Heterocyclic analogs of 5,12-naphthacenequinone 9*. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-<Emphasis Type="Italic">f</Emphasis>]isatin-5,10-diones |
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Authors: | A N Nikitina A E Shchekotikhin Y N Luzikov A M Korolev V N Buyanov M N Preobrazhenskaya |
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Institution: | (1) G. F. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, 11 B. Pirogovskaya St., Moscow, 119021, Russia;(2) D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow, 125047, Russia;; |
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Abstract: | A preparative method has been developed for N-alkyl 4,11-dimethoxynaphtho2,3-f]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding
derivatives at position 3. An efficient method has been discovered for the demethylation of the N-alkyl-4,11-dimethoxynaphtho2,3-f]isatin-5,10-diones to give a high yield of N-substituted 4,11-dihydroxynaphtho2,3-f]isatin-5,10-diones. Successive halogenation using phosphorus penta-chloride and acylation of tert-butylamine by the intermediate
2-chloro derivative converted 4,11-di-methoxynaphtho2,3-f]isatin-5,10-dione to the 2-amino-3H-naphtho2,3-f]indole-3,5,10-trione derivative. |
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