Tetrahedron

Ring D modifications of ellipticine. Part 2. Chlorination of ellipticine via its N-oxide and synthesis and selective acetylation of 5, 6, 11-trimethyl-5H-benzo [b] carbazole.

AT Boogaard, UK Pandit, GJ Koomen

Index: Boogaard, Adrian T.; Pandit, Upendra K.; Koomen, Gerrit-Jan Tetrahedron, 1994 , vol. 50, # 16 p. 4811 - 4828

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Citation Number: 27

Abstract

The N-oxide of ellipticine can be used for the introduction of a chlorine atom at carbon-3 of the ellipticine nucleus. According to model studies with 5, 8-dimethylisoquinoline-N-oxide the reaction is guided both by steric hindrance and by nitrogen-6 of the ellipticine system. Attempted nucleophilic substitution reactions of 3-chloro-ellipticines failed. The high cytostatic activity observed for 9-acetylellipticine stimulated us to prepare the ...