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A Facile and Practical One-Pot Synthesis of 2-[(Methylselenyl)Methyl]Benzoic Acid

The structures of organo-selenium compounds are similar to those of organo-sulfur compounds, but they vary drastically in some of their properties. Because of the toxicity and enormously unpleasant odor of organo-selenium compounds, they have not been as well explored as could be justified. For example, organo-selenium compounds are reported as active antibacterial, antiviral, antifungal, anti-parastitic, anti-inflammatory and antihistamine agents. Recently, Liotta and his co-workers reported the use of phenyl selenide anion as the key reagent for the conversion of lactones to x-vinylcarboxylic acids. The choice of phenyl selenide anion as the ring-opening reagent seemed attractive for two reasons. First, a simple lactone possesses two sites which are potentially reactive to nucleophiles, the carbonyl carbon and the carbinolic carbon. Based on hard-soft acid-base theory, a soft nucleophile, such as phenyl selenide anion, should exhibit a preference for SN2-type attack at the carbinolic carbon and thus generate x-vinylcarboxylic acids. An ample variety of aromatic acids have been used as key intermediates for the synthesis of 1,3,4-oxadiazole rings, which occupy a key place in medicinal chemistry due to their significant biological properties, including antimicrobial, antituberculosis and anticancer activity. It is well-known that the combination of two or more types of heterocycles into one molecule may provide increased bioactivities due to the structural synergistic effect. The synthesis of 1,3,4-oxadiazoles bearing selenium requires aromatic acids containing selenium. These acids are difficult to synthesize. In the course of our current research, we developed a new process for the preparation of an aromatic acid containing selenium, namely 2-[(methylselenyl)methyl]benzoic acid, by the SN2type cleavage of 2-benzofuran-1(3H)-one with methyl selenide anion generated from dimethyl diselenide. We observed good yield and purity. Only two methods are reported for the synthesis of 2-[(methylselenyl)methyl]benzoic acid. But both the methods involved multistep protocols with expensive starting