Vas'kevich A. The reaction of arylsulfenyl chlorides with S-alkenyl and S-alkynyl substituted di-, tri- and tetranitrogen-containing heterocycles

The thesis is devoted to study of chemo- and regioselectivity of the reaction of arylsulfenyl chlorides with alkenyl(alkynyl)substituted nitrogen-containing heterocyclic thioethers. It has been shown that the reaction of 2-allylthio- and 2-(2-propynylthio)pyrimidin-4(3H)-ones with arylsulfenyl chlorides in chloroform proceeds predominantly as АdЕ reaction with formation of anti-Markovnikov addition products. In polar solvents the yields of addition products go down, while the yields of products of electrophilic intramolecular cyclization increase. The addition of equimolar amount of LiClO4 in the reaction medium leads to formation of the products of electrophilic intramolecular cyclization. The reaction of cinnamylsubstituted heterocyclic substrates with ArSCl in chloroform proceeds with predominant formation of the products of intramolecular ring closure. On the base of the electrophilic intramolecular cyclization reaction with sulfenyl chlorides it has been elaborated the methods of obtaining of functionallysubstituted condensed derivatives of thieno[2,3-d]pyrimidin-4(3H)-one, quinazolin-4(3Н)-one, pyrimidin-4(3H)-one, 1,2,4-triazin-5(4Н)-one, 1,2,4-triazino[5,6-b]indole, benzimidazole.