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Short Paper | Special issue | Vol 93, No. 1, 2016, pp.399-405
Published online, 28th March, 2016
DOI: 10.3987/COM-15-S(T)18
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


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.