Modular, Concise, and Efficient Synthesis of Highly Functionalized 5-Fluoropyridazines by a [2 + 1]/[3 + 2]-Cycloaddition Sequence

Organic Letters

Volumn 17, Issue 14, 2015, Pages 3414-3417

  Tran, Gaël ^a   Gomez Pardo, Domingo ^a   Tsuchiya, Tomoki ^a   Hillebrand, Stefan ^a   Vors, Jean Pierre ^a   Cossy, Janine ^a  

^a ESPCI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZO COMPOUND; DIFLUOROCARBENE; FLUORINATED HYDROCARBON; PYRIDAZINE DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; SYNTHESIS;

ALKYNES; AZO COMPOUNDS; CATALYSIS; CYCLOADDITION REACTION; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; PYRIDAZINES;

EID: 84937611584     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b01370     Document Type: Article

References (27)

1. Wermuth, C. G. Med. Chem. Commun. 2011, 2, 935-941
2. Amoo, V. E.; Harrison, C. R.; Lahm, G. P.; Lowder, P. D.; Stevenson, T. M.; Long, J. K.; Shapiro, R.; March, R. W.; Allen, D. E.; Richmond, M. D.; March, W. A.; Chun, G.; Folgar, M. P.; Griswold, S. M. In Synthesis and Chemistry of Agrochemicals; Baker, D. R.; Fenyes, J. G.; Lahm, G. P.; Selby, T. P.; Stevenson, T. M., Eds.; American Chemical Society: Washington, DC, 2001; Vol. 6, pp 156-165.
3. Achelle, S.; Plé, N.; Turck, A. RSC Adv. 2011, 1, 364-388
4. Ritchie, T. J.; Macdonald, S. J. F.; Peace, S.; Pickett, S. D.; Luscombe, C. N. Med. Chem. Commun. 2012, 3, 1062-1069
5. Maes, B. U. W.; Lemière, G. L. F. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier Ltd.: Antwerp, 2008; Vol. 8, pp 1-116.
6. Klauke, E.; Oehlmann, L.; Baasner, B. J. Fluorine Chem. 1983, 23, 304-308
7. Fier, P. S.; Hartwig, J. F. Science 2013, 342, 956-960
8. Bégué, J.-P.; Bonnet-Delpon, D. In Bioorganic and Medicinal Chemistry of Fluorine; John Wiley and Sons, Inc.: Hoboken, NJ, 2008.
9. Dehmlow, E.; Ud-Din, N. J. Chem. Res., Synop. 1978, 40
10. Aue, D. H.; Lorens, R. B.; Helwig, G. S. J. Org. Chem. 1979, 44, 1202-1207
11. Regitz, M.; Welter, W.; Hartmann, A. Chem. Ber. 1979, 112, 2509-2527
12. Heydt, H.; Breiner, W. H.; Hell, V.; Reigitz, M. Z. Naturforsch., B: Chem. Sci. 1987, 42, 210-216
13. Al Dulayymi, A. R.; Baird, M. S. Tetrahedron 1998, 54, 12897-12906
14. Sheshenev, A. E.; Baird, M. S.; Croft, A. K.; Bolesov, I. G. Tetrahedron 2009, 65, 10036-10046
15. Dolbier, W. R., Jr.; Merle, M. A. Chem. Rev. 2003, 103, 1071-1098
16. Ni, C.; Hu, J. Synthesis 2014, 46, 842-863
17. Wang, F.; Luo, T.; Hu, J.; Wang, Y.; Krishnan, H. S.; Jog, P. V.; Ganesh, S. K.; Prakash, G. S. K.; Olah, G. A. Angew. Chem., Int. Ed. 2011, 50, 7153-7157
18. Tian, F.; Kruger, V.; Bautista, O.; Duan, J.-X.; Li, A.-R.; Dolbier, W. R., Jr.; Chen, Q. Y. Org. Lett. 2000, 2, 563-564
19. Dolbier, W. R., Jr.; Tian, F.; Duan, J.-X.; Li, A.-R.; Ait-Mohand, S.; Bautista, O.; Buathong, S.; Baker, J. M.; Crawford, J.; Anselme, P.; Hong Cai, X.; Modzelewska, A.; Koroniak, H.; Battiste, M. A.; Chen, Q. Y. J. Fluorine Chem. 2004, 125, 459-469
20. Zheng, Z.; Dolbier, W. R., Jr. J. Fluorine Chem. 2013, 149, 119-124
21. Cheng, Z.-L.; Chen, Q.-Y. Synlett 2006, 478-480
22. Hang, W.-C.; Gu, W.-P.; Chen, Q. Y.; Xiao, J.-C. Tetrahedron 2009, 65, 6320-6324
23. Babin, D.; Pilorge, F.; Delbarre, L. M.; Demoute, J.-P. Tetrahedron 1995, 51, 9603-9610
24. Sang, R.; Yang, H. B.; Min, S. Tetrahedron Lett. 2013, 54, 3591-3594
25. see: Ni, C.; Hu, J. Synthesis 2014, 46, 842-863
26. Lin, W.; Baron, O.; Knochel, P. Org. Lett. 2006, 8, 5673-5676
27. Wunderlich, S. H.; Knochel, P. Chem. Commun. 2008, 6387-6389