Efficient di-bromination of 5-pyrazolones and 5-hydroxypyrazoles by N-bromobenzamide

Tetrahedron

Volumn 65, Issue 46, 2009, Pages 9592-9597

  Huang, Yu Ying ^a   Lin, Hui Chang ^a   Cheng, Kaung Min ^a   Su, Wei Nien ^a   Sung, Kuan Chin ^b   Lin, Tsung Ping ^a   Huang, Jiann Jyh ^c   Lin, Shao Kai ^d   Wong, Fung Fuh ^a  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b Department of Surgery ^*  (Taiwan)

^c DEVELOPMENT CENTER FOR BIOTECHNOLOGY   (Taiwan)

^d NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDE DERIVATIVE; N BROMOBENZAMIDE; PYRAZOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; CYCLIZATION; POLYMERIZATION; PRIORITY JOURNAL; ROOM TEMPERATURE; THERMAL CONDUCTIVITY;

EID: 70349823216     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.055     Document Type: Article

References (39)

1. Golden J.E., Sanders S.D., Muller K.M., and Bürli R.W. Tetrahedron Lett. 49 (2008) 794-798
2. Bürli R.W., Hu H., Zou X., Muller K., Golden J., Frohn M., Adlam M., Plant M.H., Wong M., McElvain M., Regal K., Viswanadhan V.N., Tagari P., and Hungate R. Bioorg. Med. Chem. Lett. 16 (2006) 3713-3718
3. Banner, B. L.; Bilotta, J. A.; Fotouhi, N.; Gillespie, P.; Goodnow, R. A.; Hamilton, M. M.; Haynes, N.-E.; Kowalczyk, A.; Myers, M. P.; Pietranico-Cole, S. L; Sctto, N. R.; Thakkar, K. C.; Tilley, J. W. U.S. Patent Appl. 2,007,049,632, 2007;
4. Tripathy R., Ghose A., Singh J., Bacon E.R., Angeles T.S., Yang S.X., Albom M.S., Aimone L.D., Herman J.L., and Mallamo J.P. Bioorg. Med. Chem. Lett. 17 (2007) 1793-1798
5. Balestra, M.; Bunting, H.; Chen, D.; Egle, I.; Forst, J.; Frey, J.; Isaac, M.; Ma, F.; Nugiel, D.; Slassi, A.; Steelman, G.; Sun, G.-R.; Sundar, B.; Ukkiramapandian, R.; Urbanek, R.A.; Walsh, S. Patent Appl. WO 2,006,071,730, 2006;
6. Pégurier C., Collart P., Danhaive P., Defays S., Gillard M., Gilson F., Kogej T., Pasau P., Houtvin N.V., Thuyne M.V., and van Keulen B. Bioorg. Med. Chem. Lett. 17 (2007) 4228-4231
7. Costa D., Marques A.P., Reis R.L., Lima J.L.C., and Fernandes E. Free Radical Biol. Med. 40 (2006) 632-640
8. Ramesh Kakarla G.L., and Gerritz S.W. Tetrahedron Lett. 48 (2007) 4595-4599
9. Haddad N., Salvango A., and Busacca C. Tetrahedron Lett. 45 (2004) 5935-5937
10. Tanitam A., Oyamada Y., Ofugi K., Fujimoto M., Iwai N., Hiyama Y., Suzuki K., Ito H., Terauchi H., Kawasaki M., Nagai K., Wachi M., and Yamagishi J. J. Med. Chem. 47 (2004) 3693-3696
11. Cali P., Naerum L., Mukhija S., and Hjelmencrantz A. Bioorg. Med. Chem. Lett. 14 (2004) 5997-6000
12. Tsurumi K., Abe A., Fujimura H., Asai H., Nagasaka M., and Mikaye H. Folia Pharmacol. Jpn. 72 (1976) 41-52
13. Rapposelli S., Lapucci A., Minutolo F., Orlandimi E., Ortore G., Pinza M., and Balsamo A. Farmaco 59 (2004) 25-31
14. Souza F.R., Souza V.T., Ratzlaff V., Borges L.P., Oliverira M.R., Bonacorso H.G., Zanatta N., Martins M.A.P., and Mello C.F. Eur. J. Pharmacol. 451 (2002) 141-147
15. Al-Omran F., and El-Khair A.A. J. Heterocycl. Chem. 41 (2004) 327-333
16. Sechi M., Sannia L., Carta F., Palomba M., Dallochio R., Dessi A., Derudas M., Zawahir Z., and Neamati N. Antiviral Chem. Chemother. 16 (2005) 41-61
17. Cottineau B., Toto P., Marot C., Pipaud A., and Chenault J. Bioorg. Med. Chem. Lett. 12 (2002) 2105-2108
18. Kakiuchi Y., Sasaki N., Satoh-Masuoka M., Murofushi H., and Murakami-Murofushi K. Biochem. Biophys. Res. Commun. 320 (2004) 1351-1358
19. Sarojbasinidas A.N., Mishra C.R., and Mittra A.S. J. Indian Chem. Soc. LIV (1977) 485-487
20. Fuminori, K.; Hirohiko, K. J.P. Patent Augest 10-45588, 1998.
21. Basaif S.A., Hassan M.A., and Gobouri A.A. Dyes Pigments 72 (2007) 387-391
22. Karci F., and Ertan N. Dyes Pigments 55 (2002) 99-108
23. Ho Y.W. Dyes Pigments 64 (2005) 223-230
24. Kirscuke K., Luize G., and Schmttz E. J. Prakt. Chem. 326 (1984) 367-373
25. Chande M.S., Bhandari J.D., Joshi V.R., and Joshi V.R. India J. Chem. B. 32B (1993) 1218-1228
26. El-Saraf G.A., and El-Sayed A.M. Heteroat. Chem. 14 (2003) 211-217
27. Ahmed S.A., Award D.M.A., and Abdel-Wahab A.-M. A. Chem. Commun. 1 (2002) 84-86
28. Schuetz R.D., and Millard F.W. J. Org. Chem. 24 (1959) 297-300
29. Buckles R.E., and Prosst W.J. J. Org. Chem. 22 (1957) 1728-1729
30. Buckles R.E., Johnson R.C., and Probst W.J. J. Org. Chem. 22 (1957) 55-59
31. Chowdhury K., and Banerji K.K. J. Org. Chem. 55 (1990) 5391-5393
32. Song C.E., Oh C.R., Roh E.J., Lee S.-G., and Choi J.H. Tetrahedron: Asymmetry 10 (1999) 671-674
33. Demko Z.P., Bartsch M., and Sharpless K.B. Org. Lett. 15 (2000) 2221-2223
34. Wang X.-j., Tan J., and Grozinger K. Tetrahedron Lett. 41 (2000) 4713-4716
35. DeRuiter J., Carter D.A., Arledge W.S., and Sullivan P.J. J. Heterocycl. Chem. 24 (1987) 149-153
36. Braňa M.F., Gradillas A., Ovalles A.G., López B., Acero N., Llinares F., and Mingarro D.M. Bioorg. Med. Chem. 14 (2006) 9-16
37. McFerrin C.A., Hammer R.P., Fronczek F.R., and Watkins S.F. Acta. Crystallogr. E62 (2006) 2518-2519
38. Kimata A., Nakagawa H., Ohyama R., Fukuuchi T., Ohta S., Suzuki T., and Miyata N. J. Med. Chem. 50 (2007) 5053-5056
39. Mojtahedi M.M., Javadpour M., and Abaee M.S. Utrason. SonoChem. 15 (2008) 828-832