22031-64-7Relevant articles and documents
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Galat
, p. 2596 (1948)
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Ammonium salts from polymer-bound N-hydroxysuccinimide as solid-supported reagents for EDC-mediated amidations
Chinchilla, Rafael,Dodsworth, David J.,Nájera, Carmen,Soriano, José M.
, p. 463 - 466 (2003)
New ammonium and alkylammonium salts derived from a polymeric N-hydroxysuccinimide (P-HOSu) have been prepared and used for the amidation of carboxylic acids and amino acids mediated by 1-ethyl-3-(3′-dimethylamino-propyl)carbodiimide hydrochloride (EDC). These polymer-supported ammonium salts afforded the corresponding amides in good yield, without detectable α-racemization and with easy recovery of the P-HOSu after the amidation reaction, being especially suitable for the amidation of Fmoc-protected amino acids.
Facile and highly selective conversion of nitriles to amides via indirect acid-catalyzed hydration using TFA or AcOH-H2SO4
Moorthy, Jarugu Narasimha,Singhal, Nidhi
, p. 1926 - 1929 (2005)
(Chemical Equation Presented) Both aliphatic and aromatic nitriles are conveniently and selectively converted in a single step, via an indirect acid-catalyzed hydration, into the corresponding amides in 1-8 h using a TFA-H2SO4 mixture as a reagent system. Although the same reagent did not work for the sterically hindered nitriles such as mesitonitrile, the transformation could be accomplished by changing TFA to AcOH at higher temperatures (>90°C).
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Morsch
, p. 299,302, 305 (1932)
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Iron-catalyzed hydroaminocarbonylation of alkynes: Selective and efficient synthesis of primary α,β-unsaturated amides
Huang, Zijun,Jiang, Xiongwei,Lan, Donghui,Li, Yuehui,Pi, Shaofeng,Tan, Zhengde,Tang, Jia,Xie, Tianle,Yi, Bing,Zhang, Minmin
supporting information, (2022/02/22)
α,β-Unsaturated primary amides are important intermediates and building blocks in organic synthesis. Herein, we report a ligand-free iron-catalyzed hydroaminocarbonylation of alkynes using NH4HCO3 as the ammonia source, enabling the highly efficient and regioselective synthesis of linear α,β-unsaturated primary amides. Various aromatic and aliphatic alkynes are transformed into the desired linear α,β-unsaturated primary amides in good to excellent yields. Further studies show that using NH4HCO3 as the ammonia source is key to obtain good yields and selectivity. The utility of this route is demonstrated with the synthesis of linear α,β-unsaturated amides including vanilloid receptor-1 antagonist TRPV-1.
Manganese Catalyzed Enantioselective Epoxidation of α,β-Unsaturated Amides with H2O2
Ottenbacher, Roman V.,Kurganskiy, Vladimir I.,Talsi, Evgenii P.,Bryliakov, Konstantin P.
supporting information, p. 2778 - 2782 (2021/04/29)
Herewith, we report the enantioselective epoxidation of electron-deficient cis- and trans-α,β-unsaturated amides with the environmentally benign oxidant H2O2. The catalysts - manganese complexes with bis-amino-bis-pyridine and structurally related ligands - exhibit reasonably high efficiency (up to 100 TON) and excellent chemo- and enantioselectivity (up to 100% and 99% ee, respectively). Crucially, the cis-enamides epoxidation enantioselectivity and yield are dramatically enhanced by the presence of NH-moiety, which effect can be explained by the hydrogen bonding interaction between the cis-enamide substrate and the manganese based oxygen transferring species. (Figure presented.).
