Amides, anhydrides, esters, and thioesters of 2-azirine-2-carboxylic acids were prepared by a rapid procedure at room temperature involving FeCl-catalyzed isomerization of 5-chloroisoxazoles to 2-azirine-2-carbonyl chlorides, followed by reaction with N-, O-, or S-nucleophiles mediated by an -substituted pyridine. With readily available chloroisoxazoles and a nucleophile, 2-picoline can be used as an inexpensive base. When a high yield of the acylation product is important, the reagent 2-(trimethylsilyl)pyridine/ethyl chloroformate is more suitable for the acylation with 2-azirine-2-carbonyl chlorides.
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| http://dx.doi.org/10.3390/molecules28010275 | DOI Listing |
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