title: An expedient and divergent tandem one-pot synthesis of pyrimidin-2,4-diones using the Blaise reaction intermediate.
abstract: A novel divergent tandem one-pot method for the synthesis of 3,5,6-trisubstituted 1H-pyrimidin-2,4-dione derivatives is developed. In the presence of 10 mol % of Cu(OAc)2, the α-substituted Blaise reaction intermediates (R(2) ≠ H) reacted with isocyanates chemoselectively to afford pyrimidin-2,4-diones, whereas the α-unsubstituted Blaise reaction intermediate (R(2) = H) showed a propensity to be a C-nucleophile toward electrophiles, permitting the installation of different functionalities at the 5-position through sequential tandem reactions.
authors.affiliation: Department of Chemistry and Nano Science, Ewha Womans University , Seoul 120-750, Korea.
authors.forename: Yu Sung
authors.initials: YS
authors.lastname: Chun
authors.forename: Zi
authors.initials: Z
authors.lastname: Xuan
authors.forename: Ju Hyun
authors.initials: JH
authors.lastname: Kim
authors.forename: Sang-gi
authors.initials: SG
authors.lastname: Lee
mesh_terms: D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D017953:Isocyanates / Q000737:chemistry*; D015394:Molecular Structure; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D017953:Isocyanates; D011744:Pyrimidinones; D003300:Copper