Indium bromide catalysed, ultrasound-assisted, regio-selective synthesis of ethyl-5-(trifluoromethyl)-1-(3-substituted-isoquinolin-1-yl)-1H-pyrazole-4- carboxylates

Research on Chemical Intermediates

Volumn 38, Issue 2, 2012, Pages 429-441

  Prabakaran, K ^a   Khan, F Nawaz ^a,b   Jin, Jong Sung ^b   Manivel, P ^a  

^a VIT UNIVERSITY   (India)

^b Korea Basic Science Institute (KBSI)   (South Korea)

Author keywords

1 (3 Substituted isoquinolin 1 yl) hydrazines; Cyclisation; Indium bromide; Microwave; Pyrazole 4 carboxylates; Regio selectivity; Ultrasonic irradiation

Indexed keywords

CYCLISATIONS; INDIUM BROMIDE; INDIUM BROMIDES; NUCLEAR OVERHAUSER EFFECTS; PYRAZOLE-4-CARBOXYLATES; REGIO-SELECTIVE; TRIFLUOROMETHYL; ULTRASONIC IRRADIATION;

BROMINE COMPOUNDS; CARBOXYLATION; CATALYSTS; CYCLIZATION; ETHANOL; IRRADIATION; MICROWAVES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS;

INDIUM;

EID: 84856704608     PISSN: 09226168     EISSN: 15685675     Source Type: Journal    
DOI: 10.1007/s11164-011-0360-5     Document Type: Article

References (38)

1. V. Polshettiwar, R.S. Varma, Tetrahedron Lett. 49, 397 (2008)
2. E. McDonald, K. Jones, P.A. Brough, M.J. Drysdale, P. Workman, Curr. Top. Med. Chem. 6, 1193 (2006)
3. L. Buriol, C.P. Frizzo, R.B. Mara, D.N. Marzari, L.D. Moreira, T. Prola, N. Zanatta, H.G. Bonacorso, A.P.M. Martins, J. Braz. Chem. Soc. 21, 1037 (2010)
4. A.K. Tewari, A. Mishra, Bioorg. Med. Chem. 9, 715 (2001)
5. R.H. Wiley, P. Wiley, Pyrazolones, pyrazolidinones and derivatives (Wiley, New York, 1964)
6. E.V. Pimerova, E.V. Voronina, Pharm. Chem. J. 35, 18 (2001)
7. S.L. Janus, A.Z. Magdif, B.P. Erik, N. Claus, Monatsh. Chem. 130, 1167 (1999)
8. H.J. Park, K. Lee, S. Park, B. Ahn, J.C. Lee, H.Y. Cho, K.ǐ Lee, Bioorg. Med. Chem. Lett. 15, 3307 (2005)
9. V. Michon, C.H. du Penhoat, F. Tombret, J.M. Gillardin, F. Lepagez, L. Berthon, Eur. J. Med. Chem. 30, 147 (1995)
10. ǐ Yildirim, N. Ozdemir, Y. Akcamur, M. Dincer, O. Andac, Acta Crystallogr. E61, 256 (2005)
11. D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. Defelice, M.E. Feigenson, J. Med. Chem. 28, 256 (1985)
12. H. Cheng, K.M. Lundy DeMello, J. Li, S.M. Sakya, K. Ando, K. Kawamura, T. Kato, R.J. Rafka, B.H. Jaynes, C.B. Ziegler, R. Stevens, L.A. Lund, D.W. Mann, C. Kilroy, M.L. Haven, E.L. Nimz, J.K. Dutra, C. Li, M.L. Minich, N.L. Kolosko, C. Petras, A.M. Silivia, S.B. Seibel, Bioorg. Med. Chem. Lett. 16, 2076 (2006)
13. S. Radi, S. Salhi, A. Radi, Lett. Drug Design Discov. 7, 27 (2010)
14. S.T. Heller, S.R. Natarajan, Org. Lett. 8, 2675 (2006)
15. M.S.M. Ahmed, K. Kobayashi, A. Mori, Org. Lett. 7, 4487 (2005)
16. X. Deng, N.S. Mani, Org. Lett. 8, 3505 (2006)
17. P. Waldo, S. Mehta, R. Larock, J. Org. Chem. 73, 6666 (2008)
18. P. Manivel, F. Nawaz Khan, J. Chil. Chem. Soc. 54, 180 (2009)
19. P. Manivel, S. Mohana Roopan, R. Sathish Kumar, F. Nawaz Khan, J. Chil. Chem. Soc 54, 183 (2009)
20. P. Manivel, F. Nawaz Khan, Ind J. Chem. 48B, 825 (2009)
21. F.N. Khan, P. Manivel, K. Prabakaran, V.R. Hathwar, M. Akkurt, Acta Cryst. E66, o1081 (2010)
22. F.N. Khan, P. Manivel, K. Prabakaran, V.R. Hathwar, Mehmet. Akkurt, Acta Cryst. E66, o1094 (2010)
23. N.T. Patil, F.N. Khan, Y. Yamamoto, Tetrahedron Lett. 45, 8497 (2004)
24. P. Manivel, S. Mohana Roopan, F. Nawaz Khan, Ind. J. Het. Chem. 18, 21 (2008)
25. P. Manivel, S. Mohana Roopan, F. Nawaz Khan, J. Chil. Chem. Soc. 53, 1609 (2008)
26. K. Prabakaran, P. Manivel, F.N. Khan, Tetrahedron Lett. 51, 4340 (2010)
27. F.N. Khan, P. Manivel, K. Prabakaran, V.R. Hathwar, S.W. Ng, Acta Cryst. E66, o370 (2010)
28. P. Manivel, F. Nawaz Khan, V.R. Hathwar, Phosphorus Sulphur Silicon Relat. Elem. 185, 1932 (2010)
29. F.N. Khan, P. Manivel, K. Prabakaran, V.R. Hathwar, S.W. Ng, Acta Cryst. E65, o2732 (2009)
30. F.N. Khan, P. Manivel, K. Prabakaran, V.R. Hathwar, S.W. Ng, Acta Cryst. E66, o488 (2010)
31. P. Manivel, F. Nawaz Khan, Phosphorus Sulphur Silicon Relat. Elem. 184, 2910 (2009)
32. S. Mohana Roopan, T.R. Sakthi Sri, B. Ramakrishna Reddy, F. Nawaz Khan, Ind. J. Heterocyclic Chem. 19, 77 (2009)
33. S.S. Tajudeen, F.N. Khan, Synth. Commun. 37, 3649 (2007)
34. S.M. Roopan, T. Maiyalagan, F.N. Khan, Can. J. Chem. 86, 1019 (2008)
35. V.R. Hathwar, P. Manivel, F. Nawaz Khan, T.N.G. Row, Acta Cryst. E 63, o3707 (2007)
36. V.R. Hathwar, P. Manivel, F. Nawaz Khan, T.N.G. Row, Acta Cryst. E 63, o3708 (2007)
37. S.M. Roopan, F.R.N. Khan, Arkivoc 13, 161 (2009)
38. V.R. Hathwar, P. Manivel, F. Nawaz Khan, T.N. Guru Row, Cryst. Eng. Comm. 11, 284 (2009)