Abstract
The reactions of 1-amino-2-phenylethynyl-and 2-acylethynyl-1-amino-9,10-anthraquinones with HNO2 in a mixture of dioxane and a mineral acid at 20 °C were studied. Under these conditions, 2-alkynyl-1-amino-9,10-anthraquinones, irrespective of the structure of the C=CR substituent, are cyclized into 3-substituted 1H-naphtho[2,3-glindazole-6,11-diones. The nature of the acetylenic group in the initial compound and the choice of the mineral acid determine the structure of the substitutent in position 3 of the product (1,1-dichloroalkyl or acyl) but have no effect on the regiospecificity of cyclization.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 110–114, January, 1997.
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Ivanchikova, I.D., Fedenok, L.G. & Shvartsberg, M.S. Reaction of 1-amino-2-phenylethynyl-and 2-acylethynyl-1-amino-9,10-anthraquinones with HNO2. Synthesis of 1H-3-acylnaphtho[2,3-g]indazole-6,11-diones. Russ Chem Bull 46, 105–109 (1997). https://doi.org/10.1007/BF02495357
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DOI: https://doi.org/10.1007/BF02495357