Heterocyclic analogs of 5,12-naphthacene-quinone. 3. Synthesis of 4,11-diaminonaphtho-[2,3-f]indole-5,10-dione and certain of its derivatives |
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Authors: | A. E. Shchekotikhin Yu. N. Luzikov V. N. Buyanov M. N. Preobrazhenskaya |
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Affiliation: | (1) G. F. Gauze Institute of New Antibiotics, the Russian Academy of Medical Science Moscow, 119021, Russia;(2) Russian D. I. Mendeleev University of Chemical Technology, Moscow, 125190 |
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Abstract: | ![]() Nucleophilic substitution of methoxy groups in 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione by the action of primary and secondary alkylamines, or arylamines leads to the formation of N-alkyl or N-aryl derivatives of 4,11-diaminonaphtho[2,3-f]indole-5,10-dione respectively. 4,11-Diamino-1H-naphtho-[2,3-f]indole-5,10-dione is obtained by the dealkylation of 4,11-bis[(1-phenylethyl)amino]-1Hnaphtho[ 2,3-f]indole-5,10-dione in the presence of a Lewis acid (BBr3). __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 854–861, June, 2006. |
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Keywords: | 4,11-diamino-1H-naphtho[2,3-f]indole-5,10-dione 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione dealkylation of alkylamino groups nucleophilic aromatic substitution solvatochromism |
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