Practical Method for the Preparation of 2,2-Dimethyl-5-{aryl[(hetero)aryl]methyl}-1,3-dioxane-4,6-diones: Synthesis and Mechanistic Study

Ewelina Najda; Anna Zakaszewska; Karolina Janikowska; Sławomir Makowiec

doi:10.1055/s-0035-1561656

Synthesis, Table of Contents

Synthesis 2016; 48(20): 3589-3596
DOI: 10.1055/s-0035-1561656

paper

Practical Method for the Preparation of 2,2-Dimethyl-5-{aryl[(hetero)aryl]methyl}-1,3-dioxane-4,6-diones: Synthesis and Mechanistic Study

Ewelina Najda

Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland Email: mak@pg.gda.pl

,

Anna Zakaszewska

Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland Email: mak@pg.gda.pl

,

Karolina Janikowska*

Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland Email: mak@pg.gda.pl

,

Sławomir Makowiec*

Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland Email: mak@pg.gda.pl

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Abstract

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Abstract

An efficient practical synthetic procedure has been developed for the synthesis of 2,2-dimethyl-5-{aryl[(hetero)aryl]methyl}-1,3-dioxane-4,6-diones through Friedel–Crafts alkylation. The scope and limitation of the reaction of 2,2-dimethyl-5-arylidene-1,3-dioxane-4,6-diones with π-excess aromatic systems have been delineated.

Key words

heterocycles - indoles - pyrroles - electrophilic aromatic substitution - Lewis acids

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References

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