Abstract
Abstract Photolysis of aminated 1,4-naphthoquinones 1a–c in liquid phase was investigated. After photolysis and successive autoxidation, 2-(3-pyrrolin-1-yl)-1,4-naphthoquinone 1a gave 2-(1-pyrrolyl)-1,4-naphthoquinone 3 quantitatively. However, in the reaction, 2-(1-pyrrolydinyl)-1,4-naphthoquinone 1b and 2-(2-methoxycarbonyl-1-pyrrolidinyl)-1,4-naphthoquinone 1c afforded the corresponding hetero-ring opened products; 2-(4-oxobutylamino)-1,4-naphthoquinone 5 and 2-(4-methoxycarbonyl-4-oxobutylamino)-1,4-naphthoquinone 8 in good yields. Possible mechanisms for the formation of 3, 5, and 8 are presented.
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