Palladium-catalyzed coupling of aldehyde-derived hydrazones: Practical synthesis of triazolopyridines and related heterocycles

Angewandte Chemie - International Edition

Volumn 49, Issue 45, 2010, Pages 8395-8398

  Thiel, Oliver R ^a   Achmatowicz, Michal M ^a   Reichelt, Andreas ^a   Larsen, Robert D ^a  

^a AMGEN INC   (United States)

Author keywords

Amination; Cyclization; Heterocycles; Hydrazones; Palladium

Indexed keywords

CATALYZED COUPLING; DRUG DISCOVERY; HETEROCYCLES; HYDRAZONES; INTERMOLECULAR COUPLING; OXIDATIVE CYCLIZATION;

ALDEHYDES; AMINES; CATALYSIS; PALLADIUM;

CYCLIZATION;

ALDEHYDE; HETEROCYCLIC COMPOUND; HYDRAZONE DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALDEHYDES; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; HYDRAZONES; OXIDATION-REDUCTION; PALLADIUM; PYRIDINES; TRIAZOLES;

EID: 78149441182     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201001999     Document Type: Article

References (32)

1. G. Jones, Adv. Heterocycl. Chem. 2002, 83, 1.
2. Y. Yoshimura, K. Tomimatsu, T. Nishimura, A. Miyake, N. Hashimoto, J. Antibiot. 1992, 45, 721
3. A. K. Sadana, Y. Mirza, K. R. Aneja, O. Prakash, Eur. J. Med. Chem. 2003, 38, 533
4. E. C. Lawson, W. J. Hoekstra, M. F. Addo, P. Andrade-Gordon, B. P. Damiano, J. A. Kauffman, J. A. Mitchell, B. E. Maryanoff, Bioorg. Med. Chem. Lett. 2001, 11, 2619
5. A. S. Kalgutkar, H. L. Hatch, F. Kosea, H. T. Nguyen, E. F. Choo, K. F. McClure, T. J. Taylor, K. R. Henne, A. V. Kuperman, M. A. Dombroski, M. A. Letavic, Biopharm. Drug Dispos. 2006, 27, 371
6. K. F. McClure, Y. A. Abramov, E. R. Laird, J. T. Barberia, W. Cai, T. J. Carty, S. R. Cotina, D. E. Danley, A. J. Dipesa, K. M. Donahue, M. A. Dombroski, N. C. Elliott, C. A. Gabel, S. Han, T. R. Hynes, P. K. LeMotte, M. N. Mansour, E. S. Marr, M. A. Letavic, J. Pandit, D. B. Ripin, F. J. Sweeney, D. Tan, Y. Tao, J. Med. Chem. 2005, 48, 5728.
7. A. Reichelt, J. R. Falsey, R. M. Rzasa, O. R. Thiel, M. M. Achmatowicz, R. D. Larsen, D. Zhang, Org. Lett. 2010, 12, 792.
8. S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 6621
9. S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 10251.
10. A. Takemiya, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 14800. This reference includes a single example of the N-arylation of N-phenylhydrazone butanal with bromobenzene.
11. The intramolecular variant has been used for the synthesis of indazoles, see A. Y. Lebedev, A. S. Khartulyari, A. Z. Yoskoboynikov, J. Org. Chem. 2005, 70, 596
12. C. S. Cho, D. B. Patel, Tetrahedron 2006, 62, 6388
13. C. S. Cho, D. K. Lim, N. H. Heo, T. Kim, S. C. Shim, Chem. Commun. 2004, 104.
14. A. Abad, C. Agulló, A. C. Cu-at, C. Vilanova, Synthesis 2005, 915.
15. C. R. Kolder, H. J. den-Hertog, Recl. Trav. Chim. Pays-Bas 1953, 72, 285.
16. D. Kumar, K. V. G. Chandra-Sekhar, H. Dhillon, V. S. Rao, R. S. Varma, Green Chem. 2004, 6, 156
17. M. Ciesielski, D. Puffky, M. Doering, Tetrahedron 2005, 61, 5942
18. M. S. Gibson, Tetrahedron 1963, 19, 1587
19. A. Pollak, M. Tisler, Tetrahedron 1966, 22, 2073
20. P. Bourgeois, R. Cantegril, A. Chene, J. Gelin, J. Mortier, J. Moyroud, Synth. Commun. 1993, 23, 3195.
21. Q. Shen, S. Shekhar, J. P. Stambuli, J. F. Hartwig, Angew. Chem. 2005, 117, 1395
22. Angew. Chem. Int. Ed. 2005, 44, 1371.
23. NAr reaction products were observed in low quantities (-6 %).
24. H. N. Hafez, A. B. A. El-Gazzar, Bioorg. Med. Chem. Lett. 2009, 19, 4143
25. B. A. Albrecht, J.-C. Harmange, D. Bauer, L. Berry, C. Bode, A. A. Boezio, A. Chen, D. Choquette, I. Dussault, C. Fridrich, S. Hirai, D. Hoffman, J. F. Larrow, P. Kaplan-Lefko, J. Lin, J. Lohma, A. M. Long, J. Moriguchi, A. O-Connor, M. H. Potashman, M. Reese, K. Rex, A. Siegmund, K. Shah, R. Shimanovich, S. K. Springer, Y. Teffera, Y. Yang, Y. Zhang, S. F. Bellon, J. Med. Chem. 2008, 51, 2879
26. O. Prakash, V. Bhardwaj, R. Kumar, P. Tyagi, K. R. Aneja, Eur. J. Med. Chem. 2004, 39, 1073
27. A. Hirabayahi, H. Mukaiyama, H. Kobayashi, H. Shiohara, S. Nakayama, M. Ozawa, K. Miyazawa, K. Misawa, H. Ohnota, M. Isaji, Bioorg. Med. Chem. 2008, 16, 7347
28. R. Sarges, H. R. Howard, R. G. Browne, L. A. Lebel, P. A. Seymour, B. K. Koe, J. Med. Chem. 1990, 33, 2240
29. S. C. Goodacre, L. J. Street, D. J. Hallett, J. M. Crawforth, S. Kelly, A. P. Owens, W. P. Blackaby, R. T. Lewis, J. Stanley, A. J. Smith, P. Ferris, B. Sohal, S. M. Cook, A. Pike, N. Brown, K. A. Wafford, G. Marshall, J. L. Castro, J. R. Atack, J. Med. Chem. 2006, 49, 35.
30. D. J. Brown, T. Nagamatsu, Aust. J. Chem. 1977, 30, 2515
31. D. J. Brown, K. Shinozuka, Aust. J. Chem. 1980, 33, 1147
32. E. S. H. El-Ashry, Y. El-Kilany, N. Rashed, H. Assafir, Adv. Heterocycl. Chem. 2000, 75, 79.