Modulating the reactivity of α-isocyanoacetates: Multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones

Angewandte Chemie - International Edition

Volumn 46, Issue 14, 2007, Pages 2485-2488

  Bonne, Damien ^a   Dekhane, Mouloud ^b   Zhu, Jieping ^a  

^a CNRS   (France)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Furopyrrolones; Isocyanides; Multicomponent reactions; Oxazoles; Ugi reaction

Indexed keywords

CHEMICAL BONDS; NITROGEN COMPOUNDS; NUCLEOPHILES; REACTION KINETICS;

CONJUGATE BASE; ISOCYANOACETATES; MULTICOMPONENT REACTIONS;

ESTERS;

ACETIC ACID DERIVATIVE; OXAZOLE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ACETATES; OXAZOLES; PYRROLES;

EID: 34250857457     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200605005     Document Type: Article

References (59)

1. a) D. Hoppe, Angew. Chem. 1974, 86, 878-893;
2. Angew. Chem. Int. Ed. Engl. 1974, 13, 789-804;
3. b) U. Schöllkopf, Angew. Chem. 1977, 89, 351-360;
4. Angew. Chem. Int. Ed. Engl. 1977, 16, 339-348;
5. c) S. Marcaccini, T. Torroba, Org. Prep. Proced. Int. 1993, 25, 141-208.
6. For selected examples of metal-mediated C-H activation of α-isocyanoacetates for the synthesis of heterocycles, see: a) T. Saegusa, Y. Ito, H. Kinoshita, S. Tomita, J. Org. Chem. 1971, 36, 3316-3323;
7. b) H. Takaya, S. Kojima, S. Murahashi, Org. Lett. 2001, 3, 421-424;
8. c) Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405-6406;
9. d) A. Tongi, S. D. Pastor, J. Org. Chem. 1990, 55, 1649-1664;
10. e) T. Hayashi, E. Kishi, V. A. Soloshonok, Y. Uozumi, Tetrahedron Lett. 1996, 37, 4969-4972;
11. f) Y.-R. Lin, X.-T. Zhou, L.-X. Dai, J. Sun, J. Org. Chem. 1997, 62, 1799-1803;
12. g) R. Grigg, M. I. Lansdell, M. Thornton-Pett, Tetrahedron 1999, 55, 2025-2044;
13. h) S. Kamijo, C. Kanazawa, Y. Yamamoto, J. Am. Chem. Soc. 2005, 127, 9260-9266;
14. i) C. Kanazawa, S. Kamijo, Y. Yamamoto, J. Am. Chem. Soc. 2006, 128, 10 662-10 663.
15. a) R. S. Bon, C. Hong, M. J. Bouma, R. F. Schmitz, F. J. J. De Kanter, M. Lutz, A. L. Spek, R. V. A. Orru, Org. Lett. 2003, 5, 3759-3762;
16. b) R. S. Bon, B. Van Vliet, N. E. Sprenkels, R. F. Schmitz, F. J. J. De Kanter, C. V. Stevens, M. Swart, F. M. Bickelhaupt, M. B. Groen, R. V. A. Orru, J. Org. Chem. 2005, 70, 3542-3553.
17. For an alternative reaction pathway, see: M. Suzuki, K.-I. Nunami, T. Moriya, K. Matsumoto, N. Yoneda, J. Org. Chem. 1978, 43, 4933-4935.
18. For recent reviews, see: a) C. Hulme, V. Gore, Curr. Med. Chem. 2003, 10, 51-80;
19. b) R. V. A. Orru, M. De Greef, Synthesis 2003, 1471-1499;
20. c) A. Jacobi von Wangelin, H. Neumann, D. Gördes, S. Klaus, D. Strübing, M. Beller, Chem. Eur. J. 2003, 9, 4286-4294;
21. d) V. Nair, C. Rajesh, A. U. Vinod, S. Bindu, A. R. Sreekanth, J. S. Mathen, L. Balagopal, Acc. Chem. Res. 2003, 36, 899-907;
22. e) J. Zhu, Eur. J. Org. Chem. 2003, 1133-1144;
23. f) G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 2003, 4101-4111;
24. g) C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 4957-4980;
25. h) P. Tempest, Curr. Opin. Drug Discovery Dev. 2005, 8, 776-788;
26. i) A. Dömling, Chem. Rev. 2006, 106, 17-89.
27. For a monograph, see: Multicomponent Reactions (Eds: J. Zhu, H. Bienaymé), Wiley-VCH, Weinheim, 2005.
28. For α-isocyanoacetamide, see: a) X. Sun, P. Janvier, G. Zhao, H. Bienaymé, J. Zhu, Org. Lett. 2001, 3, 877-880;
29. b) P. Janvier, X. Sun, H. Bienaymé, J. Zhu, J. Am. Chem. Soc. 2002, 124, 2560-2567;
30. c) P. Janvier, M. Bois-Choussy, H. Bienaymé, J. Zhu, Angew. Chem. 2003, 115, 835-838;
31. Angew. Chem. Int. Ed. 2003, 42, 811-814.
32. For ortho-isocyanobenzamide, see: D. Bonne, M. Dekhane, J. Zhu, Org. Lett. 2005, 7, 5285-5288.
33. For α-isocyanoacetic acid, see: a) D. Bonne, M. Dekhane, J. Zhu, Org. Lett. 2004, 6, 4771-4774;
34. b) D. Bonne, M. Dekhane, J. Zhu, J. Am. Chem. Soc. 2005, 127, 6926-6927.
35. A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344;
36. Angew. Chem. Int. Ed. 2000, 39, 3168-3210.
37. For recent innovative development of Ugi-type reactions, see: a) L. El Kaïm, L. Grimaud, J. Oble, Angew. Chem. 2005, 117, 8175-8178;
38. Angew. Chem. Int. Ed. 2005, 44, 7961-7964;
39. b) L. El Kaïm, M. Gizolme, L. Grimaud, J. Oble, Org. Lett. 2006, 8, 4019-4021;
40. c) G. B. Giovenzana, G. C. Tron, S. D. Paola, I. G. Menegotto, T. Pirali, Angew. Chem. 2006, 118, 1117-1120;
41. Angew. Chem. Int. Ed. 2006, 45, 1099-1102.
42. a) C. Housseman, J. Zhu, Synlett 2006, 1777-1779;
43. b) R. Beugelmans, A. Bigot, J. Zhu, Tetrahedron Lett. 1994, 35, 5649-5652.
44. For examples of Ugi-type reactions in toluene in the absence of additives, see: a) A. Fayol, J. Zhu, Org. Lett. 2005, 7, 239-242;
45. b) R. Gámez-Montaño, E. González-Zamora, P. Potier, J. Zhu, Tetrahedron 2002, 58, 6351-6358.
46. L. Banfi, R. Riva, Org. React. 2005, 65, 1-140.
47. For recent reviews on the chemistry of oxazoles, see: a) V. S. C. Yeh, Tetrahedron 2004, 60, 11 995-12 042;
48. b) J. Zhong, Nat. Prod. Rep. 2005, 22, 186-229.
49. G. Cuny, R. Gámez-Montaño, J. Zhu, Tetrahedron 2004, 60, 4879-4885.
50. For reviews on the Diels-Alder reaction of oxazoles with alkynes, see: a) M. Y. Karpeiskii, V. L. Florent'ev, Russ. Chem. Rev. 1969, 38, 540-546;
51. b) P. A. Jacobi in Adv. in Heterocyclic Nat. Prod. Syn., Vol. 2 (Ed.: W. H. Pearson), 1992, pp. 251-298;
52. for examples of the cycloaddition of 5-aminooxazoles with alkynes, see: c) P. Janvier, H. Bienaymé, J. Zhu, Angew. Chem. 2002, 114, 4467-4470;
53. Angew. Chem. Int. Ed. 2002, 41, 4291-4294;
54. d) A. Fayol, J. Zhu, Angew. Chem. 2002, 114, 3785-3787;
55. Angew. Chem. Int. Ed. 2002, 41, 3633-3635.
56. We are exploiting other α-isocyanoacetates that have α C-H bonds with reinforced acidity; see: a) M. Bergemann, R. Neidlein, Helv. Chim. Acta 1999, 82, 909-918;
57. b) S. Müller, R. Neidlein, Helv. Chim. Acta 2002, 85, 2222-2231.
58. B. H. Lipshutz, Chem. Rev. 1986, 86, 795-819, and references therein.
59. M. Chapdelaine, WO Patent 2005/100351A1, 2005 [Chem. Abstr. 2005, 143, 422508].