Studies on the chemical synthesis of potential antimetabolites. XXV. Synthesis of (.+-.)-isowillardiine by application of a four-component condensation involving 2-picolylamine 1-oxide and 2-picolyl isocyanide 1-oxide.

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3-(2-Amino-2-carboxyethyl)uracil (racemic isowillardiine) was synthesized by the use of a four-component (aldehyde, amine, isocyanide, and carboxylic acid) condensation as the key reaction. Thus, 1-(2-picolyl 1-oxide)-3-(formylmethyl) uracil was allowed to react with 2-picolylamine 1-oxide and cyclohexyl isocyanide or 2-picolyl isocyanide 1-oxide in the presence of acetic acid in methanol to afford the corresponding condensation product, which after deblocking, gave (±)-isowillardiine in fair yield.

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