Journal of the Chemical Society. Perkin transactions I p. 747 - 751 (1996)
Update date:2022-07-29
Topics:
Aitken, R. Alan
Raut, Swati V.
A series of substituted Δ2-1,2,4-oxadiazolines (4,5-dihydro-1,2,4-oxadiazoles) 12 have been prepared by 1,3-dipolar cycloaddition of nitrile oxides to imines and are found, upon treatment with KOBut, to undergo cycloreversion to give nitriles and amide anions. These can be protonated to give secondary amides or treated in situ with alkyl halides to give tertiary amides in moderate to good overall yield, although the reaction is restricted to examples with an aromatic substituent at the 5-position. The 1,4,2-dioxazoles 15, formed by cycloaddition of benzonitrile oxide to aromatic aldehydes, similarly undergo cycloreversion allowing direct conversion either into substituted benzoic acids or their methyl esters. Copyright 1996 by the Royal Society of Chemistry.
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