Synthesis of ferrocenyl and ruthenocenyl thioamide derivatives using a single-step three-component reaction

Organometallics

Volumn 32, Issue 20, 2013, Pages 6098-6105

  Patra, Malay ^a   Hess, Jeannine ^a   Konatschnig, Sandro ^a   Spingler, Bernhard ^a   Gasser, Gilles ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EFFICIENT SYNTHESIS; ELEMENTAL SULFUR; FERROCENES; FERROCENYL; ORGANIC AMINE; SINGLE-STEP; THREE COMPONENT REACTIONS; THREE-COMPONENT;

CONDENSATION REACTIONS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

ORGANOMETALLICS;

EID: 84887116242     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om400715m     Document Type: Article

References (56)

1. Mehanna, A. S.; Belani, J. D.; Kelley, C. J.; Pallansch, L. A. Med. Chem. 2007, 3, 513-519
2. Yu, K.-L.; Torri, A. F.; Luo, G.; Cianci, C.; Grant-Young, K.; Danetz, S.; Tiley, L.; Krystal, M.; Meanwell, N. A. Bioorg. Med. Chem. Lett. 2002, 12, 3379-3382
3. Lo, W.-S.; Hu, W.-P.; Lo, H.-P.; Chen, C.-Y.; Kao, C.-L.; Vandavasi, J. K.; Wang, J.-J. Org. Lett. 2010, 12, 5570-5572
4. Goossen, L. J.; Blanchot, M.; Salih, K. S. M.; Karch, R.; Rivas-Nass, A. Org. Lett. 2008, 10, 4497-4499
5. Hu, W.-P.; Chen, Y.-K.; Liao, C.-C.; Yu, H.-S.; Tsai, Y.-M.; Huang, S.-M.; Tsai, F.-Y.; Shen, H.-C.; Chang, L.-S.; Wang, J.-J. Bioorg. Med. Chem. 2010, 18, 6197-6207
6. Shi, D.-F.; Bradshaw, T. D.; Wrigley, S.; McCall, C. J.; Lelieveld, P.; Fichtner, I.; Stevens, M. F. G. J. Med. Chem. 1996, 39, 3375-3384
7. Stevens, M. F. G.; McCall, C. J.; Lelieveld, P.; Alexander, P.; Richter, J. A.; Davies, D. E. J. Med. Chem. 1994, 37, 1689-1695
8. Batjargal, S.; Wang, Y. J.; Goldberg, J. M.; Wissner, R. F.; Petersson, E. J. J. Am. Chem. Soc. 2012, 124, 9172-9182
9. Goldberg, J. M.; Batjargal, S.; Petersson, E. J. J. Am. Chem. Soc. 2010, 132, 14718-14720
10. Goldberg, J. M.; Wissner, R. F.; Klein, A. M.; Petersson, E. J. Chem. Commun. 2012, 48, 1550-1552
11. Chae, M. Y.; Czarnik, A. W. J. Am. Chem. Soc. 1992, 114, 9704-9705
12. Hwang, J.; Choi, M. G.; Eor, S.; Chang, S.-K. Inorg. Chem. 2012, 51, 1634-1639
13. Nolan, E. M.; Lippard, S. J. Chem. Rev. 2008, 108, 3443-3480
14. Kealy, T. J.; Pauson, P. L. Nature 1951, 168, 1039-1040
15. Štěpnička, P. Ferrocenes: Ligands, Materials and Biomolecules; Wiley-VCH: Chichester, U.K., 2008.
16. Štěpnička, P. Ferrocenes: Ligands, Materials and Biomolecules; Wiley-VCH: Chichester, U.K., 2008; Part 1, Ferrocene Ligands.
17. Deschenaux, R. In Ferrocenes: Ligands, Materials and Biomolecules; Štěpnička, P., Ed.; Wiley-VCH: Chichester, U.K., 2008; pp 447-463.
18. Long, N. J.; Kowalski, K. In Ferrocenes: Ligands, Materials and Biomolecules; Štěpnička, P., Ed.; Wiley-VCH: Chichester, U.K., 2008; pp 393-446.
19. Heck, J.; Dede, M. In Ferrocenes: Ligands, Materials and Biomolecules; Štěpnička, P., Ed.; Wiley-VCH: Chichester, U.K., 2008; pp 319-392.
20. Tucker, J. H. R.; Collinson, S. R. Chem. Soc. Rev. 2002, 31, 147-156 and references therein
21. Tucker, J. H. R. In Encyclopaedia of Supramolecular Chemistry; Atwood, J. L.; Steed, J. W., Eds.; Marcel Dekker: New York, 2004; pp 505-519.
22. van Staveren, D. R.; Metzler-Nolte, N. Chem. Rev. 2004, 104, 5931-5985
23. Patra, M.; Gasser, G.; Metzler-Nolte, N. Dalton Trans. 2012, 41, 6350-6358
24. Gasser, G.; Ott, I.; Metzler-Nolte, N. J. Med. Chem. 2011, 54, 3-25
25. Biot, C.; Dive, D. In Medicinal Organometallic Chemistry; Jaouen, G.; Metzler-Nolte, N., Eds.; Springer: Heidelberg, Germany, 2010; Topics in Organometallic Chemistry 32, pp 155-193.
26. Biot, C.; Castro, W.; Botte, C. Y.; Navarro, M. Dalton Trans. 2012, 41, 6321-6580
27. Jaouen, G. Bioorganometallics: Biomolecules, Labelling, Medicine; Wiley-VCH: Weinheim, Germany, 2006.
28. Gasser, G.; Metzler-Nolte, N. Curr. Opin. Chem. Biol. 2012, 16, 84-91
29. Hartinger, C. G.; Dyson, P. J. Chem. Soc. Rev. 2009, 38, 391-401
30. Patra, M.; Gasser, G. ChemBioChem 2012, 13, 1232-1252
31. Nonoyama, M.; Hamamura, K. J. Organomet. Chem. 1991, 407, 271-277
32. Hauck, T.; Sünkel, K.; Beck, W. Z. Anorg. Allg. Chem. 2006, 632, 2305-2309
33. Jautze, S.; Seiler, P.; Peters, R. Angew. Chem., Int. Ed. 2007, 46, 1260-1264
34. Jautze, S.; Seiler, P.; Peters, R. Chem. Eur. J. 2008, 14, 1430-1444
35. Beer, P. D.; Graydon, A. R.; Johnson, A. O. M.; Smith, D. K. Inorg. Chem. 1997, 36, 2112-2118
36. Hall, C. D.; Danks, I. P.; Sharpe, N. W. J. Organomet. Chem. 1990, 390, 227-235
37. Sandoval-Chávez, C.; López-Cortés, J. G.; Gutiérrez-Hernández, A. I.; Ortega-Alfaro, M. C.; Toscano, A.; Alvarez-Toledano, C. J. Organomet. Chem. 2009, 694, 3692-3700
38. Kato, S.; Wakamatsu, M.; Mizuta, M. J. Organomet. Chem. 1974, 78, 405-414
39. Kato, S.; Fukushima, T.; Ishihara, H.; Murai, T. Bull. Chem. Soc. Jpn. 1990, 63, 638-639
40. DeHope, A.; Mendoza-Espinosa, D.; Donnadieu, B.; Bertrand, G. New J. Chem. 2011, 35, 2037-2042
41. Hamamura, K.; Kita, M.; Nonoyama, M.; Fujita, J. J. Organomet. Chem. 1993, 463, 169-177
42. Plazuk, D.; Zakrzewski, J.; Rybarczyk-Pirek, A.; Domagała, S. J. Organomet. Chem. 2005, 690, 4302-4308
43. McMillan, F. H. J. Am. Chem. Soc. 1948, 70, 868-869
44. Nguyen, T. B.; Ermolenko, L.; Al-Mourabit, A. Org. Lett. 2012, 14, 4274-4277
45. Beer, P. D.; Smith, D. K. J. Chem. Soc., Dalton Trans. 1998, 417-424
46. Maity, S. K.; Pradhan, N. C.; Patwardhan, A. V. Ind. Eng. Chem. Res. 2006, 45, 7767-7774
47. Ratcliffe, C. T.; Pap, G. J. Chem. Soc., Chem. Commun. 1980, 260-261
48. Leonidova, A.; Joshi, T.; Nipkow, D.; Frei, A.; Penner, J.-E.; Konatschnig, S.; Patra, M.; Gasser, G. Organometallics 2013, 32, 2037-2040
49. Dubar, F.; Egan, T. J.; Pradines, B.; Kuter, D.; Ncokazi, K. K.; Forge, D.; Paul, J.-F.; Pierrot, C.; Kalamou, H.; Khalife, J.; Buisine, E.; Rogier, C.; Vezin, H.; Forfar, I.; Slomianny, C.; Trivelli, X.; Kapishnikov, S.; Leiserowitz, L.; Dive, D.; Biot, C. ACS Chem. Biol. 2012, 6, 275-287
50. Beagley, P.; Blackie, M. A. L.; Chibale, K.; Clarkson, C.; Moss, J. R.; Smith, P. J. Dalton Trans. 2002, 4426-4433
51. Glidewell, C.; Royles, B. J. L.; Smith, D. M. J. Organomet. Chem. 1997, 527, 259-261
52. Chantson, J. T.; Falzacappa, M. V. V; Crovella, S.; Metzler-Nolte, N. ChemMedChem 2006, 1268-1274
53. Pro, 171.32 ed.; Oxford Diffraction Ltd., Oxford, U.K., 2007.
54. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119
55. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
56. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13