Facile Synthesis of Imidazoisoindolones and Quinoxalinediones from 2,3-diamino-1,4-naphthoquinone

Abstract

In aqueous acetic acid, 2,3-diamino-1,4-naphthoquinone reacted with phthalic anhydride and 4,5,6,7-tetrabromophthalic anhydride to give naphtho[2’,3’:4,5]imidazo[2,1- a]isoindole-6,11,13-triones. In the same solvent, the reaction of diaminonaphthoquinone with 2,2-dihydroxy-1 H-indene-1,3(2 H)-dione gave 11 H-benzo[ g]indeno [1,2- b]quinoxaline-6,11,13-trione. Under the same conditions, diaminonaphthoquinone reacted with succinic anhydride and with maleic anhydride, the corresponding 4-(3-amino-1,4-dioxo-1,4-dihydronaphthalene-2-ylamino)-4-oxobutanoic acid and 3,5,10-trioxo-3,4,5,10-tetrahydrobenzo[ g]-quinoxaline-2(1 H)-ylidene-acetic acid derivatives were obtained. The reaction of 2,3-diamino-1,4-naphthoquinone with ( E)-1,2-dibenzoylethylene and 1,4-diphenylbut-2-yne-1,4-dione in aqueous acetic acid afforded dihydrobenzo[ g]quinoxaline-5,10-diones.