Direct Transamidation Reactions: Mechanism and Recent Advances
Open Access
- 18 September 2018
- Vol. 23 (9), 2382
- https://doi.org/10.3390/molecules23092382
Abstract
Amides are undeniably some of the most important compounds in Nature and the chemical industry, being present in biomolecules, materials, pharmaceuticals and many other substances. Unfortunately, the traditional synthesis of amides suffers from some important drawbacks, principally the use of stoichiometric activators or the need to use highly reactive carboxylic acid derivatives. In recent years, the transamidation reaction has emerged as a valuable alternative to prepare amides. The reactivity of amides makes their direct reaction with nitrogen nucleophiles difficult; thus, the direct transamidation reaction needs a catalyst in order to activate the amide moiety and to promote the completion of the reaction because equilibrium is established. In this review, we present research on direct transamidation reactions ranging from studies of the mechanism to the recent developments of more applicable and versatile methodologies, emphasizing those reactions involving activation with metal catalysts.This publication has 53 references indexed in Scilit:
- Recent Developments in Amide Synthesis Using Nonactivated Starting MaterialsThe Journal of Organic Chemistry, 2016
- Nonclassical Routes for Amide Bond FormationChemical Reviews, 2016
- Catalytic amide formation from non-activated carboxylic acids and aminesChemical Society Reviews, 2014
- Recent Developments in Amide Synthesis: Direct Amidation of Carboxylic Acids and Transamidation ReactionsEuropean Journal of Organic Chemistry, 2013
- The Medicinal Chemist’s Toolbox: An Analysis of Reactions Used in the Pursuit of Drug CandidatesJournal of Medicinal Chemistry, 2011
- Key green chemistry research areas—a perspective from pharmaceutical manufacturersGreen Chemistry, 2007
- Analysis of the reactions used for the preparation of drug candidate moleculesOrganic & Biomolecular Chemistry, 2006
- Notes- Potential Cancerocidal Agents. III. Formanilides.The Journal of Organic Chemistry, 1961
- The Interaction of Amides with Amines: A General Method of Acylation1Journal of the American Chemical Society, 1943
- Ueber Bildung von AzoverbindungenEuropean Journal of Inorganic Chemistry, 1876