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■ Synthesis of Phenanthroline and Indole Based Hybrid Cyclophane Derivatives via Ring-Closing Metathesis

Sambasivarao Kotha,* Mukesh E. Shirbhate, Ajay Kumar Chinnam, and Gaddamedi Sreevani

*Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India

Abstract

Here, we report new phenanthroline-based cyclophane derivatives via Fischer indolization and ring-closing metathesis (RCM) as key steps. Addition of Grignard reagent to 1,10-phenanthroline-2,9-dicarbaldehyde 2 and subsequent autoxidation gave the bis-alkene dione derivative 3. Further, Fischer indolization of 3 followed by RCM under mild reaction conditions gave indole and phenanthroline containing hybrid cyclophanes such as 6a and 6b.