Modification of conditions for the selective preparation of 2-amino-3-cyano-4-phenylpyridines

Arkivoc

Volumn 2011, Issue 2, 2011, Pages 283-296

  Alvarez Pére, Mónica ^a   Marco Contelles, José ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Bicyclic compounds; Condensation; Heterocycles; Medicinal chemistry; Pyridines

Indexed keywords

EID: 79953166482     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0012.223     Document Type: Article

References (16)

1. Samadi, A.; Marco-Contelles, J.; Soriano, E.; Álvarez- Pérez, M.; Chioua, M.; Romero, A.; González-Lafuente, L.; Gandía, L.; Roda, J. M.; G. López, M.; Villarroya, M.; García, A. G.; de los Ríos, C. Bioorg. Med. Chem. 2010, 18, 5861.
2. Goldfarb, D. S. U.S. Pat. Appl. Publ. 163 545, 2009.
3. Gangjee, A.; Zeng, Y.; McGuire, J. J.; Kisliuk, R. L. J. Med. Chem. 2002, 45, 5173.
4. Benderitter, P.; Xavier de Araujo Junior; J.; Schmitt, M.; Bourguignon, J.-J. Tetrahedron 2007, 63, 12465.
5. (a) Kambe, S.; Saito, K.; Sakurai, A.; Midorikawa, H. Synthesis 1980, 366.
6. (b) Mantri, M.; de Graaf, O.; van Veldhoven, J.; Goblyos, A.; von F. D. Künzel, J. K.; Mulder-Krieger, T.; Link, R.; de Vries, H.; Beukers, M. W.; Brussee, J.; Jzerman, A. P. J. Med. Chem. 2008, 51, 4449.
7. Papin, C.; Doisneau, G.; Beau, J.-M. Chem.-Eur J. 2009, 15, 53.
8. Vitnik, V. D. Synthetic Comm. 2009, 39, 1457.
9. TLC analysis showed many spots along the TLC plate, most part of which did not give rise to defined compounds after isolation.
10. 4/AcOH: Marco, J. L.; de los Ríos, C.; Carreiras, M. C.; Baños, J. E.; Badía, A.; Vivas, N. M. Bioorg. Med. Chem. 2001, 9, 727.
11. This mechanism is in accordance with the one proposed by Tu in a related type of reaction. See: Tu, S.; Jiang, B.; Zhang, Y.; Jia, R.; Zhang, J.; Yao, C.; Shi, F. Org. Biomol. Chem. 2007, 5, 355.
12. In general, we have observed some degree of decomposition when using the described method, especially in its one-pot version. This degree of decomposition accounts for the observed low yields. Decomposition was critical in this example and the yield of compound 15 could not be increased.
13. This analysis has been carried out by Mr. César Pastor, SIDI, Facultad de Ciencias, UAM, Madrid, Spain. Single-crystal data and CIF file of compound 15 (CCDC 763716) have been deposited at the Cambridge Crystallographic Data Centre and can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1123-336-033; or email: deposit@ccdc.ac.uk).
14. Verniest, G.; Padwa, A. Org. Lett. 2008, 10, 4379.
15. Kuthan, J. Adv. Heterocyclic Chem. 1995, 62, 20. Ethyl acetoacetate has been previously used in our group to produce substituted pyridines. See ref. 9.
16. Srivastava, S.; Batra, S.; Bhaduri, A. P. Indian J. Chem, Sect. B 1996, 35B, 602.