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Paper | Regular issue | Vol 32, No. 6, 1991, pp.1199-1202
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5739
[4+2] Cycloaddition Reaction of N-Ethoxycarbonyl-2-[(1-trimethylsiloxy)vinyl]pyrrole with Acetylenic Carboxylates

Masatomi Ohno, Sadahiro Shimizu, and Shoji Eguchi*

*Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan


The title reaction resulted in the formation of functionalized indoles through rearomatization via ene reaction followed by elimination reaction or via competitive air oxidation reaction. Under an atmosphere of oxygen the latter process predominated to give majorly 7-hydroxy substituted indoles.