A synthetic method of highly substituted quinolines has been developed from N-(2-alkynylaryl)enamine carboxylates under Cu-catalyzed aerobic conditions via intramolecular carbo-oxygenation of alkynes. This strategy was further applied for N-alkynylamidines for amino-oxygenation of alkynes, leading to imidazole and quinazoline derivatives.
A method for amination of aliphatic C-H bonds of N-alkylamidines is described that utilizes Cu(OAc)(2) as the catalyst in the presence of PhI(OAc)(2) and K(3)PO(4). The resulting products, dihydroimidazoles and tetrahydropyrimidines, could be converted into the corresponding diamines by hydride reduction.
A Cu-catalyzed aminoacetoxylation of N-alkenylamidines has been achieved using PhI(OAc)(2) as an oxygen source for synthesis of 4-acetoxymethyl-4,5-dihydroimidazoles, which could be further converted into 2,3-diaminopropanol derivatives using AlH(3) as a reductant.
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