Site reactivity of indole derivatives with pentachloropyridine

Abstract

The reaction of pentachloropyridine with indoles and bis(indolyl)methanes (BIMs) were investigated. Indoles in basic medium exclusively react with pentachloropyridine to give the corresponding N-perhalopyridine substituted indoles. Furthermore, BIMs in reaction with pentachloropyridine gave N-perfluoropyridinated BIMs and N,N´-bis(perfluoropyridyl) bis(indolyl)methane derivatives, as major and minor products, respectively. The structures of all the compounds were confirmed by elemental analysis, IR, ¹H NMR and ¹³C NMR spectroscopy.

Graphical Abstract

Keywords:

• Pentachloropyridine
• Indole
• Bis(indolyl)methanes
• Heterocycle
• Nucleophilic substitution

Acknowledgements

We are grateful to the research council of the Vali-e-Asr University of Rafsanjan for financial support of this work.