Polysubstituted pyridazinones from sequential nucleophilic substitution reactions of tetrafluoropyridazine

Journal of Organic Chemistry

Volumn 74, Issue 15, 2009, Pages 5533-5540

  Pattison, Graham ^a   Sandford, Graham ^a   Yufit, Dmitry S ^a   Howard, Judith A K ^a   Christopher, John A ^b   Miller, David D ^b  

^a DURHAM UNIVERSITY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVES; BUTYLAMINE; CHEMICAL EQUATIONS; DRUG DISCOVERY; MORPHOLINE; NITROGEN NUCLEOPHILES; NUCLEOPHILIC AROMATIC SUBSTITUTION; NUCLEOPHILIC SUBSTITUTION REACTIONS; NUCLEOPHILIC SUBSTITUTIONS; PRIMARY AND SECONDARY AMINE;

AMINES; FLUORINE; ISOMERS; NUCLEOPHILES; ORGANIC POLYMERS; SUBSTITUTION REACTIONS;

AMINATION;

4,5,6 TRIFLUOROPYRIDAZINE 3 (2H) ONE; ANILINE DERIVATIVE; BUTYLAMINE; FLUORINE; MORPHOLINE DERIVATIVE; N,N' DIMETHYLETHYLENEDIAMINE; NITROGEN; NUCLEOPHILE; PYRIDAZINE; PYRIDAZINONE DERIVATIVE; TETRAFLUOROPYRIDAZINE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMER; SUBSTITUTION REACTION; SYNTHESIS;

MOLECULAR STRUCTURE; PYRIDAZINES; STEREOISOMERISM;

EID: 68049087826     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9006943     Document Type: Article

References (29)

1. Patel, D. V.; Gordon, E. M. Drug Discovery Today 1996, 1, 134-144.
2. Leach, A. R.; Hann, M. M. Drug Discovery Today 2000, 5, 326-336.
3. Bailey, D.; Brown, D. Drug Discovery Today 2001, 6, 57-59.
4. Sugiyama, Y. Drug Discovery Today 2005, 10, 1577-1579.
5. Walters, W. P.; Murcko, A.; Murcko, M. A. Curr. Opin. Chem. Biol. 1999, 3, 384-387.
6. Walters, W. P.; Murcko, M. A. Adv. Drug Delivery Rev. 2002, 54, 255-271.
7. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 2001, 46, 3-26.
8. Lipinski, C. A. Drug Discov. Today: Technol. 2004, 1, 337-341.
9. Katritzky, A. R.; Rees, C. W. Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford, 1984.
10. Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles; Thieme: Stuttgart, 1995.
11. Brooke, G. M. J. Fluorine Chem. 1997, 86, 1-76.
12. Cartwright, M. W.; Christopher, J. A.; Miller, D. D.; Sandford, G.; Slater, R.; Smith, P. W.; Vong, A. Chim. Oggi 2007, 25, 40-44.
13. Ng, H. P.; Buckman, B. O.; Eagen, K. A.; Guilford, W. J.; Kochanny, M. J.; Mohan, R.; Shaw, K. J.; Wu, S. C.; Lentz, D.; Liang, A.; Ho, L. T. E.; Smith, D.; Subramanyam, B.; Vergona, R.; Walters, J.; White, K. A.; Sullivan, M. E.; Morrissey, M. M.; Phillips, G. B. Biorg. Med. Chem. 2002, 657-666.
14. Kranjc, A.; Kikelj, D.; Peterlin-Masic, L. Curr. Pharm. Des. 2005, 11, 4207-4227.
15. Walenga, J. M.; Jeske, W. P.; Hoppensteadt, D.; Fareed, J. Curr. Opin. Investig. Drugs 2003, 4, 272-281.
16. Sandford, G.; Slater, R.; Yufit, D. S.; Howard, J. A. K.; Vong, A. J. Org. Chem. 2005, 70, 7208-7216.
17. Baron, A.; Sandford, G.; Slater, R.; Yufit, D. S.; Howard, J. A. K.; Vong, A. J. Org. Chem. 2005, 70, 9377-9381.
18. Hargreaves, C. A.; Sandford, G.; Slater, R.; Yufit, D. S.; Howard, J. A. K.; Vong, A. Tetrahedron 2007, 63, 5204-5211.
19. Cartwright, M. W.; Sandford, G.; Bousbaa, J.; Yufit, D. S.; Howard, J. A. K.; Christopher, J. A.; Miller, D. D. Tetrahedron 2007, 63, 7027-7035.
20. Chambers, R. D.; Macbride, J. A. H.; Musgrave, W. K. R. J. Chem. Soc. C 1968, 2989-2994.
21. DalPiaz, V.; Giovannoni, M. P.; Ciciani, G.; Barlocco, D.; Giardina, G.; Petrone, G.; Clarke, G. D. Eur. J. Med. Chem. 1996, 31, 65-70.
22. Kerdesky, F. A. J.; Leanna, M. R.; Zhang, J.; Li, W. K.; Lallamann, J. E.; Ji, J. G.; Morton, H. E. Org. Proc. Res. Dev. 2006, 10, 512-517.
23. Zhang, J.; Morton, H. E.; Li, J. G. Tetrahedron Lett. 2006, 47, 8733-8735.
24. Saracoglu, N. Tetrahedron 2007, 63, 4199-4236.
25. Maes, B. U. W.; R'Kyek, O.; Kosmrlj, J.; Lemiere, G. L. F.; Esmans, E.; Rozenski, J.; Dommisse, R. A.; Haemers, A. Tetrahedron 2001, 57, 1323-1330.
26. Maes, B. U. W.; Monsieurs, K.; Loones, K. T. J.; Lemiere, G. L. F.; Dommisse, R.; Matyus, M.; Riedl, Z.; Hajos, G. Tetrahedron 2002, 58, 9713-9721.
27. Monsieurs, K.; Tapolcsanyi, P.; Loones, K. T. J.; Neumajer, G.; Ridder, J. A. D. D.; Goubitz, K.; Lemiere, G. L. F.; Dommisse, R. A.; Matyus, P.; Maes, B. U. W. Tetrahedron 2007, 63, 3870-3881.
28. Dajka-Halasz, B.; Monsieurs, K.; Elias, O.; Karolyhazy, L.; Tapolcsanyi, P.; Maes, B. U. W.; Riedl, Z.; Hajos, G.; Dommisse, R. A.; Lemiere, G. L. F.; Kosmrlj, J.; Matyus, P. Tetrahedron 2004, 60, 2283-2291.
29. Helm, M. D.; Plant, A.; Harrity, J. P. A. Org. Biomol. Chem. 2006, 4, 4278-4280.