Synthesis of new halo-containing acetylenes and their application to the synthesis of azoles

Tetrahedron Letters

Volumn 45, Issue 25, 2004, Pages 4935-4938

  Martins, Marcos A P ^a   Emmerich, Daniel J ^a   Pereira, Claudio M P ^a   Cunico, Wilson ^a   Rossato, Marcelo ^a   Zanatta, Nilo ^a   Bonacorso, Helio G ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Acetylenes; Heterocycles; Isoxazoles; Pyrazoles

Indexed keywords

ACETYLENE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; GRIGNARD REACTION; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

TRIFLUORO;

EID: 2942571689     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.106     Document Type: Article

References (53)

1. Pierce M.E., Parsoms R.L. Jr., Radesca L.A., Lo Y.S., Silvermamn S., Moore J.R., Islan Q., Choudhury A., Fortunak J.M.D., Nguyen D., Luo C., Morgan S.J., Davis W.P., Conalone P.N. J. Org. Chem. 63:1998;8536
2. Rodriguez-Franco M.I., Dorronso I., Castro A., Martínez A., Badía A., Bãnos J.E. Bioorg. Med. Chem. 11:2003;2263
3. Zweifel G., Lewis W., On H.P. J. Am. Chem. Soc. 101:1979;5101
4. Legros J., Crousse B., Delpon D.-.B., Bégué J.-.P. J. Fluorine Chem. 107:2001;121
5. Tykwinski R.R., Zhao Synlett. 12:2002;1939
6. Brown H.C., Racherla U.S., Sing S.M. Tetrahedron Lett. 25:1984;2411
7. Degl'lnnocenti A., Scafato P., Capperucci Bartoletti L.A., Mordini A., Reginato G. Tetrahedron Lett. 36:1995;9031
8. Kroeger J.W., Niewland J.A. J. Am. Chem. Soc. 58:1936;1861
9. Normant J.F., Bourgain M. Tetrahedron Lett. 11:1970;2659
10. Yashina G., Zarva T.V., Kaigordova T.D., Vereshchagin L.I. Zh. Org. Khim. 4:1968;2104
11. Utimoto K., Tanaka M., Kitai M., Nozaki H. Tetrahedron Lett. 18:1978;405
12. Davis R.B., Scheiber D.H. J. Am. Chem. Soc. 78:1956;1675
13. Himbert G. Angew. Chem. 91:1979;432
14. Angew. Chem., Int. Ed. Engl. 18:1979;405
15. Kroeger J.W., Nieuwland J.A.J. J. Am. Chem. Soc. 58:1936;1861
16. Colla A., Martins M.A.P., Clar G., Krimmer S., Fischer P. Synthesis. 6:1991;483
17. Martins M.A.P., Zoch A.N., Flores A.F.C., Clar G., Zanatta N., Bonacorso H.G. J. Heterocycl. Chem. 32:1995;739
18. Martins M.A.P., Bastos G.P., Bonacorso H.G., Zanatta N., Flores A.F.C., Siqueira G.M. Tetrahedron Lett. 40:1999;4309
19. Bonacorso H.G., Martins M.A.P., Bittencourt S.R.T., Lourega R.V., Zanatta N., Flores A.F.C. J. Fluorine Chem. 99:1999;177
20. Martins M.A.P., Flores A.C., Freitag R., Zanatta N. J. Heterocycl. Chem. 32:1995;731
21. Martins M.A.P., Flores A.C., Freitag R.A., Zanatta N. J. Heterocycl. Chem. 33:1996;1223
22. Martins M.A.P., Siqueira G.M., Bastos G.P., Bonacorso H.G., Zanatta N. J. Heterocycl. Chem. 33:1996;1619
23. Martins M.A.P., Flores A.F.C., Bastos G.P., Zanatta N., Bonacorso H.G. J. Heterocycl. Chem. 36:1999;837
24. Martins M.A.P., Neto M., Sinhorin A.P., Bastos G.P., Zimmermann N.E.K., Rosa A., Bonacorso H.G., Zanatta N. Synth. Commun. 32:2002;425
25. Martins M.A.P., Sinhorin A.P., Zimmermann N.E.K., Zanatta N., Bonacorso H.G., Bastos G.P. Synthesis. 13:2001;1959
26. Braibante M.E.F., Martins M.A.P., Clar G. J. Heterocycl. Chem. 30:1993;1159
27. Flores A.C.F., Martins M.A.P., Rosa A., Flores D.C., Zanatta N., Bonacorso H.G. Synth. Commun. 32:2002;1585
28. Martins M.A.P., Pereira C.M.P., Sinhorin A.P., Bastos G.P., Zimmermann N.E.K., Rosa A., Bonacorso H., Zanatta N. Synth. Commun. 32:2002;419
29. Martins M.A.P., Blanco R.F., Pereira C.M.P., Beck P., Brondani S., Cunico W., Zimmermann N.E.K., Bonacorso H.G., Zanatta N. J. Fluorine Chem. 118:2002;69
30. Zanatta N., Rosa L.S., Loro E., Bonacorso H.G., Martins M.A.P. J. Fluorine Chem. 107:2001;149
31. Madruga C.C., Clerici E., Martins M.A.P., Zanatta N. J. Heterocycl. Chem. 32:1995;735
32. Zanatta N., Cortelini M.F.M., Carpes M.J.S., Bonacorso H.G., Martins M.A.P. J. Heterocycl. Chem. 34:1997;509
33. Zanatta N., Madruga C.C., Marisco P.C., Flores D.C., Bonacorso H.G., Martins M.A.P. J. Heterocycl. Chem. 37:2000;1213
34. Zanatta N., Pacholski I.L., Faoro D., Bonacorso H.G., Martins M.A.P. Synth. Commun. 31:2001;2855
35. Zanatta N., Barichello R., Bonacorso H.G., Martins M.A.P. Synthesis. 5:1999;765
36. Bonacorso H.G., Bittencourt S.R.T., Lourega R.V., Flores A.F.C., Zanatta N., Martins M.A.P. Synthesis. 2000;1
37. Bonacorso H.G., Bittencourt S.R.T., Wastowski A.D., Wentz A.P., Zanatta N., Martins M.A.P. Tetrahedron Lett. 37:1996;9155
38. Bonacorso H.G., Bittencourt S.R.T., Wastowski A.D., Wentz A.P., Zanatta N., Martins M.A.P. J. Heterocycl. Chem. 36:1999;45
39. Ziegler G.R., Welch C.A., Orzech C.E., Kikkawa S., Miller S.I. J. Am. Chem. Soc. 85:1963;1648
40. Andrew R.J., Mellor J.M. Tetrahedron. 56:2000;7261
41. Ishii, S.; Yagi, K.; Umehara, T.; Kudo, M.; Nawamaki, T.; Watanabe, S. Japan Kokai, Tokkyo Koho JP 02, 129, 171. Chem. Abstr. 1990, 113, 17201a
42. Buntain, I. G.; Hatton, L. R.; Hawkins, D. W.; Pearson, C. J.; Roberts, D. A. Eur. Pat. Appl. EP 295, 117. Chem. Abstr. 1990, 112, 35845n
43. Moser, H.; Bohner, B.; Foery, W. Eur. Pat. Appl. EP 268, 554; Chem. Abstr. 1988, 110, 23879
44. Ishii, T.; Shimotori, H.; Tanaka, Y.; Ishikawa, K. Japan Kokai, Tokkyo Koho JP 01, 168, 675. Chem. Abstr. 1989, 112, 35854
45. Okada, I.; Yoshida, K.; Sekine, K. Japan Kokai, Tokkyo Koho, JP 02, 292, 263. Chem. Abstr. 1990, 114, 185497
46. Sohn, E.; Handle, R.; Mildenberger, H.; Buerstell, H.; Bauer, K.; Bieringer, H. German Patent 3, 633, 840. Chem. Abstr. 1988, 110, 8202
47. Casida, J. E.; Pulman, D. A. In Advances in the Chemistry of Insect Control III; Briggs, G. G., Ed.; Proc 3rd Int. Symp. Adv. Chem. of Insect Control, Spec. Publ. 1994, 147, p 36
48. Bloomquist J.R. Ishaaya I. Biochemical Sites of Insecticide Action and Resistance. 2001;17 Springer, Berlin
49. Colliot, F.; Kukorowski, K. A.; Hawkins, D. W.; Roberts, D. A. In Brighton Crop Protection Conference - Pests and Diseases; British Crop Protection Council: Farnham, UK, 1992; Vol. 1, p 29
50. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., Isakson P.C. J. Med. Chem. 40:1997;1347
51. Linderman R.J., Lonicar M.S. J. Org. Chem. 53:1988;6013
52. Martins M.A.P., Beck P., Cunico W., Pereira C.M.P., Sinhorin Blanco R.F., Peres, Bonacorso H.G., Zanatta N. Tetrahedron Lett. 43:2002;7005
53. 15c, 17b, 30