Keteneおよびその誘導体の研究(第40報) : N-Ethylideneisopropylamine, N-Methylenecyclohexylamine, およびN-Methylene-tert-butylamineとDiketeneとの反応

概要

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Reaction of N-ethylideneisopropylamine (Id) with diketene at room temperature results in the formation of N, N'-diisopropyl-5-hydroxy-3,5-dimethyl-1-oxocyclohexane-2,4-dicarboxamide (VII). If this reaction is carried out at-5° to 0°, N, N'-diisopropyl-2,4-diacetyl-3-methylglutaramide (Vd) is formed. Treatment of VII and Vd with conc. hydrochloric acid results in their transition to N, N'-diisopropyl-3,5-dimethyl-1-oxo-2-cyclohexene-4,6-dicarboxamide (VIII) whose catalytic reduction over palladium-carbon gives N, N'-diisopropyl-3,5-dimethyl-1-oxocyclohexane-2,4-dicarboxamide (IX). Treatment of Vd with ammonia gives N, N'-diisopropyl-2,4,6-trimethylpyridine-3,5-dicarboxamide (VId). VII is also obtained on treatment of Vd with triethylamine. Reaction of N-methylenecyclohexylamine (IB) and N-methylene-tert-butylamine (Ic) with diketene respectively affords N, N'-dicvclohexyl- (Vb) and N, N'-di-tert-butyl-2,4-diacetylglutaramide (Vc), and treatment of Vb and Vc each with ammonia results in their respective transition to N, N'-dicyclohexyl-(VIb) and N, N'-di-tert-butyl-2,6-dimethyl-3,5-dicarboxamide (VIc).
社団法人日本薬学会の論文
1970-11-25