Quinoxaline synthesis in novel tandem one-pot protocol

Tetrahedron Letters

Volumn 52, Issue 22, 2011, Pages 2862-2865

  Anil Kumar, B S P ^a   Madhav, B ^a   Harsha Vardhan Reddy, K ^a   Nageswar, Y V D ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Diketones keto esters; N Bromo succinimide; Neutral conditions; Phenylene diamines; Quinoxalines; Water

Indexed keywords

1,3 DIKETONE; N BROMOSUCCINIMIDE; PHENYLENEDIAMINE; QUINOXALINE DERIVATIVE; WATER;

ARTICLE; DRUG SYNTHESIS; ONE POT SYNTHESIS;

EID: 79955557721     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.110     Document Type: Article

References (55)

1. L.E. Seitz, W.J. Suling, and R.C. Reynolds J. Med. Chem. 45 2002 5604
2. M.M. Ali, M.M.F. Ismail, M.S.A. EI-Gabby, M.A. Zahran, and T.A. Ammar Molecules 5 2000 864
3. R. Sarges, H.R. Howard, R.C. Browne, L.A. Label, and P.A. Seymour J. Med. Chem. 33 1990 2240
4. G. Arthur, K.B. Elor, G.S. Robert, Z.Z. Guo, J.P. Richard, D. Stanley, R.K. John, and T. Sean J. Med. Chem. 48 2005 744
5. E.S. Lainne, J.S. William, and C.R. Robert J. Med. Chem. 45 2002 5604
6. J. Andres, Z. Belen, A. Ibnacio, and M. Antonio J. Med. Chem. 48 2005 2019
7. C.W. Lindsley, Z. Zhao, W.H. Leister, R.G. Robinson, S.F. Barnett, D. Defeo Jones, R.E. Jones, G.D. Hartman, J.R. Huff, H.E. Huber, and M.E. Duggan Bioorg. Med. Chem. Lett. 15 2005 761
8. M. Loriga, S. Piras, P. Sanna, and G. Paglietti Farmaco 52 1997 157
9. G. Sakata, K. Makino, and Y. Kurasawa Heterocycles 27 1988 2481
10. W. He, M.R. Meyers, B. Hanney, A. Sapada, G. Blider, H. Galzeinski, D. Amin, S. Needle, K. Page, Z. Jayyosi, and H. Perrone Bioorg. Med. Chem. Lett. 13 2003 3097
11. Y.B. Kim, Y.H. Kim, J.Y. Park, and S.K. Kim Bioorg. Med. Chem. Lett. 14 2004 541
12. Brock, E. D.; Lewis, D. M.; Yousaf, T. I.; Harper, H. H. (The Procter & Gamble Company, USA) WO 9951688, 1999.
13. S. Dailey, J.W. Feast, R.J. Peace, I.C. Sage, S. Till, and E.L. Wood J. Mater. Chem. 11 2001 2238
14. D.O'. Brien, M.S. Weaver, D.G. Lidzey, and D.D.C. Bradley Appl. Phys. Lett. 69 1996 881
15. O. Sascha, and F. Rudiger Synlett 2004 1509
16. L.S. Jonathan, M. Hiromitsu, M. Toshihisa, M.L. Vincent, and F. Hiroyuki J. Am. Chem. Soc. 124 2002 13474
17. P.C. Peter, Z. Gang, A.M. Grace, H. Carlos, and M.G.T. Linda Org. Lett. 6 2004 333
18. VOGEL'S Textbook of Practical Organic Chemistry 5th ed., 1989, p 1190.
19. D.J. Brown E.C. Taylor, P. Wipf, Chemistry of Heterocyclic Compounds 2004 John Wiley and Sons New Jersey Quinoxalines Supplements II
20. R.S. Bhosale, S.R. Sarda, S.S. Andhapure, W.N. Jadhav, S.R. Bhusare, and R.P. Pawar Tetrahedron Lett. 46 2005 7183
21. S.V. More, M.N.V. Sastry, C. Wang, and C.F. Yao Tetrahedron Lett. 46 2005 6345
22. S.A. Raw, C.D. Wilfred, and R.J.K. Taylor Org. Biomol. Chem. 2 2004 788
23. S.Y. Kim, K.H. Park, and Y.K. Chung Chem. Commun. 2005 1321
24. R.S. Robinson, and R.J.K. Taylor Synlett 2005 1003
25. C.S. Cho, W.X. Renb, and S.C. Shim Tetrahedron Lett. 48 2007 4665
26. B. Das, K. Venkateswarlu, K. Suneel, and A. Majhi Tetrahedron Lett. 48 2007 5371
27. W. Zemin, and J.E. Nicholas Tetrahedron Lett. 42 2001 8115
28. A.A. Orazio, D.C. Lucia, F. Paolino, M. Fabio, and S. Stefania Synlett 2003 1183
29. K.S. Sanjay, G. Priya, D. Srinavas, and K. Bijoy Synlett 2003 2147
30. G. Shyamaprasad, and K.A. Avijit Tetrahedron Lett. 43 2002 8371
31. Z. Zhijian, D.W. David, E.W. Scoot, H.L. William, and W.L. Craig Tetrahedron Lett. 45 2004 4873
32. A. Sylvain, and D. Elisabet Tetrahedron Lett. 43 2002 3971
33. B. Jose, A. Fernando, L. Ramon, and C. Maria-Paz Synthesis 1985 313
34. A.R. Steven, D.W. Cecilia, and J.K.T. Richard Chem. Commun. 2003 2286
35. G. Shyamaprosad, and K.A. Avijit Tetrahedron Lett. 46 2005 221
36. C. Yoram, Y.M. Amatzya, and R. Mordecai J. Am. Chem. Soc. 108 1986 7044
37. N.P. Xekoukoulotakis, M. Hadjiantoniou, and A.J. Maroulis Tetrahedron Lett. 41 2000 10299
38. D. Venu Gopal, and M. Subrahmanmyam Catal. Commun. 2 2001 219
39. H.M. Meshram, P. Ramesh, G. Santosh Kumar, and B. Chennakesava Reddy Tetrahedron Lett. 51 2010 4313
40. R. Breslow Acc. Chem. Res. 24 1991 159
41. R. Breslow Acc. Chem. Res. 37 2004 471
42. C.-J. Li, and T.H. Chan Organic Reactions in Aqueous Media 1997 Wiley New York
43. P.A. Grieco Organic Synthesis in Water 1998 Thomson Science Glasgow, Scotland
44. C.-J. Li Chem. Rev. 105 2005 3095
45. S.N. Murthy, B. Madhav, A.V. Kumar, K.R. Rao, and Y.V.D. Nageswar Tetrahedron 65 2009 5251
46. S.N. Murthy, B. Madhav, A.V. Kumar, K.R. Rao, and Y.V.D. Nageswar Helv. Chim. Acta 92 2009 2118
47. S.N. Murthy, B. Madhav, V. Prakash Reddy, K. Rama Rao, and Y.V.D. Nageswar Tetrahedron Lett. 50 2009 5009
48. B. Madhav, S.N. Murthy, K.R. Rao, and Y.V.D. Nageswar Helv. Chim. Acta 93 2010 257
49. S.N. Murthy, B. Madhav, and Y.V.D. Nageswar Helv. Chim. Acta 93 2010 1216
50. S.N. Murthy, B. Madhav, V. Prakash Reddy, and Y.V.D. Nageswar Tetrahedron Lett. 51 2010 3649
51. J. Shankar, K. Karnakar, B. Srinivas, and Y.V.D. Nageswar Tetrahedron Lett. 51 2010 3938
52. H. Bienayme, C. Hulme, G. Oddon, and P. Schmitt Chem. Eur. J. 6 2000 3321
53. B. Madhav, S.N. Murthy, V.P. Reddy, K.R. Rao, and Y.V.D. Nageswar Tetrahedron Lett. 50 2009 6025
54. +. HRMS calcd for 187.1123, found 187.1232.
55. S. Fujisaki, S. Hamura, H. Eguchi, and A. Nishida Bull. Chem. Soc. Jpn. 66 1993 2426