62685-93-2Relevant academic research and scientific papers
Preparation method of amide
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Paragraph 0055-0079; 0140-0145, (2021/08/25)
The invention relates to a preparation method of an amide, wherein, under the action of oxygen, the isothiocyanate and the aldehyde can react to form an amide, and the reaction temperature can be effectively increased only when not less than 110 °C. This process is also suitable for the reaction of isocyanates with aldehydes to produce amides. The preparation method is cheap in raw material, wide in substrate application range and free of metal catalysts in the reaction process. The initiator or other activator is green and economical, and can effectively reduce the cost.
A microwave-assisted highly practical chemoselective esterification and amidation of carboxylic acids
Pathak, Gunindra,Das, Diparjun,Rokhum, Lalthazuala
, p. 93729 - 93740 (2016/10/21)
The ubiquitousness of esters and amide functionalities makes their coupling reaction one of the most sought-after organic transformations. Herein, we have described an efficient microwave-assisted synthesis of esters and amides. Soluble triphenylphosphine, in conjugation with molecular iodine, gave the desired products without the requirement for a base/catalyst. In addition, a solid-phase synthetic route is incorporated for the said conversion, which has added advantages over solution-phase pathways, such as low moisture sensitivity, easy handling, isolation of the product by simple filtration, and reusability. In short, our method is simple, mild, green, and highly chemoselective in nature.
Cleavage of C-N bonds in guanidine derivatives and its relevance to efficient C-N bonds formation
Chang, Denghu,Zhu, Dan,Zou, Peng,Shi, Lei
, p. 1684 - 1693 (2015/03/30)
Efficient nonenzymatic decomposition of guanidine derivatives with high structural and functional diversity into anilide products is achieved in the presence of PdII/Cu(II) carboxylates/CO, relying on a dual C-N bonds cleavage strategy. In this decomposition process, the cooperative action of PdII species, Cu(II) carboxylates, and CO provides not only the N-acylating agents but also an initiator to trigger this C-N bonds cleavage sequence. The current results indicate that PdII/Cu(II) carboxylates/CO system provides a convenient and practical method for highly selective cleavage of unreactive C-N single bonds.
Rhodium-catalyzed Beckmann rearrangement
Arisawa, Mieko,Yamaguchi, Masahiko
, p. 311 - 312 (2007/10/03)
equation presented Beckmann rearrangement of oxime is catalyzed by [RhCl(cod)]2, trifluoromethanesulfonic acid, and tris(p-tolyl)phosphine in refluxing dichloroethane, giving the corresponding amide in good yield. Product/acid ratios of 10:20 can be attained in the reaction of benzophenone oximes.
Oxidation of primary alcohols to acyl fluorides using BrF3
Rozen, Shlomo,Ben-David, Iris
, p. 145 - 147 (2007/10/03)
Aliphatic and alicyclic primary alcohols when treated with BrF3 were rapidly oxidized to the corresponding acyl fluorides. The reaction is of an ionic nature. The main by-product was found to be the symmetrical ester which originates from the reaction between the acyl fluoride and unreacted starting alcohol.
Charge-directed conjugate addition reactions of silylated α-β- unsaturated amidate anions
Cooke Jr.,Pollock
, p. 7474 - 7481 (2007/10/02)
A variety of N-substituted α-silylated-α,β-unsaturated amidate anions (2) have been found to be excellent Michael acceptors in charge-directed conjugate addition reactions with Grignard and organolithium reagents. The effects of olefin substitution, Si-substitution, N-substitution, and amidate counterion have been studied. Anionic acceptors may be prepared in situ by the addition of silylated vinyllithium reagents to isocyanates and then allowed to undergo conjugate addition reactions with subsequently added nucleophiles, but it was found to be more efficient to isolate neutral acceptors and regenerate the acceptor anion through the use of excess nucleophile. β-Substituted acceptors were found to react only with reactive organolithium reagents while a β,β-disubstituted acceptor failed to undergo conjugate addition reactions. A primary amide acceptor (14d) also undergoes addition reactions with larger quantitites of nucleophiles suggesting that dianionic amidate acceptors (31) are involved. Diene acceptor 24 was found to undergo a 1,6-addition reaction with n-BuLi. Sodium and potassium amidate salts were found to be inferior to lithium and magnesium salts in addition reactions in keeping with the expectation that an increase in carbonyl-group charge burden retards conjugate reactions. Triphenylsilyl-containing acceptor 16 was found to be more reactive in reactions with n-BuMgCl but less reactive with bulkier tert-BuMgCl. Adduct dianions can be monoalkylated with alkyl iodides and used in Peterson olefination reactions.
