Synthesis of fluorinated and non-fluorinated bicyclic amidines through ring-closing metathesis

European Journal of Organic Chemistry

Volumn , Issue 36, 2011, Pages 7317-7323

  Cuñat, Ana C ^a   Flores, Sonia ^a   Oliver, Judit ^a   Fustero, Santos ^a,b  

^a UNIVERSITY OF VALENCIA   (Spain)

^b CENTRO DE INVESTIGACIÓN PRÍNCIPE FELIPE   (Spain)

Author keywords

Amidines; Fluorine; Metathesis; Nitrogen heterocycles

Indexed keywords

EID: 82955163895     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201101091     Document Type: Article

References (55)

1. R. G. S. Berlinck, A. C. B. Burtuloso, M. H. Kossuga, Nat. Prod. Rep. 2008, 25, 919-954.
2. M. Silva Dos Santos, A. M. R. Bernardino, M. Costa de Souza, Quim. Nova 2006, 29, 1301-1306.
3. L. T. Vassilev, B. T. Vu, B. Graves, D. Carvajal, F. Podlaski, Z. Filipovic, N. Kong, U. Kammlott, C. Lucacs, C. Klein, N. Fotouhi, E. A. Liu, Science 2004, 303, 844-848.
4. T. Ishikawa, T. Kumamoto, Synthesis 2006, 5, 737-752.
5. T. Ishikawa, K. Takuya, "Amidines in Organic Synthesis" in Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts (Ed.:, T. Ishikawa), Wiley, Chichester, U.K., 2009, pp. 49-91.
6. L. Peterlin-Masic, D. Kikelj, Tetrahedron 2001, 57, 7073-7105.
7. M. P. Coles, Dalton Trans. 2006, 985-1001.
8. A. A. Aly, A. M. Tour-ElDin, ARKIVOC 2008, 1, 153-194.
9. H. Liu, D.-M. Du, Adv. Synth. Catal. 2009, 351, 489-519.
10. Bicyclic amidines, which include common organic bases such as DBU and DBN, are frequently used in many base-promoted transformations:, C. Joannesse, C. Simal, C. Concellõn, J. E. Thomsom, C. D. Campbell, A. M. Z. Slawin, A. D. Smith, Org. Biomol. Chem. 2008, 6, 2900-2907.
11. N. Kumagai, S. Matsunaga, M. Shibasaki, Angew. Chem. 2004, 116, 484;
12. Angew. Chem. Int. Ed. 2004, 43, 478 - 482.
13. K. L. Tan, A. Vasudevan, R. G. Bergman, J. A. Ellman, A. J. Souers, Org. Lett. 2003, 5, 2131-2134.
14. H. Fujioka, K. Murai, Y. Ohba, H. Hirose, Y. Kita, Chem. Commun. 2006, 832-834.
15. K. L. S. Hehir, L. O'Donovan, M. P. Carty, F. Aldabbagh, Tetrahedron 2008, 64, 4196-4203.
16. Q. Zhu, Y. Yu, Org. Lett. 2010, 12, 4156-4159 and references cited therein.
17. R. Smits, C. D. Cadicamo, K. Burger, B. Koksch, Chem. Soc. Rev. 2008, 37, 1727-173.
18. W.-D, Meng, F.-L Qing, "Synthesis of gem -Difluoromethylenated Nucleosides" in Fluorine in Medicinal Chemistry and Chemical Biology (Ed.:, I. Ojima), Wiley-Blackwell, Chichester, UK, 2009, chapter 8, pp. 201-212.
19. J. L. Aceña, A. Simõn-Fuentes, S. Fustero, Curr. Org. Chem. 2010, 14, 928-949.
20. S. Fustero, J. F. Sanz-Cervera, J. L. Aceña, M. Sánchez-Rosellõ, Synlett 2009, 525-549. See, also
21. S. Fustero, M. Sánchez-Rosellõ, V. Rodrigo, J. F. Sanz-Cervera, J. Piera, A. Simõn-Fuentes, C. del Pozo, Chem. Eur. J. 2008, 14, 7019-7029.
22. S. Fustero, M. Sánchez-Rosellõ, J. L. Aceña, B. Fernández, A. Asensio, J. F. Sanz-Cervera, C. del Pozo, J. Org. Chem. 2009, 74, 3414-3423.
23. S. Fustero, S. Catalán, M. Sánchez-Rosellõ, A. Simõn-Fuentes, C. del Pozo, Org. Lett. 2010, 12, 3484-3487.
24. N. M. Cerqueira, P. A. Fernandes, M. J. Ramos, Chem. Eur. J. 2007, 13, 8507-8515.
25. J. M. Baskin, J. A. Prescher, S. T. Laughlin, N. J. Agard, P. V. Chang, I. A. Miller, A. Lo, J. A. Codelli, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2007, 104, 16793-16797.
26. Ch. Fäh, L. A. Hardegger, L. Baitsch, W. B. Schweizer, S. Meyer, D. Bur, F. Diederich, Org. Biomol. Chem. 2009, 7, 3947-3957.
27. S. N. Crane, W. C. Black, J. T. Palmer, D. E. Davis, E. Setti, J. Robichaud, J. Paquet, R. M. Oballa, Ch. I. Bayly, D. J. McKay, J. R. Somoza, N. Chauret, C. Seto, J. Scheigetz, G. Wesolowski, F. Masse, S. Desmarais, M. Ouellet, J. Med. Chem. 2006, 49, 1066-1079.
28. I. Ojima, Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Chichester, U.K., 2009. See also
29. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330.
30. K. Müller, Ch. Faeh, F. Diederich, Science 2007, 317, 1881-1886.
31. W. K. Hagmann, J. Med. Chem. 2008, 51, 4359-4369.
32. J.-P. Bégué, D. Bonnet-Delpon, J. Fluorine Chem. 2006, 127, 992-1012.
33. W. Ghattas, C. R. Hess, G. Lacazio, R. Hardré, J. P. Klinman, M. Réglier, J. Org. Chem. 2006, 71, 8618-8621.
34. K. Tsuda, E. Ohki, S. Nozoe, J. Org. Chem. 1963, 28, 783-785.
35. P. A. Crassous, C. Cardinaletti, A. Carrieri, B. Bruni, M. D. Vaira, F. Gentili, F. Ghelfi, M. Giannella, H. Paris, A. Piergentili, W. Quaglia, S. Schaaak, C. Vesprini, M. Pigini, J. Med. Chem. 2007, 50, 3964-3968 and references cited therein
36. C. A. Busacca, Y. Dong, E. M. Spinelli, Tetrahedron Lett. 1996, 37, 2935-2938.
37. V. V. Lisitskii, Z. A. Akhmetchenko, I. E. Alekhina, Y. I. Murinov, Russ. J. Appl. Chem. 2007, 80, 761-766.
38. N. A. Boland, M. Casey, S. J. Hynes, J. W. Matthews, M. P. Smyth, J. Org. Chem. 2002, 67, 3919-3922 and references cited therein.
39. M. von Rauch, S. Busch, R. Gust, J. Med. Chem. 2005, 48, 466-474.
40. E. D. Raczynska, R. Gawinecki, Trends Org. Chem. 1998, 7, 85-93.
41. P. Seckarova, R. Marek, K. Malinakova, E. Kolehmainen, D. Hockva, M. Hocek, V. Sklenar, Tetrahedron Lett. 2004, 45, 6259-6263.
42. A. F. Pozharskii, E. A. Filatova, I. V. Borovlev, N. V. Vistorovskii, Chem. Heterocycl. Compd. 2001, 37, 733-742.
43. Bussaca et al. reported that strong bases, in combination with high temperatures, favor epimerization of chiral imidazolines. In our case, however, careful manipulation allowed the preparation of allylated compounds as unique cis diastereoisomers, as indicated by their NMR spectra., C. A. Busacca, T. Bartholomeyzik, S. Cheekoori, N. Grinberg, H. Lee, S. Ma, A. Saha, S. Shen, C. H. Senanayake, J. Org. Chem. 2008, 73, 9756-9761.
44. A. H. Hoveyda, A. R. Zhugralin, Nature 2007, 450, 243-251.
45. A. J. Phillips, A. D. Abell, Aldrichim. Acta 1999, 32, 75-89.
46. A. Deiters, S. F. Martin, Chem. Rev. 2004, 104, 2199-2238.
47. P. Compain, Adv. Synth. Catal. 2007, 349, 1829-1846.
48. T. J. Donohhoe, L. P. Fishlock, P. A. Procopiou, Chem. Eur. J. 2008, 14, 5716-5726.
49. V. Gracias, A. F. Gasiecki, S. W. Djuric, Org. Lett. 2005, 7, 3183-3186.
50. B. Schmidt, J. Org. Chem. 2004, 69, 7672-7687.
51. this fact has been previously observed in other RCM reactions in our laboratories:, S. Fustero, M. Sánchez-Rosellõ, D. Jiménez, J. F. Sanz-Cervera, C. del Pozo, J. L. Aceña, J. Org. Chem. 2006, 71, 2706-2714.
52. Ch. Audouard, J. Fawcett, G. A. Griffiths, J. M. Percy, Org. Biomol. Chem. 2004, 2, 528-541.
53. Y.-Y. Yang, J. Xu, Z.-W. You, X. Xu, X.-L. Qiu, F.-L. Qing, Org. Lett. 2007, 9, 5437-5440.
54. S. Fustero, B. Fernández, J. F. Sanz-Cervera, N. Mateu, S. Mosulen, R. J. Carbajo, A. Pineda-Lucena, C. Ramírez de Arellano, J. Org. Chem. 2007, 72, 8716-8723.
55. W. L. F. Armarego, D. D. Perrin, Purification of Laboratory Chemicals, 4th ed., Butterworth Heinemann Press, Oxford, 1996.