Original synthesis of oxiranes via TDAE methodology: Reaction of 2,2-dibromomethylquinoxaline with aromatic aldehydes

Tetrahedron Letters

Volumn 46, Issue 48, 2005, Pages 8373-8376

  Montana, Marc ^a   Terme, Thierry ^a   Vanelle, Patrice ^a  

^a CNRS   (France)

Author keywords

Aromatic aldehydes; Oxiranes; Quinoxaline; TDAE

Indexed keywords

ALDEHYDE DERIVATIVE; ETHYLENE DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; QUINOXALINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CIS TRANS ISOMERISM; METHODOLOGY; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 27644547500     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.152     Document Type: Article

References (19)

1. M.A. Naylor, M.A. Stephen, J. Nolan, B. Sutton, J.H. Tocher, E.M. Fielden, J.E. Adams, and I. Strafford Anticancer Drug Des. 8 1993 439 461
2. J. Harmenberg, A. Akesson-Johansson, A. Graslund, T. Malmfors, J. Bergman, B. Wahren, S. Akerfeldt, L. Lundblad, and S. Cox Antiviral Res. 15 1991 193 204
3. A. Fournet, R. Mahieux, M.A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadere Bioorg. Med. Chem. Lett. 13 2003 891 894
4. M.-H. Munos, J. Mayrargue, A. Fournet, J.-C. Gantier, R. Hocquemiller, and H. Moskowitz Chem. Pharm. Bull. 42 1994 1914 1916
5. G.W.H. Cheeseman, and R.F. Cookson A. Weissberger E.C. Taylor The Chemistry of Heterocyclic Compounds Vol. 35 1979 John Wiley and Sons New York 1
6. T.H. Corbett, P.M. Lorusso, L. Demchick, C. Simpson, S. Pugh, K. White, J. Kushner, L. Polin, J. Meyer, J. Czarnecki, L. Heilbrun, J.P. Horwitz, J.L. Gross, C.H. Behrens, B.A. Harrison, R.J. McRipley, and G. Trainor Invest. New Drugs 16 1998 129 139
7. P.M. Lorusso, R. Parchment, L. Demchik, J. Knight, L. Polin, J. Dzubow, C. Behrens, B. Harrison, G. Trainor, and T.H. Corbett Invest. New Drugs 16 1998-1999 287 296
8. R.H. Shoemaker Cancer Treat. Rep. 70 1986 9 12
9. J.R. Rigas, V.A. Miller, W.P. Tong, N. Roistacher, M.G. Kris, J.P. Orazem, C.W. Young, and R.P. Warrell Jr. Cancer Chemother. Pharmacol. 35 1995 483 488
10. I. Erden A.R. Katritzky C.W. Rees E.F.V. Scriven Comprehensive Heterocyclic Chemistry II Vol. 1 1996 Pergamon Oxford 97 171
11. R.A. Johnson, and K.B. Sharpless I. Ojima Catalytic Asymmetric Synthesis 2nd ed. 2000 Wiley-VCH New York 231 285
12. G. Giuglio-Tonolo, T. Terme, M. Médebielle, and P. Vanelle Tetrahedron Lett. 44 2003 6433 6435
13. G. Giuglio-Tonolo, T. Terme, M. Médebielle, and P. Vanelle Tetrahedron Lett. 45 2004 5121 5124
14. O. Amiri-Attou, T. Terme, and P. Vanelle Molecules 10 2005 545 551
15. S. Goswami, S. Dey, S. Jana, and A.K. Adak Chem. Lett. 33 2004 916 917
16. N.L. Maidwell, M.R. Rezai, C.A. Roeschlaub, and P.G. Sammes J. Chem. Soc., Perkin Trans. 1 10 2000 1541 1546
17. 2O (262.31): C, 77.84; H, 5.38; N, 10.68. Found: C, 77.34; H, 5.59; N, 10.56. Compound 4e cis-isomer;
18. C. Price, and D.D. Carmelite J. Am. Chem. Soc. 88 1966 4039 4044
19. D.H. Williams, and I. Fleming Spectroscopic Methods in Organic Chemistry 4th ed. 1991 Mc Graw-Hill New York 76 101