Regiospecific synthesis of 4-(2-oxoalkyl)pyridines

Organic Letters

Volumn 3, Issue 18, 2001, Pages 2807-2809

  Katritzky, Alan R ^a   Zhang, Suoming ^a,c   Kurz, Thomas ^a,d   Wang, Mingyi ^a   Steel, Peter J ^b  

^a University of Florida ^*  (United States)

^b UNIVERSITY OF CANTERBURY   (New Zealand)

^c NEUROGEN CORPORATION   (United States)

^d UNIVERSITY OF HAMBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001727119     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010116f     Document Type: Article

References (15)

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2. (b) Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Comprehensive Heterocyclic Chemistry II; Pergamon Press: Oxford, 1996; Vol. 2.
3. Comins, D. L.; Brown, J. D. Tetrahedron Lett. 1984, 25, 3297.
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5. (b) Wada, M.; Nishihara, Y.; Akiba, Y. Tetrahedron Lett. 1985, 26, 3267.
6. Doering, W. von E.; McEwen, W. E. J. Am. Chem. Soc. 1951, 73, 2104.
7. (a) Katritzky, A. R.; Beltrami, H.; Keay, J. G.; Rogers, D. N.; Sammes, M. P.; Leung, C. W. F.; Lee, C. M. Angew. Chem., Int. Ed. Engl. 1979, 18, 792.
8. (b) Lee, C. M.; Sammes, M. P.; Katritzky, A. R. J. Chem. Soc., Perkin Trans. 1 1980, 2458.
9. 4. The crude products were purified by recrystallization or chromatography to afford the desired 1,4-dihydropyridines 5 in good to excellent yields.
10. (a) Toscano, R. A.; Hernadez-Galindo, M. del C.; Rosas, R.; Garcia-Mellado, O.; Portilla, F. del R.; Amabile-Cuevas, C.; Alvarez-Toledano, C. Chem. Pharm. Bull. 1997, 45, 957.
11. (b) Toscano, R. A.; Rosas, R.; Hernadez-Galindo, M. del C.; Alvarez-Toledano, C.; Garcia-Mellado, O. Transition Met. Chem. 1998, 23, 113.
12. 4. Recrystallization from hexanes-ethyl acetate afforded product 6 in 81-97% yields.
13. Anders, E.; Will, W.; Stankowiak, A. Chem. Ber. 1983, 116, 3192.
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15. Chia, W.-L.; Shiao, M.-J. Tetrahedron Lett. 1991, 32, 2033.