Synthesis of [1,2,4]triazolo[4,3-alpha]piperazines via highly reactive chloromethyloxadiazoles.
[reaction: see text] A concise, modular approach for the synthesis of [1,2,4]triazolo[4,3-alpha]piperazines via condensation of highly reactive chloromethyloxadiazoles with ethylenediamines is described. NMR studies of this reaction provide evidence that suggests a novel activation mechanism for electron-deficient chloromethyloxadiazoles.
Balsells
Jaume
J
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA.
Dimichele
Lisa
L
Liu
Jinchu
J
Kubryk
Michele
M
Hansen
Karl
K
Armstrong
Joseph D
JD
D002384:Catalysis; D005029:Ethylenediamines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010069:Oxadiazoles / Q000737:chemistry*; D010084:Oxidation-Reduction; D010879:Piperazines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis*
D005029:Ethylenediamines; D010069:Oxadiazoles; D010879:Piperazines; D014230:Triazoles