Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agents

Journal of the Brazilian Chemical Society

Norbert Haider²  Brigitte Marian¹  Thomas Nagel²  Markus Tarnai²  Katharina Tropper² 

[1] ,University of Vienna Faculty of Life Sciences Department of Pharmaceutical ChemistryVienna,Austria

关键词: carbazoles;    electrophilic substitution;    bromination;    nitration;    antitumor activity;   

DOI  :  10.5935/0103-5053.20140178

来源: SciELO

【 摘 要 】

1-Methylcarbazole-2,3-dicarboxylic acid dimethyl ester, a key intermediate in the synthesis of b-fused carbazoles, was successfully transformed into its 6-bromo and 6-nitro derivative via electrophilic substitution in acetic acid solution, using N-bromosuccinimide or urea nitrate, respectively, as reagents. With N-chlorosuccinimide, a 6,8-dichloro congener was also obtained in substantial amounts. The 6-substituted carbazolediesters were used as building blocks for the preparation of several new pyridazine- or pyrrole-fused carbazoles with basic side chains, featuring the core structure of previously developed antitumor compounds.

【 授权许可】

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