Volume 19, Issue 2
Heterocyclic Compounds
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ChemInform Abstract: Intramolecular Ring Closure of α,β-Unsaturated 3-Acylindoles.

J. BERGMAN

J. BERGMAN

Dep. Org. Chem., R. Inst. Technol., S-100 44 Stockholm, Swed.

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L. VENEMALM

L. VENEMALM

Dep. Org. Chem., R. Inst. Technol., S-100 44 Stockholm, Swed.

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First published: January 12, 1988

Abstract

The indole Grignard reagent (I) is coupled with the alkenoyl chlorides (II), producing the 2-alkenoylindoles (III).

ChemInform Abstract

The indole Grignard reagent (I) is coupled with the alkenoyl chlorides (II), producing the 2-alkenoylindoles (III). These are cyclized in a NaCl-AlCl3 melt to give the heterocyclic ketones (IV) or (V). Treatment of (III) with hydrochloric acid in dioxane yields a number of products as a result of various processes such as cleavage or ring closure.

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