Synthesis of 2-aryl-oxazolo[4,5-c]quinoline-4(5H)-ones and 2-aryl-thiazolo[4,5-c]quinoline-4(5H)-ones

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2911-2914

  Hodgetts, Kevin J ^a   Kershaw, Mark T ^a  

^a NEUROGEN CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYL 2 BROMO 5 CHLOROTHIAZOLE 4 CARBOXYLATE; ETHYL 2 CHLOROOXAZOLE 4 CARBOXYLATE; KETONE DERIVATIVE; OXAZOLE DERIVATIVE; QUINOLINE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLIZATION; CYCLIZATION; HECK REACTION; RECEPTOR BINDING; SYNTHESIS;

EID: 0141855223     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0350285     Document Type: Article

References (45)

1. For excellent reviews of this strategy see: (a) Collins, I. J. Chem. Soc., Perkin Trans. 1 2002, 1921. (b) Collins, I. J. Chem. Soc., Perkin Trans. 1 2000, 2845. (c) Snieckus, V. Med. Res. Rev. 1999, 19, 342.
2. For excellent reviews of this strategy see: (a) Collins, I. J. Chem. Soc., Perkin Trans. 1 2002, 1921. (b) Collins, I. J. Chem. Soc., Perkin Trans. 1 2000, 2845. (c) Snieckus, V. Med. Res. Rev. 1999, 19, 342.
3. (c) Snieckus, V. Med. Res. Rev. 1999, 19, 342.
4. Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2002, 4, 1363.
5. Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2002, 4, 2905.
6. Albaugh, P. U.S. Patent 5,182,290, 1993.
7. For related series, see: (a) Albaugh, P. A.; Marshall, L.; Gregory, J.; White, G.; Hutchison, A.; Ross, P. C.; Gallagher, D. W.; Tallman, J. F.; Crago, M.; Cassella, J. V. J. Med. Chem. 2002, 45, 5043. (b) Forbes, I. T.; Johnson, C. N.; Jones, G. E.; Loudon, J.; Nicholass, J. M. Thompson, M. J. Med. Chem. 2002, 45, 2640 and references therein.
8. For related series, see: (a) Albaugh, P. A.; Marshall, L.; Gregory, J.; White, G.; Hutchison, A.; Ross, P. C.; Gallagher, D. W.; Tallman, J. F.; Crago, M.; Cassella, J. V. J. Med. Chem. 2002, 45, 5043. (b) Forbes, I. T.; Johnson, C. N.; Jones, G. E.; Loudon, J.; Nicholass, J. M. Thompson, M. J. Med. Chem. 2002, 45, 2640 and references therein.
9. For recent reviews of the therapeutic areas addressed through modulation of GABA, see: (a) Chebib, M.; Johnston, G. A. R. J. Med. Chem. 2000, 43, 1427. (b) Tallman, J. F.; Cassella, J. V.; White, G.; Gallagher, D. W. Neuroscientist 1999, 5, 351.
10. For recent reviews of the therapeutic areas addressed through modulation of GABA, see: (a) Chebib, M.; Johnston, G. A. R. J. Med. Chem. 2000, 43, 1427. (b) Tallman, J. F.; Cassella, J. V.; White, G.; Gallagher, D. W. Neuroscientist 1999, 5, 351.
11. (a) Merchant, J. R.; Shirali, S. S. Bull. Chem. Soc. Jpn. 1977, 50, 3075.
12. (b) Ponomarev, O. A.; Brusilt'sev, Y. N.; Grif, V. K.; Mitina, V. G. Ukr. Khim. Zh. 1990, 56, 272.
13. (c) Ukrainets, I. V.; Taran, S. G.; Sidorenko, L. V.; Gorokhova, O. V.; Turov, A. V. Chem. Het. Compds. 1997, 33, 1328.
14. Zoorob, H. H.; Hamama, W. S. Egypt. J. Chem. 1986, 29, 325.
15. Suzuki, M.; Matsumoto, K.; Miyoshi, M.; Yoneda, N.; Ishida, R. Chem. Pharm Bull. 1977, 25, 2602.
16. Steinschifter, W.; Fiala, W.; Stadlbauer, W. J. Het. Chem. 1994, 31, 1647 and references therein.
17. Ukrainets, I. V.; Taran, S. G.; Sidorenko, L. V.; Gorokhova, O. V.; Turov, A. V.; Ogirenko, A. A. Chem. Heterocycl. Compd. 1997, 33, 815.
18. For other examples of palladium-catalyzed reactions of oxazoles, see: (a) Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon Press: Elmsford, Oxford, 2000; Chapter 8, pp 321-333. (b) Sakamoto, T.; Nagata, H.; Kondo, Y.; Shiraiwa, M.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 823. (c) Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415. (d) Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4633. (e) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640. (f) Boto, A.; Ling, M.; Meek, G.; Pattenden G. Tetrahedron Lett. 1998, 39, 8167. (g) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011. (h) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469. (i) Smith, A. B., III; Minibiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942. (j) Clapham, B.; Sutherland, A. J. J. Org. Chem. 2001, 66, 9033.
19. For other examples of palladium-catalyzed reactions of oxazoles, see: (a) Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon Press: Elmsford, Oxford, 2000; Chapter 8, pp 321-333. (b) Sakamoto, T.; Nagata, H.; Kondo, Y.; Shiraiwa, M.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 823. (c) Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415. (d) Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4633. (e) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640. (f) Boto, A.; Ling, M.; Meek, G.; Pattenden G. Tetrahedron Lett. 1998, 39, 8167. (g) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011. (h) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469. (i) Smith, A. B., III; Minibiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942. (j) Clapham, B.; Sutherland, A. J. J. Org. Chem. 2001, 66, 9033.
20. For other examples of palladium-catalyzed reactions of oxazoles, see: (a) Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon Press: Elmsford, Oxford, 2000; Chapter 8, pp 321-333. (b) Sakamoto, T.; Nagata, H.; Kondo, Y.; Shiraiwa, M.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 823. (c) Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415. (d) Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4633. (e) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640. (f) Boto, A.; Ling, M.; Meek, G.; Pattenden G. Tetrahedron Lett. 1998, 39, 8167. (g) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011. (h) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469. (i) Smith, A. B., III; Minibiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942. (j) Clapham, B.; Sutherland, A. J. J. Org. Chem. 2001, 66, 9033.
21. For other examples of palladium-catalyzed reactions of oxazoles, see: (a) Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon Press: Elmsford, Oxford, 2000; Chapter 8, pp 321-333. (b) Sakamoto, T.; Nagata, H.; Kondo, Y.; Shiraiwa, M.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 823. (c) Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415. (d) Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4633. (e) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640. (f) Boto, A.; Ling, M.; Meek, G.; Pattenden G. Tetrahedron Lett. 1998, 39, 8167. (g) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011. (h) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469. (i) Smith, A. B., III; Minibiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942. (j) Clapham, B.; Sutherland, A. J. J. Org. Chem. 2001, 66, 9033.
22. For other examples of palladium-catalyzed reactions of oxazoles, see: (a) Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon Press: Elmsford, Oxford, 2000; Chapter 8, pp 321-333. (b) Sakamoto, T.; Nagata, H.; Kondo, Y.; Shiraiwa, M.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 823. (c) Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415. (d) Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4633. (e) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640. (f) Boto, A.; Ling, M.; Meek, G.; Pattenden G. Tetrahedron Lett. 1998, 39, 8167. (g) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011. (h) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469. (i) Smith, A. B., III; Minibiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942. (j) Clapham, B.; Sutherland, A. J. J. Org. Chem. 2001, 66, 9033.
23. For other examples of palladium-catalyzed reactions of oxazoles, see: (a) Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon Press: Elmsford, Oxford, 2000; Chapter 8, pp 321-333. (b) Sakamoto, T.; Nagata, H.; Kondo, Y.; Shiraiwa, M.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 823. (c) Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415. (d) Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4633. (e) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640. (f) Boto, A.; Ling, M.; Meek, G.; Pattenden G. Tetrahedron Lett. 1998, 39, 8167. (g) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011. (h) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469. (i) Smith, A. B., III; Minibiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942. (j) Clapham, B.; Sutherland, A. J. J. Org. Chem. 2001, 66, 9033.
24. For other examples of palladium-catalyzed reactions of oxazoles, see: (a) Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon Press: Elmsford, Oxford, 2000; Chapter 8, pp 321-333. (b) Sakamoto, T.; Nagata, H.; Kondo, Y.; Shiraiwa, M.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 823. (c) Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415. (d) Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4633. (e) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640. (f) Boto, A.; Ling, M.; Meek, G.; Pattenden G. Tetrahedron Lett. 1998, 39, 8167. (g) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011. (h) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469. (i) Smith, A. B., III; Minibiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942. (j) Clapham, B.; Sutherland, A. J. J. Org. Chem. 2001, 66, 9033.
25. For other examples of palladium-catalyzed reactions of oxazoles, see: (a) Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon Press: Elmsford, Oxford, 2000; Chapter 8, pp 321-333. (b) Sakamoto, T.; Nagata, H.; Kondo, Y.; Shiraiwa, M.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 823. (c) Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415. (d) Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4633. (e) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640. (f) Boto, A.; Ling, M.; Meek, G.; Pattenden G. Tetrahedron Lett. 1998, 39, 8167. (g) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011. (h) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469. (i) Smith, A. B., III; Minibiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942. (j) Clapham, B.; Sutherland, A. J. J. Org. Chem. 2001, 66, 9033.
26. For other examples of palladium-catalyzed reactions of oxazoles, see: (a) Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon Press: Elmsford, Oxford, 2000; Chapter 8, pp 321-333. (b) Sakamoto, T.; Nagata, H.; Kondo, Y.; Shiraiwa, M.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 823. (c) Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415. (d) Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4633. (e) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640. (f) Boto, A.; Ling, M.; Meek, G.; Pattenden G. Tetrahedron Lett. 1998, 39, 8167. (g) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011. (h) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469. (i) Smith, A. B., III; Minibiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942. (j) Clapham, B.; Sutherland, A. J. J. Org. Chem. 2001, 66, 9033.
27. For other examples of palladium-catalyzed reactions of oxazoles, see: (a) Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon Press: Elmsford, Oxford, 2000; Chapter 8, pp 321-333. (b) Sakamoto, T.; Nagata, H.; Kondo, Y.; Shiraiwa, M.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 823. (c) Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415. (d) Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4633. (e) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640. (f) Boto, A.; Ling, M.; Meek, G.; Pattenden G. Tetrahedron Lett. 1998, 39, 8167. (g) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011. (h) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469. (i) Smith, A. B., III; Minibiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942. (j) Clapham, B.; Sutherland, A. J. J. Org. Chem. 2001, 66, 9033.
28. For reviews, see: (a) Heck, R. F. Org. React. 1982, 27, 345-390. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. For mechanistic insight, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427. (d) Amatore, C.; Jutland, A. Acc. Chem. Res. 2000, 33, 314.
29. For reviews, see: (a) Heck, R. F. Org. React. 1982, 27, 345-390. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. For mechanistic insight, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427. (d) Amatore, C.; Jutland, A. Acc. Chem. Res. 2000, 33, 314.
30. For reviews, see: (a) Heck, R. F. Org. React. 1982, 27, 345-390. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. For mechanistic insight, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427. (d) Amatore, C.; Jutland, A. Acc. Chem. Res. 2000, 33, 314.
31. For reviews, see: (a) Heck, R. F. Org. React. 1982, 27, 345-390. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. For mechanistic insight, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427. (d) Amatore, C.; Jutland, A. Acc. Chem. Res. 2000, 33, 314.
32. For an example of a Heck reaction at the 5-position of an oxazole, see: (a) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467. For other heteroaryl Heck reactions, see: (b) Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. F. Org. Lett. 2003, 5, 301. (c) McClure, M. S.; Glover, B.; McSorley, E.; Maillar, A.; Osterhout, M. H.; Roschangar, F. Org. Lett. 2001, 3, 1677. (d) Hii, K. K.; Claridge, T. D. W. ; Brown, J. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (e) Itahara, T. J. J. Org. Chem. 1985, 50, 5272.
33. For an example of a Heck reaction at the 5-position of an oxazole, see: (a) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467. For other heteroaryl Heck reactions, see: (b) Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. F. Org. Lett. 2003, 5, 301. (c) McClure, M. S.; Glover, B.; McSorley, E.; Maillar, A.; Osterhout, M. H.; Roschangar, F. Org. Lett. 2001, 3, 1677. (d) Hii, K. K.; Claridge, T. D. W. ; Brown, J. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (e) Itahara, T. J. J. Org. Chem. 1985, 50, 5272.
34. For an example of a Heck reaction at the 5-position of an oxazole, see: (a) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467. For other heteroaryl Heck reactions, see: (b) Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. F. Org. Lett. 2003, 5, 301. (c) McClure, M. S.; Glover, B.; McSorley, E.; Maillar, A.; Osterhout, M. H.; Roschangar, F. Org. Lett. 2001, 3, 1677. (d) Hii, K. K.; Claridge, T. D. W. ; Brown, J. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (e) Itahara, T. J. J. Org. Chem. 1985, 50, 5272.
35. For an example of a Heck reaction at the 5-position of an oxazole, see: (a) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467. For other heteroaryl Heck reactions, see: (b) Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. F. Org. Lett. 2003, 5, 301. (c) McClure, M. S.; Glover, B.; McSorley, E.; Maillar, A.; Osterhout, M. H.; Roschangar, F. Org. Lett. 2001, 3, 1677. (d) Hii, K. K.; Claridge, T. D. W. ; Brown, J. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (e) Itahara, T. J. J. Org. Chem. 1985, 50, 5272.
36. For an example of a Heck reaction at the 5-position of an oxazole, see: (a) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467. For other heteroaryl Heck reactions, see: (b) Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. F. Org. Lett. 2003, 5, 301. (c) McClure, M. S.; Glover, B.; McSorley, E.; Maillar, A.; Osterhout, M. H.; Roschangar, F. Org. Lett. 2001, 3, 1677. (d) Hii, K. K.; Claridge, T. D. W. ; Brown, J. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 984. (e) Itahara, T. J. J. Org. Chem. 1985, 50, 5272.
37. For reviews, see: (a) Miyaura, N.; Suzuki, A. Chem Rev. 1995, 95, 2457. (b) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
38. For reviews, see: (a) Miyaura, N.; Suzuki, A. Chem Rev. 1995, 95, 2457. (b) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
39. Ziegler, C. B.; Heck, R. F. J. Org. Chem. 1978, 43, 2941.
40. For examples, see: (a) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919. (b) Kuroda, T.; Suzuki, F. Tetrahedron Lett. 1991, 32, 6915. (c) Hernandez, S.; SanMartin, R.; Tellitu, I.; Dominguez, E. Org. Lett. 2003, 5, 1095. For a general review, see: (d) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447.
41. For examples, see: (a) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919. (b) Kuroda, T.; Suzuki, F. Tetrahedron Lett. 1991, 32, 6915. (c) Hernandez, S.; SanMartin, R.; Tellitu, I.; Dominguez, E. Org. Lett. 2003, 5, 1095. For a general review, see: (d) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447.
42. For examples, see: (a) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919. (b) Kuroda, T.; Suzuki, F. Tetrahedron Lett. 1991, 32, 6915. (c) Hernandez, S.; SanMartin, R.; Tellitu, I.; Dominguez, E. Org. Lett. 2003, 5, 1095. For a general review, see: (d) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447.
43. For examples, see: (a) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919. (b) Kuroda, T.; Suzuki, F. Tetrahedron Lett. 1991, 32, 6915. (c) Hernandez, S.; SanMartin, R.; Tellitu, I.; Dominguez, E. Org. Lett. 2003, 5, 1095. For a general review, see: (d) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447.
44. Castro, B.; Dormoy, J. R.; Evin, G.; Selvey, C. Tetrahedron Lett. 1975, 1219.
45. Okonya, J. F.; Al-Obeidi, F. Tetrahedron Lett. 2002, 43, 7051.