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Synthesis 2012; 44(15): 2353-2358
DOI: 10.1055/s-0031-1290988
DOI: 10.1055/s-0031-1290988
paper
Click Reaction of Epoxides with Anthranilic Acids Using Neat Grinding To Access Benzoxazepines
Further Information
Publication History
Received: 05 March 2012
Accepted after revision: 13 June 2012
Publication Date:
04 July 2012 (online)
Abstract
An atom-economic, efficient, rapid (5 min), and highly regioselective one-pot click reaction has been developed for the synthesis of benzo[e][1,4]oxazepin-5-ones in excellent yields (78–92%). The method involves epoxide ring-opening–ring-closing cascade with anthranilic acids using neat grinding at room temperature in the presence of lithium bromide as a mild catalyst. In this procedure, pure products are obtained simply by washing the reaction mixture with warm water, thus hazardous solvents, tedious workup processes, and purification steps, such as column chromatography and recrystallization, are avoided.
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