This work introduces a [2+2]-type double nucleophilic substitution reaction between 1,2-dibromoethane and hydrozones for direct construction of 1,2-diazetidin derivatives. The reaction employs disulfonylhydrazones as reactant, which was deprotonated by n-butyllithium to afford a dianionic nucleophile at low temperature. DMF was proven to be a suitable solvent for a sequential intermolecular and intramolecular nucleophilic substitution. Precise temperature control appeared to be a key to ensure high yields as the vicinal dianionic intermediates need to be stabilized as well as kept homogenous. As a synthetic application of the resulting 1,2-diazetidines, a practical ring-opening process has been developed for a facile synthesis of N-thioiminoethanamine derivatives.

Direct synthesis of 1,2-disulfonyl diazetidine derivatives and their synthetic applications

255th National Meeting (2018)

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