Tetrahedron p. 2283 - 2292 (1986)
Update date:2022-08-03
Topics:
Benhaoua, Hadj
Texier, Fernand
Carrie, R.
The addition of azomethine ylids resulting from the thermal ring opening of the corresponding 2-cyanoaziridines on methyl and phenyl isocyanates occured exclusively at the C=N double bond.Only one orientation of the addition was observed and a mixture of diastereoisomeric imidazolidones was obtained in each case.On the basis of X ray structure of one diastereoisomer the stereochemistry of the other imidazolidones was established by NMR considering the long range coupling constants values between H2 and H5 (Jcis < Jtrans).The reaction of sodium methylate with the imidazolones led to imidates resulting from a nucleophilic addition on the nitrile function on the C2 carbon atom of the heterocycles.These imidates are easily hydrolyzed to the corresponding esters.If the reaction was carried out in the presence of oxygen the CHCN group was transformed into C=O group via the oxidation of the C2 carbanion.
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