Tandem reactions of 6-phenylethynylpyrimidine-5-carbaldehydes with alcohols: regioselective synthesis of 5-alkoxy-(7Z)-7-benzylidene-5,7-dihydrofuro[3,4-d]pyrimidines and 5-alkoxy-7-phenyl-5H-pyrano[4,3-d]pyrimidines |
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Authors: | Inga Cikotiene Rita Buksnaitiene Simonas Rudys Marius Morkunas Dainius Motiejaitis |
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Affiliation: | Department of Organic Chemistry, Faculty of Chemistry, Vilnius University, Naugarduko 24, LT-03225, Vilnius, Lithuania |
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Abstract: | An efficient and versatile tandem processes of acetalisation and cycloisomerization reactions have been developed for the reactions of 6-phenylethynylpyrimidine-5-carbaldehydes. The influence of the catalyst and role of the substituent in the position 4 of the pyrimidine ring have been studied. Regioselective synthesis of 5,7-dihydrofuro[3,4-d]pyrimidine and pyrano[4,3-d]pyrimidine cores is described. |
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Keywords: | Acetalisation 5-exo-Dig or 6-endo-dig cyclization Tandem reactions Furo[3,4-d]pyrimidines Pyrano[4,3-d]pyrimidines |
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