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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| Institution: | (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-dimethoxynaphtho2,3-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-diaminonaphtho2,3-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).
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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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