Recyclization of pyrimidinium salts into 1,2,4-triazole derivatives
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The interaction of the iodomethylates of pyrimidinyl-2-acetic acid derivatives with monosubstituted hydrazines, in addition to the products of a Kost-Sagitullin rearrangement, leads also to N-substituted triazoles. The structure of the triazoles was demonstrated by NOESY NMR experiments. The structure of the reaction products was determined on the basis of the response observed in the spectra between the methyl group protons of the triazole ring and the spatially close proton of the substituent in position 1 and a conclusion was drawn on the direction of the primary attack of nucleophile in the recyclization process of the pyrimidinium salts into a 1,2,4-triazole.
Keywordsarylhydrazines pyrimidinium salts 1,2,4-triazole 2-methylaminonicotinic acid ester NOESY method rearrangement recyclization NMR spectroscopy
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