A facile one-pot three-component synthesis of ferrocene-grafted dispiro pyrrolidine/pyrrolizidine scaffolds through intermolecular [3+2] cycloaddition reaction of ferrocenyl Baylis-Hillman adduct

Tetrahedron Letters

Volumn 50, Issue 45, 2009, Pages 6116-6120

  Kathiravan, Subban ^a   Raghunathan, Raghavachary ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

Baylis Hillman adduct; Cycloaddition; Dispiropyrrolidine pyrrolizidines; Ferrocene; Spiroheterocycles

Indexed keywords

AMINO ACID; AZOMETHINE YLIDE; DIKETONE; DSPIROPYRROLIDINE; FERROCENE DERIVATIVE; FERROCENECARBALDEHYDE; METHYL 2 (2,3 DIHYDRO 2 HYDROXY 1H FERROCENE 2 YL) ACRYLATE; PYRROLIDINE DERIVATIVE; PYRROLIZIDINE DERIVATIVE; SCAFFOLD PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CYCLOADDITION; DRUG SYNTHESIS; ONE POT SYNTHESIS; SPECTROSCOPY; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 70349197606     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.08.047     Document Type: Article

References (53)

1. Domling A., and Ugi I. Angew. Chem. 112 (2000) 3300-3344
2. Angew. Chem., Int. Ed. 39 (2000) 3168-3210
3. López C., Pérez S., Solans X., Font-Bardía M., Roig A., Molins E., Van Leeuwen P.W.N.M., and Van Strijdonck G.P.F. Organometallics 26 (2007) 571-576
4. Pérez S., López C., Caubet A., Solans X., Font-Bardía M., Roig A., and Molins E. Organometallics 25 (2006) 596-601
5. Moyano A., Rosol M., Moreno R.M., López C., and Maestro M.A. Angew. Chem., Int. Ed. 44 (2005) 1865-1869
6. Gómez Arrayas R., Adrio J., and Carretero J.C. Angew. Chem., Int. Ed. 45 (2006) 7674-7715
7. Anderson C.E., Donde Y., Yariv D., Christopher J., and Overman L.E. J. Org. Chem. 70 (2005) 648-657
8. Kelly P.N., Prêtre A., Devoy S., O'Rielly I., Devery R., Goel A., Gallagher J.F., Lough A.J., and Kenny P.T.M. J. Organomet. Chem. 692 (2007) 1327-1331
9. Lehn J.M. Angew. Chem., Int. Ed. 29 (1990) 1304-1319
10. Beer P.D., Dickson C.A.P., Fletcher N., Goulden A.J., Grieve A., Hodacora J., and Wear T. Chem. Commun. 10 (1993) 828-830
11. Miller J.S., and Epstein A.J. Angew. Chem., Int. Ed. 33 (1994) 385-415
12. Hanzlik R.P., Soine P., and Soine W.N. J. Med. Chem. 22 (1979) 424-428
13. Osella D., Nervi C., Galeotti F., Cavigiolio G., Vessieres A., and Jaouen G. Helv. Chim. Acta 84 (2001) 3289-3298
14. Inouye M., and Takase M. Angew. Chem., Int. Ed. 40 (2001) 1746-1748
15. Yu C.J., Wan Y.J., Yowonto H., Li J., Tao C.L., James M.D., Tan C.L., Blackburn G.F., and Maede T.J. J. Am. Chem. Soc. 123 (2001) 1111-1122
16. Ihara T., Nakayama M., Murata M., Nakano K., and Maeda M. Chem. Commun. (1997) 1609-1610
17. Biot C., Delhaes L., Maciejewaski L.A., Mortuaire M., Camus D., Dive D., and Brocard J.S. Eur. J. Med. Chem. 35 (2000) 707-714
18. Biot C., Glorian G., Maciejewaski L.A., and Brocard J.S. J. Med. Chem. 40 (1997) 3715-3718
19. Biot C., Delhaes L., N'Diaye M., Maciejewaski L.A., Camus D., Dive D., and Brocard J.S. Bioorg. Med. Chem. 7 (1999) 2843-2847
20. Cottineau B., Toto P., Marot C., Pipaud A., and Chenault J. Bioorg. Med. Chem. Lett. 12 (2002) 2105-2108
21. Yu H., Shao L., and Fang J. J. Organomet. Chem. 692 (2007) 987-993
22. Zora M., and Görmen M. J. Organomet. Chem. 692 (2007) 5026-5032
23. In: Monlineux R.J., and Pelletier S.W. (Eds). Alkaloids Chemical and Biological Perspectives (1987), Wiley, New York Chapter 1
24. Fujimori, S. Jap. Pat. Appl. 88-2912; Chem. Abstr., 1990, 112, 98409.
25. Basavaiah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811-891
26. Derewes S.E., and Roos G.H.P. Tetrahedron 44 (1988) 4653-5670
27. Lee K.Y., Gowrisankar S., and Kim J.N. Bull. Korean Chem. Soc. 26 (2005) 1481-1490
28. Pereira S.I., Adrio J., Silva A.M.S., and Carretero J.C. J. Org. Chem. 70 (2005) 10175-10177
29. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry Vols. 1 and 2 (1984), Wiley, New York
30. Tsuge O., and Kanemasa S. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry Vol. 45 (1989), Academic, San Diego 231-252
31. In: Grigg R., Sridharan V., and Curran D.P. (Eds). Advances in Cycloaddition Vol. 3 (1993), Jai, London 161-180
32. Nyerges M., Feges I., and Toke L. Tetrahedron Lett. 41 (2000) 7951-7954
33. Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., and Suganthan S. Tetrahedron Lett. 41 (2000) 967-970
34. Grigg R., Thornton-Pett M., and Yoganathan G. Tetrahedron 55 (1999) 1763-1780
35. Grigg R., Thornton-Pett M., Xu J., and Xu L.-H. Tetrahedron 55 (1999) 13841-13866
36. Pearson W.H., and Clark R.B. Tetrahedron Lett. 38 (1997) 7669-7672
37. Pearson W.H., and Mi Y. Tetrahedron Lett. 38 (1997) 5441-5444
38. Waldmann H., Blaser E., Jansen M., and Letschert H.-P. Angew. Chem., Int. Ed. 33 (1994) 683 and references cited therein
39. Sebahar P.R., and Williams R.M. J. Am. Chem. Soc. 122 (2000) 5666-5667
40. Pandey G., Banerjee P., and Gadre S.R. Chem. Rev. 106 (2006) 4484-4517
41. Coldham I., and Hufton R. Chem. Rev. 105 (2005) 2765-2809
42. Jayashankaran J., Durga R., Manian R.S., and Raghunathan R. Synthesis (2006) 1028-1034
43. Nair V., and Suja T.D. Tetrahedron 63 (2007) 12247-12275
44. Suresh Babu A.R., Raghunathan R., and Baskaran S. Tetrahedron 65 (2009) 2239-2243
45. Suresh Babu A.R., and Raghunathan R. Tetrahedron Lett. 49 (2008) 4487-4490
46. Ramesh E., and Raghunathan R. Tetrahedron Lett. 48 (2007) 6809-6813
47. Jayashankaran J., Rathna Durga R.S.M., and Raghunathan R. Tetrahedron Lett. 45 (2004) 7303-7305
48. Kathiravan S., and Raghunathan R. Synlett (2009) 1167-1170
49. Ramesh E., Kathiresan M., and Raghunathan R. Tetrahedron Lett. 48 (2007) 1835-1839
50. Jayashankaran J., Rathna Durga R.S.M., Sivaguru M., and Raghunathan R. Tetrahedron Lett. 47 (2006) 5535-5538
51. Theboral Sugi Kamala E., Nirmala S., Sudha L., Kathiravan S., and Raghunathan R. Acta Crystallogr. Sect. E 65 (2009) m531-m532
52. 5Fe: C, 64.06; H, 5.13; N, 2.87. Found: C, 64.20; H, 5.24; N, 3.00.
53. Theboral Sugi Kamala E., Nirmala S., Sudha L., Kathiravan S., and Raghunathan R. Acta Crystallogr. Sect. E 65 (2009) 687-688