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
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.
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.
