Synthesis of substituted 2,3-dihydro-1H-2-benzazepines and 1,2-dihydroisoquinolines using an isomerization-ring-closing metathesis strategy: Scope and limitations

European Journal of Organic Chemistry

Volumn , Issue 29, 2007, Pages 4953-4961

  Panayides, Jenny Lee ^a   Pathak, Rakhi ^a   De Koning, Charles B ^a   Van Otterlo, Willem A L ^a  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

Benzazepines; Dihydroisoquinolines; Isomerization; Ring closing metathesis

Indexed keywords

EID: 35348939078     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700473     Document Type: Article

References (39)

1. See: J. Lee, J. Lee, T. Szabo, A. F. Gonzalez, J. D. Welter, P. M. Blumberg, Bioorg. Med. Chem. Lett. 2001, 9, 1713 and references cited therein.
2. P. D. Johnson, P. A. Aristoff, G. E. Zurenko, R. D. Schaadt, B. H. Yagi, C. W. Ford, J. C. Hamel, D. Stapert, J. K. Moerman, Bioorg. Med. Chem. Lett. 2003, 13, 4197.
3. C. D. Jesudason, L. S. Beavers, J. W. Cramer, J. Dill, D. R. Finley, C. W. Lindsley, F. C. Stevens, R. A. Gadski, S. W. Oldham, R. T. Pickard, C. S. Siedem, D. K. Sindelar, A. Singh, B. M. Watson, P. A. Hipskind, Bioorg. Med. Chem. Lett. 2006, 16, 3415.
4. J. Jurayj, R. D. Haugwitz, R. K. Varma, K. D. Pauli, J. F. Barrett, M. Cushman, J. Med. Chem. 1994, 37, 2190.
5. M. M. Sheha, N. A. El-Koussi, H. H. Farag, Arch. Pharm. Pharm. Med. Chem. 2003, 336, 47.
6. a) H. Kogen, N. Toda, K. Tago, S. Marumoto, K. Takami, M. Ori, N. Yamada, K. Koyama, S. Naruto, K. Abe, R. Yamazaki, T. Hara, A. Aoyagi, Y. Abe, T. Kaneko, Org. Lett. 2002, 4, 3359;
7. b) N. Toda, K. Tago, S. Marumoto, K. Takami, M. Ori, N. Yamada, K. Koyama, S. Naruto, K. Abe, R. Yamazaki, T. Hara, A. Aoyagi, Y. Abe, T. Kaneko, H. Kogen, Bioorg. Med. Chem. 2003, 11, 4389.
8. N. Dieltiens, C. V. Stevens, Synlett 2006, 2771.
9. M. L. Bennasar, T. Roca, M. Monerris, D. García-Díaz, J. Org. Chem. 2006, 71, 7028.
10. For a review discussing the interesting relationship between metathesis and isomerization see: B. Schmidt, Eur. J. Org. Chem. 2004, 1865.
11. a) J.-L. Panayides, R. Pathak, H. Panagiotopoulos, H. Davids, M. A. Fernandes, C. B. de Koning, W. A. L. van Otterlo, Tetrahedron 2007, 63, 4737;
12. b) R. Pathak, J.-L. Panayides, T. D. Jeftic, C. B. de Koning, W. A. L. van Otterlo, S. Afr. J. Chem. 2007, 60, 1 (http://blues.sabinet.co.za/sajchem/);
13. c) E. M. Coyanis, J.-L. Panayides, M. A. Fernandes, C. B. de Koning, W. A. L. van Otterlo, J. Organomet. Chem. 2006, 691, 5222;
14. d) W. A. L. van Otterlo, E. L. Ngidi, S. Kuzvidza, G. L. Morgans, S. S. Moleele, C. B. de Koning, Tetrahedron 2005, 61, 9996;
15. e) W. A. L. van Otterlo, G. L. Morgans, L. G. Madeley, S. Kuzvidza, S. S. Moleele, N. Thornton, C. B. de Koning, Tetrahedron 2005, 61, 7746;
16. f) W. A. L. van Otterlo, E. M. Coyanis, J.-L. Panayides, C. B. de Koning, M. A. Fernandes, Synlett 2005, 501;
17. g) W. A. L. van Otterlo, E. L. Ngidi, C. B. de Koning, M. A. Fernandes, Tetrahedron Lett. 2004, 45, 659.
18. W. A. L. van Otterlo, R. Pathak, C. B. de Koning, Synlett 2003, 1859.
19. a) N. Kuźnik, S. Krompiec, Coord. Chem. Rev. 2007, 251, 222;
20. b) S. Krompiec, N. Kuźnik, M. Krompiec, R. Penczek, J. Mrzigod, A. Tórz, J. Mol. Catal. A 2006, 253, 132;
21. c) S. Krompiec, N. Kuźnik, M. Urbala, J. Rzepa, J. Mol. Catal. A 2006, 248, 198.
22. For representative examples describing an isomerization process followed by RCM and related papers see: a) A. Vik, L.-L. Gundersen, Tetrahedron Lett. 2007, 48, 1931;
23. b) E. Banaszak, C. Comoy, Y. Fort, Tetrahedron Lett. 2006, 47, 6235;
24. c) A. Núňez, A. M. Cuadro, J. Alvarez-Builla, J. J. Vaquera, Org. Lett. 2004, 6, 4125;
25. d) T. Nguyen Van, N. De Kimpe, Tetrahedron Lett. 2004, 45, 3443;
26. e) T. Nguyen Van, S. Debenedetti, N. De Kimpe, Tetrahedron Lett. 2003, 44, 4199;
27. f) U. Martínez-Estíbalez, N. Sotomayor, E. Lete, Tetrahedron Lett. 2007, 48, 2919.
28. C. B. de Koning, J. P. Michael, A. L. Rousseau, J. Chem. Soc. Perkin Trans. 1 2000, 787.
29. For an interesting review highlighting side-reactions occurring during RCM see: B. Alcaide, P. Almendros, Chem. Eur. J. 2003, 9, 1259.
30. For a related example where the RCM was successful see: S.-R. Li, L.-Y. Chen, J.-C. Tsai, J.-Y. Tzeng, I.-L. Tsai, E.-C. Wang, Tetrahedron Lett. 2007, 48, 2139.
31. W. A. L. van Otterlo, J.-L. Panayides, M. A. Fernandes, Acta Crystallogr., Sect. E 2004, 60, o1586.
32. For examples see the following references and citations listed therein: a) B. Alcaide, P. Almendros, J. M. Alonso, Chem. Eur. J. 2003, 9, 5793;
33. b) B. Alcaide, P. Almendros, J. M. Alonso, Chem. Eur. J. 2006, 12, 2874.
34. See an example in the following paper: W. A. L. van Otterlo, G. L. Morgans, S. D. Khanye, B. A. A. Aderibigbe, J. P. Michael, D. G. Billing, Tetrahedron Lett. 2004, 45, 9171.
35. See the following two reviews concerning metathesis with heteroatom-bearing alkenes: a) R. C. D. Brown, V. Satcharoen, Heterocycles 2006, 70, 705;
36. b) P. Van de Weghe, P. Bisseret, N. Blanchard, J. Eustache, J. Organomet. Chem. 2006, 691, 5078;
37. See the following recent representative examples: c) G. Liu, W.-Y. Tai, Y.-L. Li, F.-J. Nan, Tetrahedron Lett. 2006, 47, 3295;
38. d) S. Fustero, M. Sánchez-Roselló, D. Jiménez, J. F. Sanz-Cervera, C. del Pozo, J. L. Aceňa, J. Org. Chem. 2006, 71, 2706.
39. D. D. Perrin, W. L. F. Armarego, Purification of laboratory chemicals, Pergamon Press, London, 1988.