In this diploma work I present the synthesis of some 2H-pyran-2-ones and their conversion in the Diels–Alder reaction. 2H-Pyran-2-ones are aromatic organic molecules that naturally form compounds in many organisms, but in organic chemistry they are mainly very useful synthetic intermediates. Their synthesis in this work was carried out by the so-called one-pot synthesis method, in which all reactions are done without isolation of the intermediates. The products obtained by the method are pure and have rarely required further purification. The synthesized 3-benzoylamino-6-(2-thienyl)-2H-pyran-2-one was used as a diene in the Diels–Alder reaction (also known as [4+2] cycloaddition) with maleic anhydride under reflux to give the bicyclo[2.2.2.2]octene product. 5,6-Disubstituted 3-benzoylamino-2H-pyran-2-one was subjected to removal of the protecting group by hydrolysis of the amide bond. The resulting amine is not very stable, so a new protecting group using cyclopropanecarbonyl chloride was introduced. All the products synthesized were characterized by appropriate analytical methods (IR spectroscopy, TLC chromatography).
|