30334-17-9Relevant academic research and scientific papers
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.).
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.
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.
Oxidative Cleavage of Enamides with Hypervalent Iodine(III)/TMSN 3 under an Air Atmosphere
Liu, Ge,Li, Yan,Sheng, Jie,Wang, Xi-Sheng
supporting information, p. 3968 - 3974 (2017/08/29)
An oxidative cleavage of C-C double bonds of enamides promoted by hypervalent iodine(III)/TMSN 3 under an air atmosphere is developed. This reaction provides a new approach to construct various cyanobenzamides, which offers further synthetic potential for the preparation of industrial and pharmaceutical nitrogen- and oxygen-containing molecules, and exhibits good functional group tolerance, broad substrate scope and mild conditions.
2-Chloroanthraquinone-catalyzed aerobic photo-oxidative synthesis of diacylamines from benzylamides
Itoh, Izuho,Matsusaki, Yoko,Fujiya, Akitoshi,Tada, Norihiro,Miura, Tsuyoshi,Itoh, Akichika
, p. 3160 - 3162 (2014/05/20)
In this Letter, we report the aerobic photo-oxidative synthesis of diacylamines from benzylamides in the presence of molecular oxygen and catalytic amounts of 2-chloroanthraquinones under visible light irradiation from a fluorescent lamp.
N-Butylammonium carboxylates/Tf2O: Ionic liquid based systems for the synthesis of unsymmetrical imides via a Ritter-type reaction
Khodaei, Mohammad Mehdi,Nazari, Ehsan
experimental part, p. 2881 - 2884 (2012/07/28)
We have developed a new method for the preparation of unsymmetrical imides using liquid carboxylate salts via a Ritter-type process. The reactions were carried out with nitriles and n-butylammonium carboxylates as ionic liquids in the presence of triflic anhydride (Tf2O) as the promoter. Mild reaction conditions, simplicity of the procedure, and proton-free conditions are the main advantages of this procedure.
Ultrasound-assisted catalytic synthesis of acyclic imides in the presence of p-toluenesulfonic acid under solvent-free conditions
Nasr-Esfahani, Masoud,Montazerozohori, Morteza,Filvan, Najmeh
experimental part, p. 415 - 421 (2012/06/29)
A rapid and convenient preparation of acyclic imides by the reaction of aliphatic and aromatic nitriles with acyclic carboxylic anhydride in the presence of catalytic amounts of p-toluenesulfonic acid under thermal or ultrasonic conditions is reported. The advantages of this procedure are moderate reaction times, good to excellent yields, and use of an inexpensive and ecofriendly catalyst. The reaction of nitriles with aliphatic anhydrides proceeds under thermal conditions, while they are accelerated by the use of ultrasound irradiation.
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.
Efficient synthesis of symmetrical and unsymmetrical acyclic imides catalyzed by reusable 12-tungstophosphoric acid under thermal conditions and microwave irradiation
Mohammadpoor-Baltork,Tangestaninejad,Moghadam,Mirkhani,Nasr-Esfahani
experimental part, p. 401 - 410 (2012/06/16)
An efficient and environmentally friendly procedure has been developed for the synthesis of symmetrical and unsymmetrical acyclic imides by the reaction of nitriles with acyclic anhydrides in the presence of catalytic amounts of 12-tungstophosphoric acid (H3PW12O40) under thermal conditions and microwave irradiation. It was found that microwave improves the yields and significantly reduces the reaction times. Furthermore, the catalyst could be recovered and reused several times without decrease in its activity.
Aerobic photooxidation of benzylamide under visible light irradiation with a combination of 48% aq HBr and Ca(OH)2
Tada, Norihiro,Ban, Kazunori,Yoshida, Momoko,Hirashima, Shin-Ichi,Miura, Tsuyoshi,Itoh, Akichika
experimental part, p. 6098 - 6100 (2011/01/04)
Benzylamides were found to be oxidized to their corresponding diacylamines in the presence of molecular oxygen, catalytic 48% aq HBr, and Ca(OH) 2 under visible light irradiation of a fluorescent lamp.
