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Synthesis 2013; 45(20): 2853-2860
DOI: 10.1055/s-0033-1339651
DOI: 10.1055/s-0033-1339651
paper
Synthesis of 1,2-Diaryl-6,6-dimethyl-5,6-dihydro-1H-indole-4,7-diones from Arylglyoxals and Enamines through Domino Condensation and Allylic Hydroxylation
Further Information
Publication History
Received: 17 June 2013
Accepted after revision: 30 July 2013
Publication Date:
29 August 2013 (online)
Abstract
A series of fused pyrrole derivatives, 1,2-diaryl-7-hydroxy-6,6-dimethyl-1,5,6,7-tetrahydro-4H-indol-4-ones, have been synthesized by refluxing mixtures of enamines of 5,5-dimethyl-1,3-cyclohexadione (dimedone) and arylglyoxals in the non-nucleophilic solvent acetonitrile. These pyrrole derivatives are formed through domino condensation of the enamines and arylglyoxals followed by annulation and allylic hydroxylation. Oxidation of the pyrrole derivatives with chromium trioxide in pyridine produced the oxidized products, 1,2-diaryl-6,6-dimethyl-5,6-dihydro-1H-indole-4,7-diones, in good yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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