The sulfonylureas are bioactive molecules used to treat a variety of diseases from diabetes to bacterial infection. Recent identification of the inwardly-rectifying potassium channels SUR1 and SUR2 as the therapeutic target of sulfonylureas has generated new interest in this class of compounds. Examination of the physical/chemical properties of aryl sulfonylureas in our laboratories required development of new synthetic methodology. The methodology presented prepares sulfonylureas with in-situ formation of isocyanates from precursor carbamic chlorides with direct capture using sulfonamides in the presence of excess potassium carbonate in refluxing toluene. This new methodology generates sulfonyl ureas in an atom-efficient manner with identical chemical characterization to prior methods proceeding via carbamate, carbonate, or externally prepared isocyante intermediates. A manuscript describing the optimization of this synthetic strategy is in preparation.

Use of new procedure for the synthesis of sulfonylureas

ACS Spring 2022

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