Regio- and stereoselective modification of cytosine with cyanopropargylic alcohols

摘要

Cyanopropargylic alcohols (4-hydroxyalk-2-ynenitriles) add cytosine at the triple bond under mild conditions (3-5 mol K2CO3, DMF, 20-25 degrees C, 2-3 h) to afford regio- and stereoselectively the Michael adducts, (Z)-3-4-amino-2-oxo-1(2H)-pyrimidinyl-4-hydroxy-4-alkylalk-2-enenitriles, in 80-88 yield.