Regiospecific synthesis of 2-allyl-1,2,3-triazoles by palladium-catalyzed 1,3-dipolar cycloaddition

Tetrahedron Letters

Volumn 43, Issue 52, 2002, Pages 9707-9710

  Kamijo, Shin ^a   Jin, Tienan ^a   Huo, Zhibao ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; ALKYNE; ALLYL COMPOUND; AZIDE; CARBONIC ACID DERIVATIVE; PALLADIUM; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; COUPLING REACTION; CYCLOADDITION; DRUG SYNTHESIS;

EID: 0037164658     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02206-2     Document Type: Article

References (29)

1. Reviews on 1,2,3-triazoles, see: (a) Dehne, H. In Methoden der Organischen Chemie (Houben-Weyl); Schumann, E., Ed.; Thieme: Stuttgart, 1994; Vol. E8d, pp. 305-405; (b) Wamhoff, H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 5, pp. 669-732; (c) Sheradsky, T. In The Chemistry of the Azido Group; Patai, S., Ed.; Interscience: London, 1971; pp. 377-382; (d) Abu-Orabi, S. T.; Atfah, M. A.; Jibril, I.; Mari'i, F. M.; Ali, A. A.-S. J. Heterocyclic. Chem. 1989, 26, 1461-1468.
2. Reviews on 1,2,3-triazoles, see: (a) Dehne, H. In Methoden der Organischen Chemie (Houben-Weyl); Schumann, E., Ed.; Thieme: Stuttgart, 1994; Vol. E8d, pp. 305-405; (b) Wamhoff, H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 5, pp. 669-732; (c) Sheradsky, T. In The Chemistry of the Azido Group; Patai, S., Ed.; Interscience: London, 1971; pp. 377-382; (d) Abu-Orabi, S. T.; Atfah, M. A.; Jibril, I.; Mari'i, F. M.; Ali, A. A.-S. J. Heterocyclic. Chem. 1989, 26, 1461-1468.
3. Reviews on 1,2,3-triazoles, see: (a) Dehne, H. In Methoden der Organischen Chemie (Houben-Weyl); Schumann, E., Ed.; Thieme: Stuttgart, 1994; Vol. E8d, pp. 305-405; (b) Wamhoff, H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 5, pp. 669-732; (c) Sheradsky, T. In The Chemistry of the Azido Group; Patai, S., Ed.; Interscience: London, 1971; pp. 377-382; (d) Abu-Orabi, S. T.; Atfah, M. A.; Jibril, I.; Mari'i, F. M.; Ali, A. A.-S. J. Heterocyclic. Chem. 1989, 26, 1461-1468.
4. Reviews on 1,2,3-triazoles, see: (a) Dehne, H. In Methoden der Organischen Chemie (Houben-Weyl); Schumann, E., Ed.; Thieme: Stuttgart, 1994; Vol. E8d, pp. 305-405; (b) Wamhoff, H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 5, pp. 669-732; (c) Sheradsky, T. In The Chemistry of the Azido Group; Patai, S., Ed.; Interscience: London, 1971; pp. 377-382; (d) Abu-Orabi, S. T.; Atfah, M. A.; Jibril, I.; Mari'i, F. M.; Ali, A. A.-S. J. Heterocyclic. Chem. 1989, 26, 1461-1468.
5. Buckle D.R., Rockell C.J.M. J. Chem. Soc., Perkin Trans. 1. 1982;627-630.
6. Buckle D.R., Outred D.J., Rockell C.J.M., Smith H., Spicer B.A. J. Med. Chem. 26:1983;251-254.
7. Buckle D.R., Rockell C.J.M., Smith H., Spicer B.A. J. Med. Chem. 29:1986;2262-2267.
8. Alvarez R., Velázquez S., San-Félix A., Aquaro S., Clercq E.D., Perno C.-F., Karlsson A., Balzarini J., Camarasa M.J. J. Med. Chem. 37:1994;4185-4194.
9. Genin M.J., Allwine D.A., Anderson D.J., Barbachyn M.R., Emmert D.E., Garmon S.A., Graber D.R., Grega K.C., Hester J.B., Hutchinson D.K., Morris J., Reischer R.J., Ford C.W., Zurenko G.E., Hamel J.C., Schaadt R.D., Stapert D., Yagi B.H. J. Med. Chem. 43:2000;953-970.
10. Rheingold A.L., Liable-Sands L.M., Trofimenko S. Angew. Chem., Int. Ed. 39:2000;3321-3324.
11. Reviews on 1,3-dipolar cycloadditions, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990; pp. 269-331; (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909; (c) L'abbé, G. Chem. Rev. 1969, 69, 345-363.
12. Reviews on 1,3-dipolar cycloadditions, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990; pp. 269-331; (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909; (c) L'abbé, G. Chem. Rev. 1969, 69, 345-363.
13. Reviews on 1,3-dipolar cycloadditions, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990; pp. 269-331; (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909; (c) L'abbé, G. Chem. Rev. 1969, 69, 345-363.
14. Recent advances on the synthesis of 1,2,3-triazoles, see: (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599; (b) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021; (c) Lewis, G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057; (d) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064; (e) Journet, M.; Cai, D.; Kowal, J. J.; Larsen, R. D. Tetrahedron Lett. 2001, 42, 9117-9118.
15. Recent advances on the synthesis of 1,2,3-triazoles, see: (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599; (b) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021; (c) Lewis, G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057; (d) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064; (e) Journet, M.; Cai, D.; Kowal, J. J.; Larsen, R. D. Tetrahedron Lett. 2001, 42, 9117-9118.
16. Recent advances on the synthesis of 1,2,3-triazoles, see: (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599; (b) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021; (c) Lewis, G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057; (d) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064; (e) Journet, M.; Cai, D.; Kowal, J. J.; Larsen, R. D. Tetrahedron Lett. 2001, 42, 9117-9118.
17. Recent advances on the synthesis of 1,2,3-triazoles, see: (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599; (b) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021; (c) Lewis, G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057; (d) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064; (e) Journet, M.; Cai, D.; Kowal, J. J.; Larsen, R. D. Tetrahedron Lett. 2001, 42, 9117-9118.
18. Recent advances on the synthesis of 1,2,3-triazoles, see: (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599; (b) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021; (c) Lewis, G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057; (d) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064; (e) Journet, M.; Cai, D.; Kowal, J. J.; Larsen, R. D. Tetrahedron Lett. 2001, 42, 9117-9118.
19. Diz-Barra E., Hoz A.d.l., Loupy A., Sánchez-Migallón A. Heterocycles. 38:1994;1367-1374.
20. Konkel M.J., Vince R. J. Org. Chem. 61:1996;6199-6204.
21. Mashraqui S.H., Kumar S., Mudliar C.D. Bull. Chem. Soc. Jpn. 74:2001;2133-2138.
22. +) 225.0750. Found 225.0749.
23. 5a.
24. Busetto L., Palazzi A. Inorg. Chim. Acta. 13:1975;233-238.
25. Shaw B.L., Shaw G. J. Chem. Soc. (A). 1971;3533-3535.
26. For reactions involving a π-allylpalladium azide complex, see: (a) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453-9454; (b) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 11940-11945 (indole synthesis); (c) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Org. Chem. 2002, 67, 7413-7417 (tetrazole synthesis).
27. For reactions involving a π-allylpalladium azide complex, see: (a) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453-9454; (b) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 11940-11945 (indole synthesis); (c) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Org. Chem. 2002, 67, 7413-7417 (tetrazole synthesis).
28. For reactions involving a π-allylpalladium azide complex, see: (a) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453-9454; (b) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 11940-11945 (indole synthesis); (c) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Org. Chem. 2002, 67, 7413-7417 (tetrazole synthesis).
29. Tatsuno Y., Yoshida T., Otsuka S. Inorg. Synth. 19:1979;221-223.