77695-65-9Relevant academic research and scientific papers
Convenient synthesis of N1-substituted orotic acid derivatives
Bowler, Jeannette T.,Clausen, Caitlin R.,Blackburn, Daniel J.,Wu, Weiming
, p. 6465 - 6466 (2014/12/11)
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.
THROUGH-SPACE ELECTROSTATIC CONTROL IN A NOVEL REGIOSPECIFIC RING TRANSFORMATION OF 1,3,4-TRISUBSTITUTED MALEIMIDES
Seres, J.,Naray-Szabo, G.,Sinom, K.,Daroczi-Csuka, K.,Szilagyi, I.,Parkanyi, L.
, p. 1565 - 1570 (2007/10/02)
Ring transformation of 1-ethoxycarbonyl-3,4-disubstituted maleimide in alkaline solution yielded exclusively 1,5-disubstituted orotic acid.No hydantoin derivatives were detected.These findings can be best explained by assuming that the initial attack of the hydroxylate anion occurs at C2 and not at C5.X-ray diffraction and quantum chemical investigation indicate that stereospecificity is mainly due to through-space electrostatic effects.
