Efficient synthesis of 5-fluoroalkylated 1H-1,2,3-triazoles and application of the bromodifluoromethylated triazole to the synthesis of novel bicyclic gem-difluorinated 1H-pyrano[3,4-d][1,2,3]-triazol-4-one compounds

Tetrahedron

Volumn 59, Issue 24, 2003, Pages 4395-4404

  Peng, Weimin ^a   Zhu, Shizheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

1,3 dipolar cycloaddition; Acrylates; Fluoroalkylated 1H 1,2,3 triazole; Gem difluorinated compounds; Tetrakis (dimethylamino)ethylene

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; AZIDE; ETHYLENE DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFONIC ACID DERIVATIVE; TOLUENE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHROMATOGRAPHY; CYCLOADDITION; FLUORINATION; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS; TEMPERATURE; THIN LAYER CHROMATOGRAPHY;

EID: 0038361093     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00621-5     Document Type: Article

References (51)

1. Wamhoff H. Katritzky A.R., Rees C.W. Comprehensive of Heterocyclic Chemistry. Vol. 5:1984;669-732 Pergamon, Oxford.
2. For review see: (a) Finley K.T. Montgomery J.A. Heterocyclic Compounds. Heterocyclic Compounds. Vol. 39:1980;Wiley, New York, (b) Gilchrist T.L., Gymer G.E. Katritzky A.R., Boulton A.J. Advance in Heterocyclic Chemistry. Vol. 16:1974;33-85 Academic, New York, (c) Gilchrist T.L. Heterocyclic Chemistry. 3rd ed. 1997;Addison Wesley Longman, Beijing. pp 304-319 (d) Fan W.Q., Katritzky A.R. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive of Heterocyclic Chemistry II: A Review of the Literature 1982-1995; The Structure, Reactions, Synthesis, and Use of the Heterocyclic Compounds. Vol. 4:1996;1-126 Elsevier, New York.
3. For review see: (a) Finley K.T. Montgomery J.A. Heterocyclic Compounds. Heterocyclic Compounds. Vol. 39:1980;Wiley, New York, (b) Gilchrist T.L., Gymer G.E. Katritzky A.R., Boulton A.J. Advance in Heterocyclic Chemistry. Vol. 16:1974;33-85 Academic, New York, (c) Gilchrist T.L. Heterocyclic Chemistry. 3rd ed. 1997;Addison Wesley Longman, Beijing. pp 304-319 (d) Fan W.Q., Katritzky A.R. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive of Heterocyclic Chemistry II: A Review of the Literature 1982-1995; The Structure, Reactions, Synthesis, and Use of the Heterocyclic Compounds. Vol. 4:1996;1-126 Elsevier, New York.
4. For review see: (a) Finley K.T. Montgomery J.A. Heterocyclic Compounds. Heterocyclic Compounds. Vol. 39:1980;Wiley, New York, (b) Gilchrist T.L., Gymer G.E. Katritzky A.R., Boulton A.J. Advance in Heterocyclic Chemistry. Vol. 16:1974;33-85 Academic, New York, (c) Gilchrist T.L. Heterocyclic Chemistry. 3rd ed. 1997;Addison Wesley Longman, Beijing. pp 304-319 (d) Fan W.Q., Katritzky A.R. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive of Heterocyclic Chemistry II: A Review of the Literature 1982-1995; The Structure, Reactions, Synthesis, and Use of the Heterocyclic Compounds. Vol. 4:1996;1-126 Elsevier, New York.
5. For review see: (a) Finley K.T. Montgomery J.A. Heterocyclic Compounds. Heterocyclic Compounds. Vol. 39:1980;Wiley, New York, (b) Gilchrist T.L., Gymer G.E. Katritzky A.R., Boulton A.J. Advance in Heterocyclic Chemistry. Vol. 16:1974;33-85 Academic, New York, (c) Gilchrist T.L. Heterocyclic Chemistry. 3rd ed. 1997;Addison Wesley Longman, Beijing. pp 304-319 (d) Fan W.Q., Katritzky A.R. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive of Heterocyclic Chemistry II: A Review of the Literature 1982-1995; The Structure, Reactions, Synthesis, and Use of the Heterocyclic Compounds. Vol. 4:1996;1-126 Elsevier, New York.
6. (a) Abu-Orabi S.T., Al-Hamdany R., Shahateet S., Abu-Shandi K. Heterocycl. Commun. 6:2000;443-449.
7. (b) Katritzky A.R., Vvedensky V.Y., Tymoshenko D.O. J. Chem. Soc., Perkin Trans. 1. 2001;2483-2486.
8. (a) Bertelli L., Biagi G., Calderone V., Giorgi I., Livi O., Scartoni V., Barili P.L. J. Heterocycl. Chem. 37:2000;1169-1176.
9. (b) Lonning P.E. Eur. J. Cancer. 36:(Suppl. 4):2000;S81-S82.
10. (c) Lang, G.; Plos, G. PCT Int. Appl. WO 2002007689; Chem. Abstr. 2002, 136, 139633.
11. (d) Biagi G., Calderone V., Giorgi I., Livi O., Scartoni V., Baragatti B., Martinotti E. Farmaco. 56:2001;841-849.
12. (a) Kirk R.E. 2nd ed. Encycopedia of Chemical Technology. Vol. 3:1964;Interscience, New York. pp 737-748
13. (b) Hatanoka, K. Jpn. Pat. 89287190; Chem. Abstr. 1990, 113, 102285.
14. (a) Itoh Y., Ma F.H., Hoshi H., Oka M., Noda K., Ukai Y., Kojima H., Nagano T., Toda N. Anal. Biochem. 287:2000;203-209.
15. (b) Plater M.J., Greig I., Helfrich M.H., Ralston S.H. J. Chem. Soc., Perkin Trans. 1. 2001;2553-2559.
16. (a) Mori, Y.; Osawa, M.; Hori, M.; Nagashima, T. Eur. Pat. Appl. EP 1081250; Chem. Abstr. 2001, 134, 210398.
17. (b) Han, J. H. US Pat. Appl. Publ. US 20020034876; Chem. Abstr. 2002, 136, 255766.
18. (c) Umawatari, T.; Kondo, S. Jpn. Kokai Tokkyo Koho JP 2002105672; Chem. Abstr. 2002, 136, 298315.
19. (a) Philips D. Photochemistry, Chemical Society, London. 2:1971;795-799.
20. (b) Konishi, M., Nakata, Y. PCT Int. Appl. WO 2002014386; Chem. Abstr. 2002, 136, 175527.
21. (a) Yanase, Y.; Yoshikawa, Y.; Kawashima, H.; Takashi, A.; Akase, T. Jpn. Kokai Tokkyo Koho JP 2001072507; Chem. Abstr. 2001, 134, 233062.
22. (b) Yanase, Y.; Yoshikawa, Y.; Takashi, A. Jpn. Kokai Tokkyo Koho JP 2001072512; Chem. Abstr. 2001, 134, 233064.
23. (c) Woodcroft K.J., Bond J.R. Can. J. Physiol. Pharmocol. 68:1990;1278-1285.
24. For example see: (a) Stepanova N.P., Orlova N.A., Galishev V.A., Turbanova E.S., Petrov A.A. Zh. Org. Khim. 21:1985;979-983 (b) Kobayashi Y., Yamashita T., Takahashi K., Kuroda H., Kumadaki I. Chem. Pharm. Bull. 32:1984;4402-4404.
25. For example see: (a) Stepanova N.P., Orlova N.A., Galishev V.A., Turbanova E.S., Petrov A.A. Zh. Org. Khim. 21:1985;979-983 (b) Kobayashi Y., Yamashita T., Takahashi K., Kuroda H., Kumadaki I. Chem. Pharm. Bull. 32:1984;4402-4404.
26. For example see: Kadaba P.K., Stanovnik B., Tisler M. Katritzky A.R. Advances in Heterocyclic Chemistry. Vol. 37:1980;217-349 Academic, Orlando.
27. (a) Filler R., Kobayashi Y., Yagupolskii L.M. Organofluorine Compounds in Medical Chemistry and Biochemical Applications. 1993;Elsevier, Amsterdam, (b) Smart B.E. J. Fluorine Chem. 109:2001;3-11.
28. (a) Filler R., Kobayashi Y., Yagupolskii L.M. Organofluorine Compounds in Medical Chemistry and Biochemical Applications. 1993;Elsevier, Amsterdam, (b) Smart B.E. J. Fluorine Chem. 109:2001;3-11.
29. (a) Carpenter W., Haymaker A., Moore D.W. J. Org. Chem. 31:1966;789-792.
30. (b) Saunier Y.M., Danion-Bougot R., Danoin D., Carrie R. Tetrahedron. 32:1976;1995-1999.
31. (c) Kobayashi Y., Fujino S., Hamana H., Hanzawa Y., Morita S., Kumadaki I. J. Org. Chem. 45:1980;4683-4685.
32. Peng W.M., Zhu S.Z., Jin G.F. Tetrahedron. 57:2001;5781-5784.
33. (a) Tozer M.J., Herpin T. Tetrahedron. 52:1996;8619-8683.
34. (b) Burkholder C.R., Dolbier W.R. Jr., Medebielle M. J. Fluorine Chem. 109:2001;39-48.
35. Burkholder C.R., Dolbier W.R. Jr., Medebielle M. J. Org. Chem. 63:1998;5385-5394.
36. Chen Q.Y., Jiang X.K., Chen B.Q. Sci. Sin. 4:1966;498-503.
37. Metzger J.O. Angew. Chem. Int. Ed. Engl. 37:1998;2975-2978.
38. Balicki R. Pol. J. Chem. 58:1984;85-95.
39. Basketter N.S., Plunkett A.O. J. Chem. Soc., Chem. Commun. 1973;188-189.
40. (a) Goldsmith D., Soria J.J. Tetrahedron Lett. 32:1991;2457-2460.
41. (b) Funicello M., Spagnolo P., Zanirato P. J. Chem. Soc., Perkin Trans. 1. 1990;2971-2978.
42. Chu Q.L., Wang Z.M., Huang Q.C., Yan C.H., Zhu S.Z. J. Am. Chem. Soc. 123:2001;11069-11070.
43. Chen Q.Y., Li Z.T. J. Chem. Soc., Perkin Trans. 1. 1993;645-648.
44. The reaction of benzyl azide with double activated methene compound in the presence of base were well documented in literatures, for example: EI-Khadem H., Mansour H.A.R., Meshreki M.H. J. Chem. Soc. (C). 1968;1329-1331.
45. Medebielle M., Kato K., Dolbier W.R. Jr. Synlett. 2002;1541-1543. and references cited therein.
46. (a) Burkholder C., Dolbier W.R. Jr., Medebielle M., Ait-moliand S. Tetrahedron Lett. 42:2001;3077-3080.
47. (b) Burkholder C., Dolbier W.R. Jr., Medebielle M. Tetrahedron Lett. 38:1997;821-824.
48. Silva C.B.-D., Benkouider A., Pale P. Tetrahedron Lett. 41:2000;3077-3081.
49. (a) Lindsay R.O., Allen C.F.H. Organic Syntheses. Collect. Vol. 3:1955;Wiely, New York. pp 710-711
50. (b) Grieco P.A., Galatsis P., Spohn R.F. Tetrahedron. 42:1986;2847-2853.
51. (c) Dutt P.V., Whitehead H.R., Wormall A. J. Chem. Soc. 119:1921;2088-2095.