1979 Volume 99 Issue 10 Pages 982-988
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.
