Synthesis of fused dihydropyrano(furano)pyridines via [4 + 2]-cycloaddition of 5-alkenoxy substituted oxazoles

Organic Letters

Volumn 14, Issue 6, 2012, Pages 1604-1607

  Goodman, Steven N ^a   Mans, Douglas M ^a   Sisko, Joseph ^a   Yin, Hao ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; OXAZOLE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

AMINO ACIDS; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; OXAZOLES; PYRIDINES;

EID: 84858651718     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300351v     Document Type: Article

References (15)

1. Kiyoto, T., Ando, J., Tanaka, T., Tsutsui, Y., Yokotani, M., Noguchi, T., Ushiyama, F., Urabe, H., and Horikiri, H. WO2007138974A1, 2007.
2. Brooks, G., Giordano, I., Hennessy, A. J., and Pearson, N. D. WO2007122258A1, 2007.
3. Kozikowski, A. P.; Hasan, N. M. J. Org. Chem. 1977, 42, 2039
4. Levin, J. I.; Weinreb, S. M. J. Am. Chem. Soc. 1983, 105, 1397
5. Levin, J. I.; Weinreb, S. M. J. Org. Chem. 1984, 49, 4325
6. Subramanyam, C.; Noguchi, M.; Weinreb, S. M. J. Org. Chem. 1989, 54, 5580
7. Levin, J. I.; Laakso, L. M., Oxazoles: Synthesis, Reactivity, and Spectroscopy; Palmer, D. C., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2003; Vol. 60, Chapter 3, pp 417.
8. Karpeiskii, M. Y.; Florent'ev, V. L. Russ. Chem. Rev. 1969, 38, 540
9. We are aware of only one failed report concerning oxazole cycloadditions involving substrates with the dienophile tether being incoroporated at the 5-alkoxy position; see: Padwa, A.; Cohen, L. A. J. Org. Chem. 1984, 49, 399
10. Thalhammer, A.; Mecinovic, J.; Schofield, C. J. Tetrahedron Lett. 2009, 50, 1045
11. Maeda, I.; Takehara, M.; Togo, K.; Asai, S.; Yoshida, R. Bull. Chem. Soc. Jpn. 1969, 42, 1435
12. Han, W.; Egberton, M.; Wai, J.; Zhuang, L.; Ruzek, R. D.; Perlow, D.; Isaacs, R. C.; Cameron, M.; Foster, B.; Dolling, U. H.; Hoerrner, R.; Obligado, V. E.; Neilson, L. A.; Kim, B.; Payne, L. S.; Morrisette, M. M.; Williams, P. D.; Pye, P. J.; Angelaud, R.; Mancheno, D. E.; Askin, D. WO2005087768, 2005.
13. Kondrat'eva, G. Y Khim. Nauka Prom. 1957, 2, 666
14. Kondrat'eva, G. Y. Chem. Abstr. 1958, 52, 6345
15. Lakhan, R.; Ternai, B. Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J., Eds.; Academic Press: New York, NY, 1974; Vol. 17, Chapter 4, p 100.