Recyclable supported catalysts in microwave-assisted reactions: first Diels-Alder cycloaddition of a triazole ring

Tetrahedron Letters

Volumn 47, Issue 49, 2006, Pages 8761-8764

  Díaz Ortiz, Ángel ^a   de Cózar, Abel ^a   Prieto, Pilar ^a   de la Hoz, Antonio ^a   Moreno, Andrés ^a  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALKADIENE; LEWIS ACID; NITRILE; PYRAZOLE DERIVATIVE; TRIAZOLE;

ARTICLE; CATALYST SUPPORT; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; MICROWAVE IRRADIATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

BETULACEAE;

EID: 33750447664     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.006     Document Type: Article

References (33)

1. Carruthers W. Cycloaddition Reactions in Organic Synthesis (1990), Pergamon Press, Oxford, UK
2. Gottardt H., and Reiter F. Chem. Ber. 112 (1979) 1206
3. Hunnur R.K., Latthe P.R., and Badami B.V. J. Chem. Res. (2005) 592
4. See, for example:. Grigg R., Hayes R., and Jackson J.L. J. Chem. Soc., Chem. Commun. (1969) 1167
5. Potts K.T., and Marshall J. J. Chem. Soc., Chem. Commun. (1972) 1000
6. Cook M.J., and Forbes E.J. Tetrahedron 24 (1968) 4501
7. Mavoungon-Gomès L., Bruneton J., and Aicart M. J. Heterocycl. Chem. 22 (1985) 1233
8. Noland W.E., and Lee C.K. J. Org. Chem. 45 (1980) 4573
9. Corral C., Lissavetzky J., and Manzanares I. Synthesis (1997) 29
10. Loupy A., Maurel F., and Sabatié-Gogová A. Tetrahedron 60 (2004) 1683
11. Mack A., Bergsträßer U., Reiß G.J., and Regitz M. Eur. J. Org. Chem. (1999) 587
12. Kaval N., Van der Eycken J., Caroen J., Kappe C.O., Dehaen W., Strohmeier G.A., and Van der Eycken E. J. Comb. Chem. 5 (2003) 560
13. Kaval N., Ermolat'es D., Appukkuttan P., Dehaen W., Kappe C.O., and Van der Eycken E. J. Comb. Chem. 7 (2005) 490
14. Ölgen S., and Chung K.C. Z. Naturforsch., B: Chem. Sci. 56 (2001) 804
15. Genin M.J., Alwine D.A., Anderson D.J., Barbachyn M.R., Emmert D.E., Garmon S.A., Graber D.R., Grega K.C., Hester J.B., Hutchison D.K., Morris J., Reischer R.J., Ford C.W., Zurenko G.E., Hamel J.C., Schaadt R.D., Staper D., and Yagi B.H. J. Med. Chem. 43 (2000) 953
16. Brockunier L.L., Parmee E.R., Ok H.O., Candelore M.R., Cascieri M.A., Colwell L.F., Deng L., Feeney W.P., Forrest M.J., Hom G.J., MacIntyre D.E., Tota L., Wyvratt M.J., Fisher M.H., and Weber A.E. Bioorg. Med. Chem. Lett. 10 (2000) 2111
17. Huisgen R. Proc. Chem. Soc. (1961) 357
18. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem. 114 (2002) 2708
19. Amantini D., Fringuelli F., Piermatti O., Pizzo F., Zunino E., and Vaccaro L. J. Org. Chem. 70 (2005) 6526
20. McKillop A., and Young K.W. Synthesis (1979) 401 and 481
21. Laszlo P. Preparative Chemistry using Supported Reagents (1987), Academic Press, San Diego, USA
22. Smith K. Solid Supports and Catalyst in Organic Synthesis (1992), Ellis Horwood, Chichester
23. Clark J.H., and Rhodes C.N. Clean Synthesis using Porous Inorganic Solid Acid Catalysts and Supported Reagents (2000), RSC Clean Technology Monographs, Cambrigde, UK
24. See, for example:. Díaz-Ortiz A., Díez-Barra E., de la Hoz A., Prieto P., Moreno A., Langa F., Prangé T., and Neuman A. J. Org. Chem. 60 (1995) 4160
25. Díaz-Ortiz A., Langa F., de la Hoz A., and Moreno A. Eur. J. Org. Chem. 4 (2000) 3659
26. De la Hoz A., Díaz-Ortiz A., and Langa F. In: Loupy A. (Ed). Microwaves in Organic Synthesis (2002), Wiley-VCH, Weinheim, Germany 295-344
27. Aluminium chloride functionalized silica gel (particle size 70-120 mesh, extent of labeling: 1.5 mmol/g) was supplied by Sigma-Aldrich Co.
28. +: calcd: 316.1423. Found: 316.1429.
29. 3 was recovered by filtration and drying at 80 °C under reduced pressure for 2 h. The use of this recycled catalyst for five consecutive experiments in the cycloaddition of 1f with DMAD afforded 3c in 89%, 89%, 88%, 88% and 89% yield, respectively.
30. Boger D.L., and Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis (1987), Academic Press, London, UK
31. Tietze L.F., and Kettschau G. Hetero Diels-Alder Reactions in Organic Chemistry. Topics in Current Chemistry 190 (1998) 1-121
32. +: calcd 211.0593. Found: 211.0601.
33. Elguero J., de la Hoz A., and Pardo C. J. Chem. Soc., Perkin Trans 2 (1985) 427