A General Approach to the Synthesis of 1,6-, 1,7-, and 1,8-Naphthyridines

Journal of Organic Chemistry

Volumn 55, Issue 15, 1990, Pages 4744-4750

  Turner, James A ^a  

^a Discovery Research Group   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001032752     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00302a049     Document Type: Article

References (30)

1. Presented in part at the 10th International Congress of Heterocyclic Chemistry; August, 1985; Waterloo. Ontario.
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4. A notable exception is the series of pyridonecarboxylic acid antibiotics related to nalidixic acid. For leading references see: (a) Parikh, V. D.; Fray, A. H.; Kleinman, E. F. J. Heterocycl. Chem. 1988, 25, 1567.
5. Miyamoto, T.; Egawa, H.; Shibamori, K.; Matsumoto, J. J. Heterocycl. Chem. 1987, 24, 1333.
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8. U. S. Patent 4.536, 208. 1985.
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10. For a successful example of the use of this approach for preparation of 1,5-naphthyridine see: Hamada, Y.; Takeuchi, I. Chem. Pharm. Bull. 1971, 19, 1857.
11. This approach is technically equivalent to the Friedlander synthesis of quinolines. For a recent review see: Cheng, C.C.; Yan, S. J. Org. React. 1982. 28. 37.
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17. An apparently improved procedure for ortho lithiation of 3-(pivaloylamino)pyridine has recently been reported: Estel, L.; Linard, F.; Marsais, F.: Godard, A.; Queguiner, G. J. Heterocycl. Chem. 1989, 26,105.
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19. Similar treatment of nicotinaldehyde 2a with 1 mol equiv of tert-butyl lithioacetate gave a 3:2 mixture of β-hydroxy ester 10a and starting aldehyde (NMR analysis).
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