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6. Regiospecific Synthesis of Mono-N-substituted Indolopyrrolocarbazoles

Author

Frohner, W., Monse, B., Braxmeier, T. M., Casiraghi, L., Sahagun, H., and Seneci, P.

Abstract

Two complementary and efficient strategies have been developed for the regiospecific synthesis of unsymmetrical indolopyrrolocarbazoles (IPCs) mono-N-substituted with a pentacycle. A halogen in position 2 of the intermediate bisindolylmaleimides 3a−e allows a selective Mitsunobu coupling by exploiting the increased acidity of the 2-chloro-substituted indole nitrogen. It also promotes an easier cyclization of bisindolylmaleimides 4a−e and 7b−e to IPCs. Alkylation of the 2-unsubstituted indole-3-carboxamides 2a,b and further processing to the corresponding IPCs gives access to the opposite regioisomers.

Published
2005

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