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Transamidation reactions of 2-(2-sulfonylguanidino)acetamides |
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| Authors: | M Eugenia González-Rosende Belén Asíns José Sepúlveda-Arques |
| Institution: | a Department of Chemistry, Biochemistry and Molecular Biology, University CEU-Cardenal Herrera, Edificio Seminario s/n, 46113 Moncada, Valencia, Spain b Department of Physiology, Pharmacology and Toxicology, University CEU-Cardenal Herrera, Edificio Seminario s/n, 46113 Moncada, Valencia, Spain c Department of Organic Chemistry, University of Valencia, Avda, Vicent Andrés Estellés s/n, 46180 Burjassot, Valencia, Spain |
| 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. |
| Keywords: | Transamidation Guanidines Acetamides Dihydropyrimidines Imidazolidinones |
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