A simple and efficient method for the synthesis of 5,6-dihydropyrazin-2(1H)-one O-(tert-butyl)oximes, quinoxalin-2(1H)-one O-(tert-butyl)oximes and its derivatives

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A simple and efficient method was developed for the synthesis of 5,6-dihydropyrazin-2(1H)-one O-(tert-butyl)oximes, quinoxalin-2(1H)-one O-(tert-butyl)oximes and its derivatives from N-tert-butoxy acyl imidoyl bromide and diamines. Twenty three novel compounds were readily synthesized using this procedure in excellent yields. The products possessed Z-stereochemistry with regard to the CN double bond. In these reactions, the amino group first attacked an imidoyl carbon of the N-tert-butoxy acyl imidoyl bromide in order to obtain the Z-intermediate; then another amino group attacked the carbonyl carbon of the intermediate. The rate of intramolecular cyclization of the intermediate was dependent on the position of the diamino groups.