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Journal articles on the topic 'Furan opening'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 February 2022

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1

Yadav, Maruti B., and Yeon Tae Jeong. "A one-pot ring-closure and ring-opening sequence for the cascade synthesis of dihydrofurofurans and functionalized furans." Organic & Biomolecular Chemistry 19, no. 34 (2021): 7409–19. http://dx.doi.org/10.1039/d1ob01300a.

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2

Butin, Alexander V., and Sergey K. Smirnov. "Furan ring opening—indole ring closure: pseudooxidative furan ring opening in the synthesis of indoles." Tetrahedron Letters 46, no. 48 (2005): 8443–45. http://dx.doi.org/10.1016/j.tetlet.2005.09.057.

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3

Yuliati, Frita, Peter J. Deuss, Hero J. Heeres, and Francesco Picchioni. "Towards Thermally Reversible Networks Based on Furan-Functionalization of Jatropha Oil." Molecules 25, no. 16 (2020): 3641. http://dx.doi.org/10.3390/molecules25163641.

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A novel biobased monomer for the preparation of thermally reversible networks based on the Diels-Alder reaction was synthesized from jatropha oil. The oil was epoxidized and subsequently reacted with furfurylamine to attach furan groups via an epoxide ring opening reaction. However, furfurylamine also reacted with the ester groups of the triglycerides via aminolysis, thus resulting in short-chain molecules that ultimately yielded brittle thermally reversible polymers upon cross-linking via a Diels-Alder reaction. A full-factorial experimental design was used in finding the optimum conditions t

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4

A. Valderrama, Jaime, M. Florencia Gonz�ez, Patricia Arias, Hern� Pessoa-Mahana, and Ricardo Tapia. "Furan Ring Opening Reactions of 5-Hydroxy-2,3-dihydrobenzo[b]furans." HETEROCYCLES 36, no. 12 (1993): 2819. http://dx.doi.org/10.3987/com-93-6529.

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5

Mel’chin, Vladimir V., and Alexander V. Butin. "Furan ring opening–furan ring closure: cascade rearrangement of novel 4-acetoxy-9-furylnaphtho[2,3-b]furans." Tetrahedron Letters 47, no. 25 (2006): 4117–20. http://dx.doi.org/10.1016/j.tetlet.2006.04.081.

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6

Babu, Suresh D., Michael D. Hrytsak, and Tony Durst. "Intramolecular rhodium carbenoid insertions into aromatic C—H bonds. Preparation of 1,3-dihydrothiophene 2,2-dioxides fused onto aromatic rings." Canadian Journal of Chemistry 67, no. 6 (1989): 1071–76. http://dx.doi.org/10.1139/v89-162.

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The preparation of 1-carboalkoxy-1,3-dihydrobenzo[b]thiophene 2,2-dioxides via rhodium acetate or rhodium trifiuoro-acetate catalyzed decomposition of α-diazo-β-arylmethanesulfonyl esters is described. The reaction has been extended to yield 1,3-dihydrothiophene 2,2-dioxides fused to the 2,3 position of thiophene and indole, but not of furans. In the latter case products derived from the opening of the furan ring were obtained. Keywords: synthesis, 1-carboalkoxy-1,3-dihydrobenzo[b]thiophene 2,2-dioxides, intramolecular carbenoid insertions, rhodium acetate catalysis.

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7

VALDERRAMA, J. A., M. F. GONZALEZ, P. ARIAS, H. PESSOA-MAHANA, and R. TAPIA. "ChemInform Abstract: Furan Ring Opening Reactions of 5-Hydroxy-2,3-Dihydrobenzo(b)furans." ChemInform 25, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199417057.

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8

Gromov, E. V., A. B. Trofimov, F. Gatti, and H. Köppel. "Theoretical study of photoinduced ring-opening in furan." Journal of Chemical Physics 133, no. 16 (2010): 164309. http://dx.doi.org/10.1063/1.3493451.

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9

Jurczak, Janusz, and Stanisław Pikul. "Novel oxidative opening of 2,5-disubstituted furan ring." Tetrahedron Letters 26, no. 25 (1985): 3039–40. http://dx.doi.org/10.1016/s0040-4039(00)98612-x.

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10

PING, XIAOFAN, YONG GUO, HUA ZHU, YING XUE, and DAIQIAN XIE. "THEORETICAL STUDY ON THE STRUCTURE TRANSFORMATIONS OF CRYPTOTANSHINONE AND TANSHINONE I WITH HYDRION OR HYDROXIDE ION." Journal of Theoretical and Computational Chemistry 08, no. 02 (2009): 203–13. http://dx.doi.org/10.1142/s0219633609004757.

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The effects of hydrion and hydroxide ions on the structure transformations of Cryptotanshinone and Tanshinone I were investigated using the density functional theory at the Becke three-parameter hybrid functional combined with Lee–Yang–Parr correlation functional B3LYP/6-31+G(d) level. The solvent effects were assessed using the polarized continuum model. Our results revealed that the furan ring of Tanshinone I and dihydrofuran ring of Cryptotanshinone could be opened with the attack of hydroxide ion. The reaction of furan ring-opening proceeds via two pathways, while the reaction of dihydrofu

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11

Martin, S. F. "Unified strategy for the synthesis of C-aryl glycosides." Pure and Applied Chemistry 75, no. 1 (2003): 63–70. http://dx.doi.org/10.1351/pac200375010063.

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A unified approach for the synthesis of the four major groups of C-aryl glycosides has been developed. The strategy incorporates two integrated approaches, the first of which features the [4+2] cycloaddition of a glycosyl furan with a substituted benzyne followed by the acid-catalyzed opening of the resultant adduct. The second route involves the sequential palladium-catalyzed opening of a benzyne-furan cycloadduct with an iodo glycal followed by oxidation of the resultant dihydronaphthol ring and reduction of the glycal moiety. The utility of this strategy has been established by a concise fo

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12

Buttery, Jarrod H., and Dieter Wege. "Some Transformations of Adducts of 3,6-Dimethoxy-4,5-methylenedioxy-1,2-didehydrobenzene and Furans. An Approach to the 5,8-Dimethoxy-6,7-methylenedioxynaphtho[2,3-c]furan-4,9-dione Ring System of Ventilone A." Australian Journal of Chemistry 51, no. 5 (1998): 409. http://dx.doi.org/10.1071/c97209.

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Adducts derived from the aryne 3,6-dimethoxy-4,5-methylenedioxy-1,2-didehydrobenzene (19) with furan and 2-methoxyfuran have been converted into 5,8-dimethoxy-6,7-methylenedioxy-1,2-naphthoquinone (22) and 5,8-dimethoxy-6,7-methylenedioxy-1,4-naphthoquinone (24) respectively. The trapping of (19) with 1H,3H-furo[3,4-c]furan (38) yielded an unstable adduct (37), which on acid-catalysed ring opening and subsequent oxidation was transformed into 5,8-dimethoxy-6,7-methylenedioxynaphtho[2,3-c]furan-4,9-dione (36), a compound possessing the ring system of the naturally occurring quinone ventilone A.

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13

Liang, Xiao, Brian S. Haynes, and Alejandro Montoya. "Acid-Catalyzed Ring Opening of Furan in Aqueous Solution." Energy & Fuels 32, no. 4 (2017): 4139–48. http://dx.doi.org/10.1021/acs.energyfuels.7b03239.

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14

Sun, Baizhong, Honglin Liang, Deyong Che, Hongpeng Liu, and Shuai Guo. "Mechanistic investigation of CO generation by pyrolysis of furan and its main derivatives." RSC Advances 9, no. 16 (2019): 9099–105. http://dx.doi.org/10.1039/c8ra10106j.

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Quantum chemical theory has been used to study the furan and its derivatives pyrolysis reaction, nine possible reaction pathways has been studied. Results show that decarbonylation of CO after ring opening is easier than direct decarbonylation.

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15

Akai, Shuji, Shuhei Hori, Sho Ishida, et al. "Synthetic Studies on the Viridin Skeleton through Regio- and Stereoselective Functionalization of the AE-Ring Moiety." Synlett 32, no. 12 (2021): 1187–91. http://dx.doi.org/10.1055/a-1527-3781.

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Abstract4,5,6,7-Tetrahydroisobenzofurans, corresponding to the AC(D)E ring structure of viridin and equipped with required substituents on the A-ring, were synthesized with high regio- and stereoselectivities via the Diels–Alder adduct of a furan derivative and maleic anhydride. The key steps of this work include the regioselective opening of a tetrahydrofuran ring, a stereoselective epoxidation, and an AlMe3-mediated regioselective epoxide opening followed by stereoselective C-methylation.

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16

Abe, Hideki, Satoko Itaya, Kei Sasaki, Toyoharu Kobayashi, and Hisanaka Ito. "Total synthesis of the proposed structure of a polyketide from Phialomyces macrosporus." Chemical Communications 51, no. 17 (2015): 3586–89. http://dx.doi.org/10.1039/c5cc00129c.

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Total synthesis of the proposed structure of a polyketide isolated from Phialomyces macrosporus was accomplished. This synthesis features chemoselective epoxidation, regioselective epoxide ring opening, chemo- and diastereoselective dihydroxylation, and vinylation of lactone accompanied by the formation of a furan ring.

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17

Pilipenko, Arkady S., Vladimir V. Mel’chin, Igor V. Trushkov, Dmitry A. Cheshkov, and Alexander V. Butin. "Furan ring opening–indole ring closure: recyclization of 2-(2-aminophenyl)furans into 2-(2-oxoalkyl)indoles." Tetrahedron 68, no. 2 (2012): 619–27. http://dx.doi.org/10.1016/j.tet.2011.10.114.

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18

Butin, Alexander V., Maxim G. Uchuskin, Arkady S. Pilipenko, Fatima A. Tsiunchik, Dmitry A. Cheshkov, and Igor V. Trushkov. "Furan Ring-Opening/Indole Ring-Closure: Pictet-Spengler-Like Reaction of 2-(o-Aminophenyl)furans with Aldehydes." European Journal of Organic Chemistry 2010, no. 5 (2010): 920–26. http://dx.doi.org/10.1002/ejoc.200901241.

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19

Woo, Simon, Masood Parvez, and Brian A. Keay. "Regio- and stereoselective ring openings of unsymmetrical oxatricyclo adducts." Canadian Journal of Chemistry 75, no. 6 (1997): 665–80. http://dx.doi.org/10.1139/v97-081.

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SN2′ ring-opening reactions of a number of substituted 11-oxatricyclo[6.2.1.01,6]undec-9-en-5-ones prepared via the intramolecular Diels–Alder reaction employing a furan diene (IMDAF) are reported. Primary, secondary, and tertiary organolithium reagents were capable of effecting the ring-opening reaction, while methyllithium required activation before any ring opening was observed. Hydride reagents, organocuprates, and Grignard reagents were generally ineffective. The ring-opening reaction was highly regio- and stereoselective for attack at C9syn to the bridging oxygen atom provided that C8 wa

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20

Gromov, E. V., C. Lévêque, F. Gatti, I. Burghardt, and H. Köppel. "Ab initio quantum dynamical study of photoinduced ring opening in furan." Journal of Chemical Physics 135, no. 16 (2011): 164305. http://dx.doi.org/10.1063/1.3653792.

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21

Viswanathan, Tito, Jagdish Jethmalani, and Alan Toland. "Homo- and copolymers of furan–maleic anhydride and furan–dimethylacetylene dicarboxylate adducts via aqueous ring-opening metathesis polymerization." Journal of Applied Polymer Science 47, no. 8 (1993): 1477–80. http://dx.doi.org/10.1002/app.1993.070470819.

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22

Yu, Huiyue, Weiqiang Zhong, Tingyu He, Wenxiang Gu, and Biaolin Yin. "An entry to polysubstituted furans via the oxidative ring opening of furan ring employing NBS as an oxidant." Tetrahedron Letters 54, no. 10 (2013): 1256–60. http://dx.doi.org/10.1016/j.tetlet.2012.12.085.

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23

Fang, Wenting, Hualei Hu, Zhongsen Ma, Lei Wang, and Yajie Zhang. "Two Possible Side Reaction Pathways during Furanic Etherification." Catalysts 8, no. 9 (2018): 383. http://dx.doi.org/10.3390/catal8090383.

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The revealing mechanism of side reactions is crucial for obtaining theoretical yield in industrialization when 2,5-bis(methoxymethyl)furan (BMMF) yield is above 95%. By-products catalyzed by the conventional ZSM-5 (C-ZSM-5) and hierarchical porous ZSM-5 (HP-ZSM-5) catalytic systems were different, and some key by-products were identified. Thus, possible pathways were proposed, which helps to further improve BMMF selectivity. Additionally, HP-ZSM-5 exhibited quicker reaction rate, higher BMMF yield and selectivity, and slower deactivation process. The relatively weak acidity of HP-ZSM-5 suppres

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24

Abaev, Vladimir T., Artem S. Dmitriev, Sergey A. Podelyakin, Alexander V. Butin, and Andrey V. Gutnov. "Furan ring opening - isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes." Journal of Heterocyclic Chemistry 43, no. 5 (2006): 1195–204. http://dx.doi.org/10.1002/jhet.5570430510.

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25

Falco, Guillaume, Nathanael Guigo, Luc Vincent, and Nicolas Sbirrazzuoli. "Opening Furan for Tailoring Properties of Bio-based Poly(Furfuryl Alcohol) Thermoset." ChemSusChem 11, no. 11 (2018): 1805–12. http://dx.doi.org/10.1002/cssc.201800620.

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26

Wang, Shengguang, Vassili Vorotnikov, and Dionisios G. Vlachos. "A DFT study of furan hydrogenation and ring opening on Pd(111)." Green Chem. 16, no. 2 (2014): 736–47. http://dx.doi.org/10.1039/c3gc41183d.

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27

Abaev, Vladimir T., Anastasiya T. Plieva, Petrakis N. Chalikidi, Maxim G. Uchuskin, Igor V. Trushkov, and Alexander V. Butin. "A Simple Route to Polysubstituted Indoles Exploiting Azide Induced Furan Ring Opening." Organic Letters 16, no. 16 (2014): 4150–53. http://dx.doi.org/10.1021/ol5018504.

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28

Butin, Alexander V., Maxim G. Uchuskin, Arkady S. Pilipenko, Fatima A. Tsiunchik, Dmitry A. Cheshkov, and Igor V. Trushkov. "ChemInform Abstract: Furan Ring-Opening/Indole Ring-Closure: Pictet-Spengler-Like Reaction of 2-(o-Aminophenyl)furans with Aldehydes." ChemInform 41, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.201025089.

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29

Pilipenko, Arkady S., Vladimir V. Mel'chin, Igor V. Trushkov, Dmitry A. Cheshkov, and Alexander V. Butin. "ChemInform Abstract: Furan Ring Opening-Indole Ring Closure: Recyclization of 2-(2-Aminophenyl)furans into 2-(2-Oxoalkyl)indoles." ChemInform 43, no. 26 (2012): no. http://dx.doi.org/10.1002/chin.201226111.

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30

Chen, Dong-Sheng, Yu-Ling Li, Yun Liu, and Xiang-Shan Wang. "Synthesis of bis-benzoquinoline derivatives catalyzed by iodine via ring-opening of furan." Tetrahedron 69, no. 34 (2013): 7045–50. http://dx.doi.org/10.1016/j.tet.2013.06.042.

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31

Butin, Alexander V., Vladimir T. Abaev, Vladimir V. Mel’chin, and Artem S. Dmitriev. "Furan ring opening–isochromene ring closure: a new approach to isochromene ring synthesis." Tetrahedron Letters 46, no. 48 (2005): 8439–41. http://dx.doi.org/10.1016/j.tetlet.2005.09.056.

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32

Yu, Huiyue, Weiqiang Zhong, Tingyu He, Wenxiang Gu, and Biaolin Yin. "ChemInform Abstract: An Entry to Polysubstituted Furans via the Oxidative Ring-Opening of Furan Ring Employing NBS as an Oxidant." ChemInform 44, no. 24 (2013): no. http://dx.doi.org/10.1002/chin.201324082.

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33

Mincione, Enrico, Anna Sanetti, Roberta Bernini, Marcello Felici, and Paolo Bovicelli. "Selective oxidation of lignan compounds by dimethyldioxirane. Diastereoselective opening of asarinin furo-furan skeleton." Tetrahedron Letters 39, no. 47 (1998): 8699–702. http://dx.doi.org/10.1016/s0040-4039(98)01912-1.

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34

Vaitheeswaran, S., Sara K. Green, Paul Dauenhauer, and Scott M. Auerbach. "On the Way to Biofuels from Furan: Discriminating Diels–Alder and Ring-Opening Mechanisms." ACS Catalysis 3, no. 9 (2013): 2012–19. http://dx.doi.org/10.1021/cs4003904.

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35

Taylor, Kathleen H., Steven E. Kalman, T. Brent Gunnoe, and Michal Sabat. "Combined Furan C–H Activation and Furyl Ring-Opening by an Iron(II) Complex." Organometallics 35, no. 11 (2016): 1978–85. http://dx.doi.org/10.1021/acs.organomet.6b00276.

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36

Abaev, Vladimir T., Anastasiya T. Plieva, Petrakis N. Chalikidi, Maxim G. Uchuskin, Igor V. Trushkov, and Alexander V. Butin. "ChemInform Abstract: A Simple Route to Polysubstituted Indoles Exploiting Azide Induced Furan Ring Opening." ChemInform 46, no. 7 (2015): no. http://dx.doi.org/10.1002/chin.201507165.

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37

Butin, Alexander, Tatyana Nevolina, Vitaly Shcherbinin, Maxim Uchuskin, Olga Serdyuk, and Igor Trushkov. "Furan Ring Opening-Pyrrole Ring Closure: Simple Route to 5-Alkyl-2-(aminomethyl)pyrroles." Synthesis 2010, no. 17 (2010): 2969–78. http://dx.doi.org/10.1055/s-0030-1258165.

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38

Zelina, Elena Y., Tatyana A. Nevolina, Ludmila N. Sorotskaja, Dmitry A. Skvortsov, Igor V. Trushkov, and Maxim G. Uchuskin. "Route to pyrrolo[1,2-a]quinoxalines via a furan ring opening-pyrrole ring closure sequence." Tetrahedron Letters 61, no. 9 (2020): 151532. http://dx.doi.org/10.1016/j.tetlet.2019.151532.

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39

Chen, Dong-Sheng, Yu-Ling Li, Yun Liu, and Xiang-Shan Wang. "ChemInform Abstract: Synthesis of Bis-benzoquinoline Derivatives Catalyzed by Iodine via Ring-Opening of Furan." ChemInform 44, no. 50 (2013): no. http://dx.doi.org/10.1002/chin.201350187.

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40

Clerc, Michèle, Friedrich Stricker, Sebastian Ulrich, et al. "Promoting the Furan Ring‐Opening Reaction to Access New Donor–Acceptor Stenhouse Adducts with Hexafluoroisopropanol." Angewandte Chemie International Edition 60, no. 18 (2021): 10219–27. http://dx.doi.org/10.1002/anie.202100115.

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41

Clerc, Michèle, Friedrich Stricker, Sebastian Ulrich, et al. "Promoting the Furan Ring‐Opening Reaction to Access New Donor–Acceptor Stenhouse Adducts with Hexafluoroisopropanol." Angewandte Chemie 133, no. 18 (2021): 10307–15. http://dx.doi.org/10.1002/ange.202100115.

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42

Yates, Peter, and Patrick Michael Burke. "Keto ethers. IV. Products formed on reaction of dihydro-2,2,5,5-tetramethyl-3(2H)-furanone with strong acids." Canadian Journal of Chemistry 65, no. 8 (1987): 1695–704. http://dx.doi.org/10.1139/v87-284.

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Reaction of tetrahydro-2,2,5,5-tetramethyl-3(2H)-furanone (1) with 96 or ca. 100% sulfuric acid or hot polyphosphoric acid followed by aqueous quenching gave the following products: 2-hydroxy-2,5-dimethyl-4-hexen-3-one (3), 2,4,4-trimethyl-2-cyclopenten-1-one (7), 3,5,5-trimethyl-2-cyclopenten-1-one (8), tetrahydro-3,4,5,5-tetramethylfuran-2,3-diol (11), 2,5-dihydro-3,5,5-trimethyl-2-methylenefuran (17) and its dimer 20, 2,5-dihydro-2,3,5,5-tetramethyl-2-furanol (18), 4-hydroxy-2,4-dimethyl-2-pentenoic acid γ-lactone (22), 2,3,5-trimethyl-2-cyclopenten-1-one (23), and tetramethylfuran (25). In

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43

Muthusamy, Sengodagounder, Alagesan Balasubramani, and Eringathodi Suresh. "Rhodium(II) acetate catalysed intramolecular cyclopropanation followed by ring opening of furan toward oxindole incorporated macrocycles." Tetrahedron 72, no. 14 (2016): 1749–57. http://dx.doi.org/10.1016/j.tet.2016.02.032.

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44

Hua, Weijie, Sven Oesterling, Jason D. Biggs, et al. "Monitoring conical intersections in the ring opening of furan by attosecond stimulated X-ray Raman spectroscopy." Structural Dynamics 3, no. 2 (2015): 023601. http://dx.doi.org/10.1063/1.4933007.

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45

Butin, Alexander V., Tat‘yana A. Stroganova, Irina V. Lodina, and Gennady D. Krapivin. "Furan ring opening—indole ring closure: a new modification of the Reissert reaction for indole synthesis." Tetrahedron Letters 42, no. 10 (2001): 2031–33. http://dx.doi.org/10.1016/s0040-4039(01)00066-1.

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46

Butin, Alexander V., Tatyana A. Nevolina, Vitaly A. Shcherbinin, Maxim G. Uchuskin, Olga V. Serdyuk, and Igor V. Trushkov. "ChemInform Abstract: Furan Ring Opening-Pyrrole Ring Closure: Simple Route to 5-Alkyl-2-(aminomethyl)pyrroles." ChemInform 42, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.201101092.

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47

MINCIONE, E., A. SANETTI, R. BERNINI, and M. FELICI. "ChemInform Abstract: Selective Oxidation of Lignan Compounds by Dimethyldioxirane. Diastereoselective Opening of Asarinin Furo-furan Skeleton." ChemInform 30, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199907260.

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48

Butin, Alexander, Fatima Tsiunchik, Olga Kostyukova, Maxim Uchuskin, and Igor Trushkov. "Furan Ring Opening - Pyridine Ring Closure: New Route to Quinolines under the Bischler-Napieralski Reaction Conditions." Synthesis 2011, no. 16 (2011): 2629–38. http://dx.doi.org/10.1055/s-0030-1260118.

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49

Li, Yuanyuan, Yanzhen Gan, and Zexing Cao. "Computational insight into excited states of the ring‐opening radicals from the pyrolysis of furan biofuels." Journal of Computational Chemistry 40, no. 9 (2018): 1057–65. http://dx.doi.org/10.1002/jcc.25594.

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50

Stroganova, T. A., V. K. Vasilin, and E. A. Elizarova. "Opening of the furan ring in 2-R-amino- 3-furfurylthiophenes by the action of acids." Chemistry of Heterocyclic Compounds 47, no. 1 (2011): 22–28. http://dx.doi.org/10.1007/s10593-011-0715-2.

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