Abstract
Condensation of 5-arylethynyl-3-diethylaminonaphthoquinones with NH2NH2 afford 3-benzyl-9-diethylaminobenzo[de]cinnolin-7-ones. The substituents in the phenyl ring have a pronounced effect on the reaction time and the yields of benzocinnolinones and by-products. The replacement of the arylethynyl substituent in the starting naphthoquinone by the 3-hydroxyalk-1-ynyl group leads to a change in the direction of cyclization resulting in substituted naphtho[1,8-cd]-1,2-diazepin-8-ones as condensation products.
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Ivanchikova, I.D., Myasnikova, R.N. & Shvartsberg, M.S. Cyclocondensation of 5-ethynyl-1,4-naphthoquinone derivatives with hydrazine. Russian Chemical Bulletin 50, 1668–1672 (2001). https://doi.org/10.1023/A:1013007223337
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DOI: https://doi.org/10.1023/A:1013007223337