American Chemical Society
ol502783j_si_002.pdf (4.88 MB)

Brønsted Acid Mediated Alkenylation and Copper-Catalyzed Aerobic Oxidative Ring Expansion/Intramolecular Electrophilic Substitution of Indoles with Propargyl Alcohols: A Novel One-Pot Approach to Cyclopenta[c]quinolines

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journal contribution
posted on 2014-12-05, 00:00 authored by G. Gangadhararao, Anasuyamma Uruvakilli, K. C. Kumara Swamy
Copper-catalyzed oxidative ring-expansion/intramolecular electrophilic substitution of 3-dienylindoles leading to cyclo­penta­[c]­quinolines and 3-indenyl­indoles under aerobic conditions is described. The precursors, 3-dienylindoles, are formed via Friedel–Crafts alkenylation followed by isomerization reactions of 2-substituted indoles with tertiary propargyl alcohols under Brønsted acid mediation. The methyl (sp3-C) group present in the propargyl alcohol becomes a part of a six-membered ring in the final ring-expansion products, the cyclo­penta­[c]­quinolines which are fluorescence active. Based on these observations, a novel one-pot strategy for ring expansion from indole to cyclo­penta­[c]­quinoline is discovered.