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Journal articles on the topic 'Acylation reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 18 February 2022

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1

Đud, Mateja, Anamarija Briš, Iva Jušinski, Davor Gracin, and Davor Margetić. "Mechanochemical Friedel–Crafts acylations." Beilstein Journal of Organic Chemistry 15 (June 17, 2019): 1313–20. http://dx.doi.org/10.3762/bjoc.15.130.

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Friedel–Crafts (FC) acylation reactions were exploited in the preparation of ketone-functionalized aromatics. Environmentally more friendly, solvent-free mechanochemical reaction conditions of this industrially important reaction were developed. Reaction parameters such as FC catalyst, time, ratio of reagents and milling support were studied to establish the optimal reaction conditions. The scope of the reaction was explored by employment of different aromatic hydrocarbons in conjunction with anhydrides and acylation reagents. It was shown that certain FC-reactive aromatics could be effectively functionalized by FC acylations carried out under ball-milling conditions without the presence of a solvent. The reaction mechanism was studied by in situ Raman and ex situ IR spectroscopy.

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2

De Risi, Carmela, Olga Bortolini, Graziano Di Carmine, Daniele Ragno, and Alessandro Massi. "Kinetic Resolution, Dynamic Kinetic Resolution and Asymmetric Desymmetrization by N-Heterocyclic Carbene Catalysis." Synthesis 51, no. 09 (March 18, 2019): 1871–91. http://dx.doi.org/10.1055/s-0037-1612305.

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N-Heterocyclic carbenes (NHCs) are now well-established organocatalysts for a large number of asymmetric and non-asymmetric transformations. In the last 15 years, there has been significant interest in using NHCs in kinetic resolution (KR), dynamic kinetic resolution (DKR) and asymmetric desymmetrization reactions for the stereoselective synthesis of enantioenriched compounds, with diverse substrates and activation modes being adopted to this end. This short review brings into focus the progress made on NHC-catalyzed KR, DKR, and asymmetric desymmetrization from 2004 until December 2018. The literature discussed in this article is classified on the basis of the type of reaction involving the NHC catalyst.1 Introduction2 Acylation Strategies2.1 O-Acylation2.2 N-Acylation2.3 C-Acylation3 Aldol-Acylation Processes4 Benzoin Reactions5 Stetter Reactions6 Miscellaneous Approaches7 Conclusion

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3

Tran, Phuong Hoang, Thanh Duy Anh Nguyen, and Thach Ngoc Le. "Friedel-crafts acylation of aromatic compounds using Triflat bismuth." Science and Technology Development Journal 17, no. 2 (June 30, 2014): 10–14. http://dx.doi.org/10.32508/stdj.v17i2.1310.

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Friedel-Crafts acylation of aromatic compounds with acetic anhydride as acylating reagent was investigated in the presence of Lewis acid. Bismuth trifluoromethanesulfonate was found to be efficient catalyst for Friedel-Crafts acetylation under mild conditions. Bismuth triflate is safe-to-handle, simple and clean work-up, good yield and short reaction time

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4

Kawamura, Masato, Dong-Mei Cui, and Shigeru Shimada. "Friedel–Crafts acylation reaction using carboxylic acids as acylating agents." Tetrahedron 62, no. 39 (September 2006): 9201–9. http://dx.doi.org/10.1016/j.tet.2006.07.031.

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5

Kolmakov, Kirill A. "Reactions of aniline in acetic acid solutions containing cyanuric chloride and hydrogen chloride acceptors." Canadian Journal of Chemistry 85, no. 12 (December 1, 2007): 1070–74. http://dx.doi.org/10.1139/v07-129.

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Two reaction pathways in acetic acid solution containing cyanuric chloride, aniline, and some hydrogen chloride acceptors (triethylamine, sodium acetate, pyridine) were studied. Both aryl amination and acylation can be performed with high yields under proper reaction conditions. Contrary to the only known literature report on the reactions between carbonic acids and cyanuric chloride in the presence of a hydrogen chloride acceptor (triethylamine), it was established that acid chlorides are not formed. A scheme involving the replacement of chlorine atoms by acetate ion in the initial stage was proposed for the acylation of aniline promoted by cyanuric chloride.Key words: acetic acid, acylation, aniline, cyanuric chloride, aryl amination.

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6

Kuo, David L. "Magnesium chloride catalysed acylation reaction." Tetrahedron 48, no. 42 (January 1992): 9233–36. http://dx.doi.org/10.1016/s0040-4020(01)85613-1.

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7

Jiao, Yinchun, Wenjing Zhao, Shuang Deng, Zilong Tang, Wanqiang Liu, Yichao Wan, and Fuqi Zhong. "A one-pot diastereoselective synthesis of 1,3-diols and 1,3,5-triols via cascade reactions of arylalkynyl Grignard reagents with enol esters." Journal of Chemical Research 44, no. 5-6 (March 4, 2020): 255–66. http://dx.doi.org/10.1177/1747519820908513.

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An efficient cascade reaction has been developed to synthesize a series of 1,3-diols and 1,3,5-triols via reactions of arylalkynyl Grignard reagents with enol esters. The stereoselectivity of reactions and the molecular configurations of the products were confirmed by nuclear magnetic resonance, X-ray diffraction, and high-performance liquid chromatography analysis. A possible reaction mechanism was analyzed with the results indicating that it proceeded through a 1,2-addition/rearrangement and reverse O-acylation to produce the 1,3-diol and via C-acylation to form the 1,3,5-triol.

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8

Satyanarayana, Gedu, and Basuli Suchand. "Palladium-Catalyzed Direct Acylation: One-Pot Relay Synthesis of Anthraquinones." Synthesis 51, no. 03 (October 10, 2018): 769–79. http://dx.doi.org/10.1055/s-0037-1610296.

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A bis-acylation strategy to access functionalized anthraquinones via one-pot relay process, is presented. The first acylation was feasible under [Pd]-catalyzed intermolecular direct acylation reaction, while, the second acylation was accomplished by using intramolecular Friedel–Crafts acylation. Notably, benchtop aldehydes have been utilized as non-toxic acylation agents in the key [Pd]-catalyzed acylation.

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9

Shou, Haowen, Zhaoting He, Gang Peng, Weike Su, and Jingbo Yu. "Two approaches for the synthesis of levo-praziquantel." Organic & Biomolecular Chemistry 19, no. 20 (2021): 4507–14. http://dx.doi.org/10.1039/d1ob00453k.

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Two pathways for the preparation of levo-praziquantel are herein reported, which involves mechanochemical (asymmetric) aza-Henry/acylation reaction, hydrogenation reaction, (chiral resolution) and solvent-free acylation-ring closing reaction.

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10

Pelkey, Erin T., and Gordon W. Gribble. "Novel electrophilic ipso acylation - detosylation reaction of pyrroles." Canadian Journal of Chemistry 84, no. 10 (October 1, 2006): 1338–42. http://dx.doi.org/10.1139/v06-075.

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A pyrrole and two pyrroloindoles that are substituted with a p-toluenesulfonyl group undergo an ipso acylation – detosylation reaction with acid chlorides and aluminum chloride to afford the corresponding acyl-substituted pyrroles and pyrroloindoles.Key words: pyrrole, pyrroloindole, ipso acylation, detosylation, Friedel–Crafts reaction.

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11

Kurzer, Frederick, and Dennis Chapman. "The Oxidation of Partially Acylated Myoinositols." Zeitschrift für Naturforschung B 51, no. 1 (January 1, 1996): 68–78. http://dx.doi.org/10.1515/znb-1996-0114.

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Abstract 1,3,4,6-Tetrakis-and 1,3,4,5,6-pentakis-acylmyoinositols are obtained by the controlled catalyzed acylation of myoinositol. The extent of the substitution depends both on the reaction conditions and the structure of the acylating agent, including steric factors. Chromic acid oxidation converts the acylmyoinositols into the corresponding 2-ketones. Under electron impact, the compounds undergo stepwise deacylation.

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12

Čmelík, Richard, and Pavel Pazdera. "Transformation of 1,2-Dithiole-3-thiones Into 1,6,6aλ4-Trithiapentalenes via Reaction with Bromoethanones." Collection of Czechoslovak Chemical Communications 71, no. 5 (2006): 650–66. http://dx.doi.org/10.1135/cccc20060650.

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We report the reactions of derivatives of 5-amino-3-thioxo-3H-1,2-dithiole-4-carboxylic acid 1 with bromoethanones and acylation agents. Two different routes were used to obtain the products, 3-(acylmethylidene)-3H-1,2-dithioles 4. These compounds were synthesized by acylation of compounds 1 on the amino group, followed by the reaction with bromoethanones and excess of triethylamine. Another method was based on the inverted order of the mentioned reaction steps and in absence of a base. The treatment of 4 with thionyl chloride gave new unsaturated fused lactones 13 whereas thionation led to desired 1,6,6aλ4-trithiapentalenes 5. The structures of products and the reaction mechanisms are discussed.

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13

Jadhav, Arvind H., Amutha Chinnappan, Vishwanath Hiremath, and Jeong Gil Seo. "Synthesis and Characterization of AlCl3 Impregnated Molybdenum Oxide as Heterogeneous Nano-Catalyst for the Friedel-Crafts Acylation Reaction in Ambient Condition." Journal of Nanoscience and Nanotechnology 15, no. 10 (October 1, 2015): 8243–50. http://dx.doi.org/10.1166/jnn.2015.11253.

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Aluminum trichloride (AlCl3) impregnated molybdenum oxide heterogeneous nano-catalyst was prepared by using simple impregnation method. The prepared heterogeneous catalyst was characterized by powder X-ray diffraction, FT-IR spectroscopy, solid-state NMR spectroscopy, SEM imaging, and EDX mapping. The catalytic activity of this protocol was evaluated as heterogeneous catalyst for the Friedel-Crafts acylation reaction at room temperature. The impregnated MoO4(AlCl2)2 catalyst showed tremendous catalytic activity in Friedel-Crafts acylation reaction under solvent-free and mild reaction condition. As a result, 84.0% yield of acyl product with 100% consumption of reactants in 18 h reaction time at room temperature was achieved. The effects of different solvents system with MoO4(AlCl2)2 catalyst in acylation reaction was also investigated. By using optimized reaction condition various acylated derivatives were prepared. In addition, the catalyst was separated by simple filtration process after the reaction and reused several times. Therefore, heterogeneous MoO4(AlCl2)2 catalyst was found environmentally benign catalyst, very convenient, high yielding, and clean method for the Friedel-Crafts acylation reaction under solvent-free and ambient reaction condition.

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14

Rustamov, M. A., and G. A. Mirzayeva. "STUDY OF ACYLATION REACTION OF AMINES OF VARIOUS STRUCTURES WITH CHLOROANHYDRIDE OF HEXANE ACID." Chemical Problems 16, no. 2 (2018): 191–95. http://dx.doi.org/10.32737/2221-8688-2018-2-191-195.

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15

Sharma, Rajinder P., Kusum Sharma, Sunita Lakhanpal, Namita Sharma, and Bhupendra N. Misra. "Preparation and Characterization of Mixed Anhydrides of O-Acylarylcarbohydroximic Acid." Collection of Czechoslovak Chemical Communications 58, no. 9 (1993): 2150–58. http://dx.doi.org/10.1135/cccc19932150.

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A number of N,O-diacylhydroxylamines have been prepared by the reaction of potassium salts of hydroxamic acids with variety of acylating agents which include: benzoyl, p-nitrobenzoyl, anisoyl, p-chlorobenzyl and lauroyl chlorides in dioxane under reflux. The structure of resulting N,O-diacylhydroxylamines has been determined by spectral analysis, Attempted have been made to prepare mixed anhydrides of several N,O-diacylhydroxylamines by the acylation reaction in the cold (below 10 °C) using acetyl, benzoyl, p-nitrobenzoyl, anisoyl and p-toluensulfonyl chlorides as acylating agents in dioxane using triethylamine as a base. Structures of the resulting mixed anhydrides have been elucidated by spectral methods.

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16

Manhas, Maghar S., Subhendu N. Ganguly, Somdatta Mukherjee, Amit K. Jain, and Ajay K. Bose. "Microwave initiated reactions: Pechmann coumarin synthesis, Biginelli reaction, and acylation." Tetrahedron Letters 47, no. 14 (April 2006): 2423–25. http://dx.doi.org/10.1016/j.tetlet.2006.01.147.

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17

Tran, Phuong Hoang, Hai Truong Nguyen, and Thach Ngoc Le. "Benzoylation of aryl methyl ether using catalytic system of Gd(OTf)3/MSAA." Science and Technology Development Journal 18, no. 2 (June 30, 2015): 221–27. http://dx.doi.org/10.32508/stdj.v18i2.1187.

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The Friedel-Crafts acylation is an important reaction in organic synthesis. Benzoylation of aromatic compounds with benzoic acid as acylating reagent using catalytic system of Gd(OTf)3/MSAA was investigated under microwave irradiation. Catalytic system of Gd(OTf)3/MSAA was found to be an efficient catalyst for FriedelCrafts benzoylation under mild conditions. In addition, Gd(OTf)3/MSAA is safe-to-handle, simple clean work-up and gives good yield.

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18

Piegat, Agnieszka, Agata Goszczyńska, Tomasz Idzik, and Agata Niemczyk. "The Importance of Reaction Conditions on the Chemical Structure of N,O-Acylated Chitosan Derivatives." Molecules 24, no. 17 (August 22, 2019): 3047. http://dx.doi.org/10.3390/molecules24173047.

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The structure of acylated chitosan derivatives strongly determines the properties of obtained products, influencing their hydrodynamic properties and thereby their solubility or self-assembly susceptibility. In the present work, the significance of slight changes in acylation conditions on the structure and properties of the products is discussed. A series of chitosan-acylated derivatives was synthesized by varying reaction conditions in a two-step process. As reaction media, two diluted acid solutions—i.e., acetic acid and hydrochloric acid)—and two coupling systems—i.e., 1-ethyl-3-(3-dimethyl-aminopropyl)-1-carbodiimide hydrochloride (EDC) and N–hydroxysulfosuccinimide (EDC/NHS)—were used. The chemical structure of the derivatives was studied in detail by means of two spectroscopic methods, namely infrared and nuclear magnetic resonance spectroscopy, in order to analyze the preference of the systems towards N- or O-acylation reactions, depending on the synthesis conditions used. The results obtained from advanced 1H-13C HMQC spectra emphasized the challenge of achieving a selective acylation reaction path. Additionally, the study of the molecular weight and solution behavior of the derivatives revealed that even slight changes in their chemical structure have an important influence on their final properties. Therefore, an exact knowledge of the obtained structure of derivatives is essential to achieve reaction reproducibility and to target the application.

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19

Koyama, Kaichiro, Isao Mizota, and Makoto Shimizu. "Integrated reactions based on the sequential addition to α-imino esters." Pure and Applied Chemistry 86, no. 5 (May 19, 2014): 755–64. http://dx.doi.org/10.1515/pac-2013-1105.

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AbstractThis article summarizes integrated sequential reactions with α-imino esters, where the umpolung addition reaction to the imino nitrogen followed by the second addition or oxidation is the crucial step. The following four types of reactions are discussed: (1) tandem N-ethylation/Mannich reaction; (2) N-alkylation/addition reaction; (3) synthesis of indolin-3-ones and tetrahydro-4-quinolones; (4) regioselective tandem N-alkylation/ C-acylation of β,γ-alkynyl α-imino esters.

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20

Kuznetsov, Alexander A., Anna Yu Tsegelskaya, Pavel V. Buzin, Marina Yu Yablokova, and Galina K. Semenova. "High Temperature Polyimide Synthesis in ‘Active’ Medium: Reactivity Leveling of the High and the Low Basic Diamines." High Performance Polymers 19, no. 5-6 (October 2007): 711–21. http://dx.doi.org/10.1177/0954008307081214.

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The kinetics associated with the reaction of aromatic and aliphatic diamines with phthalic anhydride in glacial acetic acid was studied. This model system was intended to simulate the synthesis of polyimides from diamines and dianhydrides in molten benzoic acid. The reaction proceeds in two discrete steps, the first acylation occurs by the reaction of the diamine with phthalic anhydride followed by cy-clodehydration of the corresponding bis-(o-carboxyamides). The focus of the work was on the influence of chemical composition and basicity of the diamines on the kinetics. Kinetic and thermodynamic characteristics of model reactions were determined. It was established that acylation of aromatic and aliphatic diamines in acid medium proceeds as a reversible second-order reaction catalyzed by acid medium. On the basis of kinetic data obtained, an explanation is given for the observed phenomenon of reactivity leveling of diamines regardless of the basicity.

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21

Porfyris, Athanasios, Constantine D. Papaspyrides, Natnael Behabtu, Cristian Lenges, and Alexander Kopatsis. "High-Solids, Solvent-Free Modification of Engineered Polysaccharides." Molecules 26, no. 13 (July 2, 2021): 4058. http://dx.doi.org/10.3390/molecules26134058.

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The nature-identical engineered polysaccharide α-(1,3) glucan, produced by the enzymatic polymerization of sucrose, was chemically modified by acylation with succinic anhydride. This modification reaction was initially performed at the micro scale in a TGA reactor to access a range of reaction conditions and to study the mechanism of the reaction. Subsequently, the best performing conditions were reproduced at the larger laboratory scale. The reaction products were characterized via coupled TGA/DSC analysis, FT-IR spectroscopy, solution viscosity and pH determination. The acylation path resulted in partially modifying the polysaccharide by altering its behavior in terms of thermal properties and solubility. The acylation in a solvent-free approach was found promising for the development of novel, potentially melt-processable and fully bio-based and biodegradable ester compounds.

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22

Qazanfarzadeh, Zeinab, Mahdi Kadivar, Hajar Shekarchizadeh, and Raffaele Porta. "Functional Properties of Rye Prolamin (Secalin) and Their Improvement by Protein Lipophilization through Capric Acid Covalent Binding." Foods 10, no. 3 (March 1, 2021): 515. http://dx.doi.org/10.3390/foods10030515.

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Secalin (SCL), the prolamin fraction of rye protein, was chemically lipophilized using acylation reaction by treatment with different amounts of capric acid chloride (0, 2, 4, and 6 mmol/g) to enhance its functional properties. It was shown that SCL lipophilization increased the surface hydrophobicity and the hydrophobic interactions, leading to a reduction in protein solubility and water absorption capacity and to a greater oil absorption. In addition, SCL both emulsifying capacity and stability were improved when the protein was treated with low amount of capric acid chloride. Finally, the foaming capacity of SCL markedly increased after its treatment with increasing concentrations of the acylating agent, even though the foam of the modified protein was found to be more stable at the lower level of protein acylation. Technological application of lipophilized SCL as a protein additive in food preparations is suggested.

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23

Schmidt, Nina G., Tea Pavkov-Keller, Nina Richter, Birgit Wiltschi, Karl Gruber, and Wolfgang Kroutil. "Biocatalytic Friedel-Crafts Acylation and Fries Reaction." Angewandte Chemie International Edition 56, no. 26 (May 23, 2017): 7615–19. http://dx.doi.org/10.1002/anie.201703270.

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24

Schmidt, Nina G., Tea Pavkov-Keller, Nina Richter, Birgit Wiltschi, Karl Gruber, and Wolfgang Kroutil. "Biocatalytic Friedel-Crafts Acylation and Fries Reaction." Angewandte Chemie 129, no. 26 (May 23, 2017): 7723–27. http://dx.doi.org/10.1002/ange.201703270.

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25

KUO, D. L. "ChemInform Abstract: Magnesium Chloride Catalyzed Acylation Reaction." ChemInform 24, no. 7 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199307147.

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26

Jeong, Hye Jin, Suyeon Chae, Keunhong Jeong, and Sung Keon Namgoong. "Diverse One-Pot Electrophilic Trapping Reactions of 2-Quinolylzincates with Acyl Chlorides and Allyl Iodide." Synthesis 52, no. 03 (November 21, 2019): 378–92. http://dx.doi.org/10.1055/s-0039-1690036.

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The tandem acylation reactions of 2-quinolylzincates under one-pot reaction conditions facilitated the formation of biologically active (Z)-3-alkylidenephthalides and multifunctionalized quinoline derivatives at specific positions. The reactions of these zincates with allyl iodide produced three different types of temperature- and alkyl-ligand-dependent C-2 homologated quinolines. The reaction mechanisms for the formation of the presented products from 2-quinolylzincates are also proposed in detail.

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27

Kawamura, Masato, Dong-Mei Cui, Teruyuki Hayashi, and Shigeru Shimada. "Lewis acid-catalyzed Friedel–Crafts acylation reaction using carboxylic acids as acylating agents." Tetrahedron Letters 44, no. 42 (October 2003): 7715–17. http://dx.doi.org/10.1016/j.tetlet.2003.08.099.

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28

Li, Wenpeng, Haibo Jin, Suohe Yang, Xiaoyan Guo, Guangxiang He, and Rongyue Zhang. "An environmentally friendly acylation reaction of 2-methylnaphthalene in solvent-free condition in a micro-channel reactor." Green Processing and Synthesis 8, no. 1 (January 28, 2019): 474–79. http://dx.doi.org/10.1515/gps-2019-0015.

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Abstract An efficient and solvent-free acylation of 2-methylnaphthalene (2-MN) is presented using acid chloride as both the acylating agent and solvent in a micro channel reactor. The effect of the catalyst, reactant ratio, mixing temperature, reaction temperature and reaction time on the product yield and selectivity was investigated. At room temperature with a reaction time of only 15 min, the target product, 2-methyl-6-propionylnaphthalene (2,6-MPN), was obtained in 72.3% yield with 73.8% selectivity, and 2-methyl-6-acetylnaphthalene (2,6-MAN) was obtained in 54.1% yield with 55.4% selectivity. The route of synthesis provides a more environmentally friendly and efficient method to prepare 2,6-MPN with no other toxic solvents and efficient mass transfer and heat transfer.

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29

Wang, Jinghua, Meng Cai, Fengqi Zhao, and Kangzhen Xu. "A Review on the Reactivity of 1-Amino-2-Nitroguanidine (ANQ)." Molecules 24, no. 19 (October 8, 2019): 3616. http://dx.doi.org/10.3390/molecules24193616.

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1-Amino-2-nitroguanidine (ANQ) is a high-energy nitrogen-rich compound with good detonation properties and low sensitivities. ANQ has only a central carbon atom with three small groups around it, including an amino, a hydrazine and a nitroxyl group. Though the molecular structure of ANQ is very simple, its reactivity is surprisingly abundant. ANQ can undergo various reactions, including reduction reaction, acylation reaction, salification reaction, coordination reaction, aldimine condensation reaction, cyclization reaction and azide reaction. Many new energetic compounds were purposely obtained through these reactions. These reactions were systematically summarized in this review, and detonation properties of some energetic compounds were compared. In the field of energetic materials, ANQ and some derivatives exhibit good application prospects.

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30

Mahajan, Dinesh, Varun Kumar, Anil Rana, Chhuttan Lal Meena, Nidhi Sharma, and Yashwant Kumar. "Electrophilic Activation of Carboxylic Anhydrides for Nucleophilic Acylation Reactions." Synthesis 50, no. 19 (August 14, 2018): 3902–10. http://dx.doi.org/10.1055/s-0037-1609564.

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Nucleophilic acylation of symmetrical carboxylic anhydrides has inherited limitation of reaction efficiency along with relatively poor reactivity. Traditionally, one equivalent carboxylic acid is generated during nucleophilic acylation of a symmetrical anhydride, which always limits the yield of final product to 50% or less. This is a major drawback, which discourages the use of anhydrides for laboratory or industrial applications. Electrophilic activation of carboxylic anhydride using methanesulfonyl chloride is found to be an efficient method for nucleophilic acylation, which increases product yield by restricting the formation of corresponding acid as a side product. The developed protocol found to be a mild and high yielding methodology for one-pot nucleophilic acylation of carboxylic anhydrides with several type of N- and S-nucleophiles demonstrating appreciable functional group tolerance.

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31

Kolesinska, Beata. "P-Acylphosphonium salts and their vinyloges — application in synthesis." Open Chemistry 8, no. 6 (December 1, 2010): 1147–71. http://dx.doi.org/10.2478/s11532-010-0114-z.

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AbstractReview with 101 refs. of progress in synthetic applications and properties of P-acylphosphonium salts including acylation via P-acylphosphonium salts, enantioselective acylation using chiral phosphine ligands, nucleophilic (β)-oniovinylation, and reaction involving vinyloges of P-acylphosphonium salts formed by treatment conjugated alkenoates or alkynoates with phosphines.

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32

Lhoták, Pavel, and Antonín Kurfürst. "Synthesis of Luminophoric Derivatives of PBD Based on 2,5-Diaryl Substituted Thiazoles and Oxazoles." Collection of Czechoslovak Chemical Communications 58, no. 11 (1993): 2720–28. http://dx.doi.org/10.1135/cccc19932720.

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The Friedel-Crafts acylation of 2-(biphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole (PBD) with hippuryl chloride has been used to prepare the derivative V which on cyclization with POCl3 or P4S10 gives the respective oxazole (or thiazole) derivative of PBD, XIa or XIb. The reaction of carboxylic acid II with 4-(o-aminoacetyl)biphenyl in the presence of CDI gives N-acyl-α-aminoketone VII; the analogous compound VI has been prepared by acylating of o-aminoacetophenone with acyl chloride III. The cyclization of these compounds gives bifluorophores Xa - Xd.

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33

Mukaiyama, Teruaki, Hitoshi Nagaoka, Masahiro Ohshima, and Masahiro Murakami. "THE DIPHENYLBORYL HEXACHLOROANTIMONATE PROMOTED FRIEDEL–CRAFTS ACYLATION REACTION." Chemistry Letters 15, no. 2 (February 5, 1986): 165–68. http://dx.doi.org/10.1246/cl.1986.165.

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34

Lin, Wenwei, Praneeth Karanam, and Ganapuram Reddy. "Strategic Exploitation of the Wittig Reaction: Facile Synthesis of Heteroaromatics and Multifunctional Olefins." Synlett 29, no. 20 (August 2, 2018): 2608–22. http://dx.doi.org/10.1055/s-0037-1610486.

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In this account, our group’s efforts towards exploring new substrates as precursors for the Wittig reaction have been discussed. Several new strategies developed by our group for the generation of requisite ylides for the Wittig reaction are highlighted. The idea behind the development of some chemoselective and diversity-oriented strategies are discussed in detail in a progressive manner. These strategies encompass a wide range of substrates that are employed for the synthesis of an array of heterocycles and multifunctional olefins and present a huge scope for their application on an industrial level.1 Introduction2 Development of New Methods to Effect Intramolecular Wittig Reaction3 Development of a Catalytic Wittig Reaction4 New Synthesis of Bis-Heteroarenes5 Direct β-Acylation of 2-Arylidene-1,3-indandiones6 Doubly Chemoselective Protocol for the Diversity-Oriented Synthesis of Coumarin Derivatives7 Conclusion

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35

Tran, Phuong Hoang, Vy Hieu Huynh, Hai Ngoc Tran, and Thach Ngoc Le. "Microwave-assisted intramolecular FriedelCrafts acylation of some aryl aliphatic acids using Gd(OTf)3/ [BMI]BF4 catalytic system." Science and Technology Development Journal 19, no. 2 (June 30, 2016): 64–70. http://dx.doi.org/10.32508/stdj.v19i2.803.

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Intramolecular Friedel–Crafts acylation of aryl acids is a “green” reaction and environmentally benign, generates some valuable intermediated compounds for pharmaceutical uses. In addition, metal triflates under microwave irradiation are efficient catalysts, solving many problems when using traditional Lewis acids. Gd(OTf)3/[BMI]BF4, a good catalyst for the intramolecular Friedel–Crafts acylation under mild condition with high yield, reduced the reaction time and pollution. Furthermore, Gd(OTf)3 in [BMI]BF4 was easily recovered and reused without significant loss of its activity

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36

Yamato, Takehiko, Kiwamu Tokuhisa, and Hirohisa Tsuzuki. "Medium-sized cyclophanes. part 51. Acylation of [2.2]metaparacyclophanes: through-space electronic interactions between two benzene rings." Canadian Journal of Chemistry 78, no. 2 (February 6, 2000): 238–47. http://dx.doi.org/10.1139/v00-006.

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The acylation of 8-methyl- (1b) and 8-methoxy[2.2]metaparacyclophane 1c with 1.1 equiv. of acetyl chloride in CS2 solution in the presence of aluminum chloride afforded 15-acetyl-8-methyl- (2b) and 12-acetyl-8-methoxy[2.2]metaparacyclophanes (3c) with 65 and 41% yields, respectively. The different orientations for the electrophilic substitution were observed to be dependant on the substituent at the 8 position. On the other hand, when the same reaction was carried out under the same reaction conditions with the corresponding 5-tert-butyl derivatives (11), ipso-acetylation at the tert-butyl group was observed along with acetylation on the para-benzene ring. The substituent effect on the 8-position was also observed in the present ipso-acetylation. The ipso-acylation at the tert-butyl group of 5-tert-butyl-8-methoxy[2.2]metaparacyclophane (11c) is attributed to the highly activated character of the aryl ring and the increased stabilization of a sigma-complex intermediate arising from the dienone-type sigma-complex intermediate possible in the case of a internal methoxy substituent. However, the present ipso-acetylation has not been observed in mild reaction conditions such as acetyl chloride in the presence of TiCl4 catalyst due to deactivation of the second aromatic ring by the introduced acetyl group on the para-benzene ring. The mechanism of these novel reactions is also discussed.Key words: cyclophanes, electrophilic aromatic substitution, regioselectivity, through-space electronic interaction, ipso-acylation.

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Yusnimar. "KINETIC MODELING STUDY FOR ACYLATION REACTION OF O-XYLENE TO 3,4-DIMETHYLBENZOPHENONE OVER H-BETA." Jurnal Riset Kimia 1, no. 1 (February 11, 2015): 89. http://dx.doi.org/10.25077/jrk.v1i1.100.

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ABSTRACTThe reaction of o-xylene with benzoic anhydride has been studied by the changing molar ratio of the reactants (20:1, 10:1, and 5:1) in a batch reactor under reaction temperature 120oC. The reaction carried out without catalyst and also with catalyst Zeolite beta which was activated at 300oC overnight. HPLC analysis results showed that the yield of the product increase with the changing molar ratio of the reactants. An attempt was made in determining the kinetics of the reaction. The results show that the reaction is neither first nor second order in the acylating agent. Obtaining the reaction order even initially is unsuitable for even simple reactions that do not go to completion. It is even less applicable where more than a single process which affects the rate is taking place right from the start. These might be any one or combination of diffusion, adsorption, desorption, inhibition of the reaction by the product and multi step reactions on the surface. Postulated reaction mechanisms may be required in combination with experimental data to determine even initial reaction orders. Key words: o-xylene, catalyst, kinetics, reaction order.

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Izydore, Robert A., Juan A. Bernal-Ramirez, and Phirtu Singh. "Reaction of 4,4-diethyl-3,5-pyrazolidinedione with carboxylic acid anhydrides. N-acylation vs O-acylation." Journal of Organic Chemistry 55, no. 12 (June 1990): 3761–67. http://dx.doi.org/10.1021/jo00299a015.

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Sumita, Akinari, Jinhee Lee, Yuko Otani, and Tomohiko Ohwada. "Facile synthesis of 2,3-benzodiazepines using one-pot two-step phosphate-assisted acylation–hydrazine cyclization reactions." Organic & Biomolecular Chemistry 16, no. 21 (2018): 4013–20. http://dx.doi.org/10.1039/c8ob00708j.

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We present a one-pot two-step methodology, in which an unprotected amino is tolerated, for rapidly synthesizing 2,3-benzodiazepines via phosphate-assisted acylation reaction and hydrazine cyclization reaction.

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40

Chen, Yong, Jun Qian, Qi Xin Zhuang, and Zhe Wen Han. "The Preparation and Characterization of Polybenzoxazole Copolymerized with Multiwalled Carbon Nanotube via Direct Friedel-Crafts Acylation." Advanced Materials Research 989-994 (July 2014): 560–63. http://dx.doi.org/10.4028/www.scientific.net/amr.989-994.560.

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Multiwalled carbon nanotube (MWCNT) was subjected a copolymerization reaction with 4, 6-diaminoresorcinol salt (DAR•2HCl) and terephthalic acid (TA) in polyphosphoric acid (PPA) by Friedel-Crafts acylation reaction without any acid treatment or modification. The structure and morphology of the as-prepared poly (p-phenylene benzobisoxazole) (PBO)/MWCNT nanocomposites were characterized by X-ray diffraction (XRD) and scanning electronic microscope (SEM). The SEM images indicated that MWCNTs can disperse in PBO matrix uniformly without agglomeration and MWCNTs have been introduced into PBO matrix by covalent bonding via Friedel-Crafts acylation between MWCNTs and TA.

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41

Szabó, Balázs, Kiara Szakter, Angelika Thurner, Ferenc Faigl, János Éles, and István Greiner. "A Novel, Domino Synthesis of Tricyclic Benzimidazole Derivatives Using Continuous Flow." Periodica Polytechnica Chemical Engineering 64, no. 1 (October 17, 2019): 1–8. http://dx.doi.org/10.3311/ppch.14275.

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A novel method for synthesis of tricyclic benzimidazole derivatives by using continuous flow reactor is reported. Disadvantages of the well-known batch methods have been avoided utilizing the flow chemistry technology. Beside the one pot reductive cyclization using H-Cube Pro®, the dehydration step was also optimized producing the desired lactam compounds. Then the acylation was optimized under microwave conditions and that reaction was also integrated into the flow system using an Asia heater module. This acylation dramatically reduced the reaction time under continuous-flow conditions, with a residence time of 30 min.

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42

BAÑÓ, M. Carmen, S. Caroline JACKSON, and I. Anthony MAGEE. "Pseudo-enzymatic S-acylation of a myristoylated Yes protein tyrosine kinase peptide in vitro may reflect non-enzymatic S-acylation in vivo." Biochemical Journal 330, no. 2 (March 1, 1998): 723–31. http://dx.doi.org/10.1042/bj3300723.

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Covalent attachment of a variety of lipid groups to proteins is now recognized as a major group of post-translational modifications. S-acylation of proteins at cysteine residues is the only modification considered dynamic and thus has the potential for regulating protein function and/or localization. The activities that catalyse reversible S-acylation have not been well characterized and it is not clear whether both the acylation and the deacylation steps are regulated, since in principle it would be sufficient to control only one of them. Both apparently enzymatic and non-enzymatic S-acylation of proteins have previously been reported. Here we show that a synthetic myristoylated c-Yes protein tyrosine kinase undecapeptide undergoes spontaneous S-acylation in vitro when using a long chain acyl-CoA as acyl donor in the absence of any protein. The S-acylation was dependent on myristoylation of the substrate, the length of the incubation period, temperature and substrate concentration. When COS cell fractions were added to the S-acylation reaction no additional peptide:S-acyltransferase activity was detected. These results are consistent with the possibility that membrane-associated proteins may undergo S-acylation in vivo by non-enzymatic transfer of acyl groups from acyl-CoA. In this case, the S-acylation-deacylation process could be controlled by a regulated depalmitoylation mechanism.

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43

Zhang, Chun Yan, Min Chen, Yan Zhang, Xin Hua Yuan, and Hua Liu. "Synthesis of 1, 2-Aceanthrylenedione Catalyzed by Anhydrous AlCl₃." Materials Science Forum 561-565 (October 2007): 683–86. http://dx.doi.org/10.4028/www.scientific.net/msf.561-565.683.

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1,2-aceanthrylenedione was synthesized through the acylation reaction of anthracene and oxalyl chloride catalyzed by anhydrous AlCl3. The effects of various reaction conditions on the yield and selectivity of 1, 2-aceanthrylenedione were studied by GC analysis. The results show that the optimum synthesis conditions of the acylation reaction are as follows : the molar ratio of oxalyl chloride to anthracene being 1:2, the molar ratio of anhydrous AlCl3 to anthracene being 4:1, the reaction time being 5 h, the reaction temperature being 303k and the solvent of the reaction system being CS2. Under those conditions, the yield and selectivity of 1, 2-aceanthrylenedione is 83.8 % and 92.3% respectively. Pure 1, 2-aceanthrylenedione was prepared by extraction and recrystallation. The structure of 1, 2-aceanthrylenedione was identified by measure of melting point, GC/MS, FTIR and 1HNMR analyses.

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44

GRAVES-WOODWARD, Karen, and R. F. PRATT. "Reaction of soluble penicillin-binding protein 2a of methicillin-resistant Staphylococcus aureus with β-lactams and acyclic substrates: kinetics in homogeneous solution." Biochemical Journal 332, no. 3 (June 15, 1998): 755–61. http://dx.doi.org/10.1042/bj3320755.

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The kinetics of reaction of solubilized penicillin-binding protein 2a (sPBP2a) of methicillin-resistant Staphylococcus aureus with a variety of β-lactams and acyclic species was studied in homogeneous aqueous solution at 37 °C in 25 mM Hepes buffer, pH 7.0, containing 1 M NaCl. Under these conditions, but not at lower salt concentrations, protein precipitation did not occur either during or after the reaction. The reactions of β-lactams in general could be monitored by competition with a chromophoric β-lactam, nitrocefin, or directly in certain cases by protein fluorescence. Rate constants for reaction of a wide variety of β-lactams are reported. The interactions are characterized by a slow second-order acylation reaction followed by a slower deacylation. For example, the rate constants for benzylpenicillin were 12 M-1·s-1 and 3×10-5 s-1 respectively. The acylation is slow in comparison with those of normal non-resistant high-molecular-mass penicillin-binding proteins. sPBP2a also seemed to catalyse the slow hydrolysis of a variety of acyclic depsipeptides but not that of a d-Ala-d-Ala peptide. The reactions with certain depsipeptides also led to protein precipitation. These reactions were, however, not affected by prior blockage of the β-lactam-binding site by benzylpenicillin and thus might take place elsewhere on the enzyme. Two classes of potential transition- state analogue inhibitors, phosphonate monoesters and boronates, seemed to have little effect on the rate of reaction of sPBP2a with nitrocefin and therefore seem to have little affinity for the β-lactam-binding/d,d-peptidase site.

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45

Elvas-Leitão, Ruben, Filomena Martins, Leonor Borbinha, Catarina Marranita, Angela Martins, and Nelson Nunes. "Probing Substrate/Catalyst Effects Using QSPR Analysis on Friedel-Crafts Acylation Reactions over Hierarchical BEA Zeolites." Molecules 25, no. 23 (December 2, 2020): 5682. http://dx.doi.org/10.3390/molecules25235682.

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Attempts to optimize heterogeneous catalysis often lack quantitative comparative analysis. The use of kinetic modelling leads to rate (k) and relative sorption equilibrium constants (K), which can be further rationalized using Quantitative Structure-Property Relationships (QSPR) based on Multiple Linear Regressions (MLR). Friedel-Crafts acylation using commercial and hierarchical BEA zeolites as heterogeneous catalysts, acetic anhydride as the acylating agent, and a set of seven substrates with different sizes and chemical functionalities were herein studied. Catalytic results were correlated with the physicochemical properties of substrates and catalysts. From this analysis, a robust set of equations was obtained allowing inferences about the dominant factors governing the processes. Not entirely surprising, the rate and sorption equilibrium constants were found to be explained in part by common factors but of opposite signs: higher and stronger adsorption forces increase reaction rates, but they also make the zeolite active sites less accessible to new reactant molecules. The most relevant parameters are related to the substrates’ molecular size, which can be associated with different reaction steps, namely accessibility to micropores, diffusion capacity, and polarizability of molecules. The relatively large set of substrates used here reinforces previous findings and brings further insights into the factors that hamper/speed up Friedel-Crafts reactions in heterogeneous media.

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46

Schroeder, H., R. Leventis, S. Shahinian, P. A. Walton, and J. R. Silvius. "Lipid-modified, cysteinyl-containing peptides of diverse structures are efficiently S-acylated at the plasma membrane of mammalian cells." Journal of Cell Biology 134, no. 3 (August 1, 1996): 647–60. http://dx.doi.org/10.1083/jcb.134.3.647.

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A variety of cysteine-containing, lipid-modified peptides are found to be S-acylated by cultured mammalian cells. The acylation reaction is highly specific for cysteinyl over serinyl residues and for lipid-modified peptides over hydrophilic peptides. The S-acylation process appears by various criteria to be enzymatic and resembles the S-acylation of plasma membrane-associated proteins in various characteristics, including inhibition by tunicamycin. The substrate range of the S-acylation reaction encompasses, but is not limited to, lipopeptides incorporating the motifs myristoylGC- and -CXC(farnesyl)-OCH3, which are reversibly S-acylated in various intracellular proteins. Mass-spectrometric analysis indicates that palmitoyl residues constitute the predominant but not the only type of S-acyl group coupled to a lipopeptide carrying the myristoylGC- motif, with smaller amounts of S-stearoyl and S-oleoyl substituents also detectable. Fluorescence microscopy using NBD-labeled cysteinyl lipopeptides reveals that the products of lipopeptide S-acylation, which cannot diffuse between membranes, are in almost all cases localized preferentially to the plasma membrane. This preferential localization is found even at reduced temperatures where vesicular transport from the Golgi complex to the plasma membrane is suppressed, strongly suggesting that the plasma membrane itself is the preferred site of S-acylation of these species. Uniquely among the lipopeptides studied, species incorporating an unphysiological N-myristoylcysteinyl- motif also show substantial formation of S-acylated products in a second, intracellular compartment identified as the Golgi complex by its labeling with a fluorescent ceramide. Our results suggest that distinct S-acyltransferases exist in the Golgi complex and plasma membrane compartments and that S-acylation of motifs such as myristoylGC- occurs specifically at the plasma membrane, affording efficient targeting of cellular proteins bearing such motifs to this membrane compartment.

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47

Warden, Elizabeth, Libero Bartolotti, Shouquan Huo, and Yumin Li. "Theoretical Probe to the Mechanism of Pt-Catalyzed C–H Acylation Reaction: Possible Pathways for the Acylation Reaction of a Platinacycle." Inorganic Chemistry 59, no. 1 (December 13, 2019): 555–62. http://dx.doi.org/10.1021/acs.inorgchem.9b02835.

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48

de Cristofaro, R., B. Rocca, B. Bizzi, and R. Landolfi. "The linkage between binding of the C-terminal domain of hirudin and amidase activity in human α-thrombin." Biochemical Journal 289, no. 2 (January 15, 1993): 475–80. http://dx.doi.org/10.1042/bj2890475.

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A method derived from the analysis of viscosity effects on the hydrolysis of the amide substrates D-phenylalanylpipecolyl-arginine-p-nitroaniline, tosylglycylprolylarginine-p-nitroanaline and cyclohexylglycylalanylarginine-p-nitroalanine by human alpha-thrombin was developed to dissect the Michaelis-Menten parameters Km and kcat into the individual rate constants of the binding, acylation and deacylation reactions. This method was used to analyse the effect of the C-terminal hirudin (residues 54-65) [hir-(54-65)] domain on the binding and hydrolysis of the three substrates. The results showed that the C-terminal hir-(54-65) fragment affects only the acylation rate, which is increased approx. 1.2-fold for all the substrates. Analysis of the dependence of acylation rate constants on hirudin-fragment concentration, allowed the determination of the equilibrium binding constant of C-terminal hir-(54-65) (Kd approximately 0.7 microM). In addition this peptide was found to competitively inhibit thrombin-fibrinogen interaction with a Ki which is in excellent agreement with the equilibrium constant derived from viscosity experiments. These results demonstrate that binding of hir-(54-65) to the fibrinogen recognition site of thrombin does not affect the equilibrium binding of amide substrates, but induces only a small increase in the acylation rate of the hydrolysis reaction.

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49

Roemer, Max, Brian W. Skelton, Matthew J. Piggott, and George A. Koutsantonis. "1,1′-Diacetyloctamethylferrocene: an overlooked and overdue synthon leading to the facile synthesis of an octamethylferrocenophane." Dalton Transactions 45, no. 47 (2016): 18817–21. http://dx.doi.org/10.1039/c6dt03820d.

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50

Ghosh, Arun K., Hannah M. Simpson, and Anne M. Veitschegger. "Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction." Organic & Biomolecular Chemistry 16, no. 33 (2018): 5979–86. http://dx.doi.org/10.1039/c8ob01529e.

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