Isoxazoles from 1,1-disubstituted bromoalkenes

Tetrahedron Letters

Volumn 48, Issue 7, 2007, Pages 1295-1298

  Dadiboyena, Sureshbabu ^a   Xu, Jianping ^a   Hamme II, Ashton T ^a  

^a JACKSON STATE UNIVERSITY   (United States)

Author keywords

Alkyne surrogate; Cycloaddition; Dehydrohalogenation; Heterocycles; Regioselectivity

Indexed keywords

5 BROMOISOXAZOLINE; ALKENE DERIVATIVE; BROMINE; BROMINE DERIVATIVE; FUNCTIONAL GROUP; HYDROGEN; ISOXAZOLE DERIVATIVE; ISOXAZOLINE DERIVATIVE; NITRILE OXIDE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CYCLOADDITION; SYNTHESIS;

EID: 33846242658     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.005     Document Type: Article

References (21)

1. Talley J.J., Brown D.L., Carter J.S., Graneto M.J., Koboldt C.M., Masferrer J.L., Perkins W.E., Rogers R.S., Shaffer A.F., Zhang Y.Y., Zweifel B.S., and Seibert K. J. Med. Chem. 43 (2000) 775
2. Lee Y.-S., and Kim B.H. Bioorg. Med. Chem. Lett. 12 (2002) 1395
3. Srivastava S., Bajpai L.K., Batra S., Bhaduri A.P., Maikhuri J.P., Gupta G., and Dhar J.D. Bioorg. Med. Chem. 7 (1999) 2607
4. Simoni D., Grisolia G., Giannini G., Roberti M., Rondanin R., Piccagli L., Baruchello R., Rossi M., Romagnoli R., Invidiata F.P., Grimaudo S., Jung M.K., Hamel E., Gebbia N., Crosta L., Abbadessa V., Di Cristina A., Dusonchet L., Meli M., and Tolomeo M. J. Med. Chem. 48 (2005) 723
5. Kaffy J., Pontikis R., Carrez D., Croisy A., Monneret C., and Florent J.-C. Bioorg. Med. Chem. 14 (2006) 4067
6. Sandanayaka V.P., and Youjun Y. Org. Lett. 2 (2000) 3087
7. Croce P.D., La Rosa C., and Zecchi G. J. Chem. Soc., Perkin Trans. 1 (1985) 2621
8. For examples of highly regioselective 1,3-dipolar cycloadditions with of alkynliodonium salts please see:. Stang P.J., and Murch P. Tetrahedron Lett. 38 (1997) 8793
9. Easton C.J., Hughes C.M., Tiekink E.R.T., Lubin C.E., Savage G.P., and Simpson G.W. Tetrahedron Lett. 35 (1994) 3589
10. Easton C.J., Heath G.A., Hughes C.M.M., Lee C.K.Y., Savage G.P., Simpson G.W., Tiekink E.R.T., Vuckovic G.J., and Webster R.D. J. Chem. Soc., Perkin Trans. 1 (2001) 1168
11. Jimenez R., Perez L., Tamariz J., and Salgado H. Heterocycles 35 (1993) 591
12. The reported regioselectivites for 1,3-dipolar cycloaddition of similar terminal carbonyl alkynes range from 3:1 to 6:1 favoring the 5-isoxazole, and 4-isoxazoles are preferred over the 5-isoxazole (2:1 to 4:1) for comparable terminal phenyl sulfone alkynes.
13. Hamme II A.T., Xu J., Wang J., Cook T., and Ellis E. Heterocycles 65 (2005) 2885
14. Houk K.N., Sims J., Duke Jr. R.E., Strozier R.W., and George J.K. J. Am. Chem. Soc. 95 (1973) 7287
15. Houk K.N., Sims J., Watts C.R., and Luskus L.J. J. Am. Chem. Soc. 95 (1973) 7301
16. Houk K.N. Acc. Chem. Res. 8 (1975) 361
17. Padwa A. 1,3-Dipolar Cycloaddition Chemistry (1984), John Wiley & Sons, New York
18. 13C NMR, IR, and HRMS, and for regiochemical assignment, all analytical data is consistent with literature precedent.
19. Miyaoka H., Kajiwara Y., Hara Y., and Yamada Y. J. Org. Chem. 66 (2001) 1429
20. Trost B.M., and Bridges A.J. J. Org. Chem. 40 (1975) 2014
21. General procedure: A solution of bromoalkene (0.25 mmol) and hydroximinoyl chloride (0.25 mmol) in 5 mL dry dichloromethane was treated with triethylamine (28 mg, 0.275 mmol). The reaction mixture was stirred at rt until the disappearance of the starting materials, as evidenced by TLC. After the reaction was complete, a minimum amount of silica gel was added, and the solvent was evaporated under reduced pressure. The crude products were purified by flash column chromatography over silica gel using hexanes-ethyl acetate (4:1) as an eluant system.