Reactions of 9-chloro-1,10-anthraquinone 1-dichlorophosphorylimine with N- and C-nucleophiles |
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Authors: | M. V. Gorelik S. P. Titova T. Kh. Gladysheva |
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Affiliation: | (1) State Research Center of the Russian Federation “Research Institute of Organic Intermediates and Dyes”, 1 ul. B. Sadovaya, 103787 Moscow, Russian Federation |
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Abstract: | 9-Chloro-1,10-anthraquinone 1-dichlorophosphorylimine formed in the reaction of 1-amino-9,10-anthraquinone with PCl5 followed by dehydrochlorination reacts with primary amines with substitution of chlorine atoms. In the case of aliphatic amines, the reaction occurs further concurrently in two directions: the addition of the amine molecule with the formation of 9,9-di(alkylamino) derivatives of the anthrone and the substitution of hydrogen atom at position 4 with the formation of 4,9-di(alkylamino) derivatives of 1,10-anthraquinone 1-imine. In the case of aromatic amines, 1-amino-9,10-anthraquinone 9-arylimines are the end products. Reactions with the anions of CH-acids containing an alkoxycarbonyl or cyano group occur with substitution in position 9 followed by intramolecular cyclization with the formation of 2-alkoxy- or 2-amino-7H-dibenzo[f,ij]isoquinolin-7-one derivatives, respectively. For preliminary communication, see Ref. 1. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1179–1184, June, 1998. |
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Keywords: | 9-chloro-1,10-anthraquinone 1-dichlorophosphorylimine amines addition, substitution CH-acids, cyclization, 7H-dibenzo[f,ij]isoquinolin-7-ones |
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