331255-35-7Relevant academic research and scientific papers
A comparative study of amide-bond forming reagents in aqueous media – Substrate scope and reagent compatibility
Badland, Matthew,Crook, Robert,Delayre, Bastien,Fussell, Steven J.,Gladwell, Iain,Hawksworth, Michael,Howard, Roger M.,Walton, Robert,Weisenburger, Gerald A.
, p. 4391 - 4394 (2017)
A survey of amidation reagents demonstrating DIC-HOPO, DMT-MM, COMU-collidine, TPTU-NMI, EEDQ, CDI and EDC-Oxyma to be effective for the coupling of carboxylic acids with amines in the presence of water and the absence of problematic dipolar aprotic solvents is reported. DMT-MM was shown to provide the best yields for the coupling of a secondary amine, TPTU-NMI and COMU-collidine for aniline, whilst the combination of DIC with HOPO afforded the broadest substrate scope and the highest yields for a sterically demanding carboxylic acid.
A Hydroperoxide-Mediated Decarboxylation of α-Ketoacids Enables the Chemoselective Acylation of Amines
Nanjo, Takeshi,Kato, Natsuki,Zhang, Xuan,Takemoto, Yoshiji
supporting information, p. 15504 - 15507 (2019/11/14)
Strategies for the formation of amide bonds, that is, one of the most basic and important transformations in organic synthesis, have so far focused predominantly on dehydration reactions. Herein, we report and demonstrate the practical utility of a novel decarboxylative amidation of α-ketoacids by using inexpensive tert-butyl hydroperoxide (TBHP), which is characterized by high yields, a broad substrate scope, mild reaction conditions, and a unique chemoselectivity. These features enable the synthesis of peptides from amino acid derived α-ketoacids under preservation of the stereochemical information.
Efficient Preparation of Imidazo[1,5- a ]pyridine-1-carboxylic Acids
Tverdiy, Dmytro O.,Chekanov, Maksym O.,Savitskiy, Pavlo V.,Syniugin, Anatolii R.,Yarmoliuk, Sergiy M.,Fokin, Andrey A.
, p. 4269 - 4277 (2016/11/26)
We report a novel and efficient approach to the synthesis of imidazo[1,5-a]pyridine-1-carboxylic acids. By using the reaction of 2-(aminomethyl)pyridine with acyl chlorides followed by one-pot treatment with trifluoroacetic anhydride, 2,2,2-trifluoro-1-im
Iodination of remote ortho-C-H bonds of arenes via directed S EAr: A streamlined synthesis of tetrahydroquinolines
Nack, William A.,He, Gang,Zhang, Shu-Yu,Lu, Chengxi,Chen, Gong
supporting information, p. 3440 - 3443 (2013/07/26)
A new strategy for the synthesis of tetrahydroquinolines (THQs) via the sequential functionalizations of remote C-H bonds is reported. This method uses a single picolinamide directing/protecting group to effect Pd-catalyzed γ-C(sp3)-H arylation, metal-free ε-C(sp2)-H iodination, and Cu-catalyzed intramolecular C-N cross-coupling. The overall sequence is efficient and versatile, and offers a streamlined synthesis of THQs with complex substitution patterns from readily available aryl iodide and aliphatic amine precursors.
Synthesis of substituted imidazo[1,5-a]pyridines starting from N-2-pyridyl-methylamides using Lawesson's reagent and mercury(II) acetate
Moulin, Aline,Garcia, Sandra,Martinez, Jean,Fehrentz, Jean-Alain
, p. 2667 - 2673 (2008/03/12)
A new method for the synthesis of substituted imidazo[1,5-a]pyridines (2-azaindolizines) starting from carboxylic acid and 2-methylaminopyridine is described. The reaction of the obtained N-2-pyridylmethylamides with Lawesson's reagent gene-rated the targ
