- Synthesis of a Zeolitic Imidazolate-Zinc Metal-Organic Framework and the Combination of its Catalytic Properties with 2,2,2-Trifluoroethanol for N-Formylation
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A novel protocol is reported for the N-formylation of amines with formic acid by using the nanoporous zeolitic imidazolate framework ZIF-8 as a heterogeneous catalyst in 2,2,2-trifluoroethanol.
- Alamgholiloo, Hassan,Rostamnia, Sadegh,Hassankhani, Asadollah,Banaei, Reza
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supporting information
p. 1593 - 1596
(2018/06/08)
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- Diethyloxalate as “CO” Source for Palladium-Catalyzed Ethoxycarbonylation of Bromo- and Chloroarene Derivatives
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Palladium(II)-catalyzed ethoxycarbonylation of aryl bromides with diethyloxalate oxalate is described. Functionalized aromatic esters can be efficiently synthesized with only 0.65 mol % PdCl2(PPh3)2 catalyst under microwav
- Monrose, Amandine,Salembier, Helori,Bousquet, Till,Pellegrini, Sylvain,Pélinski, Lydie
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supporting information
p. 2699 - 2704
(2017/08/16)
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- Oxidative Cleavage of C2-C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates
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On reaction with (diacetoxyiodo)benzene, isatin and N-acetyl isatin undergo the oxidative C2-C3 bond cleavage to form carbamates of alkyl anthranilates and alkyl 2-acetamidobenzoate, respectively.
- Kalbandhe, Amit H.,Kavale, Ashish C.,Thorat, Prerana B.,Karade, Nandkishor N.
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supporting information
p. 763 - 768
(2016/03/12)
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- Reactivity of 2-methyl-4H-3,1-benzoxazin-4-ones and 2-methyl-4H-pyrido[2,3- d][1,3]oxazin-4-one under microwave irradiation conditions
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The reactivity of variably substituted 2-methyl-4H-3,1-benzoxazin-4-ones and 2-methyl-4H-pyrido[2,3-d][1,3]oxazin-4-one towards carbon and oxygen nucleophiles under microwave irradiation conditions was investigated. Optimization of the reaction conditions of oxazinones with carbon nucleophiles led to the synthesis of a series of 4-hydroxy-quinolin-2-ones and 4-hydroxy-1,8-naphthyridin-2-ones in high yields, whereas reaction with a variety of alcohols proceeded smoothly to the formation of the corresponding N-acetyl-anthranilates and nicotinates.
- Prousis, Kyriakos C.,Tzani, Andromachi,Avlonitis, Nicolaos,Calogeropoulou, Theodora,Detsi, Anastasia
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p. 1313 - 1321
(2014/01/06)
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- Efficient synthesis of anthranilic esters via Pd-catalyzed dehydrogenative/decarbonylative coupling of anilides and glyoxylates
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A novel way of synthesizing anthranilic esters was developed via Pd-catalyzed dehydrogenative/decarbonylative coupling between anilides and glyoxylates. The Royal Society of Chemistry 2012.
- Wang, Sizhuo,Yang, Zhiyong,Liu, Jidan,Xie, Kai,Wang, Anwei,Chen, Xiang,Tan, Ze
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supporting information
p. 9924 - 9926
(2012/11/07)
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- Electrochemical nuclear acetamidation of aromatic compounds at the platinum anode
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The electrochemical nuclear acetamidation of aromatic compounds ethylbenzoate, acetophenone, benzoic acid and benzene have been carried out at platinum anode under the process of nuclear oxidation. The removal of electrons from the aromatic π-electron system is achieved by the electrochemical oxidation. The electrolysis is carried out at the constant anode potential in an electrolytic cell assembly containing reaction mixture and electrodes. The products 4-acetamidoethylbenzoate, 4-acetamidoacetophenone, 4-acetamidobenzoic acid and N-phenylacetamide formed during the electrolysis are reported here.
- Sharma, Laxmi Kant,Kumar, Sanjeev,Yadav, Pragati,Singh
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p. 1277 - 1280
(2008/12/23)
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- Acylated 1,3-aminopropanols as repellents against bloodsucking arthropods
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Starting from a set of known repellent compounds, a general structural framework with high probability for repellent activity was developed by molecular modelling techniques. Synthesis, structure-biological activity relationships of acylated 1,3-aminoprop
- Boeckh,Breer,Geier,Hoever,Kruger,Nentwig,Sass
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p. 359 - 373
(2007/10/03)
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- Acylanthranils. 11. Reaction of Acylanthranils with Alcohols To Give the Corresponding Esters
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Although the reactions of acetylanthranil (1, R = CH3) with nucleophilic molecules of the type HNu usually occur "abnormally" via nucleophilic attack at the less electropositive center, C-2 (pathway A, Scheme II), it was shown that reactions of 1 with the anion form, Nu(1-), always occur "normally" via nucleophilic attack at the more electropositive center, C-4 (pathway B, Scheme II).Thus, reaction of 1 with ROH in the presence of a small amount of RO(1-) gives the corresponding o-acetamidobenzoate ester 4 in very good yields, rather than the corresponding acetimidate 3.These results are consistent with the hypothesis that the "abnormal" selectivity is attributable to formation of a molecular complex, 1*(HNu)n, via hydrogen bonding with the heterocyclic nitrogen atom of 1, which favors subsequent nucleophilic attack at the adjacent electropositive center at C-2.Since Nu(1-) cannot be restrained by the tether of hydrogen bonding to the electron donating atoms of 1, reaction occurs "normally" via direct nucleophilic attack at C-4.
- Errede, L.A.,Ashley, P.E.,McBrady, J.J.,Yarian, D.R.
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p. 3825 - 3828
(2007/10/02)
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- Ortho Vinylation of Aromatic Amides via Cyclopalladation Complexes
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The reaction of acetanilide and meta- and para-substituted acetanilides with palladium acetate has given new ortho-palladated complexes 2a-j, which reacted with carbon monoxide, ethylene, or methyl vinyl ketone to produce the corresponding N-acylanthranilic esters 4a-m, 2-acetaminostyrenes 9k-p, and 4-aryl-3-buten-2-one derivatives 9a-j, respectively.Reactions of 2a with substituted olefins proceeded readily to give the 2-olefins 8a-h.Ortho-substituted acetanilides and N-methylacetanilide did not undergo complex formation with palladium acetate.
- Horino, Hiroshi,Inoue, Naoto
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p. 4416 - 4422
(2007/10/02)
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- Acylanthranils. 9. Influence of Hydrogen Bonding on the Reaction of Acetylanthranil with Ammonia
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It was shown that hydrogen bonding has a marked influence on the reaction of acetylanthranil (1) with ammonia.The product of the reaction in anhydrous benzene is 2-methylquinazolin-4-one (5, R = H) which is formed via pathway A as shown in Scheme I, but the rate of formation is unusually slow.The rate of this conversion is about 6 times faster in pyridine than in benzene.If water is added to the benzene system, the rate of reaction is increased by orders of magnitude, but the product is o-acetamidobenzamide (4, R = H) and not 5.In contrast to this result, the addition of water to the pyridine system causes a small decrease in rate and only a slight change in selectivity.These results are consistent with postulated mechanisms whereby 1 reacts with molecular clusters of ammonia, i.e. with (NH3)n in benzene, with N(H*S)3 in strong proton acceptor solvents S, and with (NH3)n*H2O in benzene plus added water.It was verified that cyclodehydration of 4 to give 5 occurs at an appreciable rate in aqueous solution at elevated temperatures and that this rate is accelerated considerably by the presence of strong base even at room temperature.It was also observed that o-acetamidobenzamide exists in at least two crystalline forms, α and β, which have different physical properties.
- Errede, L. A.,Martinucci, P. D.,McBrady, J. J.
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p. 3009 - 3017
(2007/10/02)
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