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A series of 3(2)-phosphonylated thiazolo[3,2- a ]oxopyrimidines was synthesized for the first time by the reactions of chloroethynylphosphonates with unsubstituted and 5(6)-substituted 2-thiouracils. The reaction of chloroethynylphosphonates with 6-substituted 2-thiouracils bearing electron-donor groups (CH 3 , Ph) proceeded with high regioselectivity involving the cyclization through the N 3 -nitrogen atom to form new 3-phosphonylated thiazolo[3,2- a ]-5-oxopyrimidines with good yield. In the case of unsubstituted and 5-methyl-2-thiouracils, cyclization occurred predominantly through the N 1 atom and partially via the N 3 -nitrogen atom to form a mixture of the corresponding thiazolo[3,2- a ]-7- and 5-oxopyrimidines. A dramatic change in the reaction regioselectivity was observed in the case of 6-trifluoromethyl-2-thiouracil that afforded 2- and 3-phosphonylated 5-oxothiazolopyrimidines in a 1:1 ratio.

Synthesis of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines