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Synthesis and heterocyclization of z,e isomers of some nitroso group containing organophosphorus compounds

Virab Kirakosyan, Andranik Davinyan

The reaction of diethyl phosphite with isonitrosoacetoacetic eter and isonitrosoacetylacetone under the conditions of the Todd-Atherton reaction leads to obtaining mixture of Z and E isomers ethyl 3- (diethoxyphosphoryloxy)-2-nitroso-but-2-enoate and 4-(diethoxyphosphoryloxy) -2-nitroso-3-penten-2- on in 60 and 70% yield, respectively. The reaction of ethyl 3- (diethoxyphosphoryloxy) -2-nitrosobut-2- enoate with urea in the presence of sodium ethylate solution, is stirred at room temperature for 2 h, then refluxed 3 h giving 2,6-dihydroxy- 4-methyl-5-nitrosopyrimidine in 80 % yield.