(CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones

(CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones

A very simple and convenient reaction for 1,3-diketone preparation from carboxylic acids and aromatic ketones in TFAA/TfOH system is described. When the β-phenylpropionic acids were used as starting materials, they initially gave 1-indanones and then underwent further acylation with the formation of...

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Main Authors: JungKeun Kim, Elvira Shokova, Victor Tafeenko, Vladimir Kovalev
Format: Article
Language:English
Published: Beilstein-Institut 2014-09-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Claisen condensation
1,3-diketones
heterocycles
triflic acid
trifluoroacetic acid anhydride
Online Access:https://doi.org/10.3762/bjoc.10.236
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spelling doaj-6dd5065ebcd444bc8ce6462fa75525552021-02-02T00:48:44ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-09-011012270227810.3762/bjoc.10.2361860-5397-10-236(CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketonesJungKeun Kim0Elvira Shokova1Victor Tafeenko2Vladimir Kovalev3Laboratory of Macrocyclic Receptors, Department of Chemistry, Moscow State University, Lenin’s Hills, Moscow 119991, RussiaLaboratory of Macrocyclic Receptors, Department of Chemistry, Moscow State University, Lenin’s Hills, Moscow 119991, RussiaLaboratory of Macrocyclic Receptors, Department of Chemistry, Moscow State University, Lenin’s Hills, Moscow 119991, RussiaLaboratory of Macrocyclic Receptors, Department of Chemistry, Moscow State University, Lenin’s Hills, Moscow 119991, RussiaA very simple and convenient reaction for 1,3-diketone preparation from carboxylic acids and aromatic ketones in TFAA/TfOH system is described. When the β-phenylpropionic acids were used as starting materials, they initially gave 1-indanones and then underwent further acylation with the formation of 2-(β-phenylpropionyl)-1-indanones as the main reaction products. In addition, the application of the proposed protocol allowed for the synthesis of selected polysubstituted pyrazoles in a one-pot procedure directly from acids and ketones.https://doi.org/10.3762/bjoc.10.236Claisen condensation1,3-diketonesheterocyclestriflic acidtrifluoroacetic acid anhydride
collection DOAJ
language English
format Article
sources DOAJ
author JungKeun Kim
Elvira Shokova
Victor Tafeenko
Vladimir Kovalev
spellingShingle JungKeun Kim
Elvira Shokova
Victor Tafeenko
Vladimir Kovalev
(CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones
Beilstein Journal of Organic Chemistry
Claisen condensation
1,3-diketones
heterocycles
triflic acid
trifluoroacetic acid anhydride
author_facet JungKeun Kim
Elvira Shokova
Victor Tafeenko
Vladimir Kovalev
author_sort JungKeun Kim
title (CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones
title_short (CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones
title_full (CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones
title_fullStr (CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones
title_full_unstemmed (CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones
title_sort (cf3co)2o/cf3so3h-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2014-09-01
description A very simple and convenient reaction for 1,3-diketone preparation from carboxylic acids and aromatic ketones in TFAA/TfOH system is described. When the β-phenylpropionic acids were used as starting materials, they initially gave 1-indanones and then underwent further acylation with the formation of 2-(β-phenylpropionyl)-1-indanones as the main reaction products. In addition, the application of the proposed protocol allowed for the synthesis of selected polysubstituted pyrazoles in a one-pot procedure directly from acids and ketones.
topic Claisen condensation
1,3-diketones
heterocycles
triflic acid
trifluoroacetic acid anhydride
url https://doi.org/10.3762/bjoc.10.236
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AT elvirashokova cf3co2ocf3so3hmediatedsynthesisof13diketonesfromcarboxylicacidsandaromaticketones
AT victortafeenko cf3co2ocf3so3hmediatedsynthesisof13diketonesfromcarboxylicacidsandaromaticketones
AT vladimirkovalev cf3co2ocf3so3hmediatedsynthesisof13diketonesfromcarboxylicacidsandaromaticketones
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