A strategy for the synthesis of 2-aryl-3-dimethylaminopyrazolo-[3,4-c] pyridines that utilizes [4+1] cycloaddition reactions of 5-arylazo-2,3,6- trisubstituted pyridines

Tetrahedron

Volumn 69, Issue 49, 2013, Pages 10535-10543

  Behbehani, Haider ^a   Ibrahim, Hamada Mohamed ^a,b  

^a KUWAIT UNIVERSITY   (Kuwait)

^b Fayoum University   (Egypt)

Author keywords

(Dimethylamino)methoxycarbene; 4+1 Cycloaddition; Arylazopyridines; Azadiene; Pyrazolo 3,4 c pyridines

Indexed keywords

2,6 DIPHENYL 5 PARA TOLYLAZONICOTINONITRILE; 2,6 DIPHENYL 5 PHENYLAZONICOTINONITRILE; 3 (DIMETHYLAMINO) 2 (4 METHOXYPHENYL) 5,7 DIPHENYL 2H PYRAZOLO[3,4 C]PYRIDINE 4 CARBONITRILE; 3 (DIMETHYLAMINO) 2,5,7 TRIPHENYL 2H PYRAZOLO[3,4 C]PYRIDINE 4 CARBONITRILE; 3 (DIMETHYLAMINO) 5,7 DIPHENYL 2 PARA TOLYL 2H PYRAZOLO[3,4 C]PYRIDINE 4 CARBONITRILE; 3 (DIMETHYLAMINO) 7 (4 FLUOROPHENYL) 2,5 DIPHENYL 2H PYRAZOLO[3,4 C]PYRIDINE 4 CARBONITRILE; 3 (DIMETHYLAMINO) 7 (4 METHOXYPHENYL) 2,5 DIPHENYL 2H PYRAZOLO[3,4 C]PYRIDINE 4 CARBONITRILE; 3 (DIMETHYLAMINO) 7 (4 METHOXYPHENYL) 5 PHENYL 2 PTOLYL 2H PYRAZOLO[3,4 C]PYRIDINE 4 CARBONITRILE; 5 (4 METHOXYPHENYLAZO) 2,6 DIPHENYLNICOTINONITRILE; 6 (4 BROMOPHENYL) 2 PHENYL 5 PHENYLAZONICOTINONITRILE; 6 (4 CHLOROPHENYL) 2 PHENYL 5 PHENYLAZONICOTINONITRILE; 6 (4 CHLOROPHENYL) 2 PHENYL 5 TOLYLAZONICOTINONITRILE; 6 (4 FLUOROPHENYL) 2 PHENYL 5 PHENYLAZONICOTINONITRILE; 6 (4 FLUOROPHENYL) 2 PHENYL 5 TOLYLAZONICOTINONITRILE; 6 (4 METHOXYPHENYL) 2 PHENYL 5 PARA TOLYLAZONICOTINONITRILE; 6 (4 METHOXYPHENYL) 2 PHENYL 5 PHENYLAZONICOTINONITRILE; 7 (4 BROMOPHENYL) 3 (DIMETHYLAMINO) 2,5 DIPHENYL 2H PYRAZOLO[3,4 C]PYRIDINE 4 CARBONITRILE; 7 (4 CHLOROPHENYL) 3 (DIMETHYLAMINO) 2,5 DIPHENYL 2H PYRAZOLO[3,4 C]PYRIDINE 4 CARBONITRILE; [2 AMINO 5 (4 CHLORO 3 NITROPHENYLAZO) 6 (4 CHLOROPHENYL)PYRIDIN 3 YL]PHENYLMETHANONE; [2 AMINO 5 (4 CHLOROPHENYLAZO) 6 (4 FLUOROPHENYL)PYRIDIN 3 YL]PHENYLMETHANONE; [2 AMINO 6 (4 BROMOPHENYL) 5 (4 CHLORO 3 NITROPHENYLAZO)PYRIDIN 3 YL)]PHENYLMETHANONE; [2 AMINO 6 (4 CHLOROPHENYL) 5 (4 CHLOROPHENYLAZO)PYRIDIN 3 YL]PHENYLMETHANONE; [7 (4 BROMOPHENYL) 4 PHENYLPYRIDO[2,3 D]PYRIMIDIN 6 YL](4CHLORO 3 NITROPHENYL)DIAZENE; N,N DIMETHYLFORMAMIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON; NUCLEOPHILICITY; PRIORITY JOURNAL;

EID: 84887402776     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.10.061     Document Type: Article

References (42)

1. L.A. Zhmurenko, G.M. Molodavkin, T.A. Voronina, and V.P. Lezina Pharm. Chem. J. 46 2012 15 19
2. L.,A. Smyth, T.,P. Matthews, P.,N. Horton, M.,B. Hursthouse, and I. Collins Tetrahedron 66 2010 2843 2854
3. V. Onnis, M.T. Cocco, R. Fadda, and C. Congiu Bioorg. Med. Chem. 17 2009 6158 6165
4. M.T. Cocco, C. Congiu, V. Lilliu, and V. Onnis Bioorg. Med. Chem. 14 2004 5789 5791
5. A.F. Sherif, G.S. Hassan, and H.I. El-Subbagh Arch. Pharm. 342 2009 584 590
6. J.K. Son, L.X. Zhao, A. Basnet, P. Thapa, R. Karki, Y. Na, Y. Jahng, T.C. Jeong, B.S. Jeong, C.S. Lee, and E.S. Lee Eur. J. Med. Chem. 43 2008 675 682
7. X. Pan, F. Wang, Y. Zhang, H. Gao, Z. Hu, S. Wang, and J. Zhang Bioorg. Med. Chem. 2013 2527 2534
8. L.R.S. Dias, M.B. Santos, S. de Albuquerque, H.C. Castro, A.M.T. de Souza, A.C.C. Freitas, M.A.V. DiVaio, L.M. Cabral, and C.R. Rodrigues Bioorg. Med. Chem. 15 2007 211 219
9. A.M.R. Bernardino, L.C. da Silva Pinheiro, C.R. Rodrigues, N.I. Loureiro, H.C. Castro, A. Lanfredi-Rangel, J. Sabatini-Lopes, J.C. Borges, J.M. Carvalho, G.A. Romeiro, V.F. Ferreira, I.C.P.P. Frugulhetti, and M.A. Vannier-Santos Bioorg. Med. Chem. 14 2006 5765 5770
10. T. Suksrichavalit, S. Prachayasittikul, C. Nantasenamat, C. Isarankura-Na-Ayudhya, and V. Prachayasittikul Eur. J. Med. Chem. 44 2009 3259 3265
11. B. Leal, I.F. Afonso, C.R. Rodrigues, P.A. Abreu, R. Garrett, L.C.S. Pinheiro, A.R. Azevedo, J.C. Borges, P.F. Vegi, C.C.C. Santos, F.C.A. da Silveira, L.M. Cabral, I.C.P.P. Frugulhetti, A.M.R. Bernardino, D.O. Santos, and H.C. Castro Bioorg. Med. Chem. 16 2008 8196 8204
12. M.C.S. Lourenço, M.V.N. de Souza, A.C. Pinheiro, M. de L. Ferreira, R.S.B. Goncalves, T.C.M. Nogueira, and M.A. Peralta Arkivoc xv 2007 181 191
13. P. Brun, A. Dean, V. Di Marco, P. Surajit, I. Castagliuolo, D. Carta, and M.G. Ferlin Eur. J. Med. Chem. 62 2013 486 497
14. M. Mohammadpour, A. Sadeghi, A. Fassihi, L. Saghaei, A. Movahedian, and M. Rostami Res. Pharm. Sci. 7 2012 171 179
15. S.B. Bharate, and C.M. Thompson Chem. Biol. Drug Des. 76 2010 546 551
16. A. Li, Y. Ouyang, Z. Wang, Y. Cao, X. Liu, L. Ran, C. Li, L. Li, L. Zhang, K. Qiao, W. Xu, Y. Huang, Z. Zhang, C. Tian, Z. Liu, S. Jiang, Y. Shao, Y. Du, L. Ma, X. Wang, and J. Liu J. Med. Chem. 56 2013 3593 3608
17. Winters, G.; Sala, A.; Barone, D. Eur. Pat. Appl. EP 86422 A2 19830824, 1983.
18. Ameriks, M. K.; Axe, F. U.; Edwards, J. P.; Grice, C. A.; Cai, H.; Gleason, E. A.; Meduna, S. P.; Tays, K. L.; Wiener, J. J. M.; Wickboldt, A. T. U.S. Pat. Appl. Publ. US 20,080,200,454 A1 20,080,821, 2008.
19. A.O. Plunkett Nat. Prod. Rep. 11 1994 581 590
20. M. Balasubramanian, and J.G. Deay A.R. Katrizky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II Vol. 5 1996 Pergamon New York, NY 245
21. K. Paulvannan, and T. Chen J. Org. Chem. 65 2000 6160 6166
22. J.A. Joule, G. Smith, and K. Mills Heterocyclic Chemistry 3rd ed. 1995 Chapman and Hall London, UK 72 119
23. H.J. Roth, and A. Kleeman Pharmaceutical Chemistry, Drug Synthesis Vol. 1 1988 Prentice Hall Europe London, UK 407
24. G.D. Henry Tetrahedron 60 2004 6043 6061
25. A.-H. Li, S. Moro, N. Forsyth, N. Melman, X.-D. Ji, and K.A. Jacobsen J. Med. Chem. 42 1999 706 721
26. B. Vacher, B. Bonnaud, F. Funes, N. Jubaudt, W. Koek, M.B. Assie, C. Cosi, and M. Kleven J. Med. Chem. 42 1999 1648 1660
27. L.-C. Campeau, and K. Fagnou Org. Synth. 88 2011 22 32
28. J.Z. Deng, D.V. Paone, A.T. Ginnetti, H. Kurihara, S.D. Dreher, S.A. Weissman, S.R. Stauffer, and C.S. Burgey Org. Lett. 11 2009 345 347
29. M.R. Luzung, J.S. Patel, and J. Yin J. Org. Chem. 75 2010 8330 8332
30. J.R. Manning, and H.M.L. Manning J. Am. Chem. Soc. 130 2008 8602 8603
31. K. Parthasararathy, M. Jeganmohan, and C.-H. Cheng Org. Lett. 10 2008 325 328
32. T.J. Donohoe, J.A. Basutto, J.F. Bower, and A. Rathi Org. Lett. 13 2011 1036 1039
33. H. Behbehani, H.M. Ibrahim, and M.H. Elnagdi Tetrahedron 69 2013 6176 6184
34. H. Behbehani, H.M. Ibrahim, S. Makhseed, and H. Mahmoud Eur. J. Med. Chem. 46 2011 1813 1820
35. H. Behbehani, H.M. Ibrahim, S. Makhseed, M.H. Elnagdi, and H. Mahmoud Eur. J. Med. Chem. 52 2012 51 65
36. H. Behbehani, and H.M. Ibrahim Molecules 17 2012 6362 6385
37. H. Behbehani, and H.M. Ibrahim Chem. Cent. J. 7 2013 82
38. H.M. Ibrahim, H. Behbehani, and M.H. Elnagdi Chem. Cent. J. 7 2013 123
39. C. Gerninghaus, A. Kümmell, and G. Seitz Chem. Ber. 126 1993 733 738
40. A. Kümmell, and G. Seitz Tetrahedron Lett. 24 1991 2743 2746
41. CrystalStructure 4.0: Crystal Structure Analysis Package 2000-2010 Rigaku Corporation Tokyo 196-8666, Japan
42. G.M. Sheldrick Acta Crystallogr. A64 2008 112 122