6533b832fe1ef96bd129a244

RESEARCH PRODUCT

Transamidation reactions of 2-(2-sulfonylguanidino)acetamides

M. Eugenia González-rosendeBelén AsínsEncarna CastilloJosé Sepúlveda-arquesRachid Mamouni

subject

chemistry.chemical_compoundchemistryStereochemistryImidazolidinoneOrganic ChemistryDrug DiscoverySubstituentMoietyReactivity (chemistry)Smiles rearrangementBiochemistryAcetamide

description

Abstract The reactivity of a series of sulfonylguanidinoacetamides 2A–E towards amines is reported. Guanidinoacetamides 2A–C, containing the arylsulfonylimino moiety, undergo a facile transamidation to give substituted carboxamides 4A–C, through the imidazolidinone intermediate 3. Acetamide 2D, having a methanesulfonylimino substituent, affords the imidazolidinone 3D and no transamidated carboxamides 4 are detected. In the case of guanidinoacetamide 2E, with a p-nitrobenzenesulfonylimino substituent, a Smiles rearrangement was observed.

yearjournalcountryeditionlanguage
2007-09-01Tetrahedron
https://doi.org/10.1016/j.tet.2007.06.052