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Journal articles on the topic 'Eaton's reagent'

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Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

Yuan, Jie, Lu Jin, Runfeng Chen, Xingxing Tang, Xiang Xie, Yuting Tang, and Wei Huang. "Eaton's reagent assisted aromatic C–C coupling of carbazoles for optoelectronic applications." New Journal of Chemistry 42, no. 18 (2018): 14704–8. http://dx.doi.org/10.1039/c8nj03296c.

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2

Li, Yang, Ming-qin Chang, Feng Gao, and Wen-tao Gao. "Facile synthesis of fused quinolines via intramolecular Friedel–Crafts acylation." Journal of Chemical Research 2008, no. 11 (November 2008): 640–41. http://dx.doi.org/10.3184/030823408x375070.

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The intramolecular cyclisation of 6-[(phenoxy/phenylthio)methyl][1,3]dioxolo[4,5-g]quinoline-7-carboxylic acids to [1]benzoxepino[3,4-b][1,3]dioxolo[4,5-g]quinolin-12(6H)-onesand[1]benzothiepino[3,4-b][1,3]dioxolo[4,5-g]quinolin-12(6H)-ones in the presence of Eaton's reagent (P2O5-MeSO3H) is described. This cyclisation protocol requires milder conditions than those traditionally employed and is characterised by relatively low reaction temperatures and ease of product isolation.

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3

Ma, Zhanwei, Min Zhou, Lin Ma, and Min Zhang. "Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent." Journal of Chemical Research 44, no. 7-8 (February 24, 2020): 426–36. http://dx.doi.org/10.1177/1747519820907244.

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Cyclodehydration of α-phenoxy ketones promoted by Eaton’s reagent (phosphorus pentoxide–methanesulfonic acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare naphthofurans, furanocoumarins, benzothiophenes, and benzopyrans.

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4

Olvera-Mancilla, Jessica, Joaquín Palacios-Alquisira, and Larissa Alexandrova. "Eaton’s reagent in polybenzimidazole synthesis." High Performance Polymers 30, no. 6 (July 7, 2017): 699–709. http://dx.doi.org/10.1177/0954008317716977.

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The polycondensations of 3,3′-diaminobenzidine with two acids, 4,4′-oxybis(benzoic acid) and hexafluoroisopropylidene bis(benzoic acid), were conducted in Eaton’s reagent at the unusually high temperature of 180°C and under microwave irradiation at 90°C. Both protocols resulted in soluble polybenzimidazoles, OPBI and CF3PBI, of high molecular weights in very short reaction times. The synthesized polybenzimidazoles exhibited high thermostability and excellent mechanical properties. The influence of the reaction conditions on the polymer structure and molecular weights was studied. The “microwave effect” was demonstrated by comparison of the polycondensations conducted under microwave irradiation and conventional heating.

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5

Luque, Adriana L., Carlos M. Sanabria, Alirio Palma, Justo Cobo, and Christopher Glidewell. "Unexpected ring-closure products derived from 3-(2-allylanilino)-3-phenylacrylate esters: crystal and molecular structures of 3-acetyl-8-allyl-6-methyl-2-phenylquinolin-4-yl acetate and (2RS)-2,8-dimethyl-4-phenyl-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinolin-6-one." Acta Crystallographica Section C Structural Chemistry 72, no. 8 (July 14, 2016): 619–26. http://dx.doi.org/10.1107/s2053229616011062.

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The reactions of two 3-(2-allylanilino)-3-phenylacrylate esters with acetic anhydride and with strong acids has revealed a richly diverse reactivity providing a number of unexpected products. Thus, acetylation of ethyl 3-(2-allylanilino)-3-phenylacrylate, (Ia), or ethyl 3-(2-allyl-4-methylanilino)-3-phenylacrylate, (Ib), with acetic anhydride yields not only the expected acetylated esters, (II), as the major products but also the unexpected polysubstituted quinolines 3-acetyl-8-allyl-2-phenylquinolin-4-yl acetate, (IIIa), and 3-acetyl-8-allyl-6-methyl-2-phenylquinolin-4-yl acetate, (IIIb), as minor products. Subsequent reaction of the major product ethyl 2-[(2-allyl-4-methylanilino)(phenyl)methylidene]-3-oxobutanoate, (IIb), with concentrated sulfuric acid did not provide the expected 3-acetylquinoline derivative, but instead two unexpected products, namely ethyl 4-ethyl-2-phenyl-1,4-dihydroquinoline-3-carboxylate, (IV), and ethyl 3-acetyl-4-ethyl-2-phenyl-3,4-dihydroquinoline-3-carboxylate, (V), in yields of 39 and 22%, respectively. The reaction of (Ib) with Eaton's reagent gave both the quinoline (Z)-6-methyl-2-phenyl-8-(prop-1-en-1-yl)quinolin-4(1H)-one, (VI), and the unexpected tricyclic product (2RS)-2,8-dimethyl-4-phenyl-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinolin-6-one, (VII), in yields of 71 and 12%, respectively. The products (II)–(VII) have all been fully characterized spectroscopically and the crystal structures of two of the unexpected products,i.e.(IIIb) (C23H21NO3) and (VII) (C19H17NO), are reported here. The formation of compounds (IV), (V) and (VII) all require an isomerization of the initial allyl substituent, with migration of the C=C double bond from the terminal site to the internal site. In (IIIb), the two acetyl substituents are oriented such that the intramolecular distance between the two carbonyl O atoms is only 3.243 (2) Å, and in (VII), the five-membered ring adopts a twisted half-chair conformation. The molecules of compound (IIIb) are linked by two independent hydrogen bonds to form sheets built fromR43(20) rings and the sheets are linked by a π–π stacking interaction to form a three-dimensional framework structure. The molecules of compound (VII) are linked by a single type of C—H...O hydrogen bond to form centrosymmetricR22(14) dimers. The molecules of compound (V), which crystallizes withZ′ = 2, are linked by two N—H...O and two C—H...O hydrogen bonds, forming a chain of rings.

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6

Borse, Amulrao U., Mahesh N. Patil, and Nilesh L. Patil. "Expeditious, Mild and Solvent Free Synthesis of Bis(indolyl)methanes, Using a Mixture of Phosphorus Pentoxide in Methanesulphonic Acid." E-Journal of Chemistry 9, no. 3 (2012): 1313–19. http://dx.doi.org/10.1155/2012/637536.

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Highly rapid and efficient synthesis of Bis(indolyl)methanes has been developed by using a mixture of phosphorus pentoxide in methanesulphonic acid (Eaton’s reagent) at ambient temperature under solvent free condition.

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7

Kholkhoev, B. Ch, V. F. Burdukovskii, and D. M. Mognonov. "Synthesis of aromatic polyamidines in Eaton’s reagent." Polymer Science Series B 55, no. 11-12 (November 2013): 601–3. http://dx.doi.org/10.1134/s1560090413090029.

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8

Thimmaiah, Shubhavathi, Mallesha Ningegowda, Nanjunda Swamy Shivananju, Raghu Ningegowda, Ranjith Siddaraj, and Babu Shubha Priya. "Eaton’s reagent catalysed alacritous synthesis of 3-benzazepinones." European Journal of Chemistry 7, no. 4 (December 31, 2016): 391–96. http://dx.doi.org/10.5155/eurjchem.7.4.391-396.1477.

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9

Borse, Amulrao, Mahesh Patil, Nilesh Patil, and Rohan Shinde. "A Green, Expeditious, One-Pot Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones Using a Mixture of Phosphorus Pentoxide-Methanesulfonic Acid at Ambient Temperature." ISRN Organic Chemistry 2012 (August 8, 2012): 1–6. http://dx.doi.org/10.5402/2012/415645.

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An expeditious, one-pot method for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones using a mixture of phosphorus pentoxide-methanesulfonic acid (Eaton’s reagent) at room temperature under solvent-free conditions is described. The salient features of this method include short reaction time, green aspects, high yields, and simple procedure.

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10

Wang, Jianping, Jian Zhang, Kun Miao, Hongying Yun, Hong C. Shen, Weili Zhao, and Chungen Liang. "Eaton’s reagent-mediated metal-free and efficient synthesis of NH-sulfoximines." Tetrahedron Letters 58, no. 4 (January 2017): 333–37. http://dx.doi.org/10.1016/j.tetlet.2016.12.031.

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11

D. Tupare, Shrikrishna, Santosh V. Nalage, Sharad R. Bobe, Shivshankar N. Hallale, Sheshanath V. Bhosale, Sanjay K. Vyawahare, Satish A. Dake, Sidhanath V. Bhosale, and Rajendra P. Pawar. "Revisit: Eaton’s Reagent Catalyzed Synthesis of Mono and Bis-Chalcone Derivatives." Letters in Organic Chemistry 9, no. 7 (July 1, 2012): 526–29. http://dx.doi.org/10.2174/157017812802139627.

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12

Melzer, Benedikt C., and Franz Bracher. "A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines." Beilstein Journal of Organic Chemistry 13 (August 8, 2017): 1564–71. http://dx.doi.org/10.3762/bjoc.13.156.

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Oxoisoaporphine alkaloids are conveniently prepared via direct ring metalation of alkoxy-substituted isoquinolines at C-1, followed by reaction with iodine. Subsequent Suzuki cross-coupling of the resulting 1-iodoisoquinolines to methyl 2-(isoquinolin-1-yl)benzoates and intramolecular acylation of the corresponding carboxylic acids with Eaton’s reagent afforded five alkaloids of the oxoisoaporphine type. The yield of the cyclization step strongly depends on the electrophilic properties of ring B. An alternative cyclization protocol via directed remote metalation of ester and amide intermediates was investigated thoroughly, but found to be not feasible. Two of the alkaloids showed strong cytotoxicity against the HL-60 tumor cell line.

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13

Ghinet, Alina, Nathalie Van Hijfte, Philippe Gautret, Benoît Rigo, Hassan Oulyadi, and Jolanta Rousseau. "Studies on pyrrolidinones. Reaction of pyroglutamic acid and vinylogues with aromatics in Eaton’s reagent." Tetrahedron 68, no. 4 (January 2012): 1109–16. http://dx.doi.org/10.1016/j.tet.2011.11.080.

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14

Gao, Wentao, Guihai Lin, Yang Li, Xiyue Tao, Rui Liu, and Lianjie Sun. "An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives." Beilstein Journal of Organic Chemistry 8 (October 30, 2012): 1849–57. http://dx.doi.org/10.3762/bjoc.8.213.

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An efficient access to the tetracyclic-fused quinoline systems, 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives 4a–l, is described, involving the intramolecular Friedel–Crafts acylation reaction of 2-(phenoxymethyl)-4-phenylquinoline-3-carboxylic acid derivatives 3a–l aided by the treatment with PPA (polyphosphoric acid) or Eaton’s reagent. The required starting compound (2) was obtained by Friedländer reaction of 2-aminobenzophenone (1) with 4-chloroethylacetoacetate by using CAN (cerium ammonium nitrate, 10 mol %) as catalyst at room temperature. The substrates 3a–l were prepared through one-pot reaction of ethyl 2-(chloromethyl)-4-phenylquinoline-3-carboxylate (2) and substituted phenols. Our developed strategy, involving a three-step route, offers easy access to tetracyclic-fused quinoline systems in short reaction times, and the products are obtained in moderate to good yields.

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15

Satheeshkumar, Rajendran, and Karnam Jayarampillai Rajendra Prasad. "Solvent-free synthesis of dibenzo[b,j][1,10]phenanthroline derivatives using Eaton’s reagent as catalyst." Synthetic Communications 47, no. 10 (April 7, 2017): 990–98. http://dx.doi.org/10.1080/00397911.2017.1301480.

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16

Olvera-Mancilla, Jessica, Joaquín Palacios-Alquisira, Vladimir Alonso Escobar-Barrios, and Larissa Alexandrova. "Some aspects of polybenzimidazoles’ synthesis in Eaton reagent under different temperatures and microwave irradiation." Journal of Macromolecular Science, Part A 56, no. 6 (March 27, 2019): 609–17. http://dx.doi.org/10.1080/10601325.2019.1593046.

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17

Pawar, Rajendra P., and et al et al. "ChemInform Abstract: Revisit: Eaton′s Reagent Catalyzed Synthesis of Mono- and Bis-Chalcone Derivatives." ChemInform 44, no. 2 (January 8, 2013): no. http://dx.doi.org/10.1002/chin.201302076.

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18

Ulysse, Luckner G., Qiang Yang, Mark D. McLaws, Daniel K. Keefe, Peter R. Guzzo, and Brian P. Haney. "Process Development and Pilot-Scale Synthesis of New Cyclization Conditions of Substituted Phenylacetamides to Tetrahydroisoquinoline-2-ones Using Eaton’s Reagent." Organic Process Research & Development 14, no. 1 (January 15, 2010): 225–28. http://dx.doi.org/10.1021/op9002533.

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19

Kauthale, S., S. Tekale, A. Rode, R. Patil, J. Sangshetti, L. Kótai, and R. P. Pawar. "Eaton’s Reagent Catalyzed Synthesis, Invitro α-Amylase Inhibitory Activity and Molecular Docking Study of some Schiff’s Bases as Diabetic-II Inhibitors." European Chemical Bulletin 8, no. 10 (October 18, 2019): 356. http://dx.doi.org/10.17628/ecb.2019.8.356-362.

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20

Tagawa, Yoshinobu, Kenji Yamagata, and Kunihiro Sumoto. "Synthesis of Pyrido[3,2-c]coumarin Derivatives by an Intramolecular Cyclization of 4-Methyl-2-(ortho-methoxyphenyl)nicotinic Acid Using Eatons Reagent." Letters in Organic Chemistry 3, no. 10 (October 1, 2006): 759–63. http://dx.doi.org/10.2174/157017806779025951.

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21

Ghinet, Alina, Philippe Gautret, Nathalie Van Hijfte, Bertrand Ledé, Jean-Pierre Hénichart, Elena Bîcu, Ulrich Darbost, Benoît Rigo, and Adam Daïch. "Eaton’s Reagent-Mediated Domino π-Cationic Arylations of Aromatic Carboxylic Acids to Iasi-Red Polymethoxylated Polycyclic Aromatic Hydrocarbons: Products with Unprecedented Biological Activities as Tubulin Polymerization Inhibitors." Chemistry - A European Journal 20, no. 32 (July 7, 2014): 10117–30. http://dx.doi.org/10.1002/chem.201402377.

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22

Ghinet, Alina, Philippe Gautret, Nathalie Van Hijfte, Bertrand Lede, Jean-Pierre Henichart, Elena Bicu, Ulrich Darbost, Benoit Rigo, and Adam Daich. "ChemInform Abstract: Eaton′s Reagent-Mediated Domino π-Cationic Arylations of Aromatic Carboxylic Acids to Iasi-Red Polymethoxylated Polycyclic Aromatic Hydrocarbons: Products with Unprecedented Biological Activities as Tubulin Polymerization Inhibitors." ChemInform 46, no. 4 (January 2015): no. http://dx.doi.org/10.1002/chin.201504095.

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23

Hawkins, P. T., D. R. Poyner, T. R. Jackson, A. J. Letcher, D. A. Lander, and R. F. Irvine. "Inhibition of iron-catalysed hydroxyl radical formation by inositol polyphosphates: a possible physiological function for myo-inositol hexakisphosphate." Biochemical Journal 294, no. 3 (September 15, 1993): 929–34. http://dx.doi.org/10.1042/bj2940929.

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1. The ability of myo-inositol polyphosphates to inhibit iron-catalysed hydroxyl radical formation was studied in a hypoxanthine/xanthine oxidase system [Graf, Empson and Eaton (1987) J. Biol. Chem. 262, 11647-11650]. Fe3+ present in the assay reagents supported some radical formation, and a standard assay, with 5 microM Fe3+ added, was used to investigate the specificity of compounds which could inhibit radical generation. 2. InsP6 (phytic acid) was able to inhibit radical formation in this assay completely. In this respect it was similar to the effects of the high affinity Fe3+ chelator Desferral, and dissimilar to the effects of EDTA which, even at high concentrations, still allowed detectable radical formation to take place. 3. The six isomers of InsP5 were purified from an alkaline hydrolysate of InsP6 (four of them as two enantiomeric mixtures), and they were compared with InsP6 in this assay. Ins(1,2,3,4,6)P5 and D/L-Ins(1,2,3,4,5)P5 were similar to InsP6 in that they caused a complete inhibition of iron-catalysed radical formation at > 30 microM. Ins(1,3,4,5,6)P5 and D/L-Ins(1,2,4,5,6)P5, however, were markedly less potent than InsP6, and did not inhibit radical formation completely; even when Ins(1,3,4,5,6)P5 was added up to 600 microM, significant radical formation was still detected. Thus InsP5s lacking 2 or 1/3 phosphates are in this respect qualitatively different from InsP6 and the other InsP5s. 4. scyllo-Inositol hexakisphosphate was also tested, and although it caused a greater inhibition than Ins(1,3,4,5,6)P5, it too still allowed detectable free radical formation even at 600 microM. 5. We conclude that the 1,2,3 (equatorial-axial-equatorial) phosphate grouping in InsP6 has a conformation that uniquely provides a specific interaction with iron to inhibit totally its ability to catalyse hydroxyl radical formation; we suggest that a physiological function of InsP6 might be to act as a ‘safe’ binding site for iron during its transport through the cytosol or cellular organelles.

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24

"Preparation of Tetrahydroisoquinoline-3-ones via Cyclization of Phenyl Acetamides Using Eaton's Reagent." Organic Syntheses 89 (2012): 44. http://dx.doi.org/10.15227/orgsyn.089.0044.

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25

Kumar, Surender, and Dinesh Kumar Sharma. "Ultrasound promoted green synthesis of benzofuran substituted thiazolo[3,2-b][1,2,4]triazoles." Green Processing and Synthesis 6, no. 1 (January 1, 2017). http://dx.doi.org/10.1515/gps-2016-0099.

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AbstractA highly efficient, eco-friendly and one-pot synthesis of benzofuran substituted thiazolo[3,2-b][1,2,4]triazoles was developed involving the reaction of 2-acetyl benzofurans and 5-mercapto-3-(4-chlorophenyl)-1,2,4triazole in the presence of molecular iodine under ultrasonic conditions to give 5-(benzofuran-2-yl)-acylthio-3-(4-chlorophenyl)-1,2,4triazoles, which was further cyclised using Eaton’s reagent under microwave conditions to give 5-(benzofuran-2-yl)-2-(4-chlorophenyl)thiazolo[3,2-b][1,2,4]triazoles.

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26

Tagawa, Yoshinobu, Kenji Yamagata, and Kunihiro Sumoto. "Synthesis of Pyrido[3,2-c]coumarin Derivatives by an Intramolecular Cyclization of 4-Methyl-2-(ortho-methoxyphenyl)nicotinic Acid Using Eaton′s Reagent." ChemInform 38, no. 18 (May 1, 2007). http://dx.doi.org/10.1002/chin.200718143.

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