Tautomerism-dependent ring construction of N-heterocyclic compounds from the reactions of 1-alkynyl fischer carbene complexes and substituted pyrazolinones

Journal of Organic Chemistry

Volumn 71, Issue 26, 2006, Pages 9695-9700

  Zheng, Zhaoyan ^a   Yu, Zhengkun ^a,b   Luo, Ning ^a   Han, Xiuwen ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENES; FISCHER AMINOCARBENE COMPLEXES; HETEROCYCLIC COMPOUNDS; ORGANIC CARBONYL PRODUCTS; PYRAZOLINONES;

KETONES; OLEFINS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

2 PYRAZOLIN 5 ONE DERIVATIVE; AMINOCARBENE DERIVATIVE; CARBENOID; HETEROCYCLIC COMPOUND; ORGANIC COMPOUND; PYRAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 33845964713     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061725+     Document Type: Article

References (47)

1. (a) Negishi, E. In Comprehensive Organic Synthesis: Trost, B. M., Ed.; Pergamon: Oxford, U.K., 1991; Vol. 5, p 1163.
2. (b) Corey, E. J.; Cheng, X. The Logic of Chemical Synthesis; Wiley-Interscience: New York, 1989.
3. (a) Frühauf, H.-W. Chem. Rev. 1997, 97, 523.
4. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
5. For selected recent reviews, see: (a) Barluenga, J.; Fernández- Rodríguez, M. A.; Aguilar, E. J. Organomet. Chem. 2005, 690, 539.
6. (b) Barluenga, J.; Santamaria, J.; Tomas. M. Chem. Rev. 2004, 104, 2259.
7. (c) Herndon, J. W. Coord. Chem. Rev. 2003, 243, 3.
8. (d) Sierra, M. A. Chem. Rev. 2000, 100, 3591.
9. (e) Dötz, K. H.; Jäkel, C.; Haase, W. C. J. Organomet. Chem. 2001, 617/618, 119.
10. (f) Barluenga, J.; Floréz, J.; Fañanás, F. J. J. Organomet. Chem. 2001, 624, 5.
11. (g) de Meijere, A.; Schirmer, H.; Duetsch, M. Angew. Chem., Int. Ed. 2000, 39, 3964.
12. (h) Herndon, J. W. Tetrahedron 2000, 56, 1257.
13. (i) Barluenga, J.; Fañanás, F. J. Tetrahedron 2000, 56, 4597.
14. (j) Aumann, R. Eur. J. Org. Chem. 2000, 17.
15. (a) Capriati, V.; Florio, S.; Luisi, R.; Perna, F. M.; Barluenga, J. J. Org. Chem. 2005, 70, 5852.
16. (b) Florio, S.; Perna, F. M.; Luisi, R.; Barluenga, J.; Rodriguez, F.; Fananas, F. J. J. Org. Chem. 2004, 69, 5480.
17. (a) Hegedus, L. S. Tetrahedron 1997, 53, 4105.
18. (b) Hegedus, L. S. Top. Organomet. Chem. 2004, 13, 157.
19. For selected recent references on reactions of Fischer carbene complexes with NH/C=N bond-containing compounds, see: (a) Gu, K. C.; Chen, J. Z.; Zheng, Z. Y.; Wu, S. Z.; Wu, X. W.; Han, X. W.; Yu, Z. K. Polyhedron 2005, 24, 173, and references therein.
20. (b) Chen, J. Z.; Yu, Z. K.; Zheng, Z. Y.; Gu, K. C.; Wu, S. Z.; Zeng, F. L.; Tan, W. Q.; Wu, X. W.; Xiao, W.-J. Organometallics 2005, 24, 302.
21. (c) Llordes, A.; Sierra, M. A.; Lopez-Alberca, M. P.; Molins, E.; Ricart, S. J. Organomet. Chem. 2005, 690, 6096.
22. (d) Barluenga, J.; Suárez-Sobrino, A. L.; Tomás, M.; García-Granda, S.; Santiago-García, R. J. Am. Chem. Soc. 2001, 123, 10494.
23. (e) Barluenga, J.; Tomás, M.; Rubio, E.; López- Pelegrín, J. A.; García-Granda, S.; Priede, M. P. J. Am. Chem. Soc. 1999, 121, 3065.
24. (f) Aumann, R.; Jasper, B.; Fröhlich, R. Organometallics 1995, 14, 2447.
25. For selected leading references on preparation and properties of bimanes, see: (a) Kosower, E. M.; Pazhenchevsky, B.; Hershkowitz, E. J. Am. Chem. Soc. 1978, 100, 6516.
26. (b) Kosower, E. M.; Bernstein, J.; Goldberg, I.; Pazhenchevsky, B.; Goldstein, E. J. Am. Chem. Soc. 1979, 101, 1620.
27. (c) Kosower, E. M.; Pazhenchevsky, B. J. Am. Chem. Soc. 1980, 102, 4983.
28. (d) Kosower, E. M.; Pazhenchevsky, B.; Dodiuk, H.; Kanety, H.; Faust, D. J. Org. Chem. 1981, 46, 1666.
29. (e) Kosower, E. M.; Zbaida, D.; Baud'huin, M.; Marciano, D.; Goldberg, I. J. Am. Chem. Soc. 1990, 112, 7305.
30. (f) Shalev, D. E.; Chiacchiera, S. M.; Radkowsky, A. E.; Kosower, E. M. J. Org. Chem. 1996, 61, 1689.
31. (g) Kosower, E. M.; Ben-Shoshan, M. J. Org. Chem. 1996, 61, 5871.
32. For selected recent references, see: (a) Sosa-Peinado, A.; Gonzalez-Andrade, M. Biochemistry 2005, 44, 15083.
33. (b) Mansoor, S. E.; Farrens, D. L. Biochemistry 2004, 43, 9426.
34. (c) Lee, S.; Rosazza, J. P. N. Org. Lett. 2004, 6, 365.
35. (d) Radkowsky, A. E.; Kosower, E. M. J. Am. Chem. Soc. 1986, 108, 4527.
36. For selected references, see: (a) Camps, F.; Llebaria, A.; Moretó, J. M.; Ricart, S.; Vinas, J. M.; Ros, J.; Yáñez, R. J. Organomet. Chem. 1991, 401, C17.
37. (b) Duetsch, M.; Stein, F.; Lackmann, R.; Pohl, E.; Herbst-Irmer, R.; de Meijere, A. Chem. Ber. 1992, 125, 2051.
38. (c) Aumann, R. Chem. Ber. 1992, 125, 2773.
39. (d) Aumann, R.; Jasper, B. Organometallics 1994, 13, 3502.
40. (a) Barluenga, J.; Andina, F.; Fernández-Rodríguez, M. A.; Garcia-García, P.; Merino, I.; Aguilar, E. J. Org. Chem. 2004, 69, 7352.
41. (b) Zheng, Z. Y.; Chen, J. Z.; Yu, Z. K.; Han, X. W. J. Organomet. Chem. 2006, 691, 3679, and references therein.
42. (a) Perdicchia, D.; Licandro, E.; Maiorana, S.; Vandoni, B.; Baldoli, C. Org. Lett. 2002, 4, 827.
43. (b) Ezquerra, J.; Pedregal, C.; Merino, I.; Flórez, J.; Barluenga, J.; Garcia-Granda, S.; Llorca, M.-A. J. Org. Chem. 1999, 64, 6554.
44. (c) Beddoes, R. L.; Painter, J. E.; Quayle, P. Tetrahedron Lett. 1996, 37, 9385.
45. (a) Shu, H.-G.; Shiu, L.-H.; Wang, S.-H.; Wang, S.-L.; Lee, G.-H.; Peng, S.-M.; Liu, R.-S. J. Am. Chem. Soc. 1996, 118, 530.
46. (b) Barluenga, J.; Ballesteros, A.; de la Rúa, R. B.; Santamaría, J.; Rubio, E.; Tomás, M. J. Am. Chem. Soc. 2003, 125, 1834.
47. Aumann, R.; Fröhlich, R.; Kotila, S. Organometallics 1996, 15, 4842.