Regioselective synthesis of 3,3-diethyl-4-(methylene)-1-quinol-2-ones by an intramolecular microwave assisted heck reaction

Journal of Heterocyclic Chemistry

Volumn 42, Issue 2, 2005, Pages 327-331

  Smalley Jr , Terrence L ^a   Mills, Wendy Y ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,3 DIETHYL 4 (METHYLENE) 1 QUINOL 2 ONE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; CYCLIZATION; HECK REACTION; HYDROGENATION; MICROWAVE RADIATION; MOLECULAR INTERACTION; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 16844375375     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570420225     Document Type: Article

References (22)

1. See www.rxlist.com/top200.htm
2. M. Sattlegger, H. Buschmann, M. Przewosny, W. Englberger, B.-Y. Koegel and H. Schick, WO Patent 2003037873 (2003); authors provide Chem. Abstr., 138, 353845 (2003).
3. C. Kunick, Curr. Pharm. Design, 5, 181 (1999).
4. J. A. Lowe III, WO Patent 9315059 (1993); authors provide Chem. Abstr., 120, 191557 (1994).
5. J. C. Barrish, S. H. Spergel, S. Moreland, G. Grover, S. A. Hedberg, A. T. Pudzianowski, J. Z. Gougoutas and M. F. Malley, Bioorg. Med. Chem., 1, 309 (1993).
6. J. L. Peglion, J. Vian, P. Vilaine, N. Villeneuve, P. Janiak and J. P. Bidouard, EP Patent 534859 (1993); authors provide Chem. Abstr., 119, 117147 (1993).
7. T. Sato, T. Ito, H. Ishibashi and M. Ikeda, Chem. Pharm. Bull., 38, 3331 (1990).
8. D. M. Floyd, R. V. Moquin, K. S. Atwal, S. Z. Ahmed, S. H. Spergel, J. Z. Gougoutas and M. F. Malley J. Org. Chem., 55, 5572 (1990).
9. R. E. Gawley, Org. React., 35, 3-409 (1987).
10. [a] G. S. Coumbarides, J. Eames and N. Weerassooriya, J. Label. Compd. Radiopharm., 45, 917 (2002); [b] M. Mousseron, R. Jacquier and H. Christol, Bull. Soc. Chim. Fr., 346, 346 (1957).
11. [b] M. Mousseron, R. Jacquier and H. Christol, Bull. Soc. Chim. Fr., 346, 346 (1957)
12. T. Smalley, unpublished results.
13. A. B. Dounay, K. Hatanaka, J. J. Kodanko, M. Oestreich, L. E. Overman, L. A. Pfeifer and M. M. Weiss, J. Am. Chem. Soc., 125, 6261 (2003).
14. Y. Hayashi, S. Orikasa, K. Tanaka, K. Kanoh and Y. Kiso, J. Org. Chem., 65, 8402 (2000).
15. [14a] W. Cabri and I. Caudiani, Acc. Chem. Res., 28, 2 (1995);
16. [b] I. P. Beletskaya, A. V. Cheprakov, Chem. Rev., 100, 3009 (2000).
17. A. L. Searles and R. J. Kelly, J. Am. Chem. Soc., 78, 2242 (1956). The authors report the synthesis of 3,3-dimethyl-4-(methylene)-1-quinolin-2-one by an acid catalyzed cyclization of acetoacetanilides. This method was reported only to work for examples containing the dimethyl substitution pattern.
18. B. M. Choudary, S. Madhi, N. S. Chowdari, M. L. Kantam and B. Sreedhar, J. Am. Chem. Soc., 124, 14127 (2002).
19. Upon heating the reaction for 20 min in an oil bath an isolated yield of 63% was obtained for 3a.
20. L. A. Paquette, Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, New York, 1995.
21. A. Madin and L. E. Overman, Tetrahedron Lett., 33, 4859 (1992).
22. A. J. Clark and K. Jones, Tetrahedron, 48, 6875 (1992).