Convenient synthesis of N1-substituted orotic acid derivatives

Abstract

A convenient and efficient method for the synthesis of N1-substituted orotic acid derivatives is reported. The synthetic route utilizes substituted maleimide as synthetic intermediate and takes only four simple steps from readily available starting materials. As a result, orotic acid derivatives with various alkyl and aromatic groups at N1 can be readily synthesized.

Reductive debromination of 1,2-dibromides with anisidines

“…10 The method starts with the reaction of an amine (e.g., aniline, benzyl amine, or cyclohexyl amine) with a mixture of cis - and trans -2,3-dibromosuccinimide (1) in THF at room temperature to yield 2-arylaminoaminomaleimide (2) via a tandem dehydrobromination-conjugate addition-elimination mechanism, as shown in Scheme 1.…”