Preparative Organic Chemistry
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ChemInform Abstract: Synthetic Studies of Indoles and Related Compounds. Part 17. The Friedel-Crafts Acylation of Ethyl Pyrrole-2-carboxylate. Scope, Limitations, and Application to Synthesis of 7-Substituted Indoles.
First published: January 10, 1989
Abstract
Treatment of the ethyl pyrrole-2-carboxylate (I) with the acyl chlorides (II) under various reaction conditions results in the predominant formation of the 4-acylpyrroles (III).
ChemInform Abstract
Treatment of the ethyl pyrrole-2-carboxylate (I) with the acyl chlorides (II) under various reaction conditions results in the predominant formation of the 4-acylpyrroles (III). The tetrahydroindolone (VI), prepared from the pyrrole (I) by acylation with succinic anhydride (V) and reduction, is converted into the 7-substituted indoles (IX), (XI), and (XIV) as outlined in the reaction scheme.
