Synthesis of 5-Imino-1,2,4-Oxadiazolidin-3-One

Abstract

N-Aryl-N-cyanocarbamoyl chloride and N-aryl-N-carbomethoxy-cyanamide were reacted with N-alkylhydroxylamines to afford selectively 2-alkyl-4-aryl-5-imino-1,2, 4-oxazolidin-3-one and 2-alkyl-4-aryl-3-imino-1,2,4-oxadiazolidin-5-one, respectively.Those compounds with frameworks of 1,2,4-oxadiazolidine or its analogues have diverse biological activities. 1 For example, 1,2,4-oxadiazolidine-3,5-dione, embodies the backbone of herbicides such as methazole and BAS-3820. Relating to the structural modification of 1,2,4-oxadiazolidine-3,5-dione, the carbonyl group at C-3 or C-5 can be modified to an imino group. Several methods on the syntheses of 3-alkyl-(or aryl) imino-1,2,4-oxadiazolidin-5-one have been reported. 2-5 Nonetheless, the synthesis of 1,2,4-oxadiazolidin-5-one with free imino at 3-position has not yet been disclosed. 803