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Interest in hydroxyindoles is determined by their role in biochemistry [1][2][3][4]. In the last time, investigations on the preparation of these heterocycles have been developing intensively. One of the main methods of synthesizing hydroxyindoles is the oxidation of 2,3-dihydroindoles, obtained by the reduction of the corresponding indoles [1]. One further direct method of synthesis of 1-hydroxyindoles [4] is the reductive cyclization of 2-nitrophenylketone [5], 2-nitrostyrene [6], and 2-cyano-2-(2-nitrophenyl)acetate [7] derivatives. There is not much information in the literature on the synthesis of substituted indole-5,6-dicarbo-nitriles [8][9][10], and data on the synthesis of 2-amino-1-hydroxy-1H-indole-5,6-dicarbonitriles are in altogether absent.The aim of the present work was the synthesis of 2-amino-1-hydroxy-1H-indole-5,6-dicarbonitriles by the reductive cyclization of products of C-nucleophilic substitution of the bromine atom in 4-bromo-5-nitrophthalonitrile (1) (BNPN) with the sodium salts of 3-hydroxy-2-(4-R-phenyl)but-2-enenitriles 2a-d. The characteristic special features of the chosen highly reactive substrate 1 in S N Ar reactions were considered in [11][12][13][14][15]. It should be mentioned that the substituted ortho-dicarbonitriles are promising for obtaining hexazocyclanes [16], phthalocyanines [17,18] and a series of other compounds containing anhydride, imide, isoindoline, and tetrazole fragments.2-Amino-1-hydroxyindoles are obtained by the reductive cyclization of ortho-nitrobenzyl cyanides [7], therefore in the first stage of the investigation it was necessary for us to develop a method of synthesis of substituted 4-cyanomethyl-5-nitrophthalonitriles based on BNPN. The direct method of obtaining such

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Synthesis of Substituted Indazole-5,6-dicarbonitriles. -Two different approaches to previously unknown indazole-5,6-dicarbonitriles are developed. -(CHIRKOVA, Z. V.; SHARUNOV, V. S.; FILIMONOV*, S. I.; ABRAMOV, I. G.; FIRGANG, S. I.; STASHINA, G. A.; Russ. J. Org. Chem. 48 (2012) 12, 1557-1560, http://dx.