- Palladium-Catalyzed Solvent-Controlled Selective Synthesis of Acyl Isoureas and Imides from Amides, Isocyanides, Alcohols and Carboxylates
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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.).
- Cao, Ming,Liu, Liqiu,Tang, Shi,Peng, Zhiyuan,Wang, Yingchun
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p. 1887 - 1895
(2019/03/11)
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- Visible-Light-Driven Oxidation of N -Alkylamides to Imides Using Oxone/H 2 O and Catalytic KBr
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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.
- Mei, Chong,Hu, Yixin,Lu, Wenjun
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p. 2999 - 3005
(2018/05/25)
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- Oxidative Cleavage of Enamides with Hypervalent Iodine(III)/TMSN 3 under an Air Atmosphere
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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.
- Liu, Ge,Li, Yan,Sheng, Jie,Wang, Xi-Sheng
-
supporting information
p. 3968 - 3974
(2017/08/29)
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- Transition-Metal- and Halogen-Free Oxidation of Benzylic sp 3 C-H Bonds to Carbonyl Groups Using Potassium Persulfate
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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.
- Hu, Yixin,Zhou, Lihong,Lu, Wenjun
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p. 4007 - 4016
(2017/08/29)
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- 2-Chloroanthraquinone-catalyzed aerobic photo-oxidative synthesis of diacylamines from benzylamides
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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.
- Itoh, Izuho,Matsusaki, Yoko,Fujiya, Akitoshi,Tada, Norihiro,Miura, Tsuyoshi,Itoh, Akichika
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p. 3160 - 3162
(2014/05/20)
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- N-Butylammonium carboxylates/Tf2O: Ionic liquid based systems for the synthesis of unsymmetrical imides via a Ritter-type reaction
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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.
- Khodaei, Mohammad Mehdi,Nazari, Ehsan
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experimental part
p. 2881 - 2884
(2012/07/28)
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- Ultrasound-assisted catalytic synthesis of acyclic imides in the presence of p-toluenesulfonic acid under solvent-free conditions
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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.
- Nasr-Esfahani, Masoud,Montazerozohori, Morteza,Filvan, Najmeh
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experimental part
p. 415 - 421
(2012/06/29)
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- 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
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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.
- Lee, Jongbok,Hong, Myengchan,Jung, Yoonchul,Cho, Eun Jin,Rhee, Hakjune
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experimental part
p. 2045 - 2051
(2012/04/10)
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- Efficient synthesis of symmetrical and unsymmetrical acyclic imides catalyzed by reusable 12-tungstophosphoric acid under thermal conditions and microwave irradiation
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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.
- Mohammadpoor-Baltork,Tangestaninejad,Moghadam,Mirkhani,Nasr-Esfahani
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experimental part
p. 401 - 410
(2012/06/16)
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- Aerobic photooxidation of benzylamide under visible light irradiation with a combination of 48% aq HBr and Ca(OH)2
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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.
- Tada, Norihiro,Ban, Kazunori,Yoshida, Momoko,Hirashima, Shin-Ichi,Miura, Tsuyoshi,Itoh, Akichika
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experimental part
p. 6098 - 6100
(2011/01/04)
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- BF3 · Et2O-induced decomposition of ethyl 2-diazo-3-hydroxy-3,3-diarylpropanoates in acetonitrile: A novel approach to 2,3-diaryl β-enamino ester derivatives
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The BF3·Et2O-induced decomposition of ethyl 2-diazo-3-hydroxy-3,3-diarylpropanoates, prepared by the addition of a series of benzophenones to ethyl diazo(lithio)acetate, is reported and studied. By using acetonitrile as a solvent, the corresponding N-acyl β-enamino ester derivatives are obtained in good yields and with a diverse regioselectivity as the result of 1,2-aryl migration in the vinyl cation intermediates. The factors that govern the migratory aptitude as well as the mechanistic aspects of the reaction are discussed.
- Gioiello, Antimo,Venturoni, Francesco,Natalini, Benedetto,Pellicciari, Roberto
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supporting information; experimental part
p. 3520 - 3523
(2009/09/30)
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- Highly efficient copper-catalyzed amidation of aldehydes by C-H activation
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We have developed a highly efficient method for the copper-catalyzed amidation of aldehydes in the presence of N-bromosuccinimide (NBS). This method is simple, economical, and has practical advantages for synthesis of imides.
- Wang, Long,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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experimental part
p. 10722 - 10726
(2009/12/03)
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- Aerobic photooxidation of benzylamide in the presence of catalytic iodine
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Benzylamides were found to be oxidized to the corresponding imides in the presence of molecular oxygen and catalytic iodine under photoirradiation. Georg Thieme Verlag Stuttgart.
- Nakayama, Hiroki,Itoh, Akichika
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p. 675 - 678
(2008/12/20)
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- Aerobic oxidation with N-hydroxyphthalimide catalysts in ionic liquid
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N-Hydroxyphthalimide (NHPI)-catalyzed aerobic oxidations in the ionic liquids were examined for the first time. Both NHPI and its ionic derivative, 3-pyridinylmethyl-N-hydroxyphthalimide (Py-NHPI), were found to have better performance in the ionic liquid than in the conventional organic solvents for the aerobic oxidation of N-alkylamides to imides. On the other hand, Py-NHPI was found to be a much better catalyst than NHPI for the aerobic oxidation of benzylic compounds in the ionic liquid.
- Wang, Jia-Rui,Liu, Lei,Wang, Ye-Feng,Zhang, Ying,Deng, Wei,Guo, Qing-Xiang
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p. 4647 - 4651
(2007/10/03)
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- Mechanistic investigations on the reaction between amines or amides and an alkylperoxy-λ3-iodane
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A mechanism involving the intermediate formation of an amine radical cation by single-electron transfer is proposed for the oxidation of secondary amines with alkylperoxy-λ3-iodane. On the other hand, the oxidation of acetamides probably proceeds by a radical process, which involves the direct hydrogen abstraction of the methylene group α to the nitrogen atom.
- Sueda, Takuya,Kajishima, Daisuke,Goto, Satoru
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p. 3307 - 3310
(2007/10/03)
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- Aerobic oxidation of N-alkylamides catalyzed by N-hydroxyphthalimide under mild conditions. Polar and enthalpic effects
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The oxidation of N-alkylamides by O2, catalyzed by N-hydroxyphthalimide (NHPI) and Co(II) salt, leads under mild conditions to carbonyl derivatives (aldehydes, ketones, carboxylic acids, imides) whose distribution depends on the nature of the alkyl group and on the reaction conditions. Primary N-benzylamides lead to imides and aromatic aldehydes at room temperature without any appreciable amount of carboxylic acids, while under the same conditions nonbenzylic derivatives give carboxylic acids and imides with no trace of aldehydes, even at very low conversion. These results are explained through hydrogen abstraction by the phthalimide-N-oxyl (PINO) radical, whose reactivity with benzyl derivatives is governed by polar effects, so that benzylamides are much more reactive than the corresponding aldehydes. The enthalpic effect is, however, dominant with nonbenzylic amides, making the corresponding aldehydes much more reactive than the starting amides. The importance of the bond dissociation energy (BDE) of the O-H bond in NHPI is emphasized.
- Minisci, Francesco,Punta, Carlo,Recupero, Francesco,Fontana, Francesca,Franco Pedulli, Gian
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p. 2671 - 2676
(2007/10/03)
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- A bromine-catalysed free-radical oxidation of acetamides from primary and secondary alkylamines by H2O2
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New procedures based on the oxidation by bromine-catalysed hydrogen peroxide in a two-phase system provide simple and cheap transformations of alkylamines to carbonyl derivatives (aldehydes, ketones, carboxylic acid, imides, lactams) through the corresponding acetamides.
- Bjorsvik,Fontana,Liguori,Minisci
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p. 523 - 524
(2007/10/03)
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- Cathodic Reductions of Acid Azides. Electrolytic Studies on Vinyl Acides, VIII
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The cathodic reduction of the O=C-N3-system in aprotic solvent in the presence of anhydrides proves to be a convenient way to triacylammonia derivatives.Using the complexation of Li(+) ions with the acid azide this synthetic methods can start from non-dangerous acid halides.The complex formation constant has been estimated and the chemical stability of N,N-diacylamides produced has been investigated.Mechanistic details about the role of Li(+)-ions in these electrolyses are given.Further reduction of the triacylammonia derivatives at more negative potentials results in protected aldehydic functions, i.e. 1-acyloxy-1-diacylaminomethanes, in good yields. - Keywords: Acid azides; N,N-Diacylamides; 1-Acyloxy-1-diacetyl-aminomethanes; Lithiumion-azide complexes; Cathodic reduction
- Knittel, Dierk
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p. 379 - 388
(2007/10/02)
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- The Oxidative Decarboxylation of N-Aroylglycines to N-(Aacetoxymethyl)benzamides and N-Formylbenzamides with Lead(IV) Acetate
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Treatment of N-aroylglycines that do not bear a strong electron-withdrawing substituents with lead(IV) acetate in acetic acid/acetic anhydride mixtures at 60-100 deg C rapidly gives the corresponding N-(acetoxymethyl)benzamides and N-formylbenzamides in m
- Gledhill, Adrian P.,McCall, Carol J.,Threadgill, Michael D.
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p. 3196 - 3201
(2007/10/02)
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