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Journal articles on the topic 'Benzodioxine'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Ding, Yu, and Guangmin Yao. "Methyl 6-acetyl-1,4-benzodioxine-2-carboxylate." Acta Crystallographica Section E Structure Reports Online 63, no. 12 (November 21, 2007): o4799. http://dx.doi.org/10.1107/s1600536807057601.

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2

Vidal, B., JY Conan, G. Lamaty, and J. Vardin. "Geometry of Some Strained Oxygen Ring Compounds: 1,3-Benzodioxole and 2,3-Dihydro-1,4-benzodioxin (Benzodioxan). Application to the Geometry of (6aR-cis)-3-Methoxy-6a,12a-dihydro-6h-[1,3]dioxolo-[5,6]benzofuro[3,2-C] [1]benzopyran (Pterocarpin)." Australian Journal of Chemistry 41, no. 7 (1988): 1107. http://dx.doi.org/10.1071/ch9881107.

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The geometry of benzodioxole, benzodioxan and the strained five- membered rings of pterocarpin are studied by the MNDO method. We show that in benzodioxole there is bond alternation towards a Kekule -like structure such as in indan (Mills-Nixon effect). In benzodioxole, owing to the smaller perimeter of the fused ring and enhanced strain, alternation is more pronounced than in indan . An explanation is offered for the strong distortion in ring angles in benzodioxole compared with indan. The effect of strain in benzodioxan and pterocarpin is discussed.

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3

Ilić, Miloš, Janez Ilaš, Petra Dunkel, Péter Mátyus, Andrej Boháč, Sandra Liekens, and Danijel Kikelj. "Novel 1,4-benzoxazine and 1,4-benzodioxine inhibitors of angiogenesis." European Journal of Medicinal Chemistry 58 (December 2012): 160–70. http://dx.doi.org/10.1016/j.ejmech.2012.10.001.

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4

Srivastava, Shaifali, Madan M. Gupta, Ram K. Verma, and Sushil Kumar. "Determination of 1,3-Benzodioxanes in Piper mullesua by High-Performance Thin-Layer Chromatography." Journal of AOAC INTERNATIONAL 83, no. 6 (November 1, 2000): 1484–88. http://dx.doi.org/10.1093/jaoac/83.6.1484.

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Abstract A new, simple, precise, and rapid high-performance thin-layer chromatographic method was developed for the determination of 6 benzodioxanes in Piper mullesua extract: 1′,3′-benzodioxole-5′-(2,4,8-triene-isobutyl nonanoate), 1′,3′-benzodioxole-5′-(2,4,12-triene-isobutyl tridecanoate), fargesin, sesamin, asarinin, 1′,3′-benzodioxole-5′-(2,4,8-triene-methyl nonanoate). The ingredients were separated on a precoated Silica Gel 60 F254 plate with a solvent system of toluene–acetone (92 + 8). The 6 benzodioxanes were well separated and easily identified in this chromatographic system. The separated benzodioxanes were visualized by color development with a spray reagent consisting of 1 g vanillin dissolved in 100 mL H2SO4–ethanol (5 + 95, v/v). Quantitation was performed by scanning the spots and comparing the integrated areas of compounds in samples with those of standards. Recoveries from samples spiked with known amounts of the benzodioxanes were excellent. The results were comparable with those estimated by liquid chromatography.

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5

Fonović, Urša Pečar, Damijan Knez, Martina Hrast, Nace Zidar, Matic Proj, Stanislav Gobec, and Janko Kos. "Structure-activity relationships of triazole-benzodioxine inhibitors of cathepsin X." European Journal of Medicinal Chemistry 193 (May 2020): 112218. http://dx.doi.org/10.1016/j.ejmech.2020.112218.

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6

Kruszynski, Rafal. "Weak intermolecular interactions in isomorphous 5-(2-chloroethoxy)-2,3-dihydro-1,4-benzodioxine and 5-(2-bromoethoxy)-2,3-dihydro-1,4-benzodioxine: bonding or nonbonding interactions." Acta Crystallographica Section C Crystal Structure Communications 65, no. 8 (July 11, 2009): o396—o399. http://dx.doi.org/10.1107/s0108270109020551.

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7

Viaud-Massuard, Marie-Claude, Sophie Boyé, Gérald Guillaumet, and Marie-Claude Viaud. "Synthesis of New Arylethanolamine and Aryloxypropanolamine Derivatives Including 1,4-Benzodioxine Moiety." HETEROCYCLES 45, no. 3 (1997): 537. http://dx.doi.org/10.3987/com-96-7712.

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8

Jeong, Geum Seok, Swafvan Kaipakasseri, Sang Ryong Lee, Najat Marraiki, Gaber El‐Saber Batiha, Sanal Dev, Ashique Palakkathondi, et al. "Selected 1,3‐Benzodioxine‐Containing Chalcones as Multipotent Oxidase and Acetylcholinesterase Inhibitors." ChemMedChem 15, no. 23 (October 14, 2020): 2257–63. http://dx.doi.org/10.1002/cmdc.202000491.

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9

Dzvinchuk, I. B. "Recyclization in the hydration of 3-formyl-2-phenyl-1,4-benzodioxine." Chemistry of Heterocyclic Compounds 36, no. 3 (March 2000): 351–52. http://dx.doi.org/10.1007/bf02256876.

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10

Xie, Zhouling, Lulu Zhao, Xue Ding, Yi Kong, and Zhiyu Li. "Design, synthesis and evaluation of 1,4-benzodioxine derivatives as novel platelet aggregation inhibitors." Future Medicinal Chemistry 10, no. 4 (February 2018): 367–78. http://dx.doi.org/10.4155/fmc-2017-0161.

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11

BOYE, S., G. GUILLAUMET, and M. C. VIAUD. "ChemInform Abstract: Synthesis of New Arylethanolamine and Aryloxypropanolamine Derivatives Including 1,4-Benzodioxine Moiety." ChemInform 28, no. 33 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199733195.

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12

Dzvinchuk, I. B. "ChemInform Abstract: Recyclization in the Hydration of 3-Formyl-2-phenyl-1,4-benzodioxine." ChemInform 31, no. 50 (December 12, 2000): no. http://dx.doi.org/10.1002/chin.200050038.

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13

Hendsbee, Arthur D., Jason D. Masuda, and Adam Piórko. "(η5-Cyclopentadienyl)[(1,2,3,4,4a,12a-η)-naphtho[2,3-b][1,4]benzodioxine]iron(II) hexafluoridophosphate." Acta Crystallographica Section E Structure Reports Online 66, no. 9 (August 21, 2010): m1154. http://dx.doi.org/10.1107/s1600536810033179.

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14

Ayerbe, Nathalie, Sylvain Routier, Isabelle Gillaizeau, Sebastien Tardy, and Gerard Coudert. "Benzoxazine and Benzodioxine as Indole Isosteres in Indolocarbazoles Series: Synthesis and Biological Evaluation." Letters in Organic Chemistry 7, no. 2 (March 1, 2010): 121–26. http://dx.doi.org/10.2174/157017810790796291.

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15

Corsano, Stefano, Giovannella Strappaghetti, and Antonella Codagnone. "Synthesis and Antihypertensive Properties of Benzodioxane-pyridazinones and Benzodioxane-dihydropyridazinones Synthese und antihypertensive Eigenschaften von Benzodioxan-pyridazinonen und Benzodioxan-dihydropyridazinonen." Archiv der Pharmazie 322, no. 11 (1989): 833–35. http://dx.doi.org/10.1002/ardp.19893221113.

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16

Ayerbe, Nathalie, Sylvain Routier, Isabelle Gillaizeau, Sebastien Tardy, and Gerard Coudert. "ChemInform Abstract: Benzoxazine and Benzodioxine as Indole Isosteres in Indolocarbazoles Series: Synthesis and Biological Evaluation." ChemInform 41, no. 34 (July 29, 2010): no. http://dx.doi.org/10.1002/chin.201034183.

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17

AĞIRTAŞ, Mehmet Salih, Beyza CABİR, Selçuk GÜMÜŞ, Sadin ÖZDEMİR, and Abdurrahman DÜNDAR. "Synthesis and antioxidant, aggregation, and electronic properties of 6-tert-butyl-1,4-benzodioxine substituted phthalocyanines." TURKISH JOURNAL OF CHEMISTRY 42 (2018): 100–111. http://dx.doi.org/10.3906/kim-1605-59.

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18

Mpassi, Michel, Gérald Guillaumet, Gérard Coudert, Madeleine Tissier, and Jean Juillard. "Macrocycles polyoxygénés à structure benzodioxinique. Synthèse et étude de la complexation du sodium et du potassium dans le methanol." Canadian Journal of Chemistry 67, no. 7 (July 1, 1989): 1132–38. http://dx.doi.org/10.1139/v89-170.

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The synthesis of two new series of polyoxygenated macrocyclic derivatives, 1 and 2, was realised. All these compounds have a 1,4-benzodioxinic moiety and are related to crown ethers, benzocrown ethers, and lariat ethers. The complexing properties of sodium and potassium ions were studied using potentiometry in methanol; results thus obtained are compared to data, previously reported in the literature, for classical polyoxygenated macrocyclic compounds. Keywords: polyoxygenated macrocycles, 1,4-benzodioxin, lariat ethers, sodium and potassium complexes, solvent methanol.

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19

Mauleón, David, Cinta Lobato, and Germano Carganico. "Synthesis of (-)(s)-2-hydroxymethyl-2,3-dihydro-1,4-benzodioxine by enzyme-catalyzed resolution in organic media." Journal of Heterocyclic Chemistry 31, no. 1 (January 1994): 57–59. http://dx.doi.org/10.1002/jhet.5570310110.

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20

Kügler, Fabian, Wiebke Sihver, Johannes Ermert, Harald Hübner, Peter Gmeiner, Olaf Prante, and Heinz H. Coenen. "Evaluation of18F-Labeled Benzodioxine Piperazine-Based Dopamine D4Receptor Ligands: Lipophilicity as a Determinate of Nonspecific Binding." Journal of Medicinal Chemistry 54, no. 24 (December 22, 2011): 8343–52. http://dx.doi.org/10.1021/jm200762g.

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21

Musolino, Manuele, and Fabio Aricò. "Benzo-Fused 1,4-Heterocycles via Dialkyl Carbonate Chemistry." Synthesis 51, no. 08 (February 18, 2019): 1770–78. http://dx.doi.org/10.1055/s-0037-1611710.

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A novel halogen-free synthesis of benzo-fused six-membered 1,4-heterocycles through the chemistry of dialkyl carbonates is reported. Commercially available catechol, 2-aminophenol, and 2-aminothiophenol were reacted first with ethylene carbonate in an autoclave to give O-hydroxyethyl, N-hydroxyethyl, and S-hydroxyethyl derivatives respectively, through a BAl2 mechanism. Then 2-(2-hydroxyethoxy)phenol and 2-(2-hydroxyethylamino)phenol were cyclized in excellent yields by reaction with dimethyl carbonate (DMC) and DABCO as a bicyclic organic base to give the corresponding benzodioxine and benzoxazine derivative, respectively. Moreover, 2-(2-aminophenylthio)ethanol afforded the benzothiazine derivative in good yield by reaction with DMC with an excess of a strong base such as NaH. The investigation on the cyclization reaction has highlighted that several equilibria are involved leading to the formation of carbonate and carbamate intermediates through BAc2 mechanisms. Depending on the reaction conditions employed, these intermediates may undergo either kinetic-controlled ring closure by a BAl2 mechanism or by-product formation.

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22

Harrak, Y., G. Rosell, G. Daidone, S. Plescia, D. Schillaci, and M. D. Pujol. "Synthesis and biological activity of new anti-inflammatory compounds containing the 1,4-benzodioxine and/or pyrrole system." Bioorganic & Medicinal Chemistry 15, no. 14 (July 2007): 4876–90. http://dx.doi.org/10.1016/j.bmc.2007.04.050.

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23

MAULEON, D., C. LOBATO, and G. CARGANICO. "ChemInform Abstract: Synthesis of (-)-(S)-2-Hydroxymethyl-2,3-dihydro-1,4-benzodioxine by Enzyme-Catalyzed Resolution in Organic Media." ChemInform 26, no. 11 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199511177.

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24

Lariucci, Carlito, Áurea Tamae Inumaru, Lauro Euclides Soares Barata, Neucírio Ricardo de Azevedo, Pedro Henrique Ferri, Kristian Rønning Pedersen, Muhammed Nour Homsi, et al. "Synthesis and Crystal Structure of trans-3-(4-Acetoxy-3-methoxyphenyl)-8-acetyloxy-2-methyl-2,3-dihydro-1,4-benzodioxine." Acta Chemica Scandinavica 50 (1996): 1025–29. http://dx.doi.org/10.3891/acta.chem.scand.50-1025.

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25

Shafi, Aayisha, Renuga Devi Timiri Sathyamurthy, Janani Seetharaman, Muthu Sambanthan, Raja Murugesan, Sevvanthi Sundaram, and Raajaraman Bhanumathy Ramarathinam. "Molecular docking, quantum chemical computational and vibrational studies on bicyclic heterocycle “6-nitro-2,3-dihydro-1,4-benzodioxine”: Anti-cancer agent." Computational Biology and Chemistry 86 (June 2020): 107226. http://dx.doi.org/10.1016/j.compbiolchem.2020.107226.

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26

Yavari, Issa, and Hoorieh Djahaniani. "One-step synthesis of N-alkyl-2-aryl-2-oxoacetamides and N2,N4-dialkyl-2-aryl-4H-1,3-benzodioxine-2,4-dicarboxamides." Tetrahedron Letters 47, no. 9 (February 2006): 1477–81. http://dx.doi.org/10.1016/j.tetlet.2005.12.039.

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27

Ruiz, N., and P. Rollin. "1,4-benzodioxin chemistry : A new route to C-3 functionalized 2-methylene-1,4-benzodioxans." Tetrahedron Letters 30, no. 13 (January 1989): 1637–40. http://dx.doi.org/10.1016/s0040-4039(00)99540-6.

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28

Fatoki, Toluwase H. "In Silico Investigation of Luminol, Its Analogues and Mechanism of Chemiluminescence for Blood Identification Beyond Forensics." Current Chemical Biology 14, no. 2 (November 19, 2020): 117–27. http://dx.doi.org/10.2174/2212796814999200801020729.

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Objective: This study aimed at discovering chemiluminescent analogues of luminol, predict their molecular binding to hemoglobin of bloodstains in household crime, and expound the mechanism of chemiluminescence of luminol. Materials and Methods: Similarity and clustering analyses of luminol analogues were conducted, and molecular docking was carried out using hemoglobin from Homo sapiens and four domestic organisms namely Gallus gallus, Drosophila melanogaster, Rattus norvegicus, and Canis familiaris. Results: The results showed the order of overall binding score as D. melanogaster > H. sapiens > C. familiaris > R. norvegicus > G. gallus. Seven compounds namely ZINC16958228, ZINC17023010, ZINC19915427, ZINC34928954, ZINC19915369, ZINC19915444, and ZINC82294978, were found to be consistently stable in binding with diverse hemoglobin and possibly have chemiluminescence than luminol in this in silico study. The interaction of human hemoglobin with luminol and its analogues, showed that amino acid residues His45, Lys61, Asn68, Val73, Met76, Pro77, Ala79, Ala82, Leu83, Pro95, Phe98, Lys99, Ser102, Ser133, Ala134, and Thr134, were possibly significant in the mechanism of action of presumptive test compounds. It was hypothesized that the improved mechanism of chemiluminescent for the identification of blood was based on peroxidase-like reaction, that produces nitric oxide which binds to hemoglobin (Hb) and inhibits Hb degradation without yielding fluorescent products. The compound 2,3-benzodioxine-1,4,5(6H)-trione was formed, which possibly emits light. Conclusion: This study provides novel insight on the luminol and its expanded mechanism for broader possible applications with careful development of new methodologies.

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29

Ilić, Miloš, Petra Dunkel, Janez Ilaš, Ewa Chabielska, Agnieszka Zakrzeska, Péter Mátyus, and Danijel Kikelj. "Towards dual antithrombotic compounds – Balancing thrombin inhibitory and fibrinogen GPIIb/IIIa binding inhibitory activities of 2,3-dihydro-1,4-benzodioxine derivatives through regio- and stereoisomerism." European Journal of Medicinal Chemistry 62 (April 2013): 329–40. http://dx.doi.org/10.1016/j.ejmech.2013.01.002.

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30

ITAZAKI, HIROSHI, AKIKO KAWASAKI, MUNENORI MATSUURA, MOTOHIKO UEDA, YUKIO YONETANI, and MASUHISA NAKAMURA. "Synthesis of 2,3-dihydro-1,4-benzodioxin derivatives. I. 2-Substituted-5(and 6)-sulfamoyl-2,3-dihydro-1,4-benzodioxins." CHEMICAL & PHARMACEUTICAL BULLETIN 36, no. 9 (1988): 3387–403. http://dx.doi.org/10.1248/cpb.36.3387.

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31

Bolchi, Cristiano, Ermanno Valoti, Valentina Straniero, Paola Ruggeri, and Marco Pallavicini. "From 2-Aminomethyl-1,4-benzodioxane Enantiomers to Unichiral 2-Cyano- and 2-Carbonyl-Substituted Benzodioxanes via Dichloroamine." Journal of Organic Chemistry 79, no. 14 (June 26, 2014): 6732–37. http://dx.doi.org/10.1021/jo500964y.

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32

Varadaraju, Kavitha Raj, Jajur Ramanna Kumar, Lingappa Mallesha, Archana Muruli, Kikkeri Narasimha Shetty Mohana, Chethan Kumar Mukunda, and Umesha Sharanaiah. "Virtual Screening and Biological Evaluation of Piperazine Derivatives as Human Acetylcholinesterase Inhibitors." International Journal of Alzheimer's Disease 2013 (2013): 1–13. http://dx.doi.org/10.1155/2013/653962.

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The piperazine derivatives have been shown to inhibit human acetylcholinesterase. Virtual screening by molecular docking of piperazine derivatives 1-(1,4-benzodioxane-2-carbonyl) piperazine (K), 4-(4-methyl)-benzenesulfonyl-1-(1,4-benzodioxane-2-carbonyl) piperazine (S1), and 4-(4-chloro)-benzenesulfonyl-1-(1,4-benzodioxane-2-carbonyl) piperazine (S3) has been shown to bind at peripheral anionic site and catalytic sites, whereas 4-benzenesulfonyl-1-(1,4-benzodioxane-2-carbonyl) piperazine (S4) and 4-(2,5-dichloro)-benzenesulfonyl-1-(1,4-benzodioxane-2-carbonyl) piperazine (S7) do not bind either to peripheral anionic site or catalytic site with hydrogen bond. All the derivatives have differed in number of H-bonds and hydrophobic interactions. The peripheral anionic site interacting molecules have proven to be potential therapeutics in inhibiting amyloid peptides aggregation in Alzheimer’s disease. All the piperazine derivatives follow Lipinski’s rule of five. Among all the derivatives 1-(1,4-benzodioxane-2-carbonyl) piperazine (K) was found to have the lowest TPSA value.

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33

Hudkins, Robert L., John A. Gruner, Rita Raddatz, Joanne R. Mathiasen, Lisa D. Aimone, Michael J. Marino, Edward R. Bacon, Michael Williams, and Mark A. Ator. "3-(1′-Cyclobutylspiro[4H-1,3-benzodioxine-2,4′-piperidine]-6-yl)-5,5-dimethyl-1,4-dihydropyridazin-6-one (CEP-32215), a new wake-promoting histamine H3 antagonist/inverse agonist." Neuropharmacology 106 (July 2016): 37–45. http://dx.doi.org/10.1016/j.neuropharm.2015.09.025.

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34

Daukshas, V. K., Yu Yu Ramanauskas, L. K. Labanauskas, �. B. Udrenaite, I. Yu Yautakene, V. V. Lapinskas, N. A. Lauzhikene, and R. S. Maskalyunas. "Synthesis and local anesthetic activity of 1-amino-2-phenylethyl derivatives of 1,5-benzodioxepine and 1,6-benzodioxocine." Pharmaceutical Chemistry Journal 23, no. 4 (April 1989): 298–300. http://dx.doi.org/10.1007/bf00758417.

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35

Khalilullah, Habibullah, Shamshir Khan, Mohamed Jawed Ahsan, and Bahar Ahmed. "Synthesis and Biological Evaluation of N-[2-(substituted-phenyl)-4-oxo-1,3- thiazolidin-3-yl]-2,3-dihydro-1,4-benzodioxine-2-carboxamide Analogs as Potential Antibacterial and Antifungal Agents." Anti-Infective Agents 10, no. 2 (March 25, 2012): 142–48. http://dx.doi.org/10.2174/2211362611208020142.

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36

Lee, Thomas V., Alistair J. Leigh, and Christopher B. Chapleo. "The Preparation and Coupling Reactions of 2-Bromo-1,4-benzodioxin. A Simple Synthesis of 2-(1-Alkenyl)-, 2-Alkyl-and 2-Aryl-1,4-benzodioxins." Synthesis 1989, no. 03 (1989): 208–9. http://dx.doi.org/10.1055/s-1989-27201.

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37

Matsuda, Toshio, Takashi Yoshikawa, Makoto Suzuki, Shoichi Asano, Pranee Somboonthum, Kazuhiro Takuma, Yoshihide Nakano, et al. "Novel Benzodioxan Derivative, 5-{3-[((2S)-1,4-Benzodioxan-2-ylmethyl)amino]propoxy}-l,3-benzodioxole HC1 (MKC-242), with a Highly Potent and Selective Agonist Activity at Rat Central Serotonin1A Receptors." Japanese Journal of Pharmacology 69, no. 4 (1995): 357–66. http://dx.doi.org/10.1254/jjp.69.357.

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38

Jeyamogan, Shareni, Naveed Ahmed Khan, Ayaz Anwar, Muhammad Raza Shah, and Ruqaiyyah Siddiqui. "Cytotoxic effects of Benzodioxane, Naphthalene diimide, Porphyrin and Acetamol derivatives on HeLa cells." SAGE Open Medicine 6 (January 1, 2018): 205031211878196. http://dx.doi.org/10.1177/2050312118781962.

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Objectives: To synthesize novel compounds belonging to Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrin classes and test their potential anticancer properties. Methods: Several compounds were synthesized and their molecular identity was confirmed using nuclear magnetic resonance. Potential anticancer properties were determined using cytopathogenicity assays and growth inhibition assays using cervical cancer cells (HeLa). Cells were incubated with different concentrations of compounds belonging to Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrins and effects were determined. HeLa cells cytopathogenicity was determined by measuring lactate dehydrogenase release using cytotoxicity detection assay. Growth inhibition assays were performed by incubating 50% semi-confluent HeLa cells with Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrin compounds and HeLa cell proliferation was observed. Growth inhibition and host cell death were compared in the presence and absence of drugs. Results: Cytopathogenicity assays showed that the selected compounds were cytotoxic against HeLa cells, killing up to 90% of cells. Growth inhibition assays exhibited 100% growth inhibition. These effects are likely via oxidative stress, production of reactive oxygen species, changes in cytosolic and intracellular calcium/adenine nucleotide homeostasis, inhibition of ribonucleotide reductase/cyclooxygenase and/or glutathione depletion. Conclusions: Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrins exhibited potent anticancer properties. These findings are promising and should pave the way in the rationale development of anticancer drugs. Using different cancer cell lines, future studies will determine their potential as anti-tumour agents as well as their precise molecular mode of action.

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39

Irving, A., and H. M. N. H. Irving. "6,8-Dichloro-1,3-benzodioxin." Acta Crystallographica Section C Crystal Structure Communications 45, no. 5 (May 15, 1989): 766–68. http://dx.doi.org/10.1107/s0108270188013484.

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40

Ferenczi, Renáta Kertiné, Tünde-Zita Illyés, Sándor Balázs Király, Gyula Hoffka, László Szilágyi, Attila Mándi, Sándor Antus, and Tibor Kurtán. "Evaluation of Different Synthetic Routes to (2R,3R)-3-Hydroxymethyl-2-(4-hydroxy- 3-methoxyphenyl)-1,4-Benzodioxane-6-Carbaldehyde." Current Organic Chemistry 23, no. 26 (January 1, 2020): 2960–68. http://dx.doi.org/10.2174/1385272823666191212113407.

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The reported enantioselective synthesis for the preparation of (+)-(2R,3R)-2-(4- hydroxy-3-methoxyphenyl)-3-hydroxymethyl-1,4-benzodioxane-6-carbaldehyde, precursor for the stereoselective synthesis of bioactive flavanolignans, could not be reproduced. Thus, the target molecule was prepared via the synthesis and separation of diastereomeric O-glucosides. TDDFT-ECD calculations and the 1,4-benzodioxane helicity rule were utilized to determine the absolute configuration. ECD calculations also confirmed that the 1Lb Cotton effect is governed by the helicity of the heteroring, while the higher-energy ECD transitions reflect mainly the orientation of the equatorial C-2 aryl group.

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41

Mori, Sachio, and Shozo Takechi. "Synthesis of Benzodioxane Prostacyclin Analogue." HETEROCYCLES 31, no. 7 (1990): 1189. http://dx.doi.org/10.3987/com-90-5370.

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42

Hirata, Makoto, and Eiji Taniguchi. "Synthesis of (+)-(2S, 3S)-Benzodioxane." Journal of the Faculty of Agriculture, Kyushu University 42, no. 1/2 (December 1997): 101–12. http://dx.doi.org/10.5109/24197.

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43

Daliacker, Franz, Hans-Joachim Schieuter, and Petra Schneider. "Darstellung und Reaktionen von 1,3-Benzdioxol-biscarbaldehyden. Ein Beitrag zur Strukturaufklärung des Nepenthons A / Synthesis and Reactions of 1,3-Benzodioxoledicarboxaldehydes. A Contribution to the Structure Elucidation of Nepenthone-A." Zeitschrift für Naturforschung B 41, no. 10 (October 1, 1986): 1273–80. http://dx.doi.org/10.1515/znb-1986-1014.

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We describe the preparation o f 1,3-Benzodioxole-5,6-dicarboxaldehyde (1d) and 1,3-Benzdioxole- 4,5-dicarboxaldehyde (3h). Under especially mild conditions also the synthesis of 4,7- Dimethoxy-1,3-benzodioxole-5,6-dicarboxaldehyde (4g) can be achieved. Its reaction with Hydroxyacetone leads to quinone 9a, which after methylation can be identified with the dim ethylether of Nepenthone-A .

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He, Xuefeng, Yongsu Li, Meng Wang, Hui-Xuan Chen, Bin Chen, Hao Liang, Yaqi Zhang, Jiyan Pang, and Liqin Qiu. "Highly efficient synthesis of benzodioxins with a 2-site quaternary carbon structure by secondary amine-catalyzed dual Michael cascade reactions." Organic & Biomolecular Chemistry 16, no. 30 (2018): 5533–38. http://dx.doi.org/10.1039/c8ob01029c.

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Li, Yanding, Li Shuai, Hoon Kim, Ali Hussain Motagamwala, Justin K. Mobley, Fengxia Yue, Yuki Tobimatsu, et al. "An “ideal lignin” facilitates full biomass utilization." Science Advances 4, no. 9 (September 2018): eaau2968. http://dx.doi.org/10.1126/sciadv.aau2968.

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Lignin, a major component of lignocellulosic biomass, is crucial to plant growth and development but is a major impediment to efficient biomass utilization in various processes. Valorizing lignin is increasingly realized as being essential. However, rapid condensation of lignin during acidic extraction leads to the formation of recalcitrant condensed units that, along with similar units and structural heterogeneity in native lignin, drastically limits product yield and selectivity. Catechyl lignin (C-lignin), which is essentially a benzodioxane homopolymer without condensed units, might represent an ideal lignin for valorization, as it circumvents these issues. We discovered that C-lignin is highly acid-resistant. Hydrogenolysis of C-lignin resulted in the cleavage of all benzodioxane structures to produce catechyl-type monomers in near-quantitative yield with a selectivity of 90% to a single monomer.

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Pujol, M. D., Y. Harrak, and G. Guillaumet. "The First Synthesis of Spiro(1,4-Benzodioxin-2,4′-Piperidines) and Spiro (1,4-Benzodioxin-2,3′-Pyrrolidines)." Synlett, no. 6 (2003): 0813–16. http://dx.doi.org/10.1055/s-2003-38728.

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Pilkington, Lisa I., and David Barker. "Synthesis and biology of 1,4-benzodioxane lignan natural products." Natural Product Reports 32, no. 10 (2015): 1369–88. http://dx.doi.org/10.1039/c5np00048c.

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This review describes the evolution of synthetic methods towards 1,4-benzodioxane lignan natural products, from early biomimetic approaches to recent enantiospecific syntheses. Additionally, a comprehensive report of their biosynthesis and significant biological activities is detailed.

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Straniero, Valentina, Marco Pallavicini, Giuseppe Chiodini, Carlo Zanotto, Luca Volontè, Antonia Radaelli, Cristiano Bolchi, et al. "3-(Benzodioxan-2-ylmethoxy)-2,6-difluorobenzamides bearing hydrophobic substituents at the 7-position of the benzodioxane nucleus potently inhibit methicillin-resistant Sa and Mtb cell division." European Journal of Medicinal Chemistry 120 (September 2016): 227–43. http://dx.doi.org/10.1016/j.ejmech.2016.03.068.

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Asano, Shoichi, Toshio Matsuda, Takashi Yoshikawa, Pranee Somboonthum, Hatsue Tasaki, Michikazu Abe, and Akemichi Baba. "Interaction of Orally Administered 5-{3-[((25)-1,4-Benzodioxan-2-ylmethyl)amino]propoxy}-1,3-benzodioxole (MKC-242) with 5-HT1A Receptors in Rat Brain." Japanese Journal of Pharmacology 74, no. 1 (1997): 69–75. http://dx.doi.org/10.1016/s0021-5198(19)31428-3.

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Yang, Jinliang, Suqing Shi, and Jun Nie. "Reasons for the yellowness of photocured samples by the benzophenone/1,3-benzodioxole photoinitiating system." New Journal of Chemistry 39, no. 7 (2015): 5453–58. http://dx.doi.org/10.1039/c5nj00575b.

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