One-pot three-component synthesis, structure and redox properties of ferrocenyl isoxazoles

Journal of Organometallic Chemistry

Volumn 694, Issue 6, 2009, Pages 942-949

  Willy, Benjamin ^a   Frank, Walter ^a   Rominger, Frank ^b   Müller, Thomas J J ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkynes; Cross couplings; Cycloaddition; Ferrocene; Isoxazole

Indexed keywords

CHLORINE COMPOUNDS; COUPLINGS; CYANIDES; ELECTRONIC STRUCTURE; IRON COMPOUNDS; NITROGEN OXIDES; REDOX REACTIONS;

ACID CHLORIDES; ALKYNES; CROSS-COUPLINGS; ELECTRONIC NATURES; FERROCENE; FERROCENYL; GOOD YIELDS; IN-SITU; ISOXAZOLE; ISOXAZOLES; NITRILE OXIDES; ONE POTS; REDOX ACTIVES; REDOX POTENTIALS; REDOX PROPERTIES; TERMINAL ALKYNES; THREE COMPONENTS; X-RAY STRUCTURE ANALYSIS;

ACETYLENE;

EID: 60749128311     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.10.050     Document Type: Article

References (49)

1. For a review, see e.g.: L. Carlsen, D. Döpp, H. Döpp, F. Duus, H. Hartmann, S. Lang-Fugmann, B. Schulze, R.K. Smalley, B.J. Wakefield, in: E. Schaumann (Ed.), Houben-Weyl, Methods in Organic Chemistry, vol. E8a, Georg Thieme Verlag, Stuttgart, Germany, 1992, p. 45.
2. Rowley M., Broughton H.B., Collins I., Baker R., Emms F., Marwood R., Patel S., and Ragan C.I. J. Med. Chem. 39 (1996) 1943
3. Frolund B., Jorgensen A.T., Tagmose L., Stensbol T.B., Vestergaard H.T., Engblom C., Kristiansen U., Sanchez C., Krogsgaard-Larsen P., and Liljefors T. J. Med. Chem. 45 (2002) 2454
4. Daidone G., Raffa D., Maggio B., Plescia F., Cutuli V.M.C., Mangano N.G., and Caruso A. Arch. Pharm. Pharm. Med. Chem. 332 (1999) 50
5. Talley J.J. Prog. Med. Chem. 13 (1999) 201
6. Talley J.J., Brown D.L., Carter J.S., Graneto M.J., Koboldt C.M., Masferrer J.L., Perkins W.E., Rogers R.S., Shaffer A.F., Zhang Y.Y., Zweifel B.S., and Seibert K. J. Med. Chem. 43 (2000) 775
7. Giovannoni M.P., Vergelli C., Ghelardini C., Galeotti N., Bartolini A., and Kal Piaz V. J. Med. Chem. 46 (2003) 1055
8. Li W.-T., Hwang D.-R., Chen C.-P., Shen C.-W., Huang C.-L., Chen T.-W., Lin C.-H., Chang Y.-L., Chang Y.-Y., Lo Y.-K., Tseng H.-Y., Lin C.-C., Song J.-S., Chen H.-C., Chen S.-J., Wu S.-H., and Chen C.-T. J. Med. Chem. 46 (2003) 1706
9. For a recent review, see e.g.:. Wakefield B.J. In: Shaumann E. (Ed). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, vol. 11 (2001), Georg Thieme Verlag, Stuttgart 229
10. Bandiera T., Grünanger P., and Albini F.M. J. Heterocycl. Chem. 29 (1992) 1423
11. Cuadrado P., Gonzalez-Nogal A.M., and Valero R. Tetrahedron 58 (2002) 4975
12. Vicentini C.B., Verones A.C., Poli T., Guarneri M., Giori P., and Ferretti V. J. Hetercycl. Chem. 27 (1990) 1481
13. Denmark S.E., and Kallemeyn J.M. J. Org. Chem. 70 (2005) 2839
14. Jaeger V., and Colinas P. In: Padwa A., and Pearson W.H. (Eds). Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products Chemistry of Heterocyclic Compounds, vol. 59 (2002), Wiley, Hoboken 361
15. de Champdoré M., Di Fabio G., Messere A., Montesarchio D., Piccialli G., Loddo R., La Colla M., and La Colla P. Tetrahedron 60 (2004) 6555
16. Harding M.M., and Mokdsi G. Curr. Med. Chem. 7 (2000) 1289
17. Dombrowski K.E., Baldwin W., and Sheats J.E. J. Organomet. Chem. 302 (1986) 281
18. For a recent review on bioorganic chemistry of ferrocene, see e.g.:. van Staveren D.R., and Metzler-Nolte N. Chem. Rev. 104 (2004) 5931
19. For a recent reviews on multi-component synthesis of heterocycles by transition-metal catalysis, see e.g.:. D'Souza D.M., and Müller T.J.J. Chem. Soc. Rev. 36 (2007) 1095
20. Müller T.J.J. Chim. Oggi/Chem. Today 25 (2007) 70
21. Müller T.J.J. Targets Heterocycl. Syst. 10 (2006) 54
22. Willy B., and Müller T.J.J. ARKIVOC Part I (2008) 195
23. Willy B., Rominger F., and Müller T.J.J. Synthesis (2008) 293
24. Rotaru A.V., Druta I.D., Oeser T., and Müller T.J.J. Helv. Chim. Acta 88 (2005) 1798
25. For lead reviews on Sonogashira couplings, see e.g.:. Takahashi S., Kuroyama Y., Sonogashira K., and Hagihara N. Synthesis (1980) 627
26. Sonogashira K. In: Diederich F., and Stang P.J. (Eds). Metal Catalyzed Cross-coupling Reactions (1998), Wiley-VCH, Weinheim 203
27. Sonogashira K. J. Organomet. Chem. 653 (2002) 46
28. Negishi E.-I., and Anastasia L. Chem. Rev. 103 (2003) 1979
29. Marsden J.A., and Haley M.M. In: de Meijere A., and Diederich F. (Eds). Metal Catalyzed Cross-coupling Reactions (2004), Wiley-VCH, Weinheim 319
30. Doucet H., and Hierso J.-C. Angew. Chem., Int. Ed. 46 (2007) 834
31. Yin L., and Liebscher J. Chem. Rev. 107 (2007) 133
32. Toda Y., Sonogashira K., and Hagihara N. Synthesis (1977) 777
33. Karpov A.S., and Müller T.J.J. Org. Lett. 5 (2003) 3451
34. Karpov A.S., and Müller T.J.J. Synthesis (2003) 2815
35. A.S. Karpov, E. Merkul, F. Rominger, T.J.J. Müller, Angew. Chem. 117 (2005) 7112; Angew. Chem., Int. Ed. 44 (2005) 6951.
36. Karpov A.S., Merkul E., Rominger F., and Müller T.J.J. Eur. J. Org. Chem. (2006) 2991
37. Merkul E., and Müller T.J.J. Chem. Commun. (2006) 4817
38. D'Souza D.M., and Müller T.J.J. Nat. Protoc. 3 (2008) 1660
39. Liu K.-C., Shelton B.R., and Howe R.K. J. Org. Chem. 45 (1980) 3916
40. Shaw K.N.F., McMillan A., Gudmundson A.G., and Armstrong M.D. J. Org. Chem. 23 (1958) 1171
41. Reeves P.C. Org. Syn. Coll. vol. 6 (1988) 625
42. Regitz M., and Menz F. Chem. Commun. 101 (1968) 2622
43. Graham P.J., Lindsay P.V., Parshall G.W., Peterson M.L., and Whitman G.M. J. Am. Chem. Soc. 79 (1957) 3416
44. Polin J., and Schottenberger H. Org. Syn. Coll. vol. 9 (1998) 411
45. For important reviews on 1,3-dipolar cycloadditions, see e.g.:. Huisgen R. Angew. Chem., Int. Ed. 2 (1963) 565
46. Padwa A. 1,3-Dipolar Cycloaddition Chemistry (1984), John Wiley & Sons, New York
47. Pina F., Bernardo M.A., and Garcia-Espana E. Eur. J. Inorg. Chem. 10 (2000) 2143
48. Zoltewicz J.A., and Deady L.W. Adv. Heterocycl. Chem. 22 (1978) 71
49. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A. D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M. W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, gaussian 03, Revision B.03 ed., Gaussian, Inc., Wallingford, CT, 2004.