Uracils ozonolysis

Ozonolysis of organic compounds in water also has biological and environmental93 interest. Ozone preferentially attacks the base moiety of pyrimidine nucleotides in water.94 For example, the reaction of ozone with uracil in water, having no substitutent at 1-position, gave the ozonolysis products in Scheme 3.6.95 The reactions of DNA and RNA with O3 in an aqueous environment are linked to the damage of... 

Ozonolysis of cellular substances, such as uracil and thymine derivatives, is of special interest. Ozonolysis of aqueous solutions of uracils leads to ring cleavage and subsequent ring contraction forming 5-hydroxy-hydantoins (89CL723 90JOC1396) (Scheme 158). 

Matsui, M., H. Nakazumi, K. Kamiya, C. Yatome, K. Shibata, and H. Muramatsu. 1989. Ozonolysis of uracils in water. Chem. Lett. 723-724. 

The opening of the cyclopentene moiety involved the ozonolysis of the double bond and this has been used by Hon for the synthesis of alkenyl butyrolactones. This cyclopentene cycle could also be used for the palladium-catalyzed nucleophilic substitution of the C-4 of the fused lactones. By this strategy, Aggarwal described an access to carbocyclic uracil polyoxin C and the nikkomycins analogues." " ... 

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