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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 2
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Original Articles

Tetra-n-butylammonium Fluoride–Catalyzed Eschenmoser–Claisen [3,3]-Sigmatropic Rearrangement

, , , &
Pages 332-341 | Received 09 Mar 2008, Published online: 22 Dec 2008
 

Abstract

Condensation of dibenzofuran and dibenzothiophene carboxaldehydes with various aryl acetic acids followed by esterification of the acid intermediate afforded the 2,3-diaryl acrylates in good overall yields. Reduction of the esters with diisobutylaluminium hydride afforded the allylic alcohols, which underwent a smooth Eschenmoser–Claisen [3,3]-sigmatropic rearrangement on exposure to N,N-dimethylacetamide dimethylacetal in the presence of tetra n-butylammonium fluoride as catalyst to give 3,4-diaryl γ,δ-unstaturated amides in excellent yields.

ACKNOWLEDGMENTS

The authors thank Glenmark Pharmaceuticals Limited for granting permission to carry out the present research work.

Notes

a All reactions were carried out at reflux temperature of the solvents specified in the table.

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