α‐Keto Acids as Acylating Agents in the Synthesis of 2‐Substituted Benzothiazoles and Benzoselenazoles

David B. Lima, Filipe Penteado, Marcelo M. Vieira, Diego Alves, Gelson Perin, Claudio Santi, Eder J. Lenardão

European Journal of Organic Chemistry · 2017 · 44 citations · 96 references

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Abstract

Herein, we report the first decarboxylative oxidation of α‐keto acids that is promoted by sodium metabisulfite (Na 2 S 2 O 5 ) to obtain 2‐substituted benzothiazoles and benzoselenazoles. Diaryl disulfides and diselenides were used as chalcogen sources, and the desired products were obtained in moderate to excellent yields. This protocol does not require an inert gas, transition metals, or harsh reaction conditions, and CO 2 is released as an environmentally benign coproduct. The presence of Na 2 S 2 O 5 was essential to guarantee that the reaction reached completion and afforded maximum product yields.

References

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