SYNTHESIS OF TERMINAL 2-ALKENYL(ALKYNYL)THIO-5-CYANO-6-(p-DIMETHYLAMINOPHENYL)PYRIMIDIN-4-ONES

Functionalized pyrimidines possess a wide spectrum of biological activity. In particular, they have antitumor, antiviral, and anticonvulsant activities, exhibit anti-inflammatory and analgesic effects, and they are inhibitors of aldose reductase, SecA ATPase, azide, and plant growth. The search for methods of synthesis of new functionalized and condensed pyrimidine derivatives is an urgent problem. Alkenyl-functionalized mono- and polycyclic pyrimidines are promise substrates for studying the regioselectivity of electroph  ilic heterocyclization reactions under the influence of halogen-containing electrophilic agents, and halogen- and chalcogen-functionalized cyclization products showed high antibacterial, antifungal, and antimalarial activity. The introduction of new functional groups capable to modification into such alkenylpyrimidines can significantly affect their reactivity and change/enhance the biological activity of the halocyclization products. We proposed the synthesis of 2-alkenyl(alkynyl)thio derivatives of 5-cyano-6-(p-dimethylaminophenyl)-pyrimidin-4-one containing a cyano group labile to functionalization. As a result of alkylation of 2-thioxo-5-cyano-6-(p-dimethylaminophenyl)pyrimidin-4-one with unsaturated alkyl halides in an alkaline medium, the terminal alkenyl (allyl, methallyl) and alkynyl (propargyl) thioethers of cyanopyrimidine were obtained, promising for heterocyclization with halogen-containing electrophilic reagents . Keywords: 2-thioxo-5-cyano-pyrimidin-4-one; alkylation; alkenylthiopyrimidinone; alkynylthiopyrimidinone.