95725-07-8Relevant academic research and scientific papers
Synthesis of N,N -diethylbenzamides via a nonclassical mitsunobu reaction
Hoffman, J. Mason,Miller, Justin N.,Gardner, Margaret E.,Lepar, Danielle R.,Pongdee, Rongson
, p. 976 - 980 (2014)
The use of the Mitsunobu reaction for the synthesis of N,N- diethylbenzamides affords ortho-, meta-, and para-substituted benzamides containing both electron-donating and electron-withdrawing groups. While the preparation of numerous functional groups has
Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides
Li, Zhaohui,Liu, Long,Xu, Kaiqiang,Huang, Tianzeng,Li, Xinyi,Song, Bin,Chen, Tieqiao
supporting information, p. 5517 - 5521 (2020/07/14)
A palladium-catalyzed N-acylation of tertiary amines by carboxylic acids was achieved through C-N cleavage. This reaction showed a wide substrate scope. Both aromatic and aliphatic acids served well as the acylating reagents and coupled with tertiary amines to produce the corresponding amides in good to excellent yields. With the strategy, bioactive carboxylic acids were also efficiently modified, highlighting the synthetic value of the process in organic synthesis.
Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages
Wang, Shi-Meng,Zhao, Chuang,Zhang, Xu,Qin, Hua-Li
, p. 4087 - 4101 (2019/04/30)
The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.
Selenoxanthones via directed metalations in 2-arylselenobenzamide derivatives
Brennan, Nancy K.,Donnelly, David J.,Detty, Michael R.
, p. 3344 - 3347 (2007/10/03)
The reaction of N, N-diethyl 4-(N′, N′-dimethylamino)-2-phenylselenobenzamide (7a), N, N-diethyl 4-methoxy-2-phenylselenobenzamide (7b), N, N-diethyl 4-(N′, N′-dimethylamino)-2-[(3-(N, N-dimethylamino)phenylseleno]-benzamide (7c), and N, N-diethyl 4-metho
Conversion of thioamides into their corresponding oxygen analogues using silver carbonate supported on celite
Movassagh,Lakouraj,Gholami
, p. 1507 - 1511 (2007/10/03)
Silver carbonate supported on celite (Ag2CO3/Celite) is used as a mild heterogeneous reagent for conversion of a variety of thioamides into their corresponding amides in acetonitrile at room temperature.
Conversion of thioamides into their corresponding oxygen analogues using silver carbonate supported on celite
Movassagh,Lakouraj,Gholami
, p. 1943 - 1947 (2007/10/03)
Silver carbonate supported on celite (Ag2CO3/Celite) is used as a mild heterogeneous reagent for conversion of variety of thioamides into their corresponding amides in acetonitrile at room temperature.
Palladium-Catalysed Double Carbonylation of Aryl Halides To Give α-Keto Amides. Mechanistic Studies
Ozawa, Fumiyuki,Soyama, Hidehiko,Yanagihara, Hisayoshi,Aoyama, Issei,Takino, Hiroaki,et al.
, p. 3235 - 3245 (2007/10/02)
Various aryl halides are catalytically converted into α-keto amides and amides on treatment with secondary amines and carbon monoxide.Palladium complexes containing tertiary phosphine ligands, particularly diphenylmethylphosphine and 1,4-bis(diphenylphosphino)butane, are most effective among other transition-metal complexes.Detailed examination of factors controlling the reaction rates and selectivity for α-keto amide formation revealed the following characteristics of the reactions. (a) Reactivity of phenyl halide decreases in the order PhI > PhBr >> PhCl. (b) Oxidative addition of phenyl bromide constitutes the rate-determining step in double carbonylation of phenyl bromide, whereas in the reaction of phenyl iodide the rate determinig step is associated with the reaction of a catalitically active palladium species with carbon monoxide. (c) Introduction of an electron-withdrawing substituent into the para position of phenyl halide enhances the reactivity but decreases the selectivity for α-keto amide. (d) Employment of amines of high basicity (pKb Et2NH > piperidine > hexamethyleneimine > Me2NH > pyrrolidine probably reflects the decrease in steric bulkiness of amines. (f) Although primary amines are in general not suitable for the double carbonylation, tert-butylamine can be used because of its inertness to the product α-keto amide.Reactivity of trans-PdPh(I)(PMePh2)2 and trans-Pd(COPh)I(PMePh2)2, supposed intermediates in the catalytic reaction of PhI, toward amines and CO was examined.The relative reactivity of six secondary amines with the benzoylpalladium complex increasing in the order Pr2NH Et2NH piperidine Me2NH hexamethyleneimine pyrrolidine was found to be inversely correlated with decreasing selectivity order for α-keto amide formation in the catalytic systems.On the basis of the experimental results, a mechanism consisting of two catalytic cycles to produce α-keto amides and amides has been proposed.
