Azines and Azoles: CXX. Synthesis of Acyclic Analogs of N1-Ribosides of Barbituric Acid and Its 5-ylidene Derivatives |
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| Authors: | Studentsov E P Kokhanovskii A N Ganina M B Nikolaeva N I Fedorova E V Moskvin A V Ivin B A |
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| Institution: | (1) St. Petersburg State Institute of Technology, St. Petersburg, Russia;(2) St. Petersburg State Chemical and Pharmaceutical Academy, St. Petersburg, Russia |
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| Abstract: | The reaction of 2,4,6-tris(trimethylsiloxy)pyrimidine with 2-oxabutane-1,4-diyl diacetate in methylene chloride in methylene chloride in the presence of SnCl4 proceeds regioselectively to form 1-(2-acetoxyethoxy)methyl]barbituric acid. The latter is readily deacetylated to a free acyclic analog of N-ribosides of barbituric acid. 1-(2-Acetoxy- and 2-hydroxyethoxy)methyl]barbituric acids easily react with aromatic and heterocyclic aldehydes in water and organic solvents, forming 5-ylidenebarbituric acids. The structure of the products was proved by 1H NMR and UV spectroscopy. Certain of the products exhibit a moderate antimicrobial and antiviral activity. |
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