Construction of pyrazolo[3,4-b]pyridines and pyrazolo[4,3-c]pyridines by ring closure of 3-acylpyridine N-oxide tosylhydrazones

Tetrahedron Letters

Volumn 53, Issue 8, 2012, Pages 906-909

  Lominac, William J ^a   D'Angelo, Megan L ^a   Smith, Mark D ^b   Ollison, Darius A ^a   Hanna Jr , James M ^a  

^a WINTHROP UNIVERSITY   (United States)

^b UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

Cyclization; Pyrazolo 3,4 b pyridines; Pyrazolo 4,3 c pyridines; Pyridine N oxide hydrazones

Indexed keywords

AMINE; ELECTROPHILE; HYDRAZONE DERIVATIVE; OXIDE; PYRAZOLE DERIVATIVE; PYRAZOLO[3,4 B]PYRIDINE DERIVATIVE; PYRAZOLO[4,3 C]PYRIDINE DERIVATIVE; PYRIDINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; QUANTUM YIELD; REACTION ANALYSIS; RING CLOSING METATHESIS; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 84855914200     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.12.055     Document Type: Article

References (38)

1. T. Eicher, and S. Hauptmann The Chemistry of Heterocycles. Structure, Reactions, Synthesis, and Applications 2nd ed. 2003 Wiley-VCH Weinheim
2. A. Cappelli, C. Nannicini, A. Gallelli, G. Giuliani, S. Valenti, G.P. Mohr, M. Anzini, L. Mennuni, F. Ferrari, G. Caselli, A. Giordani, W. Pereis, F. Makovec, G. Giorgi, and S. Vomero J. Med. Chem. 51 2008 2137
3. H. de Mello, A. Echevarria, A.M. Bernardino, M. Canto-Cavalheiro, and L.L. Leon J. Med. Chem. 47 2004 5427
4. A.R. Azevedo, V.F. Ferreira, H. de Mello, L.R. Leao-Ferreira, A.V. Jabor, I.C.P.P. Frugulhetti, H.S. Pereira, N. Moussatche, and A.M. Rolim Bernardino Hetererocycl. Commun. 8 2002 427
5. T. Tuccinardi, S. Schenone, F. Bondavalli, C. Brullo, O. Bruno, L. Mosti, A.T. Zizzari, C. Tintori, F. Manetti, O. Ciampi, M.L. Trincavelli, C. Martini, A. Martinelli, and M. Botta ChemMedChem 3 2008 898
6. F. Manetti, S. Schenone, F. Bondavalli, C. Brullo, O. Bruno, A. Ranise, L. Mosti, G. Menozzi, P. Fossa, M.L. Trincavelli, C. Martini, A. Martinelli, C. Tintori, and M. Botta J. Med. Chem. 48 2005 7172
7. P.A. Babu, M.L. Narasu, and K. Srinivas ARKIVOC 2007 247
8. R. Lin, P.J. Connolly, Y. Lu, G. Chiu, S. Li, Y. Yu, S. Huang, X. Li, S.L. Emanuel, S.A. Middleton, R.H. Gruninger, M. Adams, A.R. Fuentes-Pesquera, and L.M. Greenberger Bioorg. Med. Chem. Lett. 17 2007 4297
9. J. Witherington, V. Bordas, A. Gaiba, A. Naylor, A.D. Rawlings, B.P. Slingsby, D.G. Smith, A.K. Takle, and R.W. Ward Bioorg. Med. Chem. Lett. 13 2003 3059
10. J. Witherington, V. Bordas, A. Gaiba, N.S. Garton, A. Naylor, A.D. Rawlings, B.P. Slingsby, D.G. Smith, A.K. Takle, and R.W. Ward Bioorg. Med. Chem. Lett. 13 2003 3055
11. J. Witherington, V. Bordas, S.L. Garland, D.M.B. Hickey, R.J. Ife, J. Liddle, M. Saunders, D.G. Smith, and R.W. Ward Bioorg. Med. Chem. Lett. 13 2003 1577
12. For a review, see C.R. Hardy Adv. Heterocycl. Chem. 36 1984 343
13. B.M. Lynch, M.A. Khan, H.C. Teo, and F. Pedrotti Can. J. Chem. 66 1988 420
14. F.E. Goda, A.A.-M. Abdel-Aziz, and O.A. Attef Bioorg. Med. Chem. 12 2004 1845
15. G. Lavecchia, S. Berteina-Raboin, and G. Guillaumet Tetrahedron Lett. 45 2004 2389
16. N. Suryakiran, P. Prabhakar, and Y. Venkateswarlu Chem. Lett. 36 2007 1370
17. M.A.A. Elneairy, M.A.M. Gad-Elkareem, and A.M. Taha Heteroat. Chem. 18 2007 399
18. D. Viña, E. del Olmo, J.L. López-Pérez, and A. San Feliciano Org. Lett. 9 2007 525
19. R. Liu, Y. Zhu, L. Qin, and S. Ji Synth. Commun. 38 2008 249
20. M.J. Burke, and B.M. Trantow Tetrahedron Lett. 49 2008 4579
21. G.L. Beutner, J.T. Kuethe, M.M. Kim, and N. Yasuda J. Org. Chem. 74 2009 789
22. J.T. Kuethe, Y.-L. Zhong, M. Alam, A.D. Alorati, G.L. Beutner, D. Cai, F.J. Fleitz, A.D. Gibb, A. Kassim, K. Linn, D. Mancheno, B. Marcune, P.J. Pye, J.P. Scott, D.M. Tellers, B. Xiang, N. Yasuda, J. Yin, and I.W. Davies Tetrahedron 65 2009 5013
23. Y.-L. Zhong, M.G. Lindale, and N. Yasuda Tetrahedron Lett. 50 2009 2293
24. T. Umemoto, and G. Tomizawa J. Org. Chem. 54 1989 1726
25. D. Hebel, and S. Rozen J. Org. Chem. 56 1991 6298
26. R.D. Chambers, M. Parsons, G. Sandford, C.J. Skinner, M.J. Atherton, and J.S. Moilliet J. Chem. Soc., Perkin Trans. 1 1999 803
27. K.M. Janmanchi, and J.W.R. Dolbier Org. Process Res. Dev. 12 2008 349
28. W.K. Fife, and E.F.B. Scriven Heterocycles 22 1984 2375
29. J. Yin, B. Xiang, M.A. Huffman, C.E. Raab, and I.W. Davies J. Org. Chem. 72 2007 4554
30. J.M. Keith J. Org. Chem. 75 2010 2722
31. J.M. Keith J. Org. Chem. 73 2008 327
32. A.T. Londregan, S. Jennings, and L. Wei Org. Lett. 12 2010 5254
33. A.T. Londregan, S. Jennings, and L. Wei Org. Lett. 13 2011 1840
34. J.D. Street, M.M. Baradarani, R.L. Beddoes, O.S. Mills, and J.A. Joule J. Chem. Res., Synop. 1987 154
35. I.S. Poddubnyi Chem. Heterocycl. Compd. 31 1995 682
36. Highly electron-deficient aromatic rings can undergo nucleophilic substitution by an SET mechanism even with a 'hard' nucleophile like hydroxide. See R. Bacaloglu, A. Blasko, C. Bunton, E. Dorwin, F. Ortega, and C. Zucco J. Am. Chem. Soc. 113 1991 238
37. C.A. Bunnell, and P.L. Fuchs J. Org. Chem. 42 1977 2614
38. R. Hayes, and O. Meth-Cohn Tetrahedron Lett. 23 1982 1613