N-Aminopyridinium誘導体の反応(第11報) : N-Benzylideneamino Pyridinium塩誘導体とシアニドイオンとの反応 : 5-Aminooxazole誘導体の新合成法

概要

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N-Benzylideneaminopyridinium salt (II), prepared from N-aminopyridinium salt (I) and an aromatic aldehyde, was reacted with potassium cyanide in aqueous solution to afford a novel compound, "iminonitrile" (III). III is labile and is converted to the nitrile (IV) by dehydrocyanation. II was partly hydrolysed by potassium cyanide in less than equimolar amount to the aldehyde which, when further reacted with III, produced competitively 2,4-diaryl-5-aminooxazole (V) and its arylidene derivative (VI), together with main products, III and IV. III was isolated from the reaction mixture in a good yield, and reacted with an appropriate aromatic aldehyde in organic solvent to produce V and VI in a good yield, or with an aliphatic aldehyde to produce 2,4-disubstituted 5-oxazolone (VII). These procedures offer a simple and convenient route to a wide variety of compounds of V, VI, and VII series.
社団法人日本薬学会の論文
1971-08-25