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Issue 0, 1967
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Naphthyridines. Part III. Tetrahydro- and decahydro-1,5-, -1,6-, -1,7-, and -1,8-naphthyridines


Decahydro-1,5-, -1,6-, -1,7-, and -1,8-naphthyridines have been prepared by reduction of the respective naphthyridines with sodium and ethanol. Reduction of 1,5-naphthyridine with platinum oxide in acid solution gave a separable mixture of trans- and cis-decahydro-1,5-naphthyridine. It was possible to distinguish between these isomers, also those of trans- and cis-decahydroquinolines and decahydroisoquinolines, by proton magnetic resonance spectroscopy. Catalytic reduction of 1,5-, 1,6-, and 1,8-naphthyridine with palladium on charcoal in ethanol gave the corresponding 1,2,3,4-tetrahydro-derivatives, but 1,7-naphthyridine gave a separable mixture 1,2,3,4-tetrahydro-(57%) and 5,6,7,8-tetrahydro-1,7-naphthyridine (43%). The structures of the tetrahydronaphthyridines were established by ionisation measurements and by ultraviolet and proton magnetic resonance spectroscopy.

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J. Chem. Soc. C, 1967, 377-383
Article type

Naphthyridines. Part III. Tetrahydro- and decahydro-1,5-, -1,6-, -1,7-, and -1,8-naphthyridines

W. L. F. Armarego, J. Chem. Soc. C, 1967, 377
DOI: 10.1039/J39670000377

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