Synthesis of bicyclic pyridones via cyclocondensation of heterocyclic ketene aminals with β-Ketoester enol tosylates

Synlett

Volumn , Issue 17, 2009, Pages 2821-2824

  Yan, Sheng Jiao ^a   Niu, Yan Fei ^a   Huang, Rong ^a   Lin, Jun ^a  

^a YUNNAN UNIVERSITY   (China)

Author keywords

B keto ester enol tosylates; Cyclocondensation; Heterocyclic ketene aminals; Pyridones

Indexed keywords

BETA KETOESTER ENOL TOSYLATE; BICYCLIC PYRIDONE; HETEROCYCLIC KETENE AMINAL; KETENE DERIVATIVE; PYRIDONE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; CYCLOCONDENSATION; DRUG DESIGN; DRUG SYNTHESIS; ISOMERIZATION; MICHAEL ADDITION; POLYMERIZATION; SUBSTITUTION REACTION;

EID: 70449428169     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217984     Document Type: Article

References (18)

1. For reviews, see:, Huang Z.-T, Wang M.-X, Heterocycles 1994 37 1233, Huang Z.-T, Wang [nl]M.-X, Prog. Nat. Sci. 1999 11 971
2. Gupta A K., Ila H, Junjappa H, Synthesis 1988 284, Huang Z.-T, Liu Z.-R, Chem. Ber. 1989 122 95, Zhang J.-H, Wang M.-X, Huang Z.-T, J.
3. Jones R C. F., Patel P, Hirst S C., Turner I, Tetrahedron 1997 53 11781
4. Huang Z.-T, Liu Z.-R, Heterocycles 1986 24 2247, Jones R C. F., Patel P, Hirst S C., Smallridge M J., Tetrahedron 1998 54 6191, Jones R C. F., Smallridge M J., Tetrahedron
5. Zhang J.-H, Wang M.-X, Huang Z.-T, J.
6. Huang Z.-T, Tzai L H., Chem.
7. Liao J.-P, Zhang T, Yu C.-Y, Huang Z.-T, Synlett 2007 761
8. Yu C.-Y, Yan S.-J, Zhang T, Huang Z.-T, CN101041660 2006
9. Xu Z.-H, Jie Y.-F, Wang M.-X, Huang Z.-T, Synthesis 2002 523
10. Tieman C H., Kollmeyer W D., Roman S A., [nl]DE 2,445,421 1976, Tieman C H., Kollmeyer W D., US 3,948,934 1976, Porter P E., Kollmeyer W D., [nl] US 4,053,623 1977
11. Jordan A D., Vaidya A H., Rosenthal D I., Dubinsky B, Kordik C P., Sanfilippo P J., Wub W N., Reitza [nl]A B., Biomed.
12. Suryawanshi S N., Pandey S, Rashmirathi, Bhatt B A., Gupta S, Eur.
13. Abdelhalima M M., El-Saidib M M. T., Rabieb S T., ElmegeedaG A, Steroids 2007 72 459
14. Kubo K, Ito N, Isomura Y, Sozu I, Homma H, Murakami M, Chem. Pharm. Bull. 1979 27 1207, Frohn M J., Hong F.-T, Liu L, Lopez P, Siegmund A C., Tadesse S, Tamayo N, WO 2005070932 2005, Alonso-Alija C, Michels M, Schirok H, Schlemmer K.-H, Dodd S, Fitzgerald M, Bell J, Gill A, [nl]WO 2003053967 2003
15. Hehemann D G., Winnik W, J. Heterocycl. Chem. 1994 31 393
16. Cheng D.-C, Croft L, Abdi M, Lightfoot A, Gallagher T, Org. Lett. 2007 9 5175, Cheng D.-C, Gallagher T, Org. Lett. 2009 11 2639, Qacemi M E., Ricard L, Zard S Z., Chem. Commun. 2006 4422, Podhorez D E., J. Heterocycl. Chem. 1991 28 971, Sylvia S, Daniel S, Simon S, Zhang X, Volkhard A, Synthesis 2005 3107
17. Tilak B D., Ayyangar N R., Rao U S., Indian
18. Hansen L A., Skrydstrup T, J.