Heterocyclic analogs of 5,12-naphthacenequinone 7. Synthesis of naphtho-[2,3-f]isatin-5,10-dione derivatives

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 44; no. 10; pp. 1245 - 1249
• Main Authors: Shchekotikhin, A. E, Luzikov, Y. N, Sinkevich, Y. B, Buyanov, V. N, Preobrazhenskaya, M. N
• Format: Journal Article
• Language: English
• Published: Boston Boston : Springer US 01.10.2008; Springer US; Springer Nature
• Subjects: 4,11-dihydroxynaphtho[2,3-f]indole-2,3,5,10-tetraone; 4,11-dimethoxynaphtho[2,3-f]indole- 5,10-dione; Chemistry; Chemistry and Materials Science; Chemistry, Organic; chlorination; demethylation; hydrolysis; Organic Chemistry; Pharmacy; Physical Sciences; Science & Technology; 4,11-dihydroxynaphtho[2,3; demethylation; 4,11-dimethoxynaphtho[2,3; indole- 5,10-dione; chlorination; indole-2,3,5,10-tetraone; hydrolysis; 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione; 4,11-dihydroxynaphtho[2,3-f]indole-2,3,5,10-tetraone
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-009-0173-2

On chlorination of 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione with sulfuryl chloride in chloroform, its mono-, di-, and trichloro derivatives are formed depending on the conditions. Hydrolysis of the di- and trichloro derivatives gives a new polycondensed derivative of isatin, 4,11-dimethoxynaphtho-[2,3-f]isatin-5,10-dione. Its demethylation occurs effectively on extended heating with HBr in acetic acid and leads to 4,11-dihydroxynaphtho[2,3-f]isatin-5,10-dione (4,11-di-hydroxynaphtho[2,3-f]indole-2,3,5,10-tetraone).