A simple synthesis of 2-arylbenzothiazoles and its application to palladium-catalyzed Mizoroki-Heck reaction

Tetrahedron Letters

Volumn 47, Issue 25, 2006, Pages 4231-4233

  Kawashita, Yuka ^a   Ueba, Chigusa ^a   Hayashi, Masahiko ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATED CARBON; ALDEHYDE; BENZOTHIAZOLE DERIVATIVE; OXYGEN; PALLADIUM;

ARTICLE; ATMOSPHERE; CATALYSIS; CHEMICAL REACTION; HECK REACTION; SYNTHESIS;

EID: 33646527789     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.019     Document Type: Article

References (26)

1. Shi D.-F., Bradshaw T.D., Wrigley S., McCall C.J., Lelieveld P., Fichtner I., and Stevens M.F.G. J. Med. Chem. 39 (1996) 3375-3384
2. Lezcano M., Al-Soufi W., Novo M., Rodriguez-Núñez E., and Vázquez Tato J. J. Agric. Food Chem. 50 (2002) 108-112
3. Zhuang Z.-P., Kung M.-P., Wilson A., Lee C.-W., Plössl K., Hou C., Holtzman D.M., and Kung H.F. J. Med. Chem. 46 (2003) 237-243
4. Wells G., Berry J.M., Bradshaw T.D., Burger A.M., Seaton A., Wang B., Westwell A.D., and Stevens M.F.G. J. Med. Chem. 46 (2003) 532-541
5. Skalitzky D.J., Marakovits J.T., Maegley K.A., Ekker A., Yu X.-H., Hostomsky Z., Webber S.E., Eastman B.W., Almassy R., Li J., Curtin N.J., Newell D.R., Calvert A.H., Griffin R.J., and Golding B.T. J. Med. Chem. 46 (2003) 210-213
6. Chang J., Zhaob K., and Pana S. Tetrahedron Lett. 43 (2002) 951-954
7. Ranu B.C., Jana R., and Dey S.S. Chem. Lett. 33 (2004) 274-275
8. Chang W.-C., Hu A.T., Duan J.-P., Rayabarapu D.K., and Cheng C.-H. J. Organomet. Chem. 689 (2004) 4882-4888
9. Kodomari M., Tamaru Y., and Aoyama T. Synth. Commun. 34 (2004) 3029-3036
10. Itoh T., Nagata K., Ishikawa H., and Ohsawa A. Heterocycles 63 (2004) 2769-2783 and references cited therein
11. Kawashita Y., Nakamichi N., Kawabata H., and Hayashi M. Org. Lett. 5 (2003) 3713-3715
12. For example,. Jin L., Song B., Zhang G., Xu R., Zhang S., Gao X., Hu D., and Yang S. Bioorg. Med. Chem. Lett. 16 (2006) 1537-1543
13. Mizoroki T., Mori K., and Ozaki A. Bull. Chem. Soc. Jpn. 44 (1971) 581-583
14. Heck R.F., and Nolley Jr. J.P. J. Org. Chem. 37 (1972) 2320-2322
15. Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century (2004), John Wiley & Sons Chapter 3
16. Herrmann W.A., Brossmer C., Öfele K., Reisinger C.-P., Priermeier T., Beller M., and Fischer H. Angew. Chem., Int. Ed. Engl. 34 (1995) 1844-1848
17. Herrmann W.A., Böhm V.P.W., and Reisinger C.-P. J. Organomet. Chem. 576 (1999) 23-41
18. Littke A.F., and Fu G.C. J. Am. Chem. Soc. 123 (2001) 6989-7000
19. Stambuli J.P., Stauffer S.R., Shaughnessy K.H., and Hartwig J.F. J. Am. Chem. Soc. 123 (2001) 2677-2678
20. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290-1309
21. Hillier A.C., Grasa G.A., Viciu M.S., Lee H.M., Yang C., and Nolan S.P. J. Organomet. Chem. 653 (2002) 69-82
22. Jeffery T. J. Chem. Soc., Chem. Commun. (1984) 1287-1289
23. Jeffery T. Tetrahedron 52 (1996) 10113-10130
24. Ueba, C.; Eda, K.; Hayashi, M., submitted for publication.
25. General procedure for the synthesis of 2-arylbenzothiazoles (Table 1); A mixture of 2-aminothiophenol (5 mmol), aldehyde (5 mmol) and Shirasagi KL (625 mg) in xylene (8 mL) was placed in a 100 mL three-necked flask under oxygen atmosphere (using 1 L of balloon) and stirred at 50 °C for 3-4 h. The reaction mixture was then filtered using Celite. After the filtrate was concentrated, the product was isolated by recrystallization or silica-gel column chromatography.
26. 4 and filtered. After evaporation, the obtained residue was purified by silica-gel column chromatography to give methyl trans-4-methylcinnamate in 79% yield (277.5 mg).