28358-79-4Relevant articles and documents
Photoinduced one pot transformation of 2-phenyl-4-ethylidene-5(4H)- oxazolone and allylic alcohols to γ, δ-unsaturated N-henzoyl amides
Park, Bong Ser,Oh, Chul Min,Chun, Keun Ho,Lee, Jong Ook
, p. 9711 - 9714 (1998)
Photolysis of 2-Phenyl-4-ethylidene-5(4H)-oxazolones in the presence of allylic alcohols resulted in a navel one-pot transformation to γ,δ- unsaturated N-benzoyl amides via decarbonylation, nucleophilic addition of allylic alcohols, photoinduced hydrogen
Hydrogen bond directed cocrystallization and molecular recognition properties of acyclic imides
Etter, Margaret C.,Reutzel, Susan M.
, p. 2586 - 2598 (1991)
The cocrystalization behavior of acyclic is studied as a way to map out the hydrogen bond directed molecular recognition properties of a class of small biochemically molecules under where is no preorganized cavity controlling the recognition events. Cocry
REACTIONS OF 2-PHENYL-4,4-DIMETHYL-2-OXAZOLIN-5-ONE AND 2-PHENYL-4-ETHYL-2-OXAZOLIN-5-ONE with KO2 IN APROTIC SOLVENTS
Chuaqui, Claudio A.,Delaney, Sabine,Merritt, John
, p. 2947 - 2951 (1983)
The reactions of 2-phenyl-4,4-dimethyl-2-oxazolin-5-one (I) and 2-phenyl-4-ethyl-2-oxazolin-5-one (II) with KO2 in tetrahydrofuran and freon are studied.Superoxide reacts with I to yield the N-benzoyl-α-aminoacid ring-opening product, indicating that O2 produces a nucleophilic attack at the carbonyl group of the oxazolinone.The oxazolinone II yields, in addition to the N-benzoyl-α-amino derivative, N-propanoyl benzamide (III) as the main reaction product.The results strongly suggest that III is formed after O2 has abstracted a proton from II, and then, species resulting from secondary reactions, such as oxygen, attack II to yield the final products.Several mechanistic pathways are discussed.
Method for catalytically oxidizing amine to be synthesized into amide through dipyridyl-type manganese catalyst
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Paragraph 0017-0027; 0076-0078, (2019/06/30)
The invention discloses a methodfor catalytically oxidizing amine to be synthesized into amide througha dipyridyl-type manganese catalyst. According to the method, a dipyridyl manganese complex formedafter coordination of a dipyridyl-type complex and cheap metal manganese serves as the catalyst, clean and environment-friendly hydrogen peroxide serves as an oxidizing agent, oxidation of N ortho-position sp3 C-H bonds catalyzed by the cheap metal manganese is achieved, and the amine is directly oxidized to obtain the amide. Compared with existing methods, the method has the advantages that theadopted catalyst is low in price, the preparing method is simple, raw materials are easy to obtain, the use level of the catalyst is low, the substrate range is wide, the reaction condition is mild, the operation is simple and environmentally friendly, the reaction time is short, the yield is high, the selectivity is high, and the industrialization cost is low.
Visible-Light-Driven Oxidation of N -Alkylamides to Imides Using Oxone/H 2 O and Catalytic KBr
Mei, Chong,Hu, Yixin,Lu, Wenjun
, p. 2999 - 3005 (2018/05/25)
Imides are prepared conveniently by visible-light-driven oxidations of various N -alkylamides under mild conditions. The majority of the reactions proceed efficiently by using Oxone as the oxidant in the presence of a catalytic amount of KBr in H 2 O/CH 2 Cl 2 under irradiation by an 8 W white LED at room temperature. Experimental studies suggest that an imine, obtained from the substrate amide via a radical process, is the key intermediate.
CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides
Kataoka, Kengo,Wachi, Keiju,Jin, Xiongjie,Suzuki, Kosuke,Sasano, Yusuke,Iwabuchi, Yoshiharu,Hasegawa, Jun-Ya,Mizuno, Noritaka,Yamaguchi, Kazuya
, p. 4756 - 4768 (2018/06/07)
Although aerobic oxidative acylation of amides with alcohols would be a good complement to classical synthetic methods for imides (e.g., acylation of amides with activated forms of carboxylic acids), to date, there have been no reports on oxidative acylation to produce imides. In this study, we successfully developed, for the first time, an efficient method for the synthesis of imides through aerobic oxidative acylation of amides with alcohols by employing a CuCl/TMEDA/nor-AZADO catalyst system (TMEDA = teramethylethylendiamine; nor-AZADO = 9-azanoradamantane N-oxyl). The proposed acylation proceeds through the following sequential reactions: aerobic oxidation of alcohols to aldehydes, nucleophilic addition of amides to the aldehydes to form hemiamidal intermediates, and aerobic oxidation of the hemiamidal intermediates to give the corresponding imides. This catalytic system utilizes O2 as the terminal oxidant and produces water as the sole by-product. An important point for realizing this efficient acylation system is the utilization of a TMEDA ligand, which, to the best of our knowledge, has not been employed in previously reported Cu/ligand/N-oxyl systems. Based on experimental evidence, we consider that plausible roles of TMEDA involve the promotion of both hemiamidal oxidation and regeneration of an active CuII-OH species from a CuI species. Here promotion of hemiamidal oxidation is particularly important. Employing the proposed system, various types of structurally diverse imides could be synthesized from various combinations of alcohols and amides, and gram-scale acylation was also successful. In addition, the proposed system was further applicable to the synthesis of α-ketocarbonyl compounds (i.e., α-ketoimides, α-ketoamides, and α-ketoesters) from 1,2-diols and nucleophiles (i.e., amides, amines, and alcohols).
Transition-Metal- and Halogen-Free Oxidation of Benzylic sp 3 C-H Bonds to Carbonyl Groups Using Potassium Persulfate
Hu, Yixin,Zhou, Lihong,Lu, Wenjun
supporting information, p. 4007 - 4016 (2017/08/29)
Aryl carbonyl compounds including acetophenones, benzophenones, imides, and benzoic acids are prepared from benzyl substrates using potassium persulfate as oxidant with catalytic pyridine in acetonitrile under mild conditions. Neither transition metals nor halogens are involved in the reactions.
Preparation of the zinc enolate equivalent of amides by zinciomethylation of isocyanates: Catalytic asymmetric Reformatsky-type reaction
Haraguchi, Ryosuke,Matsubara, Seijiro
, p. 2272 - 2282 (2014/12/09)
Bis(iodozincio)methane [CH2(ZnI)2] transforms isocyanates (R-N=C=O) into the enolate equivalent of amides via zinciomethylation. The reactivity of the enolate equivalent as a nucleophile toward aldehydes depends on the R group of the
Replacement of BF4- by PF6- makes Selectfluor greener
Jin, Zhuang,Xu, Bo,Hammond, Gerald B.,Dimagno, Stephen G.
, p. 226 - 230,5 (2020/08/20)
A combination of F-TEDA-PF6 and CuBr (0.1 equiv.) provides a potent oxidant that readily oxidizes amides to provide imides at room temperature. Replacement of BF4-, the anion of Selectfluor (F-TEDA-BF4), by PF6-, dramatically reduces CuBr loading in this oxidative reaction. A possible rationale for this dramatic counterion effect is provided.
Synthesis of 1,3,5-trisubstituted-1,2,4-triazoles by microwave-assisted N-acylation of amide derivatives and the consecutive reaction with hydrazine hydrochlorides
Lee, Jongbok,Hong, Myengchan,Jung, Yoonchul,Cho, Eun Jin,Rhee, Hakjune
experimental part, p. 2045 - 2051 (2012/04/10)
Facile and efficient procedures for the N-acylation reaction of amide derivatives with various acid anhydrides and the cyclization reaction of N-acylated amide derivatives with various hydrazine hydrochlorides were described. The reactions were carried out under microwave irradiation to give products in good yields in a few minutes. The synthesis of 1,3,5-trisubstituted- 1,2,4-triazoles from benzamides can also be accomplished in a simple one-pot sequential reaction.
