Multicomponent synthesis of highly substituted 2-pyridones

Synlett

Volumn , Issue 2, 2007, Pages 327-329

  Neo, Ana G ^a   Carrillo, Rosa María ^a   Barriga, Susana ^a   Momán, Edelmiro ^b   Marcaccini, Stefano ^c   Marcos, Carlos F ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

^b ROYAL COLLEGE OF SURGEONS IN IRELAND   (Ireland)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Cyclisations; Drugs; Heterocycles; Multicomponent reactions; Pyridines

Indexed keywords

2 PYRIDONE DERIVATIVE; 3 FORMYL CHROMONE DERIVATIVE; CHROMONE DERIVATIVE; MILRINONE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 33847075026     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967992     Document Type: Article

References (22)

1. Dorigo, P.; Gaion, R. M.; Belluco, P.; Fraccarollo, D.; Maragno, I.; Bombieri, G.; Benetollo, F.; Mosti, L.; Orsini, F. J. Med Chem. 1993, 36, 2475.
2. Information obtained from the Investigational Drugs Database (IDDB, www.iddb3.com).
3. For recent examples, see: (a) Chen, Y. H.; Zhang, H. J.; Nan, F. J. J. Comb. Chem. 2004, 6, 684.
4. (b) Hachiya, L.; Ogura, K.; Shimizu, M. Synthesis 2004, 1349; and the references therein.
5. See, for example: (a) Fossa, P.; Menozzi, G.; Dorigo, P.; Floreani, M.; Mosti, L. Bioorg. Med. Chem. 2003, 11, 4749.
6. (b) Altomare, C.; Cellamare, S.; Summo, L.; Fossa, P.; Mosti, L.; Carotti, A. Bioorg. Med. Chem. 2000, 8, 909.
7. (c) Dorigo, P.; Fraccarollo, D.; Gaion, R. M.; Santostasi, G.; Borea, P. A.; Floreani, M.; Mosti, L.; Maragno, I. Gen. Pharmacol. 1997, 28, 781.
8. (d) Mosti, L.; Schenone, P.; Iester, M.; Dorigo, P.; Gaion, R. M.; Fraccarollo, D. Eur. J. Med. Chem. 1993, 28, 853.
9. Bossio, R.; Marcos, C. F.; Marcaccini, S.; Pepino, R. Heterocycles 1997, 45, 1589.
10. Beck, B.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2004, 6, 39.
11. (a) Marcaccini, S.; Pepino, R.; Marcos, C. F.; Polo, C.; Torroba, T. J. Heterocycl. Chem. 2000, 37, 1501.
12. (b) Bossio, R.; Marcos, C. F.; Marcaccini, S.; Pepino, R. Synthesis 1997, 1389.
13. Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synlett 2004, 2287.
14. Jeon, Y. H.; Heo, Y. S.; Kim, C. M.; Hyun, Y. L.; Lee, T. G.; Ro, S.; Cho, J. M. CMLS, Cell. Mol. Life Sci. 2005, 62, 1198.
15. 2O, yielding a product pure enough to be used in the following reaction. For analytical purposes it may be further purified by recrystallisation from EtOH.
16. 4: 443.1849; found: 443.1845.
17. 2O, yielding compound 8 in an essentially pure form.
18. 4: 482.1482; found: 482.1487.
19. 4), obtained from 4-chloroaniline and 3-formylchromone, was identical to the published data: (a) Fitton, A. O.; Frost, J. R.; Suschitzky, H. Tetrahedron Lett. 1975, 16, 2099.
20. (b) Fitton, A. O.; Frost, J. R.; Houghton, P. G.; Suschitzky, H. J. Chem. Soc., Perkin Trans. 1 1979, 1691.
21. Cristau, P.; Vors, J. P.; Zhu, J. Tetrahedron 2003, 59, 7859.
22. 4Cl were stirred in toluene for 48 h at r.t. The resulting precipitate was filtered and successively washed with i-PrOH and hexanes.