14278-35-4Relevant articles and documents
Reaction of amphipathic-type thioester and amine with hydrophobic effect in water
Torihata, Atsushi,Kuroda, Chiaki
, p. 2035 - 2038 (2011)
The title reaction was studied using sodium 3-(1-oxododec-1-yl)thio- and 3-(1-oxohept-1-yl)thiopropanoate with various chain lengths of amines. The yields of the amides were found to depend on both the chain length of the thioester and that of amine, suggesting the presence of hydrophobic interaction. The amides were obtained in better yields after addition of sodium fluoride. Acylation (dodecanoylation) of some hydrophobic amino acids was also studied to obtain the corresponding amides. Georg Thieme Verlag Stuttgart - New York.
One-Pot Amide Bond Formation from Aldehydes and Amines via a Photoorganocatalytic Activation of Aldehydes
Papadopoulos, Giorgos N.,Kokotos, Christoforos G.
, p. 7023 - 7028 (2016/08/30)
A mild, one-pot, and environmentally friendly synthesis of amides from aldehydes and amines is described. Initially, a photoorganocatalytic reaction of aldehydes with di-isopropyl azodicarboxylate leads to an intermediate carbonyl imide, which can react with a variety of amines to afford the desired amides. The initial visible light-mediated activation of a variety of monosubstituted or disubstituted aldehydes is usually fast, occurring in a few hours. Following the photocatalytic reaction, addition of the primary amine at room temperature or the secondary amine at elevated temperatures leads to the corresponding amide from moderate to excellent yields without epimerization. This methodology was applied in the synthesis of Moclobemide, a drug against depression and social anxiety.
Copper-Catalyzed Carbonylative Synthesis of Aliphatic Amides from Alkanes and Primary Amines via C(sp3)-H Bond Activation
Li, Yahui,Zhu, Fengxiang,Wang, Zechao,Wu, Xiao-Feng
, p. 5561 - 5564 (2016/08/18)
Amides are important intermediates and building blocks in organic synthesis. Among the known preparation procedures, aminocarbonylation is an interesting and powerful tool. However, most of the studies were focused on noble metal-catalyzed synthesis of ar
Catalytic chemical amide synthesis at room temperature: One more step toward peptide synthesis
Mohy El Dine, Tharwat,Erb, William,Berhault, Yohann,Rouden, Jacques,Blanchet, Jér?me
, p. 4532 - 4544 (2015/05/13)
An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.
One-pot synthesis of amides by aerobic oxidative coupling of alcohols or aldehydes with amines using supported gold and base as catalysts
Kegnaes, Soren,Mielby, Jerrik,Mentzel, Uffe V.,Jensen, Thomas,Fristrup, Peter,Riisager, Anders
, p. 2427 - 2429 (2012/03/27)
Synthesis of amides by aerobic oxidative coupling of alcohols or aldehydes with amines via intermediate formation of methyl esters is highly efficient and selective when using a catalytic system comprised of supported gold nanoparticles and added base in methanol. The Royal Society of Chemistry 2012.
Intramolecular and intermolecular Schmidt reactions of alkyl azides with aldehydes
Lee, Huey-Lih,Aubé, Jeffrey
, p. 9007 - 9015 (2008/02/10)
Despite recent advances in the use of alkyl azides in ring expansion reactions of ketones, there has been little work done on the corresponding chemistry of aldehydes. In the present study, the Lewis acid-promoted reactions of alkyl azides with aldehydes
A catalyst system for the formation of amides by reaction of carboxylic acids with blocked isocyanates
Gertzmann,Gürtler
, p. 6659 - 6662 (2007/10/03)
A catalyst for the reaction of blocked isocyanates (blocking agent diisopropylamine and dimethyl pyrazole) and carboxylic acids was identified. Magnesium and in some instances calcium salts proved to be highly active as catalyst. This reaction gives amides in quantitative yield and excellent selectivity and is suitable for coating and general chemical purposes.
