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Journal articles on the topic 'Benzofuranones'

Author: Grafiati

Published: 4 June 2021

Last updated: 22 February 2023

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1

Qiu, Renhua, Nobuaki Kambe, Zhi Tang, Zhou Tong, and Shuang-Feng Yin. "Recent Advances on Benzofuranones: Synthesis and Transformation via C–H Functionalization." Synthesis 53, no. 18 (2021): 3193–210. http://dx.doi.org/10.1055/a-1405-5761.

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AbstractThe benzofuranone structure is important in many fields, such as natural products, pharmaceuticals, building blocks, antioxidants, and dyes. The efficient synthesis and transformation of benzofuranones have attracted great attention in organic synthesis. They can be synthesized by the Friedel–Crafts reaction and intramolecular dehydration ring-closing and transition-metal-catalyzed reactions, among others. Their direct utilization in the preparation of other functional molecules further enhance their application. Due to their low pK a value and easy enolization, the transformation of b

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2

García-Lacuna, Jorge, Maialen Alonso, Gema Domínguez, and Javier Pérez Castells. "Study of the Pauson–Khand reaction in flow over alkynylphenyl vinyl ethers: towards the synthesis of tricyclic multisubstituted benzofurans." RSC Advances 12, no. 12 (2022): 7313–17. http://dx.doi.org/10.1039/d2ra01062c.

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3

Wang, Mo, Xiao Zhang, Zheng Ling, Zhenfeng Zhang, and Wanbin Zhang. "Direct enantioselective C-acylation for the construction of a quaternary stereocenter catalyzed by a chiral bicyclic imidazole." Chemical Communications 53, no. 8 (2017): 1381–84. http://dx.doi.org/10.1039/c6cc09451a.

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4

Speisky, Hernán, María Fernanda Arias-Santé, and Jocelyn Fuentes. "Oxidation of Quercetin and Kaempferol Markedly Amplifies Their Antioxidant, Cytoprotective, and Anti-Inflammatory Properties." Antioxidants 12, no. 1 (2023): 155. http://dx.doi.org/10.3390/antiox12010155.

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The contention that flavonoids’ oxidation would necessarily lead to a loss of their antioxidant properties was recently challenged by the demonstration that quercetin oxidation leads to the formation of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (Que-BZF), a metabolite whose antioxidant potency was notably higher than that of its precursor. Here, we compared and expanded the former observation to that of the quercetin analogue kaempferol. Oxidation of kaempferol led to the formation of a mixture of metabolites that included the 2-(4-hydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-ben

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5

Xu, Kunhua, Wenming Chen, Xu Chen, Biao Wang, Jun Huang, and Xu Tian. "Organocatalytic asymmetric Friedel–Crafts alkylation/hemiketalization/lactonization cascade reactions: highly enantioselective synthesis of furo[2,3-b]benzofuranones." Organic Chemistry Frontiers 7, no. 13 (2020): 1679–84. http://dx.doi.org/10.1039/d0qo00475h.

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A highly diastereo- and enantioselective organocatalytic Friedel–Crafts alkylation/hemiketalization/lactonization cascade reaction generating furo[2,3-b]benzofuranones in good to excellent yields with high stereoselectivities.

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6

Peng, Xueke, Zhiye Hu, Jing Zhang та ін. "Construction of benzofuranone library via a metal-free, one-pot intermolecular condensation, and their application as efficient estrogen receptor β modulators". Chemical Communications 55, № 97 (2019): 14570–73. http://dx.doi.org/10.1039/c9cc05756k.

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Facile synthesis of benzofuranones as efficient estrogen receptor β modulators was achieved through a metal-free, one-pot intermolecular condensation between α-hydroxy aryl ketones and resorcinol derivatives.

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7

Zhang, Xiaojie, and Christopher M. Beaudry. "Regioselective Synthesis of Benzofuranones and Benzofurans." Journal of Organic Chemistry 86, no. 9 (2021): 6931–36. http://dx.doi.org/10.1021/acs.joc.1c00341.

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8

Li, Yao, Xin Li, and Jin-Pei Cheng. "Catalytic Asymmetric Synthesis of Chiral Benzofuranones." Advanced Synthesis & Catalysis 356, no. 6 (2014): 1172–98. http://dx.doi.org/10.1002/adsc.201301038.

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9

Hu, Chen, Gang Hong, Pradip D. Nahide, et al. "C(sp3)–H hydroxylation of fluorenes, oxindoles and benzofuranones with a Mg(NO3)2–HP(O)Ph2 oxidation system." Organic Chemistry Frontiers 6, no. 17 (2019): 3167–71. http://dx.doi.org/10.1039/c9qo00778d.

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A novel oxidation system in which magnesium nitrate is used as an oxidant in the presence of diphenylphosphine oxide permits the C(sp<sup>3</sup>)–H hydroxylation of fluorenes, oxindoles, and benzofuranones.

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10

Huang, Zhusheng, Xiuqin Yang, Fulai Yang, Tao Lu та Qingfa Zhou. "Phosphine-Catalyzed Domino β/γ-Additions of Benzofuranones with Allenoates: A Method for Unsymmetrical 3,3-Disubstituted Benzofuranones". Organic Letters 19, № 13 (2017): 3524–27. http://dx.doi.org/10.1021/acs.orglett.7b01482.

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11

Barton, Derek H. R., Dervilla M. X. Donnelly, Jean-Pierre Finet, Patrick J. Guiry, and Joshua M. Kielty. "Synthesis of 2-aryl-3(2H)-benzofuranones." Tetrahedron Letters 31, no. 46 (1990): 6637–40. http://dx.doi.org/10.1016/s0040-4039(00)97134-x.

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12

Enders, Dieter, Long Zhao, and Gerhard Raabe. "Asymmetric Synthesis of 2,2-Disubstituted Benzofuranones through an Organocatalytic Alkylation with Nitroallylic Acetates." Synthesis 51, no. 06 (2018): 1391–98. http://dx.doi.org/10.1055/s-0037-1610337.

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The asymmetric allylic alkylation of benzofuran-3(2H)-ones with nitroallylic acetates has been achieved employing a bifunctional thiourea organocatalyst via SN2′ substitution. A series of 2,2-disubstituted benzofuranones bearing adjacent tetrasubstituted and tertiary stereocenters have been synthesized with moderate to good yields and very good stereoselectivities.

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13

Xin, Hai‐Long, Xiaofeng Rao, Haruro Ishitani, and Shū Kobayashi. "Sequential Continuous‐Flow Synthesis of 3‐Aryl Benzofuranones." Chemistry – An Asian Journal 16, no. 14 (2021): 1906–10. http://dx.doi.org/10.1002/asia.202100461.

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14

Gonçalves, Cleiton José, Andrey Sávio Lenoir, Pâmela Padaratz, et al. "Benzofuranones as potential antinociceptive agents: Structure–activity relationships." European Journal of Medicinal Chemistry 56 (October 2012): 120–26. http://dx.doi.org/10.1016/j.ejmech.2012.08.015.

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15

Li, Yao, Xin Li, and Jin-Pei Cheng. "ChemInform Abstract: Catalytic Asymmetric Synthesis of Chiral Benzofuranones." ChemInform 45, no. 25 (2014): no. http://dx.doi.org/10.1002/chin.201425283.

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16

Li, Xin, Feng Wang, Nan Dong, and Jin-Pei Cheng. "Phosphine-containing Lewis base catalyzed cyclization of benzofuranone type electron-deficient alkenes with allenoates: a facile synthesis of spirocyclic benzofuranones." Organic & Biomolecular Chemistry 11, no. 9 (2013): 1451. http://dx.doi.org/10.1039/c3ob27288e.

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17

Tang, Zhi, Lingteng Peng, Yu Yuan, Tianjing Li, Renhua Qiu, and Nobuaki Kambe. "Synthesis of Triarylmethanes by Decarbonylation of 3,3-Diaryl Benzofuranones." Journal of Organic Chemistry 85, no. 8 (2020): 5300–5311. http://dx.doi.org/10.1021/acs.joc.9b03433.

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18

Mikerova, N. I., and E. K. Panisheva. "Formation of substituted benzofuranones-2 by a Nenitzescu reaction." Chemistry of Heterocyclic Compounds 26, no. 10 (1990): 1194–95. http://dx.doi.org/10.1007/bf00472202.

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19

Li, Xin, Feng Wang, Nan Dong, and Jin-Pei Cheng. "ChemInform Abstract: Phosphine-Containing Lewis Base Catalyzed Cyclization of Benzofuranone Type Electron-Deficient Alkenes with Allenoates: A Facile Synthesis of Spirocyclic Benzofuranones." ChemInform 44, no. 29 (2013): no. http://dx.doi.org/10.1002/chin.201329101.

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20

Müller, Thomas J. J., та Daniel M. D'Souza. "Diversity-oriented syntheses of functional π-systems by multicomponent and domino reactions". Pure and Applied Chemistry 80, № 3 (2008): 609–20. http://dx.doi.org/10.1351/pac200880030609.

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Functional π-electron systems can be synthesized in a diversity-oriented fashion by applying multicomponent and domino reactions. Based upon alkyne activation by Sonogashira coupling, reactive triple or double bonds become the key functionality for sequential and consecutive synthesis of heterocycles, such as β-amino vinyl nitrothiophenes, δ-amino propenylidene indolones, indolizines, furans, pyrroles, annelated 2-amino pyridines, and spirocyclic benzofuranones and indolones. All these chromophores and fluorophores possess peculiar properties such as nonlinear optical (NLO) activity, pH-sensit

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21

Cassani, Carlo, Xu Tian, Eduardo C. Escudero-Adán, and Paolo Melchiorre. "Multiple approaches to enantiopure spirocyclic benzofuranones using organocatalytic cascade reactions." Chem. Commun. 47, no. 1 (2011): 233–35. http://dx.doi.org/10.1039/c0cc01957g.

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22

Bosch, Joan, Tomàs Roca, Juan-Lorenzo Catena, Carles Farrerons, and Ignasi Miquel. "A Convergent Route to 5-(Arylsulfanyl)-6-sulfonamido-3-benzofuranones." Synthesis 2000, no. 05 (2000): 721–25. http://dx.doi.org/10.1055/s-2000-6396.

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23

Adediran, S. "The synthesis and evaluation of benzofuranones as β-Lactamase substrates". Bioorganic & Medicinal Chemistry 9, № 5 (2001): 1175–83. http://dx.doi.org/10.1016/s0968-0896(00)00345-x.

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24

Hirschbeck, Vera, and Ivana Fleischer. "Synthesis of Benzofuranones via Palladium-Catalyzed Intramolecular Alkoxycarbonylation of Alkenylphenols." Chemistry - A European Journal 24, no. 12 (2018): 2854–57. http://dx.doi.org/10.1002/chem.201705808.

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25

Dyachenko, V. I., A. F. Kolomiets, and A. V. Fokin. "Preparation of substituted 3-hydroxy-3-trifluoromethyl-2(3H)benzofuranones." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 36, no. 11 (1987): 2332–37. http://dx.doi.org/10.1007/bf00957310.

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26

BARTON, D. H. R., D. M. X. DONNELLY, J. P. FINET, P. J. GUIRY, and J. M. KIELTY. "ChemInform Abstract: Synthesis of 2-Aryl-3-(2H)-benzofuranones (VII)." ChemInform 23, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.199215163.

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27

Graf, Katharina, Carmen L. Rühl, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi. "Metal-Free Oxidative Cyclization of Alkynyl Aryl Ethers to Benzofuranones." Angewandte Chemie International Edition 52, no. 48 (2013): 12727–31. http://dx.doi.org/10.1002/anie.201304813.

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28

Wang, De, Guo-Peng Wang, Yao-Liang Sun, et al. "Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones." Chemical Science 6, no. 12 (2015): 7319–25. http://dx.doi.org/10.1039/c5sc03135d.

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29

Chen, Hui, Hui Liu, Si-Han Zhao, et al. "Enantioselective Arylation of 3-Carboxamide Oxindoles with Quinone Monoimines and Synthesis of Chiral Spirooxindole-benzofuranones." Synlett 30, no. 09 (2019): 1067–72. http://dx.doi.org/10.1055/s-0037-1611782.

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A highly enantioselective arylation of 3-carboxamide oxoindoles with quinone monoimines is described. Various 3-aryl-3-carboxamide oxindoles with an all-carbon quaternary center were obtained in moderate to good yields (up to 99%) with moderate to good enantioselectivities (up to 98%) in the presence of a bifunctional thiourea-tertiary amine catalyst. The absolute configuration of one product was determined by an X-ray crystal structural analysis and the absolute configurations of the other products can be assigned by analogy. Moreover, several chiral spirooxindole-benzofuranones were synthesi

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30

Melchiorre, Paolo, Fabio Pesciaioli, Xu Tian, Giorgio Bencivenni, and Giuseppe Bartoli. "Organocatalytic Asymmetric Conjugate Additions of Oxindoles and Benzofuranones to Cyclic Enones." Synlett 2010, no. 11 (2010): 1704–8. http://dx.doi.org/10.1055/s-0029-1219955.

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31

Zhao, Long, Guanxin Huang, Beibei Guo, et al. "Diastereo- and Enantioselective Propargylation of Benzofuranones Catalyzed by Pybox-Copper Complex." Organic Letters 16, no. 21 (2014): 5584–87. http://dx.doi.org/10.1021/ol502615y.

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32

Watson, Allan, Ciaran Seath, James Fyfe, and John Molloy. "Synthesis of Oxindoles and Benzofuranones via Oxidation of 2-Heterocyclic BMIDAs." Synthesis 49, no. 04 (2016): 891–98. http://dx.doi.org/10.1055/s-0035-1562619.

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33

Heileman, Matthew J., and Harold W. Moore. "Generation and intramolecular cyclization of (2-ethenylphenyl)bisketenes. Synthesis of benzofuranones." Tetrahedron Letters 39, no. 22 (1998): 3643–46. http://dx.doi.org/10.1016/s0040-4039(98)00638-8.

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34

Magnus, Philip, and Jennifer D. Kreisberg. "Synthesis of benzofuranones related to diazonamide via an intramolecular Pummerer reaction." Tetrahedron Letters 40, no. 3 (1999): 451–54. http://dx.doi.org/10.1016/s0040-4039(98)02386-7.

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35

Chaturvedi, Rohit, and N. B. Mulchandani. "Synthesis of Benzofuran Derivatives: One Pot Synthesis of 2(3H) Benzofuranones." Synthetic Communications 20, no. 21 (1990): 3317–23. http://dx.doi.org/10.1080/00397919008051565.

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36

Liu, Ruihan, Suvratha Krishnamurthy, Zhenwei Wu, K. S. Satyanarayana Tummalapalli, and Jon C. Antilla. "Chiral Calcium Phosphate Catalyzed Enantioselective Amination of 3-Aryl-2-benzofuranones." Organic Letters 22, no. 20 (2020): 8101–5. http://dx.doi.org/10.1021/acs.orglett.0c03059.

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37

Watson, Allan, Ciaran Seath, James Fyfe, and John Molloy. "Synthesis of Oxindoles and Benzofuranones via Oxidation of 2-Heterocyclic BMIDAs." Synthesis 49, no. 04 (2017): e2-e2. http://dx.doi.org/10.1055/s-0036-1589468.

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38

Hajipour, Abdol R., and Zahra Khorsandi. "Cobalt-catalyzed C H activation/C O formation: Synthesis of benzofuranones." Tetrahedron Letters 61, no. 3 (2020): 151396. http://dx.doi.org/10.1016/j.tetlet.2019.151396.

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39

Wang, De, Guo-Peng Wang, Yao-Liang Sun, et al. "ChemInform Abstract: Chiral Phosphine-Catalyzed Tunable Cycloaddition Reactions of Allenoates with Benzofuranone-Derived Olefins for a Highly Regio-, Diastereo- and Enantioselective Synthesis of Spiro-Benzofuranones." ChemInform 47, no. 11 (2016): no. http://dx.doi.org/10.1002/chin.201611120.

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40

Verma, Nishant, Varun Kundi, and Naseem Ahmed. "Piperidine-mediated annulation of 2-acylphenols with 4-nitrobenzaldehyde to 3-benzofuranones." Tetrahedron Letters 56, no. 28 (2015): 4175–79. http://dx.doi.org/10.1016/j.tetlet.2015.05.023.

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41

Meng, Xin, Weiguang Gong, Zhong Xin, and Zhi Cai. "Study on the antioxidant activities of benzofuranones in melt processing of polypropylene." Polymer Degradation and Stability 91, no. 12 (2006): 2888–93. http://dx.doi.org/10.1016/j.polymdegradstab.2006.08.025.

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42

Yoneda, Eiji, Takashi Sugioka, Kojiro Hirao, Shi-Wei Zhang, and Shigetoshi Takahashi. "Rhodium-catalysed cyclic carbonylation of 2-alkynylphenols: synthesis of benzofuranones and coumarins." Journal of the Chemical Society, Perkin Transactions 1, no. 3 (1998): 477–84. http://dx.doi.org/10.1039/a706622h.

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43

Bosch, Joan, Tomas Roca, Juan-Lorenzo Catena, Carles Farrerons, and Ignasi Miquel. "ChemInform Abstract: A Convergent Route to 5-(Arylsulfanyl)-6-sulfonamido-3-benzofuranones." ChemInform 31, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.200036119.

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44

Dolmazon, René, and Suzanne Gelin. "Configurations and conformations of some 3-acetoxy-cis-hexahydro-2(3H)-benzofuranones." Journal of Heterocyclic Chemistry 22, no. 4 (1985): 1113–15. http://dx.doi.org/10.1002/jhet.5570220438.

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45

Cassani, Carlo, Xu Tian, Eduardo C. Escudero-Adan, and Paolo Melchiorre. "ChemInform Abstract: Multiple Approaches to Enantiopure Spirocyclic Benzofuranones Using Organocatalytic Cascade Reactions." ChemInform 42, no. 17 (2011): no. http://dx.doi.org/10.1002/chin.201117112.

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46

Hills, Ivory D., and Gregory C. Fu. "Catalytic Enantioselective Synthesis of Oxindoles and Benzofuranones That Bear a Quaternary Stereocenter." Angewandte Chemie International Edition 42, no. 33 (2003): 3921–24. http://dx.doi.org/10.1002/anie.200351666.

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47

Graf, Katharina, Carmen L. Ruehl, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi. "ChemInform Abstract: Metal-Free Oxidative Cyclization of Alkynyl Aryl Ethers to Benzofuranones." ChemInform 45, no. 17 (2014): no. http://dx.doi.org/10.1002/chin.201417117.

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48

Hills, Ivory D., and Gregory C. Fu. "Catalytic Enantioselective Synthesis of Oxindoles and Benzofuranones That Bear a Quaternary Stereocenter." Angewandte Chemie 115, no. 33 (2003): 4051–54. http://dx.doi.org/10.1002/ange.200351666.

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49

Zhang, Chunxia, Min Liu, Mingruo Ding, Hao Xie, and Fengzhi Zhang. "A Tandem Oxidative Annulation Strategy for the Synthesis of Tetracyclic 3-Spirooxindole Benzofuranones." Organic Letters 19, no. 13 (2017): 3418–21. http://dx.doi.org/10.1021/acs.orglett.7b01374.

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50

He, Jinmei, Jiyue Zheng, Jian Liu, Xuegong She, and Xinfu Pan. "N-Heterocyclic Carbene Catalyzed Nucleophilic Substitution Reaction for Construction of Benzopyrones and Benzofuranones." Organic Letters 8, no. 20 (2006): 4637–40. http://dx.doi.org/10.1021/ol061924f.

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