Abstract
This manuscript describes the convergent synthesis of aryl- and alkyl-disubstituted γ-pyrones from β-ketoacids. The reaction proceeds in the presence of trifluoromethanesulfonic anhydride via an unprecedented decarboxylative auto-condensation of the starting material. Herein, the scope and limitations of this transformation are reported.Graphical abstract
Highlights
Since their discovery in the first part of the 19th century [1], heterocyclic derivatives occupy a special place in the field of organic chemistry
This article is published with open access at Springerlink.com. This manuscript describes the convergent synthesis of aryl- and alkyl-disubstituted c-pyrones from bketoacids
During our investigations aiming to develop the potential of trifluoromethanesulfonic anhydride (Tf2O) as an electrophilic-activating reagent of unsaturated C–O bonds [21,22,23,24,25,26], we discovered that b-ketoacids can undergo an auto-condensation to form disubstituted c-pyrones
Summary
Since their discovery in the first part of the 19th century [1], heterocyclic derivatives occupy a special place in the field of organic chemistry. As a consequence of their lactonic structure, a-pyrones represent highly valuable building blocks and a rich chemistry aiming their preparation has been developed [3] Their vinologous isomers, c-pyrones, are involved in many fields of molecular sciences. During our investigations aiming to develop the potential of trifluoromethanesulfonic anhydride (Tf2O) as an electrophilic-activating reagent of unsaturated C–O bonds [21,22,23,24,25,26], we discovered that b-ketoacids can undergo an auto-condensation to form disubstituted c-pyrones This simple transformation, which we wish to present allows the obtention of alkyl- and aryl-substituted heterocycles
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