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Journal articles on the topic 'Fused pyran'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Mukherjee, Prasun, and Asish R. Das. "Facile synthesis of functionalized 6-cyano-2-oxa-7-azabicyclo[4.1.0]hept-3-en-1-yl acetates: a catalyst free approach to access the pyran fused 2-acetoxy-NH-aziridines." RSC Advances 6, no. 1 (2016): 132–39. http://dx.doi.org/10.1039/c5ra24510a.

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2

Someswarao, B., Rasvan Khan P., B. Jagan Mohan Reddy, Sridhar B., and V. Subba Reddy B. "Tandem Prins-type cyclization for the stereoselective construction of fused polycyclic ring systems." Organic Chemistry Frontiers 5, no. 8 (2018): 1320–24. http://dx.doi.org/10.1039/c7qo01164d.

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A novel strategy has been developed for the synthesis of fused tetrahydrofuro[3,2-c]pyrano[2,3-b]chromene derivatives through the condensation of 2-hydroxybenzaldehydes with 2-(3,4-dihydro-2H-pyran-5-yl)ethan-1-ol in the presence of 20 mol% TMSOTf.

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3

Li, Shihang, Aimin Yu, Jianfa Li, and Xiangtai Meng. "Synthesis of Benzothiophene-Fused Pyran Derivatives via Piperidine Promoted Domino Reaction." Heteroatom Chemistry 2019 (May 2, 2019): 1–6. http://dx.doi.org/10.1155/2019/4361410.

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A new domino reaction between thioaurones and malononitrile has been reported. This reaction allows efficient access to benzothiophene-fused pyran derivatives in good yields under mild reaction conditions. The substrate scope is broad; a series of benzothiophene-fused pyran derivatives have been synthesized.

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4

Hurtak, Jessica, and Frank McDonald. "Regioselectivity of Mercury-Promoted Oxacyclizations of Alkynyl Diols." Synlett 28, no. 20 (2017): 2951–55. http://dx.doi.org/10.1055/s-0036-1588562.

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Hg(OTf)2-catalyzed cyclization of an alkynyl alcohol on a tetrahydropyran template gives the bispyranyl ketone arising from dehydrative cyclization and alkyne hydration, rather than the targeted fused pyran-oxepane product. The combination of stoichiometric Hg(OTf)2 and triethylsilane gives reductive cyclization, but affords the fused pyran-oxocane corresponding to an 8-endo-mode oxacyclization process.

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5

Ishikawa, Yoshinobu. "Crystal structure of 3-acetyl-4H-chromen-4-one." Acta Crystallographica Section E Crystallographic Communications 71, no. 7 (2015): o527. http://dx.doi.org/10.1107/s2056989015012098.

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In the title compound, C11H8O3, the fused-ring system is almost planar (r.m.s. deviation = 0.020 Å), with the largest deviation from the least-squares plane [0.0462 (17) Å] being for a pyran C atom. The dihedral angle between the plane of the fused-ring system and acetyl plane is 5.149 (16)°. In the crystal, the fused rings are linked by aromatic π–π stacking interactions [centroid–centroid distance between the benzene and pyran rings = 3.643 (6) Å] and C—H...O hydrogen bonds, generating a three-dimensional network.

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6

Lee, Jui-Ting, Nagesh Jatangi, Sameer Vyasamudri, and Ding-Yah Yang. "Three-component synthesis of pyran-fused biscoumarins: an entry to pyridinone- and pyranone-fused coumarins." RSC Advances 14, no. 21 (2024): 14767–74. http://dx.doi.org/10.1039/d4ra01681e.

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7

Rathin, Jana. "Intramolecular palladium-catalyzed reaction β-H elimination or C–H activation: A general method for the synthesis of fused pyran rings". International Journal of HIT Transaction on ECCN Vol. 7, № 1A (2021) (2021): 90–99. https://doi.org/10.5281/zenodo.5893081.

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Department of Chemistry, Shahid Matangini Hazra Govt. General Degree College for Women, Nimtouri, West Bengal, India. Pyrans constitute an important class of 6-member heterocycles with one oxygen atom. Together with its benzo derivatives, pyrans can formulate a prevalent verity of natural and synthetic products in industrial applications. This is an important core molecule having versatile use with its derivatives in pharmaceuticals, dye industry, catalysis, agrochemicals and many more. Several methods for the preparation of pyranderivatives have been reported earlier. In this mini review we h

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8

Li, Jun-Lin, Xiao-Hui Wang, Jun-Chao Sun, Yi-Yuan Peng, Cong-Bin Ji, and Xing-Ping Zeng. "Chiral Tertiary Amine Catalyzed Asymmetric [4 + 2] Cyclization of 3-Aroylcoumarines with 2,3-Butadienoate." Molecules 26, no. 2 (2021): 489. http://dx.doi.org/10.3390/molecules26020489.

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Coumarins and 2H-pyran derivatives are among the most commonly found structural units in natural products. Therefore, the introduction of 2H-pyran moiety into the coumarin structural unit, i.e., dihydrocoumarin-fused dihydropyranones, is a potentially successful route for the identification of novel bioactive structures, and the synthesis of these structures has attracted continuing research interest. Herein, a chiral tertiary amine catalyzed [4 + 2] cyclization of 3-aroylcoumarines with benzyl 2,3-butadienoate was reported. In the presence of Kumar’s 6’-(4-biphenyl)-β-iso-cinchonine, the desi

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9

Safari, Fatemeh, Hajar Hosseini, Mohammad Bayat, and Ashkan Ranjbar. "Synthesis and evaluation of antimicrobial activity, cytotoxic and pro-apoptotic effects of novel spiro-4H-pyran derivatives." RSC Advances 9, no. 43 (2019): 24843–51. http://dx.doi.org/10.1039/c9ra03196k.

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10

Sughanya, V., and N. Sureshbabu. "9-(4-Hydroxy-3,5-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (2012): o1060. http://dx.doi.org/10.1107/s1600536812010410.

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In the title compound, C25H30O6, the two fused cyclohexanone rings have envelope conformations, whereas the central pyran ring is roughly planar [mximum deviation = 0.045 (2) Å]. The pyran and benzene rings are almost perpendicular to each other, making a dihedral angle of 86.32 (2)°. In the crystal, molecules are linkedviapairs of O—H...O hydrogen bonds, forming inversion dimers.

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11

Hammam, Abou Elfatooh G., Nagla A. Abd El-hafeza, Wanda H. Midurab, and Marian Mikołajczyk. "Chemistry of Seven-Membered Heterocycles, VI. Synthesis of Novel Bicyclic Heterocyclic Compounds as Potential Anticancer and Anti-HIV Agents." Zeitschrift für Naturforschung B 55, no. 5 (2000): 417–24. http://dx.doi.org/10.1515/znb-2000-0511.

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Several new pyridines, pyridones and pyrans fused to benzothiepine or benzoheptene ring were synthesized as potential anticancer and anti-HIV agents. The fused-ring pyridines 6. 7 and 17-19 were obtained via the reaction of the seven-membered ring ketones 1, 2 and 3 with an arylidene-malononitrile and by treatment of the ylidenemalononitriles 14, 15 and 16 with aromatic aldehydes, respectively. The corresponding pyridones 11, 12 and 13 were prepared from the ketones 1, 2 and 3 and arylmethylenecyanoacetamide. The synthesis of the fused-ring pyranes 8 and 9 involved the condensation of the keto

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12

Kumar, Sumit, Aditi Arora, Sandeep Kumar, Rajesh Kumar, Nihar Nalini Senapati, and Brajendra K. Singh. "Pyran-Fused Analogues and Their Potential Applications." Russian Journal of Bioorganic Chemistry 51, no. 2 (2025): 373–438. https://doi.org/10.1134/s1068162024606001.

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13

Ponnusamy, R., V. Sabari, G. Sivakumar, M. Bakthadoss, and S. Aravindhan. "(6bS*,14R*,14aR*)-Methyl 14-(4-methylphenyl)-7-oxo-6b,6c,7,12b,14,14a-hexahydro-1H-pyrano[3,2-c:5,4-c′]dichromene-14a-carboxylate." Acta Crystallographica Section E Structure Reports Online 69, no. 2 (2013): o267—o268. http://dx.doi.org/10.1107/s1600536813001244.

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In the title compound, C28H22O6, the chromeno ring system is almost planar, with a dihedral angle between the mean planes of the pyran and benzene rings of 1.87 (8)°. The pyran ring bearing the methylphenyl substituent has a half-chair conformation while the other pyran ring has an envelope conformation with the tetrasubstituted C atom as the flap. The benzene ring of the chromeno ring system is inclined to the benzene ring fused to the latter pyran ring by 74.66 (9)°. These aromatic rings are inclined to the 4-methylphenyl ring by 52.67 (9) and 66.63 (10)°, respectively. In the crystal, molec

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14

Mariappan, Arumugam, Kandasamy Rajaguru, Shanmugam Muthusubramanian, and Nattamai Bhuvanesh. "A facile one pot synthesis of thiazolo[3,2-a]benzimidazole and pyran fused polyheterocyclic scaffolds." Organic & Biomolecular Chemistry 17, no. 17 (2019): 4196–99. http://dx.doi.org/10.1039/c9ob00300b.

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15

Fun, Hoong-Kun, Suchada Chantrapromma, Uma Prawat, Nawong Boonnak, and Ibrahim Abdul Razak. "8-O-Acetyl-8-epi-9-deoxygoniopypyrone." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (2012): o1072—o1073. http://dx.doi.org/10.1107/s1600536812010483.

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The title compound (systematic name: 7-oxo-3-phenyl-2,6-dioxabicyclo[3.3.1]nonan-4-yl acetate), C15H16O5, is a styryllactone derivative which was isolated fromGoniothalamus macrophyllus. The molecule has two fused rings consisting of a tetrahydro-2H-pyran and a lactone ring, with the benzene ring and the acetyl group attached to the tetrahydro-2H-pyran ring. The tetrahydro-2H-pyran ring is in a standard chair conformation, whereas the lactone ring is in an envelope conformation. In the crystal, molecules are linked by weak C—H...O interactions into sheets parallel to theacplane. Weak C—H...π i

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16

Khan, Md Musawwer, Sumbulunnisan Shareef, Saigal Saigal, and Subash C. Sahoo. "A catalyst- and solvent-free protocol for the sustainable synthesis of fused 4H-pyran derivatives." RSC Advances 9, no. 45 (2019): 26393–401. http://dx.doi.org/10.1039/c9ra04370e.

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17

Abdulaeva, I. A., L. G. Minyaeva, and V. V. Mezheritskii. "Pyran derivatives peri-fused to acenaphthene and acenaphthylene." Russian Journal of Organic Chemistry 47, no. 3 (2011): 384–91. http://dx.doi.org/10.1134/s1070428011030109.

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18

Doddi, Venkata Ramana, Pavan K. Kancharla, Y. Suman Reddy, Amit Kumar, and Yashwant D. Vankar. "Synthesis of fused pyran-carbahexopyranoses as glycosidase inhibitors." Carbohydrate Research 344, no. 5 (2009): 606–12. http://dx.doi.org/10.1016/j.carres.2009.01.017.

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19

Swaminathan, K., K. Sethusankar, G. Siva Kumar, and M. Bakthadoss. "Crystal structures and conformational analyses of three pyranochromene derivatives." Acta Crystallographica Section E Crystallographic Communications 71, no. 8 (2015): 926–30. http://dx.doi.org/10.1107/s2056989015012967.

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The title compounds, C27H20O6, (I) [systematic name: methyl 7-oxo-14-phenyl-1H,7H,14H-pyrano[3,2-c:5,4-c′]dichromene-14a(6bH)-carboxylate], C24H22O5, (II) [systematic name: methyl 1-oxo-6-phenyl-2,3,4,12b-tetrahydro-1H,6H-chromeno[3,4-c]chromene-6a(7H)-carboxylate], and C25H23N3O4, (III) [systematic name: 6-(4-ethylphenyl)-2,4-dimethyl-1,3-dioxo-2,3,4,12b-tetrahydro-1H,6H-chromeno[4′,3′:4,5]pyrano[2,3-d]pyrimidine-6a(7H)-carbonitrile], are pyranochromene derivatives. The central pyran rings (B) of compounds (I) and (III) adopt half-chair conformations, whereas that of compound (II) adopts a so

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20

Saha, Arijit, Soumen Payra, and Subhash Banerjee. "On water synthesis of pyran–chromenes via a multicomponent reactions catalyzed by fluorescent t-ZrO2nanoparticles." RSC Advances 5, no. 123 (2015): 101664–71. http://dx.doi.org/10.1039/c5ra19290k.

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Here, we have reported multicomponent synthesis of diverse pyran fused chromenes namely 2-aminochromene, dihydropyrano[3,2-c]chromene, and chromeno[4,3-b]chromene derivatives using fluorescentt-ZrO<sub>2</sub>nanoparticles as reusable catalyst in water.

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21

Desmaële, Didier, Gilles Pain, and Jean d'Angelo. "Asymmetric synthesis of trans-fused octahydro pyrano-pyran subunits related to marine polyether toxins." Tetrahedron: Asymmetry 3, no. 7 (1992): 867–70. http://dx.doi.org/10.1016/s0957-4166(00)82186-2.

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22

Sagar, Ram, Jongmin Park, Minseob Koh, and Seung Bum Park. "Diastereoselective Synthesis of Polycyclic Acetal-Fused Pyrano[3,2-c]pyran-5(2H)-one Derivatives." Journal of Organic Chemistry 74, no. 5 (2009): 2171–74. http://dx.doi.org/10.1021/jo8023889.

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23

Wu, Simin, Lingxian Meng, Zhe Zhang, et al. "Molecular optimization of incorporating pyran fused acceptor–donor–acceptor type acceptors enables over 15% efficiency in organic solar cells." Journal of Materials Chemistry C 10, no. 6 (2022): 1977–83. http://dx.doi.org/10.1039/d1tc05779k.

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Three acceptor–donor–acceptor type fused-ring non-fullerene acceptors of FOR-IN, FOR-1F and FOR-2F, were synthesized with the same pyran-composed backbone but different terminals, affording over 15% efficiency in organic solar cells.

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24

Kranjc, Krištof, and Marijan Kočevar. "Intensification of a Reaction by the Addition of a Minor Amount of Solvent: Diels-Alder Reaction of 2H-Pyran-2-ones with Alkynes." Collection of Czechoslovak Chemical Communications 71, no. 5 (2006): 667–78. http://dx.doi.org/10.1135/cccc20060667.

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Diels-Alder transformation of substituted 3-benzoylamino-2H-pyran-2-ones 1 with a variety of alkynes 2 under microwave (MW) irradiation in a closed system can be intensified in a novel way by addition of a minor amount of butan-1-ol. When the reagents are not volatile under the used conditions, the reactions do not seem to be influenced by the addition of butan-1-ol, as demonstrated by the cycloaddition of a fused 2H-pyran-2-one 5 with N-ethylmaleimide (6) giving adduct 7.

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25

Wang, Xiao-Bing, and Ling-Yi Kong. "2-(2-Chlorophenyl)-7-methyl-4H-chromen-4-one." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (2007): o4340. http://dx.doi.org/10.1107/s1600536807050155.

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The title compound, C16H11ClO2, is a synthetic flavonoid. The fused-ring system is almost planar, with a mean deviation from the least-squares plane of 0.0204 (2) Å. The dihedral angle between the chromene group and the chlorophenyl ring is 50.9 (6)°, due to unfavourable steric interactions with the Cl atom. Aromatic π–π stacking interactions between the fused benzene (π-rich) and pyran (π-deficient) rings are observed, with a centroid–centroid distance of 3.578 Å.

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26

Kočevar, Marijan, and Franc Požgan. "Ring Transformations of 2H-Pyran-2-ones and Fused Pyran-2-ones with Nucleophilic Reagents." HETEROCYCLES 77, no. 2 (2009): 657. http://dx.doi.org/10.3987/rev-08-sr(f)5.

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27

Požgan, Franc, Krištof Kranjc, Vladimir Kepe, Slovenko Polanc, and Marijan Kočevar. "Synthesis of 2H-pyran-2-ones and fused pyran-2-ones as useful building blocks." Arkivoc 2007, no. 8 (2006): 97–111. http://dx.doi.org/10.3998/ark.5550190.0008.810.

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28

K., C. MAJUMDAR, and DAS U. "Studies on Sigmatropic Rearrangements : Regioselective Synthesis of Coumarins, Quinolones and Thiocoumarins with 3,4-Fused Pyran or Furan Ring Systems by Claisen Rearrangement." Journal of Indian Chemical Society Vol. 74, Nov-Dec 1997 (1997): 884–90. https://doi.org/10.5281/zenodo.5900433.

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Department of Chemistry, University of Kalyam, Kalyana-741 235 <em>Manuscript received 4 September 1997</em> A brief review of the regioselective synthesis of pyrano[3,2-<em>c</em>][1]benzopyran-5(2<em>H</em>)-ones, pyrano[3,2-<em>c</em>][1]benzothiapyran-5(2<em>H</em>)-one, pyrano[3,2-<em>c</em>]quinolin-5(2<em>H</em>)-ones, pyrano(2,3-<em>c</em>)[1]benzopyran-5(3<em>H</em>)-ones, 3<em>H</em>-pyrano[2,3-<em>c</em>)quinolin-5(6H)-ones, thiapyrano(2, 3- b) (1)benzothiapyran-5(2<em>H</em>)-ones, thiapyrano[2,3-<em>b]</em> [1]benzopyran-5(2<em>H</em>)-ones, furo[3,2-<em>c</em>] [1] benzopyra

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29

Kocevar, Marijan, Vladimir Kepe, and Slovenko Polanc. "One-Pot Synthesis of Some Fused Pyran-2-ones." HETEROCYCLES 41, no. 6 (1995): 1299. http://dx.doi.org/10.3987/com-95-7062.

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30

Shehab, Wesam S., and Amira A. Ghoneim. "Synthesis and biological activities of some fused pyran derivatives." Arabian Journal of Chemistry 9 (November 2016): S966—S970. http://dx.doi.org/10.1016/j.arabjc.2011.10.008.

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31

Bayat, Mohammad, Nader Zabarjad Shiraz, and Soheila Shafei Asayesh. "One-pot synthesis of functionalized fused 4H-pyran systems." Journal of Heterocyclic Chemistry 47, no. 4 (2010): 857–60. http://dx.doi.org/10.1002/jhet.401.

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32

Fogeron, Thibault, Pascal Retailleau, Lise-Marie Chamoreau, Marc Fontecave, and Yun Li. "The unusual ring scission of a quinoxaline-pyran-fused dithiolene system related to molybdopterin." Dalton Transactions 46, no. 13 (2017): 4161–64. http://dx.doi.org/10.1039/c7dt00377c.

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33

M, Heravi; Majid, M. Tamimi, M. Mirzaei, V. Zadsirjan, N. Lotfian, and H. Eshtiagh-Hosseini. "Ag3[PMo12O40]: An efficient and green catalyst for the synthesis of highly functionalized pyran‐annulated heterocycles via multicomponent reaction." Applied Organometallic Chemistry 33, no. 9 (2019): e5043. https://doi.org/10.1002/aoc.5043.

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A facile, efficient and eco-friendly catalytic protocol was developed for the synthesis of medicinally important pyran-annulated heterocycles via multicomponent reaction (MCR). Cyclocondensation of differently substituted aromatic aldehydes, malononitrile/ethyl cyanoacetate and various β-dicarbonyl compounds in the presence of Ag<sub>3</sub>[PMo<sub>12</sub>O<sub>40</sub>]⋅nH<sub>2</sub>O as heterogeneous catalyst, in EtOH–H<sub>2</sub>O, afforded diverse pyran-fused chromene analogues. The merits observed for this approach were it being conducted via MCR, using commercially av

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34

Chen, Daoliang, Danlei Zhu, Gaobo Lin, et al. "New fused conjugated molecules with fused thiophene and pyran units for organic electronic materials." RSC Advances 10, no. 21 (2020): 12378–83. http://dx.doi.org/10.1039/d0ra01984d.

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35

Rizwana Begum, S., R. Hema, G. Sumathi, R. Valliappan, and N. Srinivasan. "9-(2,4-Difluorophenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione." Acta Crystallographica Section E Structure Reports Online 70, no. 3 (2014): o276—o277. http://dx.doi.org/10.1107/s1600536814002761.

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In the title compound, C23H24F2O3, the central pyran ring has a flat-boat conformation, whereas the two fused cyclohexenone rings adopt envelope conformations, with the C atom bearing the dimethyl substituent being the flap atom in each case. The pyran ring mean plane and the difluorophenyl ring are almost normal to each other, making a dihedral angle of 87.55 (4)°. In the crystal, molecules are linked by pairs of C—H...O hydrogen bonds, forming inversion dimers with anR22(8) ring motif. The F atom at position 2 on the difluorophenyl ring is disordered over the 2- and 6-positions, and has a re

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36

Suresh Babu, N., V. Sughanya, D. Praveenkumar, and M. L. Sundararajan. "Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione." Acta Crystallographica Section E Crystallographic Communications 77, no. 11 (2021): 1170–74. http://dx.doi.org/10.1107/s2056989021010690.

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In the fused ring system of the title compound, C24H27BrO5, the mean plane and maximum deviations of the central pyran ring are 0.0384 (2) and 0.0733 (2) Å, respectively. The cyclohexenone rings both adopt envelope conformations with the tetra-substituted C atoms as flap atoms, whereas the central pyran ring adopts a flattened boat conformation. The central pyran and phenyl substituent rings are almost perpendicular to each other, making a dihedral angle of 89.71 (2)°. In the crystal, pairs of molecules are linked via O—H...O hydrogen bonds, forming inversion dimers with an R 2 2(20) ring moti

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37

Chai, Hongxin, Mingxing Liu, Qi Zhang, Daxin Shi, and Jiarong Li. "Pseudoaglycone of Spinosyn A." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (2012): o2488. http://dx.doi.org/10.1107/s1600536812028851.

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The title compound [systematic name: 9-ethyl-13-hydroxy-14-methyl-2-(3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yloxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione], C33H50O9, was obtained by hydrolysis of Spinosyn A. The fused cyclopentene ring adopts a twisted conformation, while the fused cyclohexene and cyclopentane rings are in envelope conformations with the same C atom at the flaps. In the crystal, molecules are linked by O—H...O and C—H...O hydrogen bonds into a layer parallel to theabplane.

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38

Ishikawa, Yoshinobu. "Crystal structure of 7,8-dichloro-4-oxo-4H-chromene-3-carbaldehyde." Acta Crystallographica Section E Crystallographic Communications 71, no. 8 (2015): 902–5. http://dx.doi.org/10.1107/s205698901501275x.

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In the title compound, C10H4Cl2O3, a dichlorinated 3-formylchromone derivative, the fused-ring system is slightly puckered [dihedral angle between the benzene and pyran rings = 3.66 (10)°]. The dihedral angle between the pyran ring and the formyl plane is 8.64 (7)°. In the crystal, molecules are linked through π–π stacking interactions [centroid–centroid distance between the benzene and pyran rings = 3.727 (2) Å], C—H...O hydrogen bonds and short C...O contacts [2.838 (4) Å]. Halogen bonds between the formyl O atoms and the Cl atoms at the 7-position [Cl...O = 2.984 (3) Å, C—Cl...O = 170.83 (1

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39

Conceição, Rafaela, Graham Hungerford, Susana P. G. Costa, and M. Sameiro T. Gonçalves. "Photolytic release of bioactive carboxylic acids from fused pyran conjugates." Dyes and Pigments 148 (January 2018): 368–79. http://dx.doi.org/10.1016/j.dyepig.2017.09.023.

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40

Aguiar, António, Andreia Leite, André M. N. Silva, et al. "Isoxazolidine-fused meso-tetraarylchlorins as key tools for the synthesis of mono- and bis-annulated chlorins." Organic & Biomolecular Chemistry 13, no. 26 (2015): 7131–35. http://dx.doi.org/10.1039/c5ob00800j.

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An efficient synthetic approach to prepare novel annulated chlorin derivatives, a meso-tetraarylchlorin bearing an azepine ring and another bearing simultaneously an azepine and a 2H-pyran ring, is described.

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41

Hirokawa, Shoma, Nagao Kobayashi, and Soji Shimizu. "Periphery-Fused Chiral A2B-Type Subporphyrin." Molecules 26, no. 4 (2021): 1140. http://dx.doi.org/10.3390/molecules26041140.

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Despite significant interest, the chiroptical properties of subporphyrins have rarely been investigated because chiral subporphyrins are elusive. Here, inherently chiral subporphyrins are elaborated by forming a fused pyran ring at the periphery of an A2B-type meso-aryl-substituted subporphyrin. Their circular dichroism (CD) properties are largely affected by the peripheral substituents and the dihedral angles between the meso-aryl substituents and the subporphyrin core: the β-perbromo subporphyrin with an orthogonal arrangement of the meso-phenyl substituents to the subporphyrin core exhibits

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42

Ding, Chunyong, Lili Wang, Haijun Chen, et al. "ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels–Alder reactions: synthesis of dihydropyran-fused diterpenoids." Org. Biomol. Chem. 12, no. 42 (2014): 8442–52. http://dx.doi.org/10.1039/c4ob01040j.

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43

Samir, Nermin, Riham F. George, Eman Z. Elrazaz, et al. "Synthesis of some tropane-based compounds targeting colon cancer." Future Medicinal Chemistry 12, no. 23 (2020): 2123–40. http://dx.doi.org/10.4155/fmc-2020-0097.

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Background: In continuation of a previous work concerned with the anticancer activity of some 8-alkyl-2,4-bisarylidene-8-nortropan-3-ones, this work focuses on further modification to the tropane/pyran fused skeleton aiming to obtain improved anticancer activity. Methodology: Reaction of 8-alkyl-2,4-bisarylidene-8-nortropan-3-ones 1–21 with malononitrile under basic conditions afforded tropane/pyran hybrids 22–40 and tropane/pyridine hybrids 41, 42. X-ray crystallography for compounds 22 and 41 as representative examples confirmed their structures. They were tested for their anticancer activit

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44

Zhang, Enshen, Mei Sun, and Lvlv Gao. "Rh(III)-Catalyzed Double Annulation of 3-Phenyl-1,2,4-oxadiazoles with 2-Diazo-1,3-diketones: Access to Pyran-Fused Isoquinolines." Molecules 30, no. 1 (2025): 149. https://doi.org/10.3390/molecules30010149.

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Efficient access to pyranoisoquinoline derivatives via rhodium-catalyzed double C-H functionalization of phenyl oxadiazoles and diazo compounds has been developed. Two C-C bonds and one C-O and C-N bond formation was realized by this tandem reaction, along with the formation of two heterocycles, affording diversified pyran-fused isoquinolines in moderate to good yields with broad functional group tolerance under mild reaction conditions.

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45

Ishikawa, Yoshinobu. "Crystal structure of 4-oxo-4H-chromene-3-carboxylic acid." Acta Crystallographica Section E Crystallographic Communications 71, no. 8 (2015): o580—o581. http://dx.doi.org/10.1107/s2056989015013456.

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In the title compound, C10H6O4, also known as 3-carboxychromone, the non-H atoms of the chromone ring are essentially coplanar (r.m.s. deviation = 0.0057 Å), with the maximum deviation from their least-squares plane [0.011 (2) Å] being for a pyran C atom. The dihedral angle between the fused ring and plane of the carboxy group is 3.06 (2)°. An intramolecular hydrogen bond is formed between the ring carbonyl O atom and the carboxy O—H atom, closing anS(6) loop. In the crystal, molecules are assembled by stacking interactions [centroid–centroid distance between the benzene and pyran rings = 3.84

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46

Raja, Rajamani, Subramani Kandhasamy, Paramasivam T. Perumal, and A. SubbiahPandi. "Crystal structure of 4-(6-bromo-4-oxo-4H-chromen-3-yl)-2-methylamino-3-nitropyrano[3,2-c]chromen-5(4H)-one chloroform monosolvate." Acta Crystallographica Section E Crystallographic Communications 71, no. 9 (2015): o648—o649. http://dx.doi.org/10.1107/s2056989015014553.

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In the title compound, C22H13BrN2O7·CHCl3, the pyran ring adopts a shallow sofa conformation with the C atom bearing the bromochromene system as the flap [deviation = 0.291 (3) Å]. The dihedral angle between the pyran fused-ring system (all atoms; r.m.s. deviation = 0.032 Å) and the bromochromene ring system (r.m.s. deviation = 0.027 Å) is 87.56 (9)°. An intramolecular N—H...O hydrogen bond closes anS(6) ring. The Cl atoms of the solvent molecule are disordered over two sets of sites in a 0.515 (6):0.485 (6) ratio. In the crystal, inversion dimers linked by pairs of N—H...O hydrogen bonds gene

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47

Bakhouch, Mohamed, Ghali Al Houari, Mohamed El Yazidi, Mohamed Saadi, and Lahcen El Ammari. "Ethyl 2-amino-4-(3-nitrophenyl)-4H-1-benzothieno[3,2-b]pyran-3-carboxylate." Acta Crystallographica Section E Structure Reports Online 70, no. 5 (2014): o587. http://dx.doi.org/10.1107/s1600536814008538.

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The molecule of the title compound, C20H16N2O5S, is built up by one fused five-membered and two fused six-membered rings linked to ethoxycarbonyl and 3-nitrophenyl groups. The benzothienopyran ring system is nearly planar (r.m.s deviation = 0.0392 Å) and forms a dihedral angle of 86.90 (6)° with the aromatic ring of the nitrobenzene group. In the crystal, molecules are linked by N—H...O hydrogen bonds and by π–π interactions between the phenyl ring and the six-membered heterocyle [intercentroid distance = 3.5819 (8) Å], forming a three-dimensional network.

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48

Kepe, Vladimir, Marijan Kocevar, Solvenko Polanc, Bojan Verc̈ek, and Miha Tis̈ler. "A simple and general one-pot synthesis of some 2h-pyran-2-ones and fused pyran-2-ones." Tetrahedron 46, no. 6 (1990): 2081–88. http://dx.doi.org/10.1016/s0040-4020(01)89774-x.

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49

Bondock, Samir, Abd El-Gaber Tarhoni, and Ahmed A. Fadda. "A Convenient Synthesis of 2H-Pyran-2-ones, Fused Pyran-2-ones, and Pyridones Bearing a Thiazole Moiety." Journal of Heterocyclic Chemistry 51, no. 1 (2013): 249–55. http://dx.doi.org/10.1002/jhet.1677.

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50

Roma, Giorgio, Mario Di Braccio, Giancarlo Grossi, Cristina Marzano, Morena Simonato, and Franco Bordin. "Pyran derivatives XX. 2-Aminochromone benzo-fused derivatives with antiproliferative properties." Il Farmaco 53, no. 7 (1998): 494–503. http://dx.doi.org/10.1016/s0014-827x(98)00055-x.

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