1-Acetylenyl-9,10-anthraquinones react with an excess of NH 2 NH 2 at 80-115°C to give a mixture of substituted 7H-dibenzo[de,h]quinolin-7-ones and anthra[9, 1-cd]-1,2-diazepin-8-ones. The latter compounds undergo reductive contraction of the seven-membered ring to give the corresponding 7H-dibenzo[de,h]quinolin-7-ones. Bulky substituents in position 2 of the initial acetylenylanthraquinones prevent the formation of the seven-membered heterocycle. A scheme of the cyclocondensation was proposed.
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