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Synlett 2006(3): 0379-0382
DOI: 10.1055/s-2006-926229
DOI: 10.1055/s-2006-926229
LETTER
© Georg Thieme Verlag Stuttgart · New York
A One-Pot Method for the Synthesis of Naphthyridines via Modified Friedländer Reaction
Weitere Informationen
Received
12 October 2005
Publikationsdatum:
06. Februar 2006 (online)
Publikationsverlauf
Publikationsdatum:
06. Februar 2006 (online)
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Abstract
A one-pot method for the preparation of 1,8-naphthyridine derivatives is reported. The method involves the dimetalation of an appropriate N-2-pyridylpivalamide or tert-butylcarbamate followed by reaction with a β-dimethylamino or β-alkoxyacrolein derivative. This method is also applicable to 1,6-naphthyridines.
Key words
pyridines - directed ortho-metalation - cyclization - naphthyridines
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References and Notes
For example, Hamada8b reported preparation of 4-methyl-1,8-naphthyridine in 38% yield. We repeatedly obtained 10-17% yield following his procedure, which is consistent with the yield reported by Paudler and Kress (17%).4b