A five-component synthesis of hexasubstituted benzene

Angewandte Chemie - International Edition

Volumn 41, Issue 22, 2002, Pages 4291-4294

  Janvier, Pierre ^a   Bienaymé, Hugues ^b   Zhu, Jieping ^a  

^a CNRS   (France)

^b Chrysalon   (France)

Author keywords

Cycloaddition; Domino reactions; Heterocycles; Multicomponent reactions; Synthetic methods

Indexed keywords

CHEMICAL BONDS; SYNTHESIS (CHEMICAL);

FUNCTIONAL GROUPS;

BENZENE;

BENZENE DERIVATIVE; CAMPHOR DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE;

EID: 2242457652     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021115)41:22<4291::AID-ANIE4291>3.0.CO;2-D     Document Type: Article

References (46)

1. a) G. W. Gribble, S. J. Berthel in Studies in Natural Products Chemistry. Vol. 12 (Ed.: Atta-Ur-Rahman), Elsevier, New York, 1993, pp. 365-409:
2. b) J. Bergman, T. Janosik, N. Wahlström in Advances in Heterocyclic Chemistry, Vol. 80 (Ed.: A. R. Katritzky), Academic Press, New York, 2001, pp. 1-71.
3. ) P. Moreau, F. Anizon, M. Sancelme, M. Prudhomme, D. Sevère, J. F. Riou, J. F. Goossens, J. P. Hénichart, C. Bailly, E. Labourier, J. Tazzi, D. Fabbro, T. Meyer, A. M. Aubertin, J. Med. Chem. 1999, 42, 1816-1822.
4. ) P. Schupp, C. Eder, P. Porksch, V. Wray, B. Schneider, M. Herderich, V. Paul, J. Nat. Prod. 1999, 62, 959-962.
5. ) U. Pindur, Y. S. Kim, F. Mehrabani, Curr. Med. Chem. 1999, 6, 29-69.
6. a) K. P. C. Vollhardt, Augew. Chem. 1984, 96, 525; Angew. Chem. Int. Ed. Engl. 1984, 23, 539-556:
7. b) A. J. Fletcher, S. D. R. Christie, J. Chem. Soc. Perkin Trans. 1 2000, 1657-1668;
8. c) S. Saito, Y. Yamamoto, Chem. Rev. 2000, 100, 2901-2916.
9. a) H. N. C. Wong, T. K. Ng, T. Y. Wong, Heterocycles 1983, 20, 1815-1840;
10. b) H. N. C. Wong, T. K. Ng, T. Y. Wong, Y. D. Xing, Heterocycles 1984, 22, 875-890;
11. c) C. O. Kappe, S. S. Murphree, A. Padwa, Tetrahedron 1997, 53, 14179-14233;
12. d) P. Vogel, J. Cossy, J. Plumet, O. Arjona. Tetrahedron 1999, 55, 13 521-13 642.
13. Recent selected examples: metal-catalyzed: a) B. Witulski, T. Stengel, Angew. Chem. 1999, 111, 2521-2524; Angew. Chem. Int. Ed. 1999, 38, 2426-2430; b) D. Suzuki, H. Urabe, F. Sato, J. Am. Chem. Soc. 2001. 123, 7925-7926; c) T Sugihara, A. Wakabayashi, Y. Nagai, H. Takao, H. Imagawa, M. Nishizawa, Chem. Commun. 2002, 576-577; d) M. Petit, G. Chouraqui, P. Phansavath, C. Aubert, M. Malacria, Org. Lett. 2002, 4, 1027-1029; cycloaddition: e) A. Padwa, J. P. Snyder, E. A. Curtis, S. M. Sheehan, K. J. Worsencroft, C. O. Kappe, J. Am. Chem. Soc. 2000, 122, 8155-8167.
14. Recent selected examples: metal-catalyzed: a) B. Witulski, T. Stengel, Angew. Chem. 1999, 111, 2521-2524; Angew. Chem. Int. Ed. 1999, 38, 2426-2430; b) D. Suzuki, H. Urabe, F. Sato, J. Am. Chem. Soc. 2001. 123, 7925-7926; c) T Sugihara, A. Wakabayashi, Y. Nagai, H. Takao, H. Imagawa, M. Nishizawa, Chem. Commun. 2002, 576-577; d) M. Petit, G. Chouraqui, P. Phansavath, C. Aubert, M. Malacria, Org. Lett. 2002, 4, 1027-1029; cycloaddition: e) A. Padwa, J. P. Snyder, E. A. Curtis, S. M. Sheehan, K. J. Worsencroft, C. O. Kappe, J. Am. Chem. Soc. 2000, 122, 8155-8167.
15. Recent selected examples: metal-catalyzed: a) B. Witulski, T. Stengel, Angew. Chem. 1999, 111, 2521-2524; Angew. Chem. Int. Ed. 1999, 38, 2426-2430; b) D. Suzuki, H. Urabe, F. Sato, J. Am. Chem. Soc. 2001. 123, 7925-7926; c) T Sugihara, A. Wakabayashi, Y. Nagai, H. Takao, H. Imagawa, M. Nishizawa, Chem. Commun. 2002, 576-577; d) M. Petit, G. Chouraqui, P. Phansavath, C. Aubert, M. Malacria, Org. Lett. 2002, 4, 1027-1029; cycloaddition: e) A. Padwa, J. P. Snyder, E. A. Curtis, S. M. Sheehan, K. J. Worsencroft, C. O. Kappe, J. Am. Chem. Soc. 2000, 122, 8155-8167.
16. Recent selected examples: metal-catalyzed: a) B. Witulski, T. Stengel, Angew. Chem. 1999, 111, 2521-2524; Angew. Chem. Int. Ed. 1999, 38, 2426-2430; b) D. Suzuki, H. Urabe, F. Sato, J. Am. Chem. Soc. 2001. 123, 7925-7926; c) T Sugihara, A. Wakabayashi, Y. Nagai, H. Takao, H. Imagawa, M. Nishizawa, Chem. Commun. 2002, 576-577; d) M. Petit, G. Chouraqui, P. Phansavath, C. Aubert, M. Malacria, Org. Lett. 2002, 4, 1027-1029; cycloaddition: e) A. Padwa, J. P. Snyder, E. A. Curtis, S. M. Sheehan, K. J. Worsencroft, C. O. Kappe, J. Am. Chem. Soc. 2000, 122, 8155-8167.
17. Recent selected examples: metal-catalyzed: a) B. Witulski, T. Stengel, Angew. Chem. 1999, 111, 2521-2524; Angew. Chem. Int. Ed. 1999, 38, 2426-2430; b) D. Suzuki, H. Urabe, F. Sato, J. Am. Chem. Soc. 2001. 123, 7925-7926; c) T Sugihara, A. Wakabayashi, Y. Nagai, H. Takao, H. Imagawa, M. Nishizawa, Chem. Commun. 2002, 576-577; d) M. Petit, G. Chouraqui, P. Phansavath, C. Aubert, M. Malacria, Org. Lett. 2002, 4, 1027-1029; cycloaddition: e) A. Padwa, J. P. Snyder, E. A. Curtis, S. M. Sheehan, K. J. Worsencroft, C. O. Kappe, J. Am. Chem. Soc. 2000, 122, 8155-8167.
18. Recent selected examples: metal-catalyzed: a) B. Witulski, T. Stengel, Angew. Chem. 1999, 111, 2521-2524; Angew. Chem. Int. Ed. 1999, 38, 2426-2430; b) D. Suzuki, H. Urabe, F. Sato, J. Am. Chem. Soc. 2001. 123, 7925-7926; c) T Sugihara, A. Wakabayashi, Y. Nagai, H. Takao, H. Imagawa, M. Nishizawa, Chem. Commun. 2002, 576-577; d) M. Petit, G. Chouraqui, P. Phansavath, C. Aubert, M. Malacria, Org. Lett. 2002, 4, 1027-1029; cycloaddition: e) A. Padwa, J. P. Snyder, E. A. Curtis, S. M. Sheehan, K. J. Worsencroft, C. O. Kappe, J. Am. Chem. Soc. 2000, 122, 8155-8167.
19. a) J. Drews, Science 2000, 287, 1960-1964;
20. b) W. Wess. M. Urmann, B. Sickenberger, Angew. Chem. 2001, 113, 3443-3453; Angew. Chem. Int. Ed. 2001, 40, 3341-3350.
21. b) W. Wess. M. Urmann, B. Sickenberger, Angew. Chem. 2001, 113, 3443-3453; Angew. Chem. Int. Ed. 2001, 40, 3341-3350.
22. For recent reviews on multicomponent reactions, see: a) G. H. Posner, Chem. Rev. 1986, 86, 831-844;
23. b) L. Weber, K. Illgen, M. Almstetter, Synlett 1999, 366-374;
24. c) A. Domling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344; Angew. Chem. Int. Ed. 2000, 39, 3168-3210;
25. c) A. Domling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344; Angew. Chem. Int. Ed. 2000, 39, 3168-3210;
26. d) H. Bienaymé, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 2000, 6, 3321-3329.
27. For recent reviews on domino process, see: a) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
28. b) M. H. Filippini, J. Rodriguez, Chem. Rev. 1999, 99, 27-76;
29. c) R. A. Bunce, Tetrahedron 1995, 51, 13 103-13 160;
30. d) L. F. Tietze, F. Haunert in Stimulating Concepts in Chemistry (Eds.: M. Shibasaki, J. F. Stoddart, F. Vögtle), 2000, pp. 39-64.
31. ) X. Sun, P. Janvier, G. Zhao, H. Bienaymé, J. Zhu, Org. Lett. 2001, 3, 877-880.
32. For a review on the intramolecular Diels-Alder reaction of oxazole and acetylene, see: P. A. Jacobi in Advances in Heterocyclic Natural Product Synthesis, Vol. 2 (Ed.: W, H. Pearson), 1992, pp. 251-298; for a recent application in natural product synthesis, see: b) B. Liu, A. Padwa, Tetrahedron Lett. 1999, 40, 1645-1648; c) P. A. Jacobi, K. Lee, J. Am. Chem. Soc. 2000, 122, 4295-4303; d) L. A. Paquette, I. Efremov, J. Am. Chem. Soc. 2001, 123, 4492-4501.
33. For a review on the intramolecular Diels-Alder reaction of oxazole and acetylene, see: P. A. Jacobi in Advances in Heterocyclic Natural Product Synthesis, Vol. 2 (Ed.: W, H. Pearson), 1992, pp. 251-298; for a recent application in natural product synthesis, see: b) B. Liu, A. Padwa, Tetrahedron Lett. 1999, 40, 1645-1648; c) P. A. Jacobi, K. Lee, J. Am. Chem. Soc. 2000, 122, 4295-4303; d) L. A. Paquette, I. Efremov, J. Am. Chem. Soc. 2001, 123, 4492-4501.
34. For a review on the intramolecular Diels-Alder reaction of oxazole and acetylene, see: P. A. Jacobi in Advances in Heterocyclic Natural Product Synthesis, Vol. 2 (Ed.: W, H. Pearson), 1992, pp. 251-298; for a recent application in natural product synthesis, see: b) B. Liu, A. Padwa, Tetrahedron Lett. 1999, 40, 1645-1648; c) P. A. Jacobi, K. Lee, J. Am. Chem. Soc. 2000, 122, 4295-4303; d) L. A. Paquette, I. Efremov, J. Am. Chem. Soc. 2001, 123, 4492-4501.
35. For a review on the intramolecular Diels-Alder reaction of oxazole and acetylene, see: P. A. Jacobi in Advances in Heterocyclic Natural Product Synthesis, Vol. 2 (Ed.: W, H. Pearson), 1992, pp. 251-298; for a recent application in natural product synthesis, see: b) B. Liu, A. Padwa, Tetrahedron Lett. 1999, 40, 1645-1648; c) P. A. Jacobi, K. Lee, J. Am. Chem. Soc. 2000, 122, 4295-4303; d) L. A. Paquette, I. Efremov, J. Am. Chem. Soc. 2001, 123, 4492-4501.
36. 3-Arylpropiolic acid was synthesized from the corresponding cinnamate according to a literature procedure: K. J. Schofield, J. C. E. Simpson, J. Chem. Soc. 1945, 512-520.
37. E. Gonzalez-Zamora, A. Fayol, M. Bois-Choussy, A. Chiaroni, J. Zhu, Chem. Commun. 2001, 1684-1685.
38. a) P. Cristau, J.-P. Vors. J. Zhu, Org. Lett. 2001, 3, 4079-4082;
39. b) P. Janvier, X. Sun, H. Bienaymé, J. Zhu, J. Am. Chem. Soc. 2002, 124, 2560-2567.
40. For a five-component synthesis of α-acylaminocarbonamide, see: a) I. Ugi, C. Steinbrückner, Chem. Ber. 1961, 94, 2802-2814; for a seven-component reaction, see: b) A. Dömling, I. Ugi, Angew. Chem. 1993, 105, 634-635; Angew. Chem. Int. Ed. Engl. 1993, 32, 563-564.
41. For a five-component synthesis of α-acylaminocarbonamide, see: a) I. Ugi, C. Steinbrückner, Chem. Ber. 1961, 94, 2802-2814; for a seven-component reaction, see: b) A. Dömling, I. Ugi, Angew. Chem. 1993, 105, 634-635; Angew. Chem. Int. Ed. Engl. 1993, 32, 563-564.
42. For a five-component synthesis of α-acylaminocarbonamide, see: a) I. Ugi, C. Steinbrückner, Chem. Ber. 1961, 94, 2802-2814; for a seven-component reaction, see: b) A. Dömling, I. Ugi, Angew. Chem. 1993, 105, 634-635; Angew. Chem. Int. Ed. Engl. 1993, 32, 563-564.
43. a) S. L. Schreiber, Science 2000, 287, 1964-1969;
44. b) P. Arya, D. T. H. Chou, M. G. Baek, Angew. Chem. 2001, 113, 3511-358; Angew. Chem. Int. Ed. 2001, 40, 339-346.
45. b) P. Arya, D. T. H. Chou, M. G. Baek, Angew. Chem. 2001, 113, 3511-358; Angew. Chem. Int. Ed. 2001, 40, 339-346.