Fischer indole synthesis of 3-acyl- and 3-alkoxy-carbonylindoles
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 636-641
- https://doi.org/10.1039/p19810000636
Abstract
N-Benzyl-N-phenylhydrazine derivatives of 1,3-diketones and 1,3-ketoesters undergo normal Fischer cyclisations to indoles, but no method could be found for the subsequent removal of the N-protecting group. No method could be found for the indolisation of N-aroyl-N-phenylhydrazine derivatives of dimedone with retention of the N-protecting group, though heating in tetralin did effect the electrocyclic step of the Fischer sequence and the formation of a carbon–carbon bond.Keywords
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