Three-component synthesis of highly functionalized 5-acetyloxazoles

Chemistry - A European Journal

Volumn 15, Issue 22, 2009, Pages 5432-5435

  Lechel, Tilman ^a   Lentz, Dieter ^a   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Cumulenes; Cyclization; Heterocycles; Multicomponent reactions; Oxazoles

Indexed keywords

ACETYL GROUPS; ALKYNYL; CUMULENES; ENAMIDE; FUNCTIONALIZED; HETEROCYCLES; LOW-YIELD; MULTICOMPONENT REACTIONS; OIL BATHS; OXAZOLES; PROPIOLIC ACID; PYRUVIC ACID; REACTION MIXTURE; SEALED TUBES; SUBSTITUTION PATTERNS; SYNTHESIS PROCEDURE; THREE-COMPONENT; TRIFLUOROACETIC ACIDS; TWO-STEP PROCEDURE;

CYCLIZATION; DISSOLUTION; ORGANIC ACIDS;

SYNTHESIS (CHEMICAL);

OXAZOLE DERIVATIVE; POLYENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; OXAZOLES; POLYENES;

EID: 66249143396     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900386     Document Type: Article

References (57)

1. a) G. V. Boyd, Science of Synthesis, Vol.11 (Ed.: E. Schaumann), Thieme, Stuttgart, 2001, pp. 383-479;
2. b) B. Iddon, Heterocycles 1994,37,1321-1346.
3. a) P. Wipf, Chem. Rev. 1995, 95, 2115-2134;
4. b) V. S. C. Yeh, Tetrahedron 2004, 60, 11995-12042;
5. c) E. Riego, D. Hernández, F. Albericio, M. Alvarez, Synthesis 2005, 1907-1922;
6. d) Z. Jin, Nat. Prod. Rep. 2006, 23, 464-496;
7. e) A. Herrera, R. Martinez-Alvarez, P. Ramiro, D. Molero, J. Almy, J. Org. Chem. 2006, 71, 3026-3032.
8. a) I. J. Turchi, M. J. S. Dewar, Chem. Rev. 1975, 75, 389-437;
9. b) F. W. Hartner Jr. in Comprehensive Heterocyclic Chemistry II, Vol.3 (Eds.: C. W Rees, E. F. V. Scriven, A. R. Katritzky), Elsevier, Oxford, 1996, pp. 261-318;
10. c) Oxazoles: Synthesis Reactions, and Spectroscopy, Part A, Vol.60 (Ed.: D. C. Palmer), Wiley, New York, 2004;
11. d) R. Martín, A. Cuenca, S. L. Buchwald, Org. Lett. 2007, 9, 5521-5524.
12. Recent multicomponent syntheses of oxazoles: a) V. Lobrégat, G. Alcaraz, H. Bienaymé, M. Vaultier, Chem. Commun. 2001, 817-818;
13. b)D. A. Black, B. A. Arndtsen, Tetrahedron 2005, 61, 11317-11321;
14. c)I.F. Clémençon, B. Ganem, Tetrahedron 2007, 63, 8665-8669;
15. d) D. Bonne, M. Dekhane, J. Zhu, Angew. Chem. 2007, 119, 2537-2540;
16. Angew. Chem. Int. Ed. 2007, 46, 2485-2488;
17. e)N Elders, E. Ruijter, F.J.J, de Kanter, M.B. Groen, R. V. A. Orru, Chem. Eur. J. 2008, 14, 4961-4973;
18. f) E. Merkul, T. J. J. Müller, Chem. Commun. 2006, 4817-4819.
19. Recent oxazole syntheses starting from a-acylaminoketones or enamides: a) P Wipf, C. P. Miller, J. Org. Chem. 1993, 58, 3604-3606;
20. b) C. T. Brain, J. M. Paul, Synlett 1999, 1642-1644;
21. c) M. Keni, J. J. Tepe,J. Org. Chem. 2005, 70, 4211-4213;
22. d) M. P. Kumar, R.-S. Liu, J. Org. Chem. 2006, 71, 4951-4955;
23. e) K. Schuh, F. Glorius, Synthesis 2007, 2297-2306;
24. f) C. Kison, T. Opatz, Chem Eur. J. 2009, 15, 843-845.
25. For reviews on alkoxyallenes: a) R. Zimmer, Synthesis 1993, 165178;
26. b)R. Zimmer, F.A. Khan, J. Prakt. Chem. 1996, 338, 92-94;
27. c) H.-U. Reissig, W. Schade, M. G. Okala Amombo, R. PuIz, A. Hausherr, Pure Appl. Chem. 2002, 74, 175-180;
28. d) "Donor-Substituted Alienes": R. Zimmer, H.-U. Reissig in Modern Allene Chemistry (Eds.: N Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004, pp. 425-492;
29. e) H.-U. Reissig, R. Zimmer, Science of Synthesis, Vol.44 (Ed.: N. Krause), Thieme, Stuttgart, 2007, pp. 301-352;
30. f) M. Brasholz, H.-U. xReissig, R. Zimmer, Acc. Chem. Res. 2009, 42, 45-56; for selected recent applications developed by our group, see:
31. g) A. Al-Harrasi, H.-U. Reissig, Angew. Chem. 2005,117, 6383-6387;
32. Angew. Chem. Int. Ed. 2005, 44, 6227-6231;
33. h) S. Kaden, H.U. Reissig, Org. Lett. 2006, 8, 4763-4766;
34. i) S. Sörgel, C. Azap, H.U. Reissig, Org. Lett. 2006, 8, 4875-4878;
35. j) M. Brasholz, H.-U. Reissig, Angew. Chem. 2007, 119, 1659-1662;
36. Angew. Chem. Int. Ed. 2007, 46, 1634-1637;
37. k) M. Gwiazda, H.-U. Reissig, Synthesis 2008, 990-994;
38. I)F. Pfrengle, D. Lentz, H.-U. Reissig, Angew. Chem. 2009, 121, 3211-3215;
39. Angew. Chem. Int. Ed. 2009, 48, 3165-3169.
40. J. Dash, T. Lechel, H.-U. Reissig, Org. Lett. 2007, 9, 5541-5544.
41. T. Lechel, S. Möhl, H.-U. Reissig, Synlett 2009,1059-1062.
42. a) O. Flögel, J. Dash, I. Brüdgam, H. Hartl, H.-U. Reissig, Chem. Eur. J. 2004, 10, 4283-4290;
43. b) O. Flögel, H.-U. Reissig, German Patent Nr. 10336497.8.Al, 2005;
44. c) T. Lechel, J. Dash, H.-U. Reissig, Eur. J. Org. Chem. 2008, 3647-3655.
45. T. Lechel, H.-U. Reissig, German Patent Application DE 102008049431.3, 2008.
46. CCDC 718587 (7h) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data-request/cif.
47. F.J. Vinick, H.H. Wasserman, J. Org. Chem. 1973, 38, 2407-2408.
48. Recent benzoxazole syntheses starting from ortto-hydroxy benze- neamides: a) E. Koyama, G. Yang, S. Tsuzuki, K. Hiratani, Eur. J. Org. Chem. 2002, 1996-2006;
49. b) G. Evindar, R. A. Batey, J. Org. Chem. 2006, 71, 1802-1808;
50. c) A. Huxley, Synlett 2006, 2658-2660;
51. d) Y-H. Yang, M. Shi, Tetrahedron 2006, 62, 2420-2427.
52. B. Kemper, R. Metternich, T. Lehmeier, R. W. Hoffmann, Liebigs Ann. Chem. 1985, 2246-2260.
53. A. Dornow, H. Hell, Chem. Ber. 1960, 93,1998-2001.
54. Syntheses of related oxazol-5-yl ketones: a) S. B. Bathia, C. D. Telefus, C. P. Smith, F. Ramirez, Tetrahedron 1969, 25, 771-782;
55. b) Y C. Lee, H. J. Choi, J. C. Lee, Tetrahedron Lett. 2002, 43, 123-125;
56. c) Y. Aoyama, T. E. Benedum, P. Wipf, Org. Lett. 2004, 6, 3593-3595;
57. d) E. Merkul, O. Grotkopp, T. J. J. Müller, Synthesis 2009, 502-507.