REARRANGEMENT OF THIAZOLO[3,2-<i>a</i>]PYRIMIDINES INTO TRIAZOLO[4,3-<i>a</i>]PYRIMIDINES INDUCED BY C=N BOND REDUCTION
DOI:
https://doi.org/10.1007/5149Keywords:
hydrazine derivatives, 2-hydrazinylidene-5H-[1, 3]thiazolo[3, 2-a]pyrimidin-3(2H)-one, [1, 2-a]pyrimidine, 2, 4]triazolo[4, 3-a]pyrimidine, rearrangement, reduction, transition cage structure.Abstract
Triazolo[4,3-a]pyrimidines were prepared by the reduction of 5,6,7-trisubstituted 2-(arylhydrazinylidene)-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with NaBH4 in the presence of V2O5 at room temperature. The structure of ethyl 3-(hydroxymethyl)-5-(4-methoxyphenyl)-7-methyl-1-phenyl-1,5-dihydro[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate was proven by the single crystal X-ray diffraction data. The mechanism of the reaction including transition cage structure is discussed.Downloads
Published
2019-12-18
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Section
Original Papers