Preparation of trifluoromethylated dihydrocoumarins, indanones, and arylpropanoic acids by tandem superacidic activation of 2-(trifluoromethyl)acrylic acid with arenes.

doi:10.1021/jo9026275

Paper

Preparation of trifluoromethylated dihydrocoumarins, indanones, and arylpropanoic acids by tandem superacidic activation of 2-(trifluoromethyl)acrylic acid with arenes.

Published Mar 10, 2010 · G. Prakash, F. Paknia, Habiba Vaghoo

The Journal of organic chemistry

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37

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Abstract

Indanones and coumarins are important intermediates for the convenient synthesis of many pharmaceutical and biologically active compounds. Fluoroorganics play a vital role in the design of very effective therapeutics due to significant enhancenment in their lipophilicity, bioavailability, and fast uptake by the presence of fluorine in these molecules. Herein, we report an efficient one-pot synthesis of trifluoromethylated arylpropanoic acids, indanones, and dihydrocoumarins using Friedel-Crafts alkylation or tandem Friedel-Crafts alkylation-cycloacylation of arenes/phenols with 2-(trifluoromethyl)acrylic acid under superacidic conditions using trifluoromethanesulfonic acid. The results have been rationalized by the structure energy calculations of the involved reaction intermediates using ab initio theoretical methods.

Study Snapshot

This study presents an efficient one-pot synthesis of trifluoromethylated arylpropanoic acids, indanones, and dihydrocoumarins using Friedel-Crafts alkylation or tandem Friedel-Crafts alkylation-cycloacylation of arenes/

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Preparation of trifluoromethylated dihydrocoumarins, indanones, and arylpropanoic acids by tandem superacidic activation of 2-(trifluoromethyl)acrylic acid with arenes.

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References

Citations

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Rhodium(III)-catalyzed synthesis of 3-trifluoromethylindanone derivatives from N-methoxybenzamides provides an efficient, straightforward route for the synthesis of these compounds.

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