title: Switching between reaction pathways by an alcohol cosolvent effect: SmI2-ethylene glycol vs SmI2-H2O mediated synthesis of uracils.
abstract: A chemoselective switch between reaction pathways by an alcohol cosolvent effect in a general SmI2-mediated synthesis of uracil derivatives is described. The method relies on the use of coordinating solvents to increase the redox potential of Sm(II) and results in a chemoselective 1,2-reduction (SmI2-H2O) or 1,2-migration via in situ generated N-acyliminium ions (SmI2-ethylene glycol, EG). This work exploits the mild conditions of the SmI2-mediated monoreduction of barbituric acids and offers an attractive protocol for the synthesis of uracil derivatives with biological activity from readily accessible building blocks.
authors.affiliation: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors.forename: Michal
authors.initials: M
authors.lastname: Szostak
authors.forename: Malcolm
authors.initials: M
authors.lastname: Spain
authors.forename: Brice
authors.initials: B
authors.lastname: Sautier
authors.forename: David J
authors.initials: DJ
authors.lastname: Procter
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001463:Barbiturates / Q000737:chemistry*; D019855:Ethylene Glycol / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D007477:Ions / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012493:Samarium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D014498:Uracil / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000438:Alcohols; D001463:Barbiturates; D007454:Iodides; D007477:Ions; D012997:Solvents; D012493:Samarium; D014498:Uracil; D019855:Ethylene Glycol; C032232:barbituric acid