Improved synthesis of three brominated analogues of the potent environmental mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX)

Tetrahedron

Volumn 56, Issue 21, 2000, Pages 3391-3397

  Lloveras, Maia ^a   Ramos, Isabel ^a   Molins, Elies ^b   Messeguer, Angel ^a  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

Bromofuranones; Mutagen; Polybrominated compounds; Synthesis

Indexed keywords

BROMINE DERIVATIVE; FURANONE DERIVATIVE; MUTAGENIC AGENT;

ARTICLE; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

EID: 0034685868     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00258-1     Document Type: Article

References (28)

1. Tikkanen L., Kronberg L. Mutat. Res. 240:1990;109-116.
2. Meier J.R., Blazak W.F., Knohl R.B. Environ. Mol. Mutagen. 10:1987;411-424.
3. Kronberg L., Holmbom B., Reunanen M., Tikkanen L. Environ. Sci. Technol. 22:1988;1097-1103.
4. Horth H. J. Fr. Hydrol. 21:1990;135-145.
5. Hemming J., Holmbom B., Reunanen M., Kronberg L. Chemosphere. 15:1986;549-556.
6. Harrington-Brock K., Doerr C.L., Moore M.M. Mutat. Res. 348:1995;105-110.
7. Jansson K., Hyttinen J.M.T. Mutat. Res. 322:1994;129-132.
8. Chang L.W., Daniel F.B., DeAngelo A.B. Teratog. Carcinog., Mutagen. 11:1991;103-114.
9. Furihata C., Yamashita M., Kinae N., Matsushima T. Water Sci. Technol. 25:1992;341-345.
10. Jansson K., Maki-Paakkanen J., Vaittinen S.L., Vartiainen T., Komulainen H., Tuomisto J. Mutat. Res. 299:1993;25-28.
11. Komulainen H., Kosma V.M., Vaittinen S.L., Vartianen T., Kaliste-Korhonen E., Lötjönen S., Tuominen R.K., Tuomisto J. J. Natl. Cancer Inst. 89:1997;848-856.
12. Le Curieux F., Munter T., Kronberg L. Chem. Res. Toxicol. 10:1997;1180-1185.
13. Munter T., Le Curieux F., Sjöholm R., Kronberg L. Chem. Res. Toxicol. 11:1998;226-233.
14. Melnick. J. Natl. Cancer Inst. 89:1997;832-833.
15. Koivusalo M., Jaakkola J.K., Vartianinen T., Hakulinen T., Karjalainen S., Pukkala E., Tuomisto J. Am. J. Public Health. 84:1994;1223-1228.
16. Horth H., Fielding M., James H.A., Thomas M.J., Gibson T., Wilcox P. Water Chlorination. 6:1990;107-124.
17. Suzuki N., Nakanishi J. Chemosphere. 30:1995;1557-1564.
18. LaLonde R.T., Bu L., Henwood A., Fiumano J., Zhang L. Chem. Res. Toxicol. 10:1997;1427-1436.
19. Padmapriya A.A., Just G., Lewis N.G., Can. J. Chem. 63:1985;828-832.
20. For previous reports on the reaction of bromine with crowded olefins, see Bellucci, G.; Bianchini, R.; Chiappe, C.; Lenoir, D.; Attar, A. J. Am. Chem. Soc. 1995, 117, 6243-6248.
21. Martin R., Chapleo C.B., Svanholt K.L., Dreidig A.S. Helv. Chim. Acta. 59:1976;2724-2727.
22. It is worth noting that a similar sequence (halogenation/dehydrohalogenation), but performed with bromine as in the synthesis of BMX-3, did not lead to the formation of the corresponding unsaturated dibromoesters.
23. For previous reports on isomerisations involved in allylic brominations, see Löffer, A.; Norris, F.; Taub, W.; Svanholt, K. L.; Dreidig, A. S. Helv. Chim. Acta. 1970, 53, 403-417.
24. Ramos, I.; Lloveras, M.; Solans, X.; Huici, A.; Messeguer, A. Submitted for publication.
25. Owen L.N. J. Chem. Soc. 1949;236-239.
26. WINGX - A Windows Program for Crystal Structure Analysis. Farrugia, L. J. University of Glasgow, Glasgow, 1998.
27. Sheldrick G.M. Acta Crystallogr. A. 46:1990;467-473.
28. Sheldrick, G. M. SHELX198; A computer program for the refinement of crystal structures, University of Gottingen, 1997.