ケテンおよびその誘導体の研究(第36報) : Acetoacetamideおよびβ-Aminocrotonamideとアルデヒドとの反応

概要

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Reaction of acetoacetamide (III) and β-aminocrotonamide (IV) with aldehydes was examined. Treatment of III with benzaldehyde in the presence of piperidine catalyst gave α-benzylideneacetoacetamide (Va). Similarly, reaction with p-dimethylamino-, p-chloro -, o-chloro-, and p-hydroxy-benzaldehyde afforded the corresponding α-substituted arylidene compounds (Vb-e). Treatment of III or IV with benzaldehyde in the presence of ammonia produced 4-phenyl-1,4-dihydropyridine-3,5-dicarboxamide (IX) whose dehydrogenation produced 2,6-dimethyl-4-phenylpyridine-3,5-dicarboxamide (X). Treatment of IV with benzaldehyde in the presence of potassium hydroxide afforded 5-benzyl-6-methyl-2-phenyl-4(3H)-pyrimidone (XIa) in a good yield. 2,5-Disubstituted pyrimidone derivatives (XIb-i) were obtained by similar reaction of IV with p-methoxy-, p-dimethylamino-, p-chloro-, p-bromo-, and o-chlorobenza1dehyde, or with 2-thienyl-, 2-furyl-, and 2-pyridinecarboxaldehyde.
公益社団法人日本薬学会の論文
1970-05-25