Quinone-Amine Reactions, VII: 5-Amino-2,3,4,6-tetrahydrobenzoquinoxalin-6-one

Article abstract of DOI:10.1002/ardp.19843170409

Aminolysis of 2,3-diphthalimido-1,4-naphthoquinone (15) by ethylenediamine (2) yields the title compound 7 as main product, which is also obtained from 18 and 2.In addition 2,3-diamino-1,4-naphthoquinone (17) and 2-amino-3-phthalimidoethylamino-1,4-naphthoquinone (18) are formed.Attempts to produce 7 from 5-acetylamino-2,3,4,6-tetrahydroquinoxalin-6-one (10) did not succed because in acidic solution 10 is preferentially hydrolyzed to 13 whereas in alkaline solution is dehydrogenated to 12.