aryl-aryl radical coupling reaction, not involving an EWG group ortho to the σ radical, see: Benati, L.; Montevecchi, P. C.; Tundo, A. J. Chem. Soc., Chem. Commun, 1978, 530.
24. a) Bowman, W. R.; Heaney, H.; Jordan, B. J. Tetrahedron, 1991, 48, 10119.
25. b) Curran, D. P.; Yu, H.; Liu, H. Tetrahedron, 1994, 50, 7343.
26. c) Beckwith, A. L. J.; Storey, J. M. D. J. Chem. Soc., Chem. Commun, 1995, 977.
27. Abramovitch, R. A.; Shi, Q. Heterocycles, 1994, 37, 1463.
28. Curran, D. P.; Liu, H. J. Chem. Soc., Perkin Trans 1, 1994, 1377.
29. Benington, F.; Morin, R. D.; Clark, L. C. J. Org. Chem., 1958, 23, 19.
30. Wheeler, T. S.; Naik, R. G. J. Chem. Soc., 1938, 1780.
31. Becker, D.; Hughes, L. R.; Raphael, R. A. J. Chem. Soc., Perkin Trans 1, 1977, 1674.
32. Supplied by Aldrich Co., Spain.
33. Bocchi, V.; Casnati, G.; Dossena, A.; Villani, F. Synthesis, 1976, 414.
34. Leibner, J. F.; Jacobus, J. J. Org. Chem., 1979, 44, 449.
35. Berge, J. M.; Roberts, S. M. Synthesis, 1979, 471.
36. Warren, F. L.; Wright, W. G. J. Chem. Soc., 1958, 4696; see also ref. 3b.
37. Onaka, T.; Kanda, Y.; Natsume, M. Tetrahedron Lett., 1974, 1179.