614-28-8Relevant articles and documents
Palladium-Catalyzed Solvent-Controlled Selective Synthesis of Acyl Isoureas and Imides from Amides, Isocyanides, Alcohols and Carboxylates
Cao, Ming,Liu, Liqiu,Tang, Shi,Peng, Zhiyuan,Wang, Yingchun
, p. 1887 - 1895 (2019/03/11)
A highly selective synthesis of acyl isoureas and imides from readily accessible amides, isocyanides, alcohols and carboxylates based on reaction solvent selection is described. In the presence of a catalytic amount of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and cupric acetate, treatment of amides and isocyanides in alcohols at 60 °C provided acyl isoureas in high yields. Interestingly, when other solvents such as acetonitrile was used instead of alcohols, imides were exclusively produced in good to excellent yields via direct N-acylation of amides with carboxylates as the acyl sources. This protocol offers an attractive alternative approach toward isoureas and imides. (Figure presented.).
Copper-Catalyzed Oxidative C?H Bond Functionalization of N-Allylbenzamide for Regioselective C?N and C?O Bond Formation
Ranjith, Jala,Krishna, Palakodety Radha
supporting information, p. 1448 - 1451 (2019/04/03)
Copper-catalyzed oxidative couplings of N-allylbenzamides for C?N and C?O bond formations have been developed through C?H bond functionalization. To demonstrate the utility of this approach, it was applied to the synthesis of β-aminoimides and imides. To the best of our knowledge, these are the first examples in which different classes of N-containing compounds have been directly prepared from the readily available N-allylbenzamides using an inexpensive catalyst/oxidant/base (CuSO4/TBHP/Cs2CO3) system.
Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation
Liou, Yan-Cheng,Su, Yin-Hsiang,Ku, Kuan-Chun,Edukondalu, Athukuri,Lin, Chun-Kai,Ke, You-Syuan,Karanam, Praneeth,Lee, Chia-Jui,Lin, Wenwei
supporting information, p. 8339 - 8343 (2019/10/16)
We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.
Symmetric imide compound and synthetic method thereof
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Paragraph 0030-0033, (2019/08/07)
The invention discloses a symmetric imide compound and a synthetic method thereof. The method comprises the steps of mixing a compound as shown in the general formula (I) and alkali in aprotic solvent, heating for reaction, and then collecting a compound as shown in the general formula (II) from the reaction product. A series of diaryl imide compounds with representative structure can be obtainedby one-step reaction of simple and easily available activated amide, which is taken as raw material.
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).
A carbonylation reaction of carbon monoxide in the method of preparing amide
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Paragraph 0024; 0025; 0026; 0027; 0028-0032; 0129-0130; 0146, (2018/07/30)
The invention belongs to the technical field of synthesis of amides, discloses a process for the carbonylation of carbon monoxide in the method of preparing amide, the method is to cheap and easy to obtain the halogenated aromatic hydrocarbon and organic amine compounds as the substrate of reaction, to carbon monoxide as carbonyl source, under light-struck, halogenated aromatic hydrocarbons are cracked to produce free radical, by free-radical addition process to obtain the amide compound. Compared with the traditional carbonylation reaction, the carbon monoxide pressure is extremely low, can react to the atmospheric pressure. This process does not need to rely on any metal catalyst of the booster, mild reaction conditions, environmental protection, with a shorter synthetic route and high utilization efficiency of the atoms, the reaction system with higher substrate tolerance, green sustainable light source as the driving force, the atom economy is high, application prospect.
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
, 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.
Organocatalytic Direct N-Acylation of Amides with Aldehydes under Oxidative Conditions
Zheng, Chenguang,Liu, Xiang,Ma, Cheng
, p. 6940 - 6945 (2017/07/13)
The direct oxidative N-acylation reaction of primary amides with aryl/α,β-unsaturated aldehydes was achieved in the presence of azolium salt C3 and an inorganic base using 3,3′,5,5′-tetra-tert-butyldiphenoquinone as the oxidant, thus providing an efficient approach for the synthesis of three types of imide compounds including N-sulfonylcarboxamides, N-sulfinylcarboxamides, and dicarboxyimides in good yield.
Direct Oxidative Cross-Coupling of Toluene Derivatives and N-Acyl-2-aminoacetophenones
Yu, Hui,Xu, Yilan,Dong, Rui,Fang, Yan
supporting information, p. 39 - 43 (2017/01/14)
The direct oxidative cross-coupling between N-acyl-2-aminoacetophenones and toluene derivatives was developed with a new C–C bond being formed under metal-free and environmentally friendly conditions with excellent atom economy. A possible reaction pathway for the formation of the products is also discussed in this paper. (Figure presented.).
Vanadium-Catalyzed Oxidative C(CO)-C(CO) Bond Cleavage for C-N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides
Digwal, Chander Singh,Yadav, Upasana,Ramya, P. V. Sri,Sana, Sravani,Swain, Baijayantimala,Kamal, Ahmed
, p. 7332 - 7345 (2017/07/26)
A novel vanadium-catalyzed one-pot domino reaction of 1,2-diketones with amidines has been identified that enables their transformation into imides and amides. The reaction proceeds by dual acylation of amidines via oxidative C(CO)-C(CO) bond cleavage of 1,2-diketones to afford N,N′-diaroyl-N-arylbenzamidine intermediates. In the reaction, these intermediates are easily hydrolyzed into imides and amides through vanadium catalysis. This method provides a practical, simple, and mild synthetic approach to access a variety of imides as well as amides in high yields. Moreover, one-step construction of imide and amide bonds with a long-chain alkyl group is an attractive feature of this protocol.
