Abstract
I-Acetylenyl-9,10-anthraquinones react with an excess of NH2NH2 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 sevenmembered 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 sevenmembered heterocycle. A scheme of the cyclocondensation was proposed.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2027–2030, October, 1998.
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Shvartsberg, M.S., Ivanchikova, I.D. & Vasilevsky, S.F. A novel heterocyclization of 1-acetylenyl-9,10-anthraquinones. Russ Chem Bull 47, 1971–1974 (1998). https://doi.org/10.1007/BF02494508
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DOI: https://doi.org/10.1007/BF02494508