| Autor: |
Mavroskoufis, Alexandros, Deckert, Samuel, Fopp, Carolin, Hertwig, Hakon, Schydlo, Jakob John, Bera, Mrinal K., Zimmer, Reinhold, Reissig, Hans-Ulrich |
| Předmět: |
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| Zdroj: |
Synthesis; Jan2025, Vol. 57 Issue 1, p125-137, 13p |
| Abstrakt: |
With the motivation to expand the compound library of specifically substituted pyrimidine derivatives, we prepared several pyrimidine-4-carbaldehydes. In most cases, the chemoselective oxidation of 4-hydroxymethyl-substituted pyrimidine derivatives could be achieved in good yields to provide the desired compounds. Alternatively, the aldehydes were prepared by Riley oxidation with selenium dioxide from the corresponding 4-methylpyrimidines. The formyl group of these compounds was employed as handle to generate alkynyl, cyano, oxazol-5-yl or β-ketoester substituents. Furthermore, two methods were found to prepare furo[3,2- d ]pyrimidines. A serendipitously discovered reaction to a 6-(pyrimidin-4-yl)furo[3,2- d ]pyrimidin-7-ol derivative involves a mechanistically interestingly 'dimerization' process with a benzoin addition as key step. Other compounds in this series contain amino, azido, or 1,2,3-triazol-1-yl groups. All these transformations to highly substituted pyrimidine derivatives demonstrate the synthetic versatility of pyrimidine-4-carbaldehydes and similar compounds. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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