Examples of Amides
Amides are common functional groups that have been studied for more than a century.
We use this methodology to convert amides to esters, which is a challenging and underdeveloped transformation.
Amides have historically been considered stable and unreactive functional groups because of resonance stabilization.
(Nature Chemistry, )
Amides are known to be poor electrophiles, which is typically attributed to the resonance stability of the amide bond.
Here, it is demonstrated that Boc-activated amides can be employed in Suzuki–Miyaura couplings using non-precious-metal catalysis.
(Nature Chemistry, )
Here we report an approach that overcomes these limitations by homolysing the N–H bonds of N-alkyl amides via proton-coupled electron transfer.
Although amides can readily be cleaved by enzymes such as proteases, it is difficult to selectively break the carbon–nitrogen bond of an amide using synthetic chemistry.
The team used the solvent-free, catalytic reaction to produce high yields of a wide range of amides, including the antidepressant moclobemide and other drug-like molecules.
(Science Daily - News, )
The genome of the poisonous mushroom Omphalotus olearius provides a potent new biocatalytic strategy for installing backbone N-methyl amides on ribosomally synthesized peptides.
(Nature Chemical Biology , )
This C–H alkylation represents a catalytic variant of the Hofmann–Löffler–Freytag reaction, using simple, unfunctionalized amides to direct the formation of new C–C bonds.
Given the prevalence of amides in pharmaceuticals and natural products, we anticipate that this method will simplify the synthesis and structural elaboration of amine-containing targets.
Despite advances in hydrogen atom transfer (HAT) catalysis, there are currently no molecular HAT catalysts that are capable of homolysing the strong nitrogen–hydrogen (N–H) bonds of N-alkyl amides.
In a recent study, Cohen et al. identified microbial N-acyl amides that mimic human signalling molecules and interact with host G protein-coupled receptors (GPCRs) to regulate gastrointestinal tract physiology.
(Nature Reviews Microbiology, )
These observations are made for a class of unsymmetrical amides that exhibits two asymmetric axes—one axis is defined through a benzamide substructure, and the other axis is associated with differentially N,N-disubstituted amides.
Our results provide a way to harness amide functional groups as synthetic building blocks and are expected to lead to the further use of amides in the construction of carbon–heteroatom or carbon–carbon bonds using non-precious-metal catalysis.
Here we describe a network of biologically relevant organic reactions (amide formation, thiolate–thioester exchange, thiolate–disulfide interchange and conjugate addition) that displays bistability and oscillations in the concentrations of organic thiols and amides.
Oscillations arise from the interaction between three subcomponents of the network: an autocatalytic cycle that generates thiols and amides from thioesters and dialkyl disulfides; a trigger that controls autocatalytic growth; and inhibitory processes that remove activating thiol species that are produced during the autocatalytic cycle.
See also examples for amide.
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