An efficient alternative route to 3,6-disubstituted-furo[2,3-d]pyrimidin-2-one analogues |
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Institution: | Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA. |
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Abstract: | Copper(I)-catalyzed 5-endo-dig cyclizations of 5-(alkyn-1-yl)uracil derivatives had given poor yields of substituted furo2,3-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 furo2,3-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 furo2,3-d]pyrinmidin-2-one analogues. |
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