Pyrazole formation: Examination of kinetics, substituent effects, and mechanistic pathways

International Journal of Chemical Kinetics

Volumn 40, Issue 7, 2008, Pages 370-383

  Sloop, Joseph C ^a   Lechner, Brent ^a   Washington, Gary ^a   Bumgardner, Carl L ^b   Loehle, W David ^a   Creasy, William ^c  

^a UNITED STATES MILITARY ACADEMY   (United States)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

^c SCIENCE APPLICATIONS INTERNATIONAL CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLHYDRAZINES; DIKETONES; MECHANISTIC PATHWAYS; PYRAZOLE; SUBSTITUENT EFFECTS;

CONDENSATION REACTIONS; KETONES; KINETICS; MICROFLUIDICS; PH; REACTION KINETICS;

PH EFFECTS;

EID: 45749090163     PISSN: 05388066     EISSN: 10974601     Source Type: Journal    
DOI: 10.1002/kin.20316     Document Type: Article

References (30)

1. Genin, M.; Biles, C.; Keiser, B. J.; Poppe, S. M.; Swaney, S. M.; Tarpley, G.; Yagi, T.; Romero, D. L. J Med Chem 2000, 43, 1034.
2. Guzman-Perez, A.; Wester, R. T.; Allen, M. C.; Brown, J. A.; Buchholz, A. R.; Cook, E. R.; Day, W. W.; Hamanaka, E. S.; Kennedy, S. P.; Knight, D. R.; Kowalczyk, P. J.; Marala, R. B.; Mularski, C. J.; Novomisle, W. A.; Ruggeri, R. B.; Tracey, W. R.; Hill, R. J. Bioorg Med Chem Lett 2001, 11(6), 803.
3. Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. E; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J Med Chem 1997, 40, 1347.
4. Ware, G. W.; Whitcare, D. M. Introduction to insecticides. In: The Pesticide Book, 6th ed.; MeisterPro Information Resources: Willoughby, OH, 2004; p. 10.
5. Stiefel, J. Unpublished research, United States Military Academy, 1993.
6. Sloop, J. C.; Bumgardner, C. L. J Fluorine Chem 1992, 56, 141.
7. Sloop, J. C.; Bumgardner, C. L.; Loehle, W. D. J Fluorine Chem 2002, 118, 135.
8. Ishikawa, N. Bull Chem Soc Jpn 1981, 59, 3221.
9. Linderman, R. J.; Kirollos, K. Tetrahedron Lett 1989, 30(16), 2049.
10. Norris, T.; Colon-Cruz, R.; Ripin, D. H. Org Biomol Chem 2005, 3, 1844.
11. Singh, S. P.; Kumar, D.; Batra, H.; Naithani, R.; Rozas, I.; Elguero, J. Can J Chem 2000, 78, 1109.
12. Katrizky, A. R.; Barczynski, P.; Ostercamp, D. L. J Chem Soc, Perkin Trans II 1987, 969.
13. Fernández, F.; Caamaño, O.; García, M. D.; Alkorta, I.; Elguero, I. Tetrahedron 2006, 62, 3362.
14. Singh, S. P.; Kumar, V.; Aggarwal, R.; Elguero, J. J Heterocyclic Chem 2006, 43, 1003.
15. Zefirov, N. S.; Kozhushkov, S. I.; Kuznetsova, T. S.; Ershov, B. A.; Selivanov, S. I. Tetrahedron 1986, 42, 709-713.
16. Alberola, A.; Calvo, L.; Gonzalez Ortega, A.; Sadaba, M. L.; Sanudo, M. C.; Garcia Granda, S.; Garcia Rodriguez, E. Heterocycles 1999, 51, 2675-2686.
17. Reid, J. C.; Calvin, M. J Am Chem Soc 1950, 72, 2948.
18. von Auwers, K.; Schmidt, W. Chem Ber 1925, 58, 528.
19. Moscovici, R.; Ferraz, J. P.; Neves, E. A.; Tognoli, M. I.; do Amaral, L. J Org Chem 1976, 41, 4093.
20. Nemukhin, A. V.; Grigorenko, B. L.; Granovsky, A. A. Moscow Univ Chem Bull 2004, 45(2), 75.
21. Chamberlin, A. C.; Pu, J.; Kelly, C. P.; Thompson, J. D.; Xidos, J. D.; Li, J.; Zhu, T.; Hawkins, G. D.; Chuang, Y.-Y.; Fast, P. L.; Lynch, B. J.; Liotard, D. A.; Rinaldi, D.; Gao, J.; Cramer, C. J.; Truhlar, D. G. University of Minnesota, 2005.
22. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J Comput Chem 1993, 14, 1347.
23. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987; Vol. 150, pp. 702-709.
24. McMurry, J. Organic Chemistry, 6th ed; Brooks-Cole: Pacific Grove, CA; 2004; p. 698.
25. Jencks, W. P. J Am Chem Soc 1959, 81, 475.
26. Sayer, J. M.; Edman, C. J Am Chem Soc 1979, 101, 3010.
27. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 3rd ed; Wiley-VCH: Weinheim, Germany, 2003; Vol. 107, pp. 329, 375.
28. Sloop,J. C.; Bumgardner, C. L.; Washington, G.; Loehle, W. D.; Sankar, S. S.; Lewis, A. B. J Fluorine Chem 2006, 127, 780.
29. Ebraheem, K. A. K. Monatsh Chem 1991, 122, 157.
30. Elguero, J.; Yranzo, G. I. J Chem Res, Synop 1990, 120.