Abstract
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).
