Electrocatalytic tandem Knoevenagel-Michael addition of barbituric acids to isatins: Facile and efficient way to substituted 5,5′-(2-oxo-2,3-dihydro- 1H-indole-3,3-diyl)bis(pyrimidine-2,4,6-(1H,3H,5H)-trione) scaffold

Electrochimica Acta

Volumn 56, Issue 24, 2011, Pages 8219-8223

  Elinson, Michail N ^a   Merkulova, Valentina M ^a   Ilovaisky, Alexey I ^a   Barba, Fructuoso ^b   Batanero, Belen ^b  

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

^b UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

5,5 (2 Oxo 2,3 dihydro 1H indole 3,3 diyl)bis(pyrimidine 2,4,6 (1H,3H,5H) triones); Barbituric acids; Electrocatalysis; Isatins; Tandem reactions

Indexed keywords

BARBITURIC ACID; CURRENT YIELDS; ELECTROCATALYTIC; ENVIRONMENTALLY BENIGN; GENERAL CHEMICALS; ISATINS; SODIUM BROMIDE; TANDEM REACTION; TANDEM REACTIONS; UNDIVIDED CELL;

ADDITION REACTIONS; BROMINE COMPOUNDS; ELECTROCATALYSIS; ETHANOL; SODIUM;

AROMATIC COMPOUNDS;

EID: 80052799304     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2011.06.059     Document Type: Article

References (29)

1. B.E. Evans, K.E. Rittle, M.G. Bock, R.M. DiPardo, R.M. Freidinger, W.L. Whitter, G.F. Lundell, D.F. Veber, P.S. Anderson, R.S.L. Chang, V.J. Lotti, D.J. Cerino, T.B. Chen, P.J. Kling, K.A. Kunkel, J.P. Springer, and J. Hirshfield J. Med. Chem. 31 1988 2235
2. R.W. DeSimone, K.S. Currie, S.A. Mitchell, J.W. Darrow, and D.A. Pippin Comb. Chem. High Throughput Screening 7 2004 473
3. D.J. Triggle Cell. Mol. Neurobiol. 23 2003 293
4. A.A. Patchett, and R.P. Nargund Annu. Rep. Med. Chem. 35 2000 289
5. J. Poupaert, P. Carato, and E. Colacino Curr. Med. Chem. 12 2005 877
6. F.R. De Sá Alves, C.A.M. Fraga, and E.J. Barreiro Mini Rev. Med. Chem. 9 2009 782
7. J.F.M. Da Silva, S.J. Garden, and A.C. Pinto J. Braz. Chem. Soc. 12 2001 273
8. S.N. Pandeya, S. Smitha, M. Jyoti, and S.K. Sridhar Acta Pharm. 55 2005 27
9. D. Sriram, T.R. Bal, and P. Yogeeswari J. Pharm. Pharm. Sci. 8 2005 565
10. D. Sriram, T.R. Bal, and P. Yogeeswari Il Farmaco 60 2005 377
11. N. Karali, A. Gursoi, F. Kandemirli, N. Shvets, F.B. Kaynak, S. Ozbey, V. Kovalishyn, and A. Dimoglo Bioorg. Med. Chem. 15 2007 5888
12. L.L. Brunton, J.S. Lazo, and K.L. Parker Goodman & Gilman's The Pharmacological Basis of Therapeutics 11th ed. 2006 The McGraw-Hill Companies, Inc.
13. M.W. Johns Drugs 9 1975 448
14. C. Uhlmann, and W. Froscher CNS Neurosci. & Ther. 15 2009 24
15. F.N.M. Naguib, D.L. Levesque, E.C. Wang, P.P. Panzica, and M.H. El Kouni Biochem. Pharmacol. 46 1993 1273
16. F. Grams, H. Brandstetter, S. D'Alo, D. Geppert, H.-W. Krell, H. Leinert, V. Livi, E. Menta, A. Oliva, and G. Zimmermann Biol. Chem. 382 2001 1277
17. E. Maquoi, N.E. Sounni, L. Devy, F. Olivier, F. Frankenne, H.-W. Krell, F. Grams, J.M. Foidart, and A. Noel Clin. Cancer Res. 10 2004 4038
18. L.R. Morgan, B.S. Jursic, C.L. Hooper, D.M. Neumann, K. Thangaraj, and B. LeBlanc Bioorg. Med. Chem. Lett. 12 2002 3407
19. F.E. King, T.J. King, and G.B. Thompson J. Chem. Soc. 1948 552
20. M. Chakrabarty, K. Mukherjee, S. Arima, and Y. Harigaya Heterocycles 78 2009 139
21. B.S. Jursic, and E.D. Stevens Tetrahedron Lett. 43 2002 5681
22. M.N. Elinson, S.K. Feducovich, T.L. Lizunova, and G.I. Nikishin Tetrahedron 56 2000 3063
23. M.N. Elinson, A.I. Ilovaisky, V.M. Merkulova, F. Barba, and B. Batanero Tetrahedron 64 2008 5915
24. M.N. Elinson, V.M. Merkulova, A.I. Ilovaisky, A.O. Chizhov, P.A. Belyakov, F. Barba, and B. Batanero Electrochim. Acta 55 2010 2129
25. M.N. Elinson, A.S. Dorofeev, R.F. Nasybullin, and G.I. Nikishin Synthesis 2008 1933
26. M.N. Elinson, A.S. Dorofeev, R.F. Nasybullin, S.K. Feducovich, and G.I. Nikishin Electrochim. Acta 53 2008 5033
27. O.M. Radul, G.I. Zhungietu, M.A. Rekhter, and S.M. Bukhanyuk Khim. Geterotsikl. Soed. 1983 353
28. S. Patai, and Y. Israeli J. Chem. Soc. 1960 2025
29. D.A. White J. Electrochem. Soc. 124 1977 1177