16697-83-9Relevant academic research and scientific papers
One-Pot Synthesis of α-Ketoamides from α-Keto Acids and Amines Using Ynamides as Coupling Reagents
Ma, Jianting,Cui, Xue,Xu, Junyu,Tan, Yinfeng,Wang, Yan,Wang, Xuesong,Li, Youbin
supporting information, p. 3661 - 3667 (2022/02/07)
A one-pot strategy for α-keto amide bond formation have been developed by using ynamides as coupling reagents under extremely mild reaction conditions. Diversely structural α-ketoamides were afforded in up to 98% yield for 36 examples. This reaction features advantages such as practical coupling procedure, wide functional group tolerance, and extremely mild conditions and has potential applications in synthetic and medicinal chemistry.
Ynamide-Mediated Intermolecular Esterification
Wang, Xuewei,Yang, Yang,Zhao, Yongli,Wang, Sheng,Hu, Wenchang,Li, Jinmei,Wang, Zihao,Yang, Fengling,Zhao, Junfeng
, p. 6188 - 6194 (2020/05/26)
An ynamide-mediated one-pot, two-step intermolecular esterification via the condensation of carboxylic acids with nucleophilic hydroxyl species was reported. A broad substrate scope with respect to carboxylic acids, alcohols, and phenols was observed. The α-acyloxyenamide intermediates formed by the addition of carboxylic acids to ynamides proved to be effective acylating reagents for the esterification of alcohol and phenol derivatives with the assistance of base catalysis. Notably, the racemization of the α-chiral center of carboxylic acids can be avoided.
Alkyne amide-mediated one-pot method for preparing macrolide
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Paragraph 0014, (2018/10/24)
The invention discloses a method for preparing macrolide by using alkyne amide as a condensation reagent and hydroxy carboxylic acid as a raw material at 10-50 DEG C; the method comprises a method formildly and efficiently preparing an alpha-acyloxy alkenyl amide compound through addition of carboxylic acid and alkyne amide at room temperature under the catalysis of cuprous salt and a method forobtaining macrocyclic lactonization through enabling the intramolecular hydroxyl of the alpha-acyloxy alkenyl amide compound to react under the catalysis of p-toluenesulfonic acid; the two reactions can be performed through a one-pot method as well, i.e., an intermediate alpha-acyloxy alkenyl amide obtained after complete reaction of carboxylic acid and the alkyne amide does not need to be separated, the p-toluenesulfonic acid is directly added to perform intramolecular condensation reaction in the next step, thereby realizing the formation of the alkyne amide-mediated macrocyclic lactonization at room temperature. The method disclosed by the invention has the characteristics of mild reaction condition, simplicity and easy operation.
The scope and regioselectivity of intramolecular N-C rearrangements of orthogonally protected sulfonamides, including cyclization to saccharin derivatives
Saidykhan, Amie,Ebert, Jenessa,Ally, Hashim,Gallagher, Richard T.,Martin, William H.C.,Bowen, Richard D.
supporting information, p. 3089 - 3091 (2017/07/18)
The scope and regiochemistry of the intramolecular N-C rearrangement involving ortholithiation of orthogonally protected sulfonamides in which an N-acyl or N-carboalkoxy group is transferred from nitrogen to the aromatic ring have been explored. Provided that excess lithium diisopropylamide is used, the process is compatible with the presence of acidic α-protons in a substituent attached to the aromatic ring or if the protons in the migrating acyl group are relatively inaccessible because of steric factors. In certain cases, the isolated product is not the ortho carboalkoxy species, but the derived saccharin; the regiochemistry found for starting materials containing a naphthalene ring is consistent with ortho lithiation at the most electron deficient position.
Indium triiodide catalyzed reductive functionalization of amides via the single-stage treatment of hydrosilanes and organosilicon nucleophiles
Inamoto, Yoshihiro,Kaga, Yuta,Nishimoto, Yoshihiro,Yasuda, Makoto,Baba, Akio
supporting information, p. 3452 - 3455 (2013/07/26)
The indium triiodide catalyzed single-stage cascade reaction of N-sulfonyl amides with hydrosilanes and two types of organosilicon nucleophiles such as silyl cyanide and silyl enolates selectively promoted deoxygenative functionalization to give α-cyanoamines and β-aminocarbonyl compounds, respectively.
Fe-exchanged montmorillonite K10 - The first heterogeneous catalyst for acylation of sulfonamides with carboxylic acid anhydrides
Singh, Devendrapratap U.,Singh, Pankajkumar R.,Samant, Shriniwas D.
, p. 4805 - 4807 (2007/10/03)
Fe-exchanged montmorillonite K10 catalyzes a highly efficient reaction between sterically and electronically diverse sulfonamides and carboxylic acid anhydrides to furnish N-acylsulfonamides in excellent yield and high selectivity. The catalyst can also be reused several times.
