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Transamidation reactions of 2-(2-sulfonylguanidino)acetamides

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
63
Issue
36
Identifiers
DOI: 10.1016/j.tet.2007.06.052
Keywords
  • Transamidation
  • Guanidines
  • Acetamides
  • Dihydropyrimidines
  • Imidazolidinones

Abstract

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.

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