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Journal articles on the topic 'Diynes'

Author: Grafiati

Published: 4 June 2021

Last updated: 17 February 2022

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1

Sanz-Marco, Amparo, Gonzalo Blay, M. Carmen Muñoz та José R. Pedro. "Highly enantioselective copper(i)-catalyzed conjugate addition of 1,3-diynes to α,β-unsaturated trifluoromethyl ketones". Chemical Communications 51, № 43 (2015): 8958–61. http://dx.doi.org/10.1039/c5cc01676b.

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The conjugate diynylation of α,β-unsaturated trifluoromethyl ketones with terminal diynes is carried out. Pre-metalation of the terminal 1,3-diyne is not required. Diynes bearing a propargylic stereogenic center are obtained with good yields and ee's.

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2

Guo, Richard, Romelo Gibe, and James R. Green. "Mono- and disubstitutions of (hepta-2,5-diyne-1,7-diol) bis(dicobalt) derivatives Selectivity in Nicholas reactions." Canadian Journal of Chemistry 82, no. 2 (2004): 366–74. http://dx.doi.org/10.1139/v03-209.

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Bis(hexacarbonyldicobalt) complexes of benzyl ether methyl ether or benzyl ether acetate derivatives of hepta-2,5-diyne-1,7-diols undergo selective Lewis-acid-mediated Nicholas reactions with enol silanes, silyl ketene acetals, and allylstannanes, preferentially replacing the methyl ether or acetate function. Hydride nucleophiles are similarly incorporated selectively using a benzyl ether alcohol derivative. Subsequent Nicholas reaction at the benzyloxy-bearing site may be accomplished with an identical or a different nucleophile, affording skipped 1,4-diyne-Co4(CO)12 complexes. In insta

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3

Gu, Kai, and Xiao Di Xu. "Synthesis of Hyperbranched Polyphenylacetylene Resins and the Influence of their Molecular Architecture on their Properties." Advanced Materials Research 1095 (March 2015): 385–92. http://dx.doi.org/10.4028/www.scientific.net/amr.1095.385.

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Hyperbranched polyphenylacetylene resins were obtained by the homo-and copolycyclotrimerizations of diynes and monoynes initiated by tantalum-based catalysts, with the aim of exploring new synthetic routes to hyperbranched polyphenylacetylene resins. A group of hyperbranched poly (alkylenephenylenes) (hb-PAPs) were synthesized by TaBr5-Ph4Sn catalyzed polycyclotrimerization of 1,7-octadiyne. To improve the solubility of the homopolymers,the diyne monomers were copolymerized with phenylacetylene. IR,and 1H NMR Spectrum confirmed that the target polymers had formed via a [2+2+2] cyclotrimerizati

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4

Zhang, Liang, Mingzhu Zhao, and Xiaoming Zhao. "The synthesis of carbonyl 2-amino-pyrimidines via tandem regioselective heterocyclization of 1,3-diynes with guanidine and selective oxidation." Chemical Communications 51, no. 45 (2015): 9370–73. http://dx.doi.org/10.1039/c5cc02238j.

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A highly efficient one-pot approach for the synthesis of carbonyl 2-amino-pyrimidines from 1,3-diynes and guanidine in the presence of Cs<sub>2</sub>CO<sub>3</sub> and DMSO has been described. This methodology proves to be a tandem regioselective heterocyclization of 1,3-diynes with guanidine and selective oxidation.

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5

Ritter, Joachim, and Rolf Gleiter. "Preparation of 1-Azacyclodeca-3,8-diynes and 1,6-Diazacyclodeca-3,8-diynes." European Journal of Organic Chemistry 1998, no. 3 (1998): 553. http://dx.doi.org/10.1002/(sici)1099-0690(199803)1998:3<553::aid-ejoc553>3.0.co;2-z.

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6

Ritter, Joachim, and Rolf Gleiter. "Preparation of 1-Azacyclododeca-3,8-diynes and 1,6-Diazacyclododeca-3,8-diynes." Liebigs Annalen 1997, no. 10 (1997): 2113–18. http://dx.doi.org/10.1002/jlac.199719971013.

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7

Ojima, Iwao, Jiawang Zhu, Ephraim S. Vidal, and Dora Fracchiolla Kass. "Silylcarbocyclizations of 1,6-Diynes." Journal of the American Chemical Society 120, no. 27 (1998): 6690–97. http://dx.doi.org/10.1021/ja980907l.

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8

Bruce, Michael I., Nancy Scoleri, and Brian W. Skelton. "Lithiation of diynyl–ruthenium complexes: Routes to novel metallated functional diynes." Journal of Organometallic Chemistry 696, no. 22 (2011): 3473–82. http://dx.doi.org/10.1016/j.jorganchem.2011.07.021.

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9

Liu, Yajing, Meng Gao, Zheng Zhao, Jacky W. Y. Lam, and Ben Zhong Tang. "Polyannulation of internal alkynes and O-acyloxime derivatives to synthesize functional poly(isoquinoline)s." Polymer Chemistry 7, no. 34 (2016): 5436–44. http://dx.doi.org/10.1039/c6py01011c.

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10

Zhang, Qian, Qiu-Ju Liang, Jian-Lin Xu, Yun-He Xu, and Teck-Peng Loh. "Palladium-catalyzed silaborative carbocyclizations of 1,6-diynes." Chemical Communications 54, no. 19 (2018): 2357–60. http://dx.doi.org/10.1039/c8cc00097b.

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11

RITTER, J., and R. GLEITER. "ChemInform Abstract: Preparation of 1-Azacyclodeca-3,8-diynes and 1,6-Diazacyclodeca-3,8-diynes." ChemInform 29, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199801187.

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12

Wang, Guohua, Chao Chen, and Jing Peng. "Copper-catalyzed intramolecular aryl-bicyclization of diynes with diaryliodonium salts via vinyl cations." Chemical Communications 52, no. 67 (2016): 10277–80. http://dx.doi.org/10.1039/c6cc05735g.

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13

Diamond, Oliver J., and Todd B. Marder. "Methodology and applications of the hexadehydro-Diels–Alder (HDDA) reaction." Organic Chemistry Frontiers 4, no. 5 (2017): 891–910. http://dx.doi.org/10.1039/c7qo00071e.

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14

Lin, Yongjia, Tao Zhou, Wei Guo, Zhenfang Teng, and Yuanzhi Xia. "The mechanism of the gold-catalyzed intramolecular [3 + 2]-cycloaddition of 1,6-diynes: a DFT study." Dalton Transactions 48, no. 17 (2019): 5698–704. http://dx.doi.org/10.1039/c9dt00553f.

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15

Zhang, Yun, Jacky W. Y. Lam, and Ben Zhong Tang. "Palladium-catalyzed alkyne polyannulation of diphenols and unactivated internal diynes: a new synthetic route to functional heterocyclic polymers." Polymer Chemistry 7, no. 2 (2016): 330–38. http://dx.doi.org/10.1039/c5py01466b.

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16

Liu, Qibo, and Donald J. Burton. "A facile synthesis of diynes." Tetrahedron Letters 38, no. 25 (1997): 4371–74. http://dx.doi.org/10.1016/s0040-4039(97)00969-6.

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17

Gleiter, Rolf, Björn Hellbach, and Frank Rominger. "Cyclic Diynes by Alkyne Metathesis." Synthesis, no. 16 (2003): 2535–41. http://dx.doi.org/10.1055/s-2003-42421.

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18

Asiri, Abdullah M., and A. Stephen K. Hashmi. "Gold-catalysed reactions of diynes." Chemical Society Reviews 45, no. 16 (2016): 4471–503. http://dx.doi.org/10.1039/c6cs00023a.

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19

Lysenko, Sergej, Jeroen Volbeda, Peter G. Jones, and Matthias Tamm. "Catalytic Metathesis of Conjugated Diynes." Angewandte Chemie 124, no. 27 (2012): 6861–65. http://dx.doi.org/10.1002/ange.201202101.

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20

Lysenko, Sergej, Jeroen Volbeda, Peter G. Jones, and Matthias Tamm. "Catalytic Metathesis of Conjugated Diynes." Angewandte Chemie International Edition 51, no. 27 (2012): 6757–61. http://dx.doi.org/10.1002/anie.201202101.

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21

Danilkina, N. A., A. E. Kulyashova, and I. A. Balova. "Intramolecular cyclizations of functionalized diynes." Chemistry of Heterocyclic Compounds 48, no. 1 (2012): 95–106. http://dx.doi.org/10.1007/s10593-012-0973-7.

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22

Nasr-Esfahani, Mahboobeh, Iraj Mohammadpoor-Baltork, Ahmad Reza Khosropour, et al. "Copper immobilized on nano-silica triazine dendrimer (Cu(ii)-TD@nSiO2) catalyzed synthesis of symmetrical and unsymmetrical 1,3-diynes under aerobic conditions at ambient temperature." RSC Adv. 4, no. 27 (2014): 14291–96. http://dx.doi.org/10.1039/c3ra47184e.

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23

Yan, Lipeng, Jingbo Lan, Hu Cheng та ін. "Regioselective addition/annulation of ferrocenyl thioamides with 1,3-diynes via a sulfur-transfer rearrangement to construct extended π-conjugated ferrocenes with luminescent properties". Chemical Science 11, № 40 (2020): 11030–36. http://dx.doi.org/10.1039/d0sc04597g.

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24

Xuan, Jun, and Armido Studer. "Radical cascade cyclization of 1,n-enynes and diynes for the synthesis of carbocycles and heterocycles." Chemical Society Reviews 46, no. 14 (2017): 4329–46. http://dx.doi.org/10.1039/c6cs00912c.

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25

Wang, Zhe, Yang Shi, Jian Wang, et al. "Indium-catalyzed polycyclotrimerization of diynes: a facile route to prepare regioregular hyperbranched polyarylenes." Polym. Chem. 5, no. 20 (2014): 5890–94. http://dx.doi.org/10.1039/c4py00859f.

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26

Cao, Tao, and Shengming Ma. "Nickel-catalyzed alkyl-zincation and carboxylation of diynes." Organic Chemistry Frontiers 3, no. 12 (2016): 1711–15. http://dx.doi.org/10.1039/c6qo00484a.

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27

Schörgenhumer, J., and M. Waser. "Transition metal-free coupling of terminal alkynes and hypervalent iodine-based alkyne-transfer reagents to access unsymmetrical 1,3-diynes." Organic & Biomolecular Chemistry 16, no. 41 (2018): 7561–63. http://dx.doi.org/10.1039/c8ob02375a.

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28

Ye, Fei, Mansour Haddad, Véronique Michelet та Virginie Ratovelomanana-Vidal. "Solvent-free ruthenium trichloride-mediated [2 + 2 + 2] cycloaddition of α,ω-diynes and cyanamides: a convenient access to 2-aminopyridines". Organic Chemistry Frontiers 4, № 6 (2017): 1063–68. http://dx.doi.org/10.1039/c7qo00058h.

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29

Yasui, Takeshi, Tomohiro Kikuchi, and Yoshihiko Yamamoto. "Rhodium-catalyzed cycloisomerization of ester-tethered 1,6-diynes with cyclopropanol moiety leading to tetralone/exocyclic diene hybrid molecules." Chemical Communications 56, no. 84 (2020): 12865–68. http://dx.doi.org/10.1039/d0cc05429a.

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30

Rao, Maddali L. N., Sk Shamim Islam, and Priyabrata Dasgupta. "Rapid access to unsymmetrical 1,3-diynes and 2,5-disubstituted thiophenes under ligand and Pd/Ni-free Cu-catalysis." RSC Advances 5, no. 95 (2015): 78090–98. http://dx.doi.org/10.1039/c5ra15705f.

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31

Curbet, Idriss, Sophie Colombel-Rouen, Romane Manguin, et al. "Expedient synthesis of conjugated triynes via alkyne metathesis." Chemical Science 11, no. 19 (2020): 4934–38. http://dx.doi.org/10.1039/d0sc01124j.

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32

Li, Baixue, Anjun Qin, and Ben Zhong Tang. "Metal-free polycycloaddition of aldehyde-activated internal diynes and diazides toward post-functionalizable poly(formyl-1,2,3-triazole)s." Polymer Chemistry 11, no. 17 (2020): 3075–83. http://dx.doi.org/10.1039/d0py00193g.

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33

Wang, Jian-Shu, Qi Wang, Yiwen Zhu, Qian Gao, Jun Ying, and Xiao-Feng Wu. "Cobalt-catalyzed carbonylative cycloaddition of substituted diynes to access complexed polycyclic compounds." Organic Chemistry Frontiers 8, no. 15 (2021): 4188–91. http://dx.doi.org/10.1039/d1qo00725d.

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34

Lai, Xiaoling, Mengwei Hu, and Yang Li. "DFT studies on Ni-catalyzed intermolecular cycloaddition of diynes with methyleneaziridines." Dalton Transactions 50, no. 35 (2021): 12308–15. http://dx.doi.org/10.1039/d1dt01734a.

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35

Ye, Fei, Fatma Boukattaya, Mansour Haddad, Virginie Ratovelomanana-Vidal, and Véronique Michelet. "Synthesis of 2-aminopyridines via ruthenium-catalyzed [2+2+2] cycloaddition of 1,6- and 1,7-diynes with cyanamides: scope and limitations." New Journal of Chemistry 42, no. 5 (2018): 3222–35. http://dx.doi.org/10.1039/c7nj04933a.

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36

Devarajan, Nainamalai, Murugan Karthik, and Palaniswamy Suresh. "Copper catalyzed oxidative homocoupling of terminal alkynes to 1,3-diynes: a Cu3(BTC)2 MOF as an efficient and ligand free catalyst for Glaser–Hay coupling." Organic & Biomolecular Chemistry 15, no. 43 (2017): 9191–99. http://dx.doi.org/10.1039/c7ob02196h.

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37

Wang, Jia, Baixue Li, Dehua Xin, et al. "Superbase catalyzed regio-selective polyhydroalkoxylation of alkynes: a facile route towards functional poly(vinyl ether)s." Polymer Chemistry 8, no. 17 (2017): 2713–22. http://dx.doi.org/10.1039/c7py00363c.

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38

Shibata, Takanori, Ayato Sekine, Mika Akino, and Mamoru Ito. "Ni-catalyzed non-activated C–S bond cleavage at ambient temperature for the synthesis of sulfur-containing polycyclic compounds." Chemical Communications 57, no. 72 (2021): 9048–51. http://dx.doi.org/10.1039/d1cc03226g.

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39

Mohanty, Anuradha, and Sujit Roy. "Glaser–Hay hetero-coupling in a bimetallic regime: a Ni(ii)/Ag(i) assisted base, ligand and additive free route to selective unsymmetrical 1,3-diynes." Chemical Communications 53, no. 78 (2017): 10796–99. http://dx.doi.org/10.1039/c7cc05605b.

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40

Yi, Xiaofei, Kai Chen, Wei Chen, Wanzhi Chen, Miaochang Liu, and Huayue Wu. "Synthesis of cyclic gem-dinitro compounds via radical nitration of 1,6-diynes with Fe(NO3)3·9H2O." Organic & Biomolecular Chemistry 17, no. 19 (2019): 4725–28. http://dx.doi.org/10.1039/c9ob00431a.

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41

Ebrahimiasl, Saeideh, Farnaz Behmagham, Shahrzad Abdolmohammadi, Rahman N. Kojabad, and Esmail Vessally. "Recent Advances in the Application of Nanometal Catalysts for Glaser Coupling." Current Organic Chemistry 23, no. 22 (2020): 2489–503. http://dx.doi.org/10.2174/1385272823666191022174928.

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: Synthesis of symmetrical 1,3-diynes from terminal alkynes through an oxidative process is generally called Glaser coupling. The classic Glaser coupling is catalyzed by copper salts under an atmosphere of molecular oxygen as an oxidant. Over the past years, different metal catalysts and oxidants were successfully used in this atom economical C-C coupling reaction. Moreover, several procedures for the preparation of unsymmetrical 1,3-diynes by coupling two different alkyne substrates have been developed. In this review, we will highlight the usefulness of transition metal nanoparticles as effi

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42

Carvalho, M. Fernanda N. N., Armando J. L. Pombeiro, Gabriele Wagner, Bjørn Pedersen, and Rudolf Herrmann. "Cascade Reaction of Camphor-Derived Diynes with Transition Metal Compounds." Zeitschrift für Naturforschung B 54, no. 6 (1999): 725–33. http://dx.doi.org/10.1515/znb-1999-0604.

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Platinum(II) catalyzes the isomerization of camphor sulfonamide diynes in a cascade reaction involving annulation of a five-membered ring to the camphor skeleton, ring-enlargement by C-C bond cleavage, reduction of sulfur(VI) to sulfur(IV), and oxidation of a hydroxy group to a ketone. The reactions of the diynes with other transition metal compounds were also studied. Copper, gold and rhenium give final products similar to those obtained with simple Brønsted acids or halogens, mainly by annulation o f a five-membered ring to the camphor moiety, accompanied by reduction of a sulfonamide to a s

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43

Ito, Yukiteru, and Mitsuhiro Yoshimatsu. "Deuterative cyclization of sulfanyl 1,6-diynes: complete and monodeuteration of functional groups on heterocycles." Organic Chemistry Frontiers 2, no. 3 (2015): 201–5. http://dx.doi.org/10.1039/c4qo00333k.

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Regioselective H/D exchange reaction of functional groups on heterocycles proceeded via a transition metal-free reductive cyclization of sulfanyl 1,6-diynes using sodium borodeuteride/ethanol-D<sub>1</sub>.

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44

Warner, Andrew J., Kieron M. Enright, John M. Cole, Kang Yuan, John S. McGough, and Michael J. Ingleson. "Borylative cyclisation of diynes using BCl3 and borocations." Organic & Biomolecular Chemistry 17, no. 22 (2019): 5520–25. http://dx.doi.org/10.1039/c9ob00991d.

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Products from the borylative cyclisation of diynes using BCl<sub>3</sub> is dependent on substituent effects, however, some control of product outcome is achieved using borocations or BCl<sub>3</sub> in the presence of [BCl<sub>4</sub>]<sup>−</sup>.

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45

Radhika, Sankaran, Nissy Ann Harry, Mohan Neetha, and Gopinathan Anilkumar. "Recent trends and applications of the Cadiot–Chodkiewicz reaction." Organic & Biomolecular Chemistry 17, no. 41 (2019): 9081–94. http://dx.doi.org/10.1039/c9ob01757g.

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46

Bai, Chiyao, Meicheng Zhang, Bo Li, et al. "Modifiable diyne-based covalent organic framework: a versatile platform for in situ multipurpose functionalization." RSC Advances 6, no. 45 (2016): 39150–58. http://dx.doi.org/10.1039/c6ra02842j.

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A COF material (TCD) containing diynes as both building blocks and active sites was prepared by microwave irradiation and employed as a versatile platform for the preparation of diverse functional materials.

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47

Ma, Kai-Qing, Yan-Hong Miao, Xiao Li, et al. "Discovery of 1,3-diyne compounds as novel and potent antidepressant agents: synthesis, cell-based assay and behavioral studies." RSC Advances 7, no. 26 (2017): 16005–14. http://dx.doi.org/10.1039/c7ra01268c.

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1,3-Diynes compound 7a protected the corticosterone-injured PC12 cells through regulation of the apoptosis related proteins and exerted antidepressant effect in mice forced swim test in a concentration-dependent manner.

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48

Qiu, Yi-Feng, Yue-Jie Niu, Xian-Rong Song, et al. "Iodine promoted cascade cycloisomerization of 1-en-6,11-diynes." Chemical Communications 56, no. 9 (2020): 1421–24. http://dx.doi.org/10.1039/c9cc08286g.

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Cascade iodocyclization: an iodine promoted cascade cycloisomerization of 1-en-6,11-diynes is presented for the easy preparation of tetrahydrobenzo[f]isoquinolines. In this transformation, two new cyclic frameworks and one carbonyl group are formed.

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49

Xu, Murong, Zhong Zheng, Mengdan Wang, Lingkai Kong, Yujuan Ao, and Yanzhong Li. "Cobalt-catalyzed regioselective syntheses of indeno[2,1-c]pyridines from nitriles and diynes bearing propargyl fragments." Organic & Biomolecular Chemistry 16, no. 45 (2018): 8761–68. http://dx.doi.org/10.1039/c8ob02419g.

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Indeno[2,1-c]pyridines were synthesized via the cobalt-catalyzed cycloaddition reaction of nitriles with diynes bearing TBS protected propargylic alcohol fragments under mild conditions with highly functional compatibility and exclusive regio-selectivity.

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50

Singha, Raju, and Jayanta K. Ray. "Transition metal free synthesis of 2,4,6-trisubstituted pyrimidines via Cope-type hydroamination of 1,4-diarylbuta-1,3-diynes." RSC Adv. 4, no. 83 (2014): 44052–55. http://dx.doi.org/10.1039/c4ra07690g.

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We have developed an efficient and transition metal free methodology for the synthesis of 2,4,6-trisubstituted pyrimidines by the Cope-type hydroamination reaction of 1,4-diarylbuta-1,3-diynes with amidines in DMSO solvent.

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