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Relevant bibliographies by topics / Tandem addition/cyclization reaction

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Journal articles

Academic literature on the topic 'Tandem addition/cyclization reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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Journal articles on the topic "Tandem addition/cyclization reaction"

1

Deng, Danfeng, Dayun Huang, Xiangyu Sun, and Biwen Gao. "Recent Advances in the Tandem Difunctionalization of Alkynes: Mechanism-Based Classification." Synthesis 53, no. 19 (2021): 3522–34. http://dx.doi.org/10.1055/a-1486-2158.

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AbstractRecent advances on the tandem difunctionalization of alkynes in the last decade (2010–2020) are summarized into five categories based on the type of mechanism: (1) radical addition and coupling for the synthesis of polysubstituted ketones and alkenes, (2) electrophilic addition of alkynes, (3) reactions mediated by haloalkynes or copper acetylides, (4) the preparation of cyclic compounds via radical processes, palladium-catalyzed reactions or conjugate additions, and (5) cyclic compounds as intermediates in ring openings. Herein, radical, electrophilic and nucleophilic reactions are discussed in detail. We hope this review will help to promote future research in this area. 1 Introduction2 Radical Addition and Coupling3 Electrophilic Addition4 Reactions Mediated by Haloalkynes or Copper Acetylides5 Cyclization6 Cyclization and Ring Opening7 Conclusions

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2

Yuan, Lang, and Hai-Tao Yu. "A Density Functional Theory Investigation of the Tandem Radical Cyclization of 1-[2-Yl-3-(2-Methoxyphenyl)-prop-2-enyl]-6-oxo-1,6-dihydropyridine-2-carbonitrile." Australian Journal of Chemistry 69, no. 3 (2016): 319. http://dx.doi.org/10.1071/ch15369.

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A density functional theory investigation of the mechanism of the titled reaction has been performed. The results suggest that the compound 1-[2-iodo-3-(2-methoxyphenyl)-prop-2-enyl]-6-oxo-1,6-dihydropyridine-2-carbonitrile would rather be converted into the titled free radical by deiodination than go by way of a Diels–Alder cycloaddition and HI-elimination to access the experimentally observed product. The deiodination of the radical precursor is followed by tandem radical cyclizations and hydrogen-loss oxidations to generate tetracyclic non-radical products. The mechanism of the tandem reaction was determined by an examination of the calculated reaction barriers, attack trajectories, and interaction energies between key orbitals. Furthermore, the H-loss oxidation of the addition intermediates by several H-abstractors were carefully analyzed. The theoretical results are in close agreement with the available experimental evidence. The detailed reaction mechanism and knowledge of such an intramolecular tandem radical cyclization presented in this study not only provide insight into the nature of tandem cyclizations but also serves as a useful guide for future experimental investigations.

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3

Li, Xuanxuan, Shengyi Zhuang, Xinxin Fang, Ping Liu, and Peipei Sun. "Addition of nitrogen dioxide to carbon–carbon double bond followed by a cyclization to construct nitromethylated isoquinolinediones." Organic & Biomolecular Chemistry 15, no. 8 (2017): 1821–27. http://dx.doi.org/10.1039/c6ob02797k.

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4

Yu, Shuling, Kun Hu, Julin Gong, et al. "Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles." Organic & Biomolecular Chemistry 15, no. 20 (2017): 4300–4307. http://dx.doi.org/10.1039/c7ob00572e.

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5

Liu, Shuyang, Wenna Pan, Songxiao Wu, et al. "Visible-light-induced tandem radical addition–cyclization of 2-aryl phenyl isocyanides catalysed by recyclable covalent organic frameworks." Green Chemistry 21, no. 11 (2019): 2905–10. http://dx.doi.org/10.1039/c9gc00022d.

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A heterogeneous visible-light-induced tandem radical addition–cyclization of isocyanides by photoactive covalent organic frameworks was developed, delivering diverse phenanthridines with high reaction efficiency and easy catalyst recyclability.

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6

Fan, Jian, Shengke Wang, Jiahui Chen, Manyi Wu, Jitan Zhang, and Meihua Xie. "Synthesis of 2-acetyl trisubstituted furans via copper-mediated deacylation cleavage of unstrained C(sp3)–C(sp2) bonds." Organic Chemistry Frontiers 6, no. 4 (2019): 437–41. http://dx.doi.org/10.1039/c8qo01139g.

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7

Hsieh, Jen-Chieh, and Haw-Lih Su. "Synthesis of N-Heterocycles via Transition-Metal-Catalyzed Tandem Addition/Cyclization of a Nitrile." Synthesis 52, no. 06 (2020): 819–33. http://dx.doi.org/10.1055/s-0039-1691561.

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The diverse methodologies to synthesize N-heterocycles through transition-metal-catalyzed cascade addition/cyclization of a nitrile are discussed in this review. Aspects relating to three types of transition-metal-catalyzed addition of a nitrile with subsequent cyclization include (1) a transition-metal acting as a Lewis acid to accelerate the nucleophilic addition of a nitrile, (2) the late-transition-metal-catalyzed 1,2-insertion of a nitrile, and (3) an in situ generated radical by transition-metal catalysis to implement a radical addition/cyclization tandem reaction. Applications for the synthesis of natural alkaloids, their derivatives, and some bioactive compounds are also summarized herein.1 Introduction2 Nucleophilic Addition of a Nitrile Accelerated by a Lewis Acid2.1 Late-Transition-Metal Catalysis2.2 Early-Transition-Metal Catalysis2.3 Lanthanide-Metal Catalysis2.4 Cyclization from N-Arylnitriliums3 Transition-Metal-Catalyzed Insertion of a Nitrile4 Transition-Metal-Catalyzed Radical Addition of a Nitrile5 Conclusions

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8

Hoffmann, Norbert, Samuel Bertrand, Siniša Marinković, and Jens Pesch. "Efficient radical addition of tertiary amines to alkenes using photochemical electron transfer." Pure and Applied Chemistry 78, no. 12 (2006): 2227–46. http://dx.doi.org/10.1351/pac200678122227.

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An efficient photoinduced radical addition of tertiary amine, mainly cyclic derivatives, to electron-deficient alkenes was developed. The reaction was applied to the asymmetric synthesis of the pyrrolizidine alkaloids laburnine and isoretronecanol. The method was then optimized for the addition of a larger variety of tertiary amines, in particular acyclic ones. Radical tandem addition cyclization reactions with unsaturated tertiary amines have also been investigated. A detailed mechanistic study using isotopic labeling enabled the optimization of a corresponding reaction with N,N-dialkylaniline derivatives. The origin of the high reaction stereoselectivity achieved with menthyloxyfuranone was elucidated. The radical addition of tertiary amines was also performed with heterogeneous photocatalysis using inorganic semiconductors as sensitizers.

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9

Fei, Weihong, Ping Xu, Jie Hou, and Weijun Yao. "Phosphine catalyzed [3+2] cyclization/Michael addition of allenoate with CS2 to form 2-thineyl vinyl sulfide." Chemical Communications 56, no. 78 (2020): 11669–72. http://dx.doi.org/10.1039/d0cc05070a.

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We have developed a DPPE-catalyzed three molecular two component tandem reaction of γ-substituted allenoate and CS<sub>2</sub> to construct 2-thineyl vinyl sulfide through phosphine catalyzed [3+2] cyclization followed by Michael addition.

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10

Behr, Jean-Bernard, Adel Kalla, Dominique Harakat, and Richard Plantier-Royon. "Tandem Nucleophilic Addition/Cyclization Reaction in the Synthesis of Ketimine-Type Iminosugars." Journal of Organic Chemistry 73, no. 9 (2008): 3612–15. http://dx.doi.org/10.1021/jo702616x.

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