Journal of Organic Chemistry p. 1202 - 1206 (1980)
Update date:2022-08-05
Topics:
Myers, John A.
Moore, Lloyd D.
Whitter, Willie L.
Council, Samuel L.
Waldo, Rosalyn M.
et al.
A general, convenient synthesis of 2H-isoindole-4,7-diones from readily available starting materials is described. 3-Methyl-2,4-diphenyloxazolium 5-oxide, formed by dehydrative cyclization of N-methyl-N-benzoyl-C-phenylglycine, combines with 1,4-quinones to produce 2H-isoindole-4,7-diones in moderate yields.Conversion of other N-acyl amino acids to the corresponding less stable oxazolium 5-oxides in solution using 1 equiv of acetic anhydride or dicyclohexylcarbodiimide and subsequent reaction with 1,4-quinones also affords 2H-isoindole-4,7-diones.
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