Trifluoroacetic anhydride-mediated solid-phase version of the Robinson-Gabriel synthesis of oxazoles

Journal of Combinatorial Chemistry

Volumn 7, Issue 3, 2005, Pages 463-473

  Pulici, Maurizio ^a   Quartieri, Francesca ^a   Felder, Eduard R ^a  

^a Nerviano Medical Sciences ^*  (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ANHYDRIDE; ALDEHYDE DERIVATIVE; AMIDE; AMINOALCOHOL; FUNCTIONAL GROUP; KETONE DERIVATIVE; OXAZOLE DERIVATIVE; RESIN; SOLVENT; TRIFLUOROACETIC ACID;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DEPROTECTION REACTION; METHODOLOGY; OXIDATION; ROBINSON GABRIEL REACTION; SOLID; SYNTHESIS; VALIDATION PROCESS;

ACYLATION; AMIDES; AMINATION; AMINES; AMINO ALCOHOLS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; KETONES; MODELS, CHEMICAL; OXAZOLES; OXIDATION-REDUCTION; RESINS, SYNTHETIC; TECHNOLOGY, PHARMACEUTICAL; TIME FACTORS; TRIFLUOROACETIC ACID;

EID: 20044380367     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc049831h     Document Type: Article

References (83)

1. (a) Lister, J.; Robinson, R. J. Chem. Soc. 1912, 1297.
2. (b) Robinson R. J. Chem. Soc. 1909, 2167.
3. (c) Gabriel, S. Chem. Ber. 1907, 40, 2647.
4. (a) Turchi, I. J. In The Chemistry of Heterocyclic Compounds; Wiley: New York, 1986; Vol. 45.
5. (b) Boyd, G. V. Oxazoles and Their Benzo Derivatives. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, pp 177-234.
6. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604-3606.
7. (a) Nishida, A.; Fuwa, M.; Nasuto, S.; Sugano, Y.; Saito, H.; Nakagawa, M. Tetrahedron Lett. 2000, 41, 4791-4794.
8. (b) Mann, E.; Kessler, H. Org. Lett. 2003, 5, 4567-4570.
9. (c) Clapham, B.; Spanka, C.; Janda, K. D. Org. Lett. 2001, 3, 2173-2176.
10. (d) Spanka, C.; Clapham, B.; Janda, K. D. J. Org. Chem. 2002, 67, 3045-3050.
11. Brain, C. T.; Paul, J. P. Synlett 1999, 10, 1642-1644.
12. Clapham, B.; Lee, S.; Koch, G.; Zimmermann, J.; Janda, K. D. Tetrahedron Lett. 2002, 43, 5407-5410.
13. Wasserman, H. H.; Vinick, F. J. J. Org. Chem. 1973, 38, 2407.
14. Clerin, D.; Kille, G.; Fleury, J.-P. Tetrahedron 1974, 30, 469-474.
15. Pinciroli, V.; Biancardi, R.; Colombo, N.; Colombo, M.; Rizzo, V. J. Comb. Chem. 2001, 3, 434-440.
16. (a) Sharma, A. K.; Hergenrother, P. J. Org Lett. 2003, 5, 2107-2109.
17. (b) Florjancic, A. S.; Sheppard, G. S. Synthesis 2003, 1653-1656.
18. Singh, J.; Gordon, T. D.; Barley, W. G.; Morgan, B. A. Tetrahedron Lett. 1993, 34, 211-214.
19. (a) Garg, N. K.; Sarpong, R.; Stoltz B. M. J. Am. Chem. Soc. 2002, 124, 13179-13184.
20. (b) Chen, B.-C.; Chao, S. T.; Sundeen, J. E.; Tellew J,; Ahmad, S. Tetrahedron Lett. 2002, 43, 1595-1596.
21. (c) Tamura, R.; Oda, D.; Kurokawa, H. Tetrahedron Lett. 1986, 27, 5759-5762.
22. (a) Krajewska, D.; Rozanski, A. J. Antibiot. 1999, 52, 1140-1142.
23. (b) Long, L. M.; Troutman, H. D. J. Am. Chem. Soc., 1949, 71, 2473.
24. (a) Kajiwara, Y.; Scott, A. I. Tetrahedron Lett. 2002, 43, 8795-8996.
25. (b) Kauffman, J. M.; Moyna, G. J. Org. Chem. 2003, 68, 839-853.
26. (a) Han, Y.; Hu, H. Synthesis 1990, 615-618.
27. (b) Han, Y.; Hu, H. Tetrahedron Lett. 1989, 30, 5285-5286.
28. (c) Baran, P. S.; Zografos, A. L.; O'Malley, D. P. J. Am. Chem. Soc. 2004, 126, 3726-3727.
29. (a) Widler, L.; Green, J.; Missbach, M.; Susa, M.; Altmann, E. Bioorg. Med. Chem. Lett. 2001, 11, 849-852.
30. (b) Jiang, B.; Gu, X.-H.; Heterocycles 2000, 53, 1559-1568.
31. (c) Unangst, P. C.; Connor, D. T.; Kostlan, C. R.; Shrum, G. P.; Miller, S. R.; Kanter, G. J. Heterocycl. Chem. 1995, 32, 1197-1200.
32. (a) Fresneda, P. M.; Molina, P.; Sanz, M. A. Synlett 2001, 218-221.
33. (b) Patonay, T.; Juhasz-Toth, E.; Benyei, A. Eur. J. Org. Chem. 2002, 2, 285-295.
34. This is, in fact, a variant of a known protocol. See: Urbansky, M.; Proska, J.; Drasar, P. Collect. Czech. Chem. Commun. 1999, 64, 1457-1470.
35. (a) Hone, N. D.; Salter, J. I.; Reader, J. C. Tetrahedron Lett. 2003, 44, 8169-8172.
36. (b) Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171-11172.
37. Yamaguchi, J.; Ueki, M. Chem. Lett. 1996, 621-622.
38. (a) Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373-6374.
39. (b) Felder, E. R.; Marzinzik, A. L. ECSOC-4, http://pages.unibas.ch/mdpi/ ecsoc-4/b0004/b0004.htm.
40. For examples of condensation of α-bromo ketones, see: (a) Tietze, L.-F.; Meier, H.; Voss, E. Synthesis 1988, 274-277.
41. (b) Joliveau, C.; Wermuth, C.-G. Tetrahedron 1983, 39, 2295-2301.
42. (c) Sasai, H.; Kirio, Y.; Shibasaki, M. J. Org. Chem. 1990, 55, 5306-5308.
43. For examples of condensation of α-sulfonylamino ketones, see: (a) Desarbre, E.; Merour, J.-Y. Synthesis 1997, 73-78.
44. (b) Croce, P. D.; Ferraccioli, R.; La Rosa, C. Synth. Commun. 1992, 22, 2621-2624.
45. (c) Desarbre, E.; Merour, J.-Y. Tetrahedron Lett. 1994, 35, 1995-1998.
46. Groarke, M.; Hartzoulakis, B.; McKervey, M. A.; Walker, B.; Williams, C. H. Bioorg. Med. Chem. Lett. 2000, 10, 153-155.
47. Miller, P. C.; Owen, T. J.; Molyneaux, J. M.; Curtis, J. M.; Jones, C. R. J. Comb. Chem. 1999, 1, 223-234.
48. Fuchi, N.; Doi, T.; Cao, B.; Kahn, M.; Takahashi, T. Synlett 2002, 285-289.
49. Bray, A. M.; Chiefari, D. S.; Valerio, R. M.; Maeji, N. J. Tetrahedron Lett. 1995, 36, 5081-5084.
50. For a similar solution-phase reaction, see: Lennon, M.; Mclean, A.; Proctor, G. R.; Sinclair, I. W. J. Chem. Soc., Perkin Trans. 1 1975, 622.
51. (a) Garro-Helion, F.; Merzouk, A.; Guibé, F J. Org. Chem. 1993, 58, 6109-6113.
52. (b) Lemaire-Audoire, S.; Savignac, M.; Dupuis, C.; Genet, J. P. Bull. Soc. Chim. Fr. 1995, 132, 1157-1166.
53. Moreau, B.; Lavielle, S.; Marquet, A. Tetrahedron Lett. 1977, 2591-2594.
54. Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Org. Lett. 2001, 3, 3781-2784.
55. Bertrand, M. P.; Escoubet, S.; Gastaldi, S.; Timokhin, V. I. Chem. Commun. 2002, 216-217.
56. For another very recent solid-phase application, see: Hotha, S.; Yarrow, J. C.; Yang, J. G.; Garret, S.; Renduchintala, K. V.; Mayer, T. U.; Kapoor, T. M. Angew. Chem., Int. Ed. 2003, 42, 2379-2382.
57. (a) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321-3329.
58. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
59. Ugi, I.; Steinbruckner, C. Angew. Chem. 1960, 72, 267-268.
60. Bastiaans, H. M. M.; Tiebes, J.; Jans, D.; Hempel, W.; Sanft, U.; Thonessen, M.-T. Patent WO2000035912, PCT Int. Appl. 2000.
61. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446.
62. Petasis, N. A.; Goodman, A.; Zavialov, I. S. Tetrahedron 1997, 53, 16463-16470.
63. Petasis, N. A. Patent WO9800398, PCT Int. Appl., January 8, 1998.
64. Tedder, J. M. Chem. Rev. 1955, 787, 7-827.
65. For instance, see: Crucianelli, M.; Bravo, P.; Arnone, A.; Corradi, E.; Meille, S. V.; Zanda, M. J. Org. Chem. 2000, 65, 2965-2971.
66. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; J. Wiley and Sons Inc.: New York, 1999.
67. Andrew, R. J.; Mellor, J. M.; Tetrahedron 2000, 56, 7267-7272 and references therein.
68. Kawase, M.; Miyame, H.; Narita, M.; Kurihara, T.; Tetrahedron Lett. 1993, 34, 859-862.
69. See, for instance: (a) Gray, A. D.; Smyth, T. P. J. Org. Chem. 2001, 66, 7113-7117.
70. (b) Veeramaneni, V. R.; Pal, M.; Yeleswarapu, K. R. Tetrahedron 2003, 59, 3283-3290.
71. See, for instance: (a) Miyata, O.; Kimura, Y.; Muroya, K.; Hiramatsu, H.; Naito, T. Tetrahedron Lett. 1999, 40, 3601-3604.
72. (b) Appell, R. B.; Duguid, R. J. Org. Process Res. Dev. 2000, 4, 172-174.
73. Connolly, P. J.; Beers, K. N.; Wetter, S. K.; Murray, W. V. Tetrahedron Lett. 2000, 41, 5187-5191.
74. (a) Schuster, M.; Pernerstorfer, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1979-1980.
75. (b) Pernerstorfer, J.; Schuster, M.; Blechert, S. Synthesis 1999, 138-144.
76. (c) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963-7966.
77. (d) Spaller, M. R.; Thielemann, W. T.; Brennan, P. E.; Bartlett P. A. J. Comb. Chem. 2002, 4, 516-522.
78. (e) Norman, T. C.; Gray, N. S.; Koh, J. T.; Schultz, P. G. J. Am. Chem. Soc. 1996, 118, 7430-7431.
79. Rolland; C.; Hanquet, G.; Ducep, J.-B.; Solladié, G. Tetrahedron Lett. 2001, 42, 7563-7566.
80. Rodenko, B.; Wanner, M. J.; Koomen, G.-J. J. Chem. Soc., Perkin Trans. 1 2002, 1247-1252.
81. Lee, H. M.; Riordan, J. F. Anal. Biochem. 1978, 89, 136-142.
82. Brill, W. K-D.; Schmidt, E.; Tommasi, R. A. Synlett 1998, 906-908.
83. Colombo, M.; Riccardi Sirtori, F.; Rizzo, V. Rapid Commun. Mass Spectrom. 2004, 18, 511-517.