Electrocatalytic fast and efficient aldol addition of pyrazoline-5-ones to isatine

Journal of the Electrochemical Society

Volumn 161, Issue 6, 2014, Pages

  Elinson, M N ^a   Merkulova, V M ^a   Ilovaisky, A I ^a   Chizhov, A O ^a   Barba, F ^b   Batanero, B ^b  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CONDENSATION REACTIONS; MEDICAL APPLICATIONS;

ALDOL ADDITION; ALDOL REACTIONS; APROTIC SOLVENTS; BIOMEDICAL APPLICATIONS; CURRENT EFFICIENCY; ELECTROCATALYTIC; ELECTROCATALYTIC SYSTEM; FUNCTIONALIZED;

KETONES;

EID: 84904812712     PISSN: 00134651     EISSN: 19457111     Source Type: Journal    
DOI: 10.1149/2.104406jes     Document Type: Article

References (39)

1. R. Mahrwald, Modern Aldol Reactions, vol. 1 and 2,Wiley-VCH Verlag, Weinheim, 2004.
2. C. H. Heathcock, in: B. M. Trost (Ed.), Comprehensive Organic Synthesis, vol. 2, Pergamon, Oxford, 1991, Ch. 1.5.
3. T. Mukaiyama, Org. React., 28, 203 (1982).
4. K. C. Nicolaou, T. Montagnon, G. Vassilikogiannakis, and C. J. N. Mathison, J. Am. Chem. Soc., 127, 8872 (2005).
5. C. Tsukano, D. R. Siegel, and S. J. Danishefsky, Angew. Chem., 119, 8996 (2007).
6. K. Rohr and R. Mahrwald, Adv. Synth. Catal., 350, 2877 (2008).
7. G. Jones, Org. React., 15, 204 (1967).
8. F. Freeman, Chem. Rev., 80, 329 (1980).
9. L. F. Tietze, Chem. Rev., 96, 115 (1996).
10. L. Henry, Compt. Rend., 120, 1265 (1895).
11. F.A. Luzzio, Tetrahedron, 57, 915 (2001).
12. G. Rosini, in: B. M. Trost (Ed.), ComprehensiveOrganic Synthesis, vol. 2, Pergamon, Oxford, 1991, Ch. 1.10.
13. S. A. M. Metwally, M. I. Younes, and H. H. Abbas, Acta Chim. Hung., 126, 591 (1989).
14. R. H. Wiley and P. Wiley, Pyrazolones, Pyrazolidones and Derivatives, Interscience Publishers, Division of John Wiley and Sons, New York, 1964.
15. J. Elguero, in: A. R. Katritzky, C. W. Rees, and E. F. V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry II, Pergamon-Elsevier Science, Oxford, 1996, vol. 3.
16. R. N. Brogden, Drugs, 32, 60 (1986).
17. F. Lepage andB. Hubiot, Eur. Pat. Appl. EP 459887 (1992) Chem. Abstr., 116:128914.
18. K. L. Kees, J. J. Fitzgerald, K. E. Steiner, J. F. Mattes, B. Mihan, T. Tosi,D.Mondoro, and M. L. McCaleb, J. Med. Chem., 39, 3920 (1996).
19. L. D. Wise, D. E. Butler, H. A. DeWald, D. M. Lustgarten, I. C. Pattison, D. N. Schweiss, L. L. Coughenour, D. A. Downs, T. G. Heffner, and T. A. Pugsley, J. Med. Chem., 30, 1807 (1987).
20. T. van Herk, J. Brussee, A. M. C. H. van den Nieuwendijk, P. A. M. van der Klein, A. P. Jzerman, C. Stannek, A. Burmeister, and A. Lorenzen, J. Med. Chem., 46, 3945 (2003).
21. C. E. Rosiere and M. E. Grossman, Science, 113, 651 (1951).
22. P. Singh, K. Paul, and W. Holzer, Bioorg. Med. Chem., 14, 5061 (2006).
23. R. J. Sundberg, The Chemistry of Indoles, Academic, New York, 1970.
24. F. R. De Śa Alves, C. A. M. Fraga, and E. J. Barreiro, Mini Rev. Med. Chem., 9, 782 (2009).
25. S. N. Pandeya, S. Smitha, M. Jyoti, and S. K. Sridhar, Acta Pharm., 55, 27 (2005).
26. D. Sriram, T. R. Bal, and P. Yogeeswari, J. Pharm. Pharm. Sci., 8, 565 (2005).
27. N. Karali, A. Gursoi, F.Kandemirli, N. Shvets, F. B.Kaynak, S. Ozbey,V.Kovalishyn, and A. Dimoglo, Bioorg. Med. Chem., 15, 5888 (2007).
28. Y. Koguchi, J. Kohno, M. Nishio, K. Takahashi, T. Okuda, T. Ohnuki, and S. Komatsubara, J. Antibiot., 53, 105 (2000).
29. T. Tokunaga,W. E. Hume, T. Umezome,K. Okazaki,Y. Ueki,K.Kumagai, S. Hourai, J. Nagamine, H. Seki, M. Taiji, H. Noguchi, and R. Nagata, J. Med. Chem., 44, 4641 (2001).
30. P. Hewawasam, M. Erway, S. L. Moon, J. Knipe, H. Weiner, C. G. Boissard, D. J. Post-Munson, Q. Gao, S. Huang, V. K. Gribkoff, and N. A. Meanwell, J. Med. Chem., 45, 1487 (2002).
31. T. Tokunaga,W. E. Hume, J. Nagamine, T. Kawamura, M. Taiji, and R. Nagata, Bioorg. Med. Chem. Lett., 15, 1789 (2005).
32. Y. N. Ogibin, M. N. Elinson, and G. I Nikishin, Russ. Chem. Rev., 78, 89 (2009).
33. M. N. Elinson, S. K. Feducovich, T. L. Lizunova, and G. I. Nikishin, Tetrahedron, 56, 3063 (2000).
34. M. N. Elinson, A. I. Ilovaisky, V. M. Merkulova, F. Barba, and B. Batanero, Tetrahedron, 64, 5915 (2008).
35. M. N. Elinson, V. M. Merkulova, A. I. Ilovaisky, A. O. Chizhov, P. A. Belyakov, F. Barba, and B. Batanero, Electrochim. Acta, 55, 2129 (2010).
36. M. N. Elinson, A. S. Dorofeev, S. K. Feducovich, R. F. Nasybullin, S. V. Gorbunov, and G. I. Nikishin, Electrochem. Commun., 8, 1567 (2006).
37. M. N. Elinson,A. S. Dorofeev, R. F. Nasybullin, S. K. Feducovich, andG. I. Nikishin, Electrochim. Acta, 53, 5033 (2008).
38. M. N. Elinson, A. I. Ilovaisky, V. M. Merkulova, D. V. Demchuk, P. A. Belyakov, Y. N. Ogibin, and G. I. Nikishin, Electrochim. Acta, 53, 8346 (2008).
39. M. N. Elinson, V. M. Merkulova, A. I. Ilovaisky, F. Barba, and B. Batanero, Electrochim. Acta, 56, 8219 (2011).