A directive effect of heterofunctions in cyclocondensation reactions of acetylenylquinones with hydrazine

The heterocycle formed in the cyclocondensation reactions of 2-acetylenyl-1-chloro-9,10-anthraquinones or 5-acetylenyl-3-diethylamino-1,4-naphthoquinones with NH₂NH₂ is influenced by the presence of a heterofunction, e.g. a hydroxyl group, in the acetylenic substituent; this directive effect was used for the synthesis of naphtho[2,3-h]cinnoline-4,7,12-trione and 4H-naphtho[1,8-cd]-1,2- diazepin-8-one derivatives.