An efficient alternative route to 3,6-disubstituted-furo[2,3-d]pyrimidin-2-one analogues.
Copper(I)-catalyzed 5-endo-dig cyclizations of 5-(alkyn-1-yl)uracil derivatives had given poor yields of substituted furo[2,3-d]pyrimidin-2-ones unless the uracil ring was substituted at N1 with alkyl or glycosyl groups. This limited flexibility for the synthesis of analogues with varied substituents at N3 and/or C6 of the furo[2,3-d]pyrimidin-2-one core has been overcome with 5-(3-hydroxyalkyn-1-yl)uracil compounds with no substituent at N1. Manipulation of the side-chain hydroxyl group gives access to additional furo[2,3-d]pyrinmidin-2-one analogues.
Janeba
Zlatko
Z
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Maklad
Noha
N
Robins
Morris J
MJ
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D014498:Uracil / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
D011744:Pyrimidinones; D014498:Uracil; D003300:Copper