The 2-azido analogue of 2'-deoxyuridine was prepared in three steps from 2'-deoxy-2-thiouridine. The sulfur atom of the 2-thio nucleoside was methylated and then displaced by hydrazine to furnish the corresponding 2-hydrazino derivative. After diazotization, the 2-azido compound that exists as its tetrazolo tautomer was obtained. Upon UV irradiation in aqueous solution, the title compound led to isocytosine.
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SnAr Reactions of 2,4-Diazidopyrido[3,2-]pyrimidine and Azide-Tetrazole Equilibrium Studies of the Obtained 5-Substituted Tetrazolo[1,5-]pyrido[2,3-]pyrimidines.
Molecules
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Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena str. 3, LV-1048 Riga, Latvia.
A straightforward method for the synthesis of 5-substituted tetrazolo[1,5-]pyrido[2,3-]pyrimidines from 2,4-diazidopyrido[3,2-]pyrimidine in SnAr reactions with -, -, and - nucleophiles has been developed. The various - and -substituted products were obtained with yields from 47% to 98%, but the substitution with -nucleophiles gave lower yields (20-32%). Furthermore, the fused tetrazolo[1,5-]pyrimidine derivatives can be regarded as 2-azidopyrimidines and functionalized in copper(I)-catalyzed azide-alkyne dipolar cycloaddition (CuAAC) and Staudinger reactions due to the presence of a sufficient concentration of the reactive azide tautomer in solution.
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Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Paula Valdena Str. 3, Riga, LV-1048, Latvia.
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Institut de Chimie Moléculaire de Reims, Université de Reims Champagne Ardenne, CNRS UMR 6229, UFR de Pharmacie, 51 rue Cognacq-Jay, 51096 Reims cedex, France.
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