6533b7d8fe1ef96bd126ab71

RESEARCH PRODUCT

1,2-Methyl shift in the reaction of 4,7-dihydro-4,5-dimethyl-7-phenyl-(1,2,4)-triazolo[1,5-a]pyrimidine with tosyl azide

Alexander S. KaganovskyV. D. OrlovSergey A. KomykhovHerbert MeierSergey M. Desenko

subject

Tosyl azidechemistry.chemical_compoundPyrimidineChemistryOrganic Chemistrychemistry.chemical_elementCarbon-13 NMRMedicinal chemistryNitrogenDerivative (chemistry)AdductEnamineMethyl group

description

The reaction of the heterocyclic enamine 1 with tosyl azide (2) leads to the tosylimino derivative 4 of 1,2,4-triazolo[1,5-a]pyrimidine. The extrusion of nitrogen from the primary adduct 3 is followed by a 1,2-shift of a methyl group. The structure determination of 4 is based on 1H and 13C nmr spectra including NOE measurements.

https://doi.org/10.1002/jhet.5570370135