Syntheses of Nitrogen-containing Heterocyclic Compounds. XLII. The Reissert Reaction of 1, 6-Naphthyridines

HAMADA YOSHIKI, SHIGEMURA KENTARO

doi:10.1248/yakushi1947.99.10_982

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Other Title

含窒素複素環化合物の合成研究(第42報)1,6-Naphthyridine類のReissert反応について
含窒素複素環化合物の合成研究-42-I,6-Naphthyridine類のReissert反応について
ガンチッソフクソカンカゴウブツノゴウセイケンキュウ 42 I 6

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Description

The Reissert reaction of 1, 6-naphthyridine (I) was carried out by the use of triethylbenzylammonium chloride as the phase transfer catalyst. When aliphatic chloride (RCOCl : R=CH₃, C₂H₅, C₃H₇) was used, the products were the Reissert compounds (IV, V, VI) and 2-(2-acylaminovinyl)-α-acyl-3-pyridineacetonitriles (VII, VIII, IX), while the use of benzoyl chloride gave only the Reissert compound X. Alkaline hydrolysis of VII, VIII, and IX gave I. As a proof of the formation mechanism of I from VII, VIII, and IX, VII was reduced with sodium borohydride to 2-(2-acetamidovinyl)-3-pyridinemethanol (XII) and its acetylation gave 2-(2-acetamidovinyl)-3-pyridinemethyl acetate (XIII). Alkaline hydrolysis of the pseudo-base III gave I. As a proof of the formation mechanism of VII, VIII, and IX, III was submitted to the Reissert reaction over a long period and 2-(2-benzoylaminovinyl)-α-benzoyl-3-pyridineacetonitrile (XIV) was obtained. The Reissert reaction of 4, 7-phenanthroline (XVII) gave the Reissert compound XVIII.

Journal

YAKUGAKU ZASSHI

YAKUGAKU ZASSHI 99 (10), 982-988, 1979

The Pharmaceutical Society of Japan

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