6533b851fe1ef96bd12a9921

RESEARCH PRODUCT

Unprecedented intermolecular transamidation reaction of N-carbamoylmethyl-N'-tosylguanidines.

Jamal LasriJosé Sepúlveda-arquesMaria Eugenia González-rosende

subject

chemistry.chemical_compoundPrimary (chemistry)TosylchemistryOrganic ChemistryIntermolecular forceOrganic chemistryPhysical and Theoretical ChemistryGuanidineBiochemistryMedicinal chemistry

description

[reaction: see text] N-Carbamoylmethyl-N'-tosyl guanidine 2 reacts easily with primary alkylamines to afford substituted carboxamides 3. The reaction proceeds via a five-membered-ring intermediate 5, which could be isolated, and features a rare example of an intermolecular transamidation reaction under mild conditions.

10.1021/ol035377zhttps://pubmed.ncbi.nlm.nih.gov/14535726