A "click and activate" Approach in one-pot synthesis of a triazolyl-pyridazinone library

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1682-1685

  Qian, Wenyuan ^a   Winternheimer, David ^a   Allen, Jennifer ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; PYRIDAZINE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINES; CATALYSIS; MOLECULAR STRUCTURE; PYRIDAZINES; STEREOISOMERISM; TRIAZOLES;

EID: 79953206308     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200183b     Document Type: Article

References (36)

1. Dömling, A. Chem. Rev. 2006, 106, 17
2. Ramon, D. J.; Miguel, Y. Angew. Chem., Int. Ed. 2005, 44, 1602
3. Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123
4. Multicomponent reactions; Zhu, J.; Bienaymé, H., Eds.; Wiley: Weinheim, 2005.
5. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
6. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596
7. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057
8. For recent reviews, see: Thematic issue: Click chemistry: Function follows form; Finn, M. G.; Fokin, V. V., Eds.; Chem. Soc. Rev. 2010, 39, 1221.
9. Wu, P.; Fokin, V. V. Aldrichimica Acta 2007, 40, 7
10. Fournier, D.; Hoogenboom, R.; Schubert, U. S. Chem. Soc. Rev. 2007, 36, 1369
11. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249
12. Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; Van der Eycken, E. Org. Lett. 2004, 6, 4223
13. Feldman, A. K.; Colasson, B.; Fokin, V. V. Org. Lett. 2004, 6, 3897
14. Chittaboina, S.; Xie, F.; Wang, Q. Tetrahedron Lett. 2005, 46, 2331
15. Kumar, D.; Reddy, V. B.; Varma, R. S. Tetrahedron Lett. 2009, 50, 2065
16. Reddy, P. S.; Sreedhar, B. Synthesis 2009, 24, 4203
17. Khanetskyy, B.; Dallinger, D.; Kappe, C. O. J. Comb. Chem. 2004, 6, 884
18. Ramachary, D. B.; Barbas, C. F., III. Chem.-Eur. J. 2004, 10, 5323
19. Akritopoulou-Zanze, I.; Gracias, V.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 8439
20. For a one-pot, modular synthesis of trisubstituted 1,2,3-triazoles involving direct arylation after click reaction, see: Ackermann, L.; Potukuchi, H. K.; Landsberg, D.; Vicente, R. Org. Lett. 2008, 10, 3081
21. Tišler, M.; Stanovnik, B. Adv. Heterocycl. Chem. 1990, 49, 385
22. Coates, W. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R; Rees, C. W., Eds.; Pergamon Press: Oxford, 1996; Vol. 6, p 1.
23. Frank, H.; Heinisch, G. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Eds.; Elsevier Science: Amsterdam, 1990; Vol. 27, p 1.
24. Frank, H.; Heinisch, G. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Eds.; Elsevier Science: Amsterdam, 1992; Vol. 29, p 141.
25. BASF Web site.
26. Maes, B. U. W.; R'kyek, O.; Košmrlj, J.; Lemière, G. L. F.; Esmans, E.; Rozenski, J.; Dommisse, R. A.; Haemers, A. Tetrahedron 2001, 57, 1323
27. Riedl, Z.; Maes, B. U. W.; Monsieurs, K.; Lemière, G. L. F.; Mètyus, P.; Hajós, G. Tetrahedron 2002, 58, 5645
28. Tapolcsányi, P.; Maes, B. U. W.; Monsieurs, K.; Lemière, G. L. F.; Riedl, Z.; Hajós, G.; Van den Driessche, B.; Dommisse, R. A.; Mátyus, P. Tetrahedron 2003, 59, 5919
29. Wu, B.; Wang, H.-L.; Pettus, L.; Wurz, R. P.; Doherty, E. M.; Henkle, B.; McBride, H. G.; Saris, C. J. M.; Wong, L. M.; Plant, M. H.; Sherman, L.; Lee, M. R.; Hsieh, F.; Tasker, A. S. J. Med. Chem. 2010, 53, 6398
30. Pilgrim, K. H.; Pollard, G. E. J. Heterocycl. Chem. 1977, 14, 1039
31. Lyga, J. W. J. Heterocycl. Chem. 1988, 25, 1757
32. Kweon, D.-H.; Kang, Y.-J.; Chung, J.-A; Yoon, Y.-J. J. Heterocycl. Chem. 1998, 35, 819
33. Chung, H.-A.; Kweon, D.-H.; Kang, Y.-J.; Park, J.-W.; Yoon, Y.-J. J. Heterocycl. Chem. 1999, 36, 905
34. To the best of our knowledge, this is the first example of one-pot, multiple component condensation sequence by a CuAAC "click and activate" approach. Early examples of 4-alkylamino-5-triazolyl-pyridazinone were synthesized in three separate steps. However, extended heating and the potential regiochemical control issue in the "nonclick" triazole formation step limits the scope of this old procedure and makes it unsuitable for one-pot operation. See: Karklins, A.; Gudriniece, E. Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija 1969, 5, 579
35. Gudriniece, E.; Urbans, V. Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija 1971, 1, 82
36. Urbans, V.; Gudriniece, E.; Urbans, V. Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija 1972, 1, 107