Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-][1,3]dioxoles.

A method for the synthesis of fused 1,3-dioxolanes was developed by self-condensation of glyoxal generated by oxidation of acetophenones with SeO in the presence of trifluoroacetic acid. Three molecules of the glyoxal generated by oxidation of ketone with SeO condensed to form architecturally novel oxygen-containing heterocycles (3a-aryldihydro-[1,3]dioxolo[4,5-][1,3] dioxole-2,5-diyl)bis(phenylmethanones). This reaction provides a unique methodology for the construction of four C-O bonds in a concerted fashion, generating highly embedded oxygen heterocycles from readily available ketones using affordable shelf reagents and simple reaction conditions.

PTSA-Catalyzed Reaction of Alkyl/Aryl Methyl Ketones with Aliphatic Alcohols in the Presence of Selenium Dioxide: A Protocol for the Generation of an α-Ketoacetals Library.

A novel approach has been developed for the synthesis of a wide range of α-ketoacetals by the reaction of alkyl/aryl methyl ketones and aliphatic alcohols in the presence of selenium dioxide catalyzed by -toluenesufonic acid. This method represents a general route to obtain a wide variety of α-ketoacetals in a simple, rapid, and practical manner. This approach is particularly attractive because of the easy availability of the starting materials, mild reaction temperature, and good yields of the products.

Selenium Dioxide As an Alternative Reagent for the Direct α-Selenoamidation of Aryl Methyl Ketones.

A general strategy for the preparation of N, N-dialkyl-2-oxo-2-arylethaneselenoamides is described. The single step method involves direct coupling of aryl methyl ketones with secondary amines and selenium dioxide in DMSO. The reactions proceeded smoothly at room temperature to provide a number of the α-oxo-selenoamides in good to excellent yields.