Traceless solid-phase synthesis of 2,4,5-trisubstituted thiazoles

Synlett

Volumn , Issue 16, 2005, Pages 2483-2485

  Lee, Ill Young ^a   Lee, Jin Young ^a   Lee, Hye Jin ^a   Gong, Young Dae ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

Cyanodithioimidocarbonic acid; Thiazoles; Traceless solid phase synthesis

Indexed keywords

ALPHA BROMOKETONE; CARBONIC ACID DERIVATIVE; CYANODITHIOIMIDOCARBONIC ACID; ISOCYANIC ACID DERIVATIVE; KETONE DERIVATIVE; POLYMER; RESIN; SULFONE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; OXIDATION; SOLID PHASE SYNTHESIS;

EID: 26844491372     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872687     Document Type: Article

References (32)

1. (a) Nicolaou, K. C.; Hanko, R.; Hatwig, W. Handbook of Combinatorial Chemistry; Wiley-VCH: Washington, 2002.
2. (b) Dolle, R. E. J. Comb. Chem. 2003, 6, 693.
3. (a) Boyle, P. H. In Comprehensive Heterocyclic Chemistry, 2nd ed., Vol. 3; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier: New York, 1996, 373.
4. (b) Lewis, J. R. Nat. Prod. Rep. 1999, 16, 389.
5. (a) Goff, D.; Fernandez, J. Tetrahedron Lett. 1999, 40, 423.
6. (b) Kazzouli, S. E.; Berteina-Raboin, S.; Mouaddib, A.; Guillaumet, G. Tetrahedron Lett. 2002, 43, 3193.
7. (c) Stieber, F.; Mazitschek, R.; Soric, N.; Giannis, A.; Waldmann, H. Angew. Chem. Int. Ed. 2002, 41, 4757.
8. (d) Katrizky, A. R.; Cai, X.; Rogovoy, B. V. J. Comb. Chem. 2003, 5, 392.
9. Chen, L.; Ding, Q.; Gillespie, P.; Kim, K.; Lovey, A. J.; Mccomas, W. W.; Mullin, J. G. Jr.; Perrotta, A. PCT Int. Appl. WO02057261, 2002.
10. Bowler, A. N.; Hansen, B. F. PCT Int. Appl. WO03011843, 2003.
11. (a) Gompper, R.; Gang, M.; Saygin, F. Tetrahedron Lett. 1966, 7, 1885.
12. (b) Gewald, K.; Blauschimit, P.; Mayer, R. J. Prakt. Chem. 1967, 35, 97.
13. (a) Rajasekharan, K. N.; Nair, K. P.; Jenardanan, G. C. Synthesis 1986, 353.
14. (b) Binu, R.; Thomas, K. K.; Jenardannan, G. C.; Rajasekharan, K. N. Org. Prep. Proced. Int. 1998, 30, 93.
15. (c) Romero-Ortega, M.; Aviles, A.; Raymundo, C.; Fuentes, A.; Gomez, R. M.; Plata, A. J. Org. Chem. 2000, 65, 7244.
16. (d) Masquelin, T.; Obrecht, D. Tetrahedron 2001, 57, 153.
17. (e) Baer, R.; Masquelin, T. J. Comb. Chem. 2001, 3, 16.
18. (a) Yamanaka, H.; Ohba, S.; Sakamoto, T. Heterocycles 1990, 31, 1115.
19. (b) Konno, S.; Masaki, A.; Mataichi, S.; Hiroshi, Y. Yakugaku Zasshi 1990, 110, 105.
20. Timmons, R. J.; Wittenbrook, L. S. J. Org. Chem. 1967, 32, 1566.
21. Hwang, J. Y.; Choi, H.-S.; Lee, D.-H.; Yoo, S.-e.; Gong, Y.-D. J. Comb. Chem. 2005, 7, 136.
22. Vernin, G.; Siv, C.; Metzger, J. J. Heterocyd. Chem. 1978, 75, 1361.
23. (a) Walchshofer, N.; Minjat, M.; Tinland, B.; Jaussaud, P.; Petavy, A. F.; Paris, J. Eur. J. Med. Chem. 1986, 59.
24. (b) Yamamoto, K.; Kondoh, K.; Horiuchi, K.; Matsui, Y.; Nagamine, M. Eur. Pat. Appl. EP 761658, 1997.
25. (a) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
26. (b) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717.
27. (c) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberin, R. J. Comb. Chem. 2002, 4, 95.
28. (d) Lee, I. Y.; Lee, J. Y.; Gong, Y.-D. Synthesis 2005, DOI: 10.1055/5-2005-872099.
29. (a) Hirai, K.; Sugimoto, H.; Ishiba, T. J. Org. Chem. 1980, 45, 253.
30. (b) Wamhoff, H.; Berressem, R.; Herrmann, S. Synthesis 1993, 107.
31. 3): δ = 11.67 (s, 1 H), (m, 2 H), 7.40-7.45 (m, 3 H), 3.17-3.20 (m, 2 H), 1.65 (q, 2 H, m), 0.96 (t, 3 H, J = 7.4 Hz). LCMS: m/z = 262 [M + 1].
32. 3): δ = 186.7, 174.2, 164.0, 158.0, 140.9, 133.8, 132.5, 131.5, 128.9, 128.6, 128.0, 127.5, 102.7, 48.0, 22.1, 11.3. LCMS: m/z = 366 [M + 1].