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Journal articles on the topic 'Cycloaddition reactions'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Grygorenko, Oleksandr O., Viktoriia S. Moskvina, Oleksandr V. Hryshchuk, and Andriy V. Tymtsunik. "Cycloadditions of Alkenylboronic Derivatives." Synthesis 52, no. 19 (2020): 2761–80. http://dx.doi.org/10.1055/s-0040-1707159.

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The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addres

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2

Svete, Jurij, Uroš Grošelj, Franc Požgan, and Bogdan Štefane. "Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)." Synthesis 50, no. 23 (2018): 4501–24. http://dx.doi.org/10.1055/s-0037-1610284.

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Although the first example of copper-catalyzed azomethine imine–alkyne cycloaddition (CuAIAC) was published only a year after the seminal papers of Meldal and Sharpless on Cu-catalyzed azide–alkyne cycloaddition (CuAAC), the CuAIAC reaction has remained overlooked by the synthetic community for almost a decade. Since 2010, however, CuAIAC reaction started to emerge as a promising supplement to the well-known CuAAC reaction. The present review surveys primarily the literature on CuAIAC reaction since 2003. Beside this, azomethine imine–alkyne cycloadditions catalyzed by other metals, selected e

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3

Zhou, You-Yun, and Christopher Uyeda. "Catalytic reductive [4 + 1]-cycloadditions of vinylidenes and dienes." Science 363, no. 6429 (2019): 857–62. http://dx.doi.org/10.1126/science.aau0364.

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Cycloaddition reactions provide direct and convergent routes to cycloalkanes, making them valuable targets for the development of synthetic methods. Whereas six-membered rings are readily accessible from Diels-Alder reactions, cycloadditions that generate five-membered rings are comparatively limited in scope. Here, we report that dinickel complexes catalyze [4 + 1]-cycloaddition reactions of 1,3-dienes. The C1partner is a vinylidene equivalent generated from the reductive activation of a 1,1-dichloroalkene in the presence of stoichiometric zinc. Intermolecular and intramolecular variants of t

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4

Kotha, Sambasivarao, Kakali Lahiri, and Gaddamedi Sreevani. "Design and Synthesis of Aromatics through [2+2+2] Cyclotrimerization." Synlett 29, no. 18 (2018): 2342–61. http://dx.doi.org/10.1055/s-0037-1609584.

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The [2+2+2] cycloaddition reaction is a useful tool to realize unusual chemical transformations which are not achievable by traditional methods. Here, we report our work during the past two decades that involve utilization of transition-metal complexes in a [2+2+2] cyclotrimerization reaction. Several key “building blocks” were assembled by a [2+2+2] cycloaddition approach and they have been further expanded by other synthetic transformations to design unusual amino acids and peptides, diphenylalkanes, bis- and trisaryl benzene derivatives, annulated benzocycloalkanes, spirocycles, and spiroox

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5

Cordero, Franca Maria, Donatella Giomi, and Fabrizio Machetti. "Synthesis of 2-Azetidinones via Cycloaddition Approaches: An Update." Reactions 5, no. 3 (2024): 492–566. http://dx.doi.org/10.3390/reactions5030026.

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The present review is a comprehensive update of the synthesis of monocyclic β-lactams via cycloaddition reactions. According to the IUPAC definition of cycloaddition, both elementary and stepwise processes (formal cycloadditions) have been considered. The years 2019–2022 are covered by the cited literature. The focus of the review is on synthetic aspects with emphasis on the structural scope, reaction conditions, mechanistic aspects, and selectivity results. Selected significant data related to biological activities and synthetic applications are also highlighted.

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6

Kalluraya, Balakrishna, Kaushik B R, and H. M. Somashekarappa. "Effect of Gamma- Irradiation on Structure, Morphology and Thermal Properties of Novel Polyamide Based Thermoset Obtained by Double Cycloaddition." Journal of Modern Materials 7, no. 1 (2020): 17–25. http://dx.doi.org/10.21467/jmm.7.1.17-25.

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Cycloaddition reactions gained prominence in macromolecular chemistry for generating macromolecules because of high yields of these reactions, which is a key tool that drives polyaddition reactions. Cycloaddition reaction plays major role in extension of polymerisation or in other words high conversions of monomers to macromolecules of high molecular weights. Until the late 1990s, the major studies regarding cycloadditions in novel polymer synthesis were related to polyaddition reactions. Since then in the field of polymer synthesis the affirmative strengths of these cycloaddition reactions ha

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7

Mlostoń, Grzegorz, Yuriy Shermolovich, and Heinz Heimgartner. "Synthesis of Fluorinated and Fluoroalkylated Heterocycles Containing at Least One Sulfur Atom via Cycloaddition Reactions." Materials 15, no. 20 (2022): 7244. http://dx.doi.org/10.3390/ma15207244.

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Fluorinated heterocycles constitute an important group of organic compounds with a rapidly growing number of applications in such areas as medicinal chemistry, agrochemicals production, polymer chemistry, as well as chemistry of advanced materials. In the latter case, fluorinated thiophenes are considered as a lead class of compounds with numerous spectacular applications. On the other hand, cycloaddition reactions offer a superior methodology for stereo-chemically controlled synthesis of heterocycles with a diverse ring size and a variable number of heteroatoms. A comprehensive review of meth

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8

Li, Jin-Heng, De-Lie An, and Jing-Hao Qin. "Recent Advances in Cycloaddition Reactions with Alkynes to Construct Heterocycles." Synthesis 52, no. 24 (2020): 3818–36. http://dx.doi.org/10.1055/s-0040-1707355.

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Heterocyclic compounds, especially N-heterocycles and O-heterocycles, are prominent structural motifs present in numerous natural products and medically and/or economically important compounds. This review aims to describe the development of transition-metal-catalyzed cycloaddition reactions of functionalized m-atom partners with alkynes to access a wide range of five-, six-, and seven-membered heterocycles, that is functionalized N-heterocycles and O-heterocycles such as azepines, isoquinolines, isocoumarins, spiroheterocycles, indoles, furans, and pyrroles, in a selectively controlled manner

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9

Tietze, L. F., G. Kettschau, J. A. Gewert, and A. Schuffenhauer. "Hetero-Diels-Aider Reactions of 1-0xa-1,3-butadienes." Current Organic Chemistry 2, no. 1 (1998): 19–62. http://dx.doi.org/10.2174/1385272802666220126210654.

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Many biologically active and widely distributed natural products contain a dihydro- or a tetrahydropyran moiety. One of the best methods for the synthesis of these compounds is the hetero Diels-Aider reaction of 1-0Xia-1,3-butadienes which leads to substituted and annulated 3,4-dihydro-2H-pyrans usually in excellent yields and high selectivity. Further transformations of these substances e.g. by hydrogenation yield the tetrahydropyrans with the basic skeleton of the carbohydrates. In this article at first theoretical aspects of the cycloaddition are discussed which include ab initio calculatio

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10

Asmita, Mondal, Banerji Avijit, and Acharjee Nivedita. "Understanding [3 + 2] cycloaddition reactions from the molecular electron density perspective : A new theoretical outlook on organic reactions." Education in Chemical Science and Technology Vol. 3, Aug 2022 (2022): 131–50. https://doi.org/10.5281/zenodo.6822007.

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Department of Chemistry, Durgapur Government College, Durgapur-713 214, West Bengal, India Central Ayurveda Research Institute (CARI), Calcutta-700 091, West Bengal, India E-mail: ablabcu@yahoo.co.uk Cycloaddition reactions share the top shelf priority in the toolbox of organic chemists owing to their diverse pharmaceutical and industrial applications. The frontiers molecular orbital (FMO) theory has been used to study the reactivity of cycloaddition reactions since nearly the last five decades, though there have been criticisms, and even instances of failures. In 2016, an appealing alternativ

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11

Aitouna, Abdelhak Ouled, Ali Barhoumi, and Abdellah Zeroual. "A Mechanism Study and an Investigation of the Reason for the Stereoselectivity in the [4+2] Cycloaddition Reaction between Cyclopentadiene and Gem-substituted Ethylene Electrophiles." Scientiae Radices 2, no. 3 (2023): 217–28. http://dx.doi.org/10.58332/scirad2023v2i3a01.

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The Molecular Electron Density Theory is applied to the [4+2] cycloaddition reaction between cyclopentadiene and gem-substituted ethylene electrophiles. Calculations are made for reactions, activation energies, and reactivity indices. The results of the experiment are perfectly consistent with activation energies, which unequivocally show that this cyclization’s are is highly stereoselective, in addition, based on ELF examination, the mechanism of these [4+2] cycloadditions occurs in two phases, The mechanisms of these reactions demonstrate that the term "pericyclic reaction" is no more releva

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12

Sadowski, Mikołaj, Ewa Dresler, Karolina Zawadzińska, Aneta Wróblewska, and Radomir Jasiński. "Syn-Propanethial S-Oxide as an Available Natural Building Block for the Preparation of Nitro-Functionalized, Sulfur-Containing Five-Membered Heterocycles: An MEDT Study." Molecules 29, no. 20 (2024): 4892. http://dx.doi.org/10.3390/molecules29204892.

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The regio- and stereoselectivity and the molecular mechanisms of the [3 + 2] cycloaddition reactions between Syn-propanethial S-oxide and selected conjugated nitroalkenes were explored theoretically in the framework of the Molecular Electron Density Theory. It was found that cycloadditions with the participation of nitroethene as well as its methyl- and chloro-substituted analogs can be realized via a single-step mechanism. On the other hand, [3 + 2] cycloaddition reactions between Syn-propanethial S-oxide and 1,1-dinitroethene can proceed according to a stepwise mechanism with a zwitterionic

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13

Zhan, Desheng, Gang Yang, Tieli Zhou, Sashirekha Nallapati, and Xiaofeng Zhang. "Decarboxylation-Driven Double Annulations: Innovative Multi-Component Reaction Pathways." Molecules 30, no. 7 (2025): 1594. https://doi.org/10.3390/molecules30071594.

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A concerted five-component reaction strategy has been developed, featuring double [3+2] cycloadditions utilizing aspartic acid. This approach provides valuable insights into mechanistic pathways, allowing for the distinction between concerted and stepwise processes based on reaction efficiency and diastereoselectivity. Both aspartic and glutamic acids have been employed for a thorough evaluation and exploration of decarboxylation-driven double annulations. This method effectively constructs pyrrolizidine frameworks through a concerted double 1,3-dipolar cycloaddition with aspartic acid, as wel

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14

Zhang, Xiaofeng, Xiaoming Ma, and Wei Zhang. "Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds." Beilstein Journal of Organic Chemistry 19 (November 6, 2023): 1677–93. http://dx.doi.org/10.3762/bjoc.19.123.

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The [3 + 2] cycloadditions of stabilized azomethine ylides (AMYs) derived from amino esters are well-established. However, the reactions of semi-stabilized AMYs generated from decarboxylative condensation of α-amino acids with arylaldehydes are much less explored. The [3 + 2] adducts of α-amino acids could be used for a second [3 + 2] cycloaddition as well as for other post-condensation modifications. This article highlights our recent work on the development of α-amino acid-based [3 + 2] cycloaddition reactions of N–H-type AMYs in multicomponent, one-pot, and stepwise reactions for the synthe

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15

Harmata, Michael, and Aswin Garimalla. "Derivatives of Alkyl 2-Hydroxy-3-oxocyclopent-1-enecarboxylates and Intermolecular [4+2] Cycloadditions of Cyclopentadienones Prepared Therefrom." Synthesis 50, no. 22 (2018): 4483–89. http://dx.doi.org/10.1055/s-0037-1610184.

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Some derivatives of alkyl 2-hydroxy-3-oxocyclopent-1-enecarboxylates have been synthesized and their reactivity as progenitors of cyclopentadienones for intermolecular [4+2]-cycloaddition reactions has been evaluated. It was found that the derivative containing a phosphate ester leaving group gave better yields in the cycloaddition reaction among the derivatives studied. The yields of the cycloaddition reactions were moderate, perhaps due side reactions not leading to the reactive intermediate cyclopentadienone.

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16

Bhunia, Sabyasachi, and Rai-Shung Liu. "Access to molecular complexity via gold- and platinum-catalyzed cascade reactions." Pure and Applied Chemistry 84, no. 8 (2012): 1749–57. http://dx.doi.org/10.1351/pac-con-11-09-13.

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We report recent progress on Au- and Pt-catalyzed cascade reactions to access complicated molecular frameworks. Reported reactions include new cyclization/cycloaddition cascades on carbonyl and epoxide substrates tethered with an allene, alkene, and alkyne. Such substrates enable Au-catalyzed cascade reactions comprising an initial cyclization to form reactive 1,n-dipole that undergoes subsequent cycloadditions with suitable dipolarophiles.

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17

Deng, Yongming, Qing-Qing Cheng, and Michael Doyle. "Asymmetric [3+3] Cycloaddition for Heterocycle Synthesis." Synlett 28, no. 14 (2017): 1695–706. http://dx.doi.org/10.1055/s-0036-1588453.

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Asymmetric syntheses of six-membered ring heterocycles are important research targets not only in synthetic organic chemistry but also in pharmaceuticals. The [3+3]-cycloaddition methodology is a complementary strategy to [4+2] cycloaddition for the synthesis of heterocyclic compounds. Recent progress in [3+3]-cycloaddition processes provide powerful asymmetric methodologies for the construction of six-membered ring heterocycles with one to three heteroatoms in the ring. In this account, synthetic efforts during the past five years toward the synthesis of enantioenriched six-membered ring hete

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18

Li, Fang, W. Felix Zhu, Claire Empel, et al. "Photosensitization enables Pauson-Khand–type reactions with nitrenes." Science 383, no. 6682 (2024): 498–503. http://dx.doi.org/10.1126/science.adm8095.

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The Pauson-Khand reaction has in the past 50 years become one of the most common cycloaddition reactions in chemistry. Coupling two unsaturated bonds with carbon monoxide, the transformation remains limited to CO as a C 1 building block. Herein we report analogous cycloaddition reactions with nitrenes as an N 1 unit. The reaction of a nonconjugated diene with a nitrene precursor produces bicyclic bioisosteres of common saturated heterocycles such as piperidine, morpholine, and piperazine. Experimental and computational mechanistic studies support relaying of the diradical nature of triplet nit

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19

Morizumi, Haruka, Kaii Nakayama, Yoshikazu Kitano, and Yohei Okada. "Electrocatalytic Radical Cation Diels-Alder Reactions Using Enol Ethers As Dienophiles." ECS Meeting Abstracts MA2024-01, no. 41 (2024): 2337. http://dx.doi.org/10.1149/ma2024-01412337mtgabs.

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Single-electron oxidation enables the conversion of electron-rich alkenes such as styrene derivatives to radical cation species. We have been developing various cycloaddition reactions of radical cations produced by single-electron oxidation using electrochemical and TiO2 photochemical methods. Introducing an electron-rich aryl group which we call a redox tag is a critical part of the process to control the reactivity of the radical cations. During carbon-carbon bonds formation the motif functions as both electron donor and electron acceptor. In addition to styrene derivatives, enol ethers can

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20

Dresler, Ewa, Aneta Wróblewska, and Radomir Jasiński. "Energetic Aspects and Molecular Mechanism of 3-Nitro-substituted 2-Isoxazolines Formation via Nitrile N-Oxide [3+2] Cycloaddition: An MEDT Computational Study." Molecules 29, no. 13 (2024): 3042. http://dx.doi.org/10.3390/molecules29133042.

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Regioselectivity and the molecular mechanism of the [3+2] cycloaddition reaction between nitro-substituted formonitrile N-oxide 1 and electron-rich alkenes were explored on the basis of the wb97xd/6-311+G(d) (PCM) quantum chemical calculations. It was established that the thermodynamic factors allow for the formation of stable cycloadducts along all considered models. The analysis of the kinetic parameters of the main processes show that all [3+2] cycloadditions should be realized with full regioselectivity. In all cases, the formation of 5-substituted 3-nitro-2-isoxazolidines is clearly prefe

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21

Lee, Hee-Yoon, Seog-Beom Song, Taek Kang, Yoon Jung Kim, and Su Jeong Geum. "Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products." Pure and Applied Chemistry 85, no. 4 (2013): 741–53. http://dx.doi.org/10.1351/pac-con-12-10-01.

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Aziridinyl imines are well-known carbene equivalents because they are precursors of diazo compounds from which reactive intermediates can be produced. These carbene equivalents can be utilized as zwitterionic species, diradicals, or 4π system for cycloaddition reactions. Thus, the intermediates derived from aziridinyl imines have been used in the sulfur-ylide-mediated epoxide formation, tandem free-radical reactions, or cyclopropanation reaction via carbene intermediates to form trimethylenemethane (TMM) diyls, which undergo [2 + 3] cycloaddition reactions to form cyclopentanoids. Diazo compou

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22

Krompiec, Stanisław, Piotr Lodowski, Aneta Kurpanik-Wójcik, et al. "Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines." Molecules 28, no. 6 (2023): 2547. http://dx.doi.org/10.3390/molecules28062547.

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The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods for synthesizing isoxazolines (other than 1,3-DP cycloaddition) were also presented briefly. Various methods of nitrile oxide preparation, especially in situ-generated procedures, are presented. Special attention was paid to the application of various combinations of 1,3-DP cycloaddition with double bond migration (DBM) and

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23

Kotha, Sambasivarao, Milind Meshram, and Nageswara Panguluri. "Advanced Approaches to Post-Assembly Modification of Peptides by Transition-Metal-Catalyzed Reactions." Synthesis 51, no. 09 (2019): 1913–22. http://dx.doi.org/10.1055/s-0037-1612418.

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We have summarized diverse synthetic approaches for the modification of peptides by employing transition-metal-catalyzed reactions. These methods can deliver unusual peptides suitable for peptidomimetics. To this end, several popular reactions such as Diels–Alder, 1,3-dipolar cycloaddition, [2+2+2] cyclotrimerization, metathesis, Suzuki–Miyaura cross-coupling, and Negishi coupling have been used to assemble modified peptides by post-assembly chemical modification strategies.1 Introduction2 Synthesis of a Cyclic α-Amino Acid Derivative via a Ring-Closing Metathesis Protocol3 Peptide Modificati

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24

Spivey, Alan, Christian Nielsen, and Hossay Abas. "Stereoselective Reactions of ortho-Quinone Methide and ortho-Quinone Methide Imines and Their Utility in Natural Product Synthesis." Synthesis 50, no. 20 (2018): 4008–18. http://dx.doi.org/10.1055/s-0037-1610241.

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Herein presented is a review of the reactivity and synthetic utility of ortho-quinone methides and ortho-quinone methide imines. These versatile intermediates have received significant attention in the literature and new methods for their preparation and reaction as well as recent applications in total synthesis are discussed.1 Introduction2 Conjugate Addition Reactions3 Concerted Cycloaddition Reactions4 Stepwise Addition Reactions5 Applications in Total Synthesis6 Conclusion

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Wiberg, N., G. Preiner, G. Wagner, and H. Köpf. "Reaktivität des labilen, durch Adduktbildung mit Ph2C=NSiMe3 gespeicherten Silaethens Me2Si=C(SiMe3)2 / Reactivity of the Labile Silaethene Me2Si = C(SiMe3)2, Stored as Ph2C =NSiMe3 Adducts." Zeitschrift für Naturforschung B 42, no. 9 (1987): 1062–74. http://dx.doi.org/10.1515/znb-1987-0902.

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Silaethene Me2Si = C(SiMe3)2 (1), stored as Ph2C=NSiMe3 adducts and regenerated from the adducts at about 100 °C as a reaction intermediate, combines with reactants a-b (e. g. HO-H, RO-H. RCOO-H, RS-H. RHN-H, Ph2CN-H, RO-SiR3, R2N-SiR3, Ph2CN-SiR3, Cl-GeR3, Cl-SnR3) with insertion into the a-b bond, with a=b (e.g. 0 = CPh2, Me3SiN = CPh2, CH2=CHOMe, cis-piperylene), a=b=c (e.g. RN = N = N, O = N=N). a=b-c=d (e.g. butadiene, isoprene, trans-piperylene, 2,3-dimethylbutadiene, cyclopentadiene, anthracene, benzophenone, N-trimethylsilylbenzophenoneimine) under [2+2]-, [2+3]- as well as [2+A]-cyclo

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26

MacKenzie, Douglas A., and John Paul Pezacki. "Kinetics studies of rapid strain-promoted [3+2] cycloadditions of nitrones with bicyclo[6.1.0]nonyne." Canadian Journal of Chemistry 92, no. 4 (2014): 337–40. http://dx.doi.org/10.1139/cjc-2013-0577.

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Strain-promoted alkyne−nitrone cycloaddition (SPANC) reactions represent a bioorthogonal labeling strategy that is both very rapid and at the same time efficient and selective. Nitrones provide increased reaction rates as well as greater susceptibility toward stereoelectronic modification when compared with organic azides. We find that strain-promoted cycloadditions of cyclic nitrones with bicyclo[6.1.0]nonyne react with second-order rate constants as large as 1.49 L mol−1 s−1 at 25 °C. These reactions display rate constants that are up to 37-fold greater than those of the analogous reactions

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27

Petko, Dina, Samuel Koh, and William Tam. "Transition Metal-Catalyzed Reactions of Alkynyl Halides." Current Organic Synthesis 16, no. 4 (2019): 546–82. http://dx.doi.org/10.2174/1570179416666190329200616.

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Background: Transition metal-catalyzed reactions of alkynyl halides are a versatile means of synthesizing a wide array of products. Their use is of particular interest in cycloaddition reactions and in constructing new carbon-carbon and carbon-heteroatom bonds. Transition metal-catalyzed reactions of alkynyl halides have successfully been used in [4+2], [2+2], [2+2+2] and [3+2] cycloaddition reactions. Many carbon-carbon coupling reactions take advantage of metal-catalyzed reactions of alkynyl halides, including Cadiot-Chodkiewicz, Suzuki-Miyaura, Stille, Kumada-Corriu and Inverse Sonogashira

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28

Echavarren, Antonio, and Cristina García-Morales. "From Straightforward Gold(I)-Catalyzed Enyne Cyclizations to more Demanding Intermolecular Reactions of Alkynes with Alkenes." Synlett 29, no. 17 (2018): 2225–37. http://dx.doi.org/10.1055/s-0037-1610203.

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Gold(I) complexes are the catalysts of choice for the selective activation of alkynes in the presence of other unsaturated functional groups. In this Account, we present the development of gold(I)-catalyzed intermolecular reactions of terminal alkynes with functionalized alkenes. In particular, we focus on the synthesis of cyclobutenes by asymmetric gold(I)-catalyzed [2+2] cycloaddition and its applications.1 Introduction2 Intramolecular Gold(I)-Catalyzed Synthesis of Cyclobutenes2.1 Role of Cyclobutenes in 1,n-Enynes Cycloisomerizations2.2 [2+2] Cycloaddition of 1,n-Enynes3 Intermolecular Gol

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29

Chen, Jia-Rong, Dong Liang, and Wen-Jing Xiao. "Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions." Synthesis 52, no. 17 (2020): 2469–82. http://dx.doi.org/10.1055/s-0040-1707160.

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1,3,5-Trisubstituted 1,3,5-triazinanes (hexahydro-1,3,5-triazines), as stable and readily available surrogates for formaldimines, have found extensive applications for the construction of various nitrogen-containing compounds. The formaldimines, formed in situ from this reagent class, can participate in various aminomethylation and cycloaddition reactions. This short review presents recent advances in this field with emphasis on the conceptual ideas behind the developed methodologies and the reaction mechanisms.1 Introduction2 Aminomethylations with 1,3,5-Triazinanes3 Cycloadditions with 1,3,

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30

Swan, Ellen, Kirsten Platts, and Anton Blencowe. "An overview of the cycloaddition chemistry of fulvenes and emerging applications." Beilstein Journal of Organic Chemistry 15 (September 6, 2019): 2113–32. http://dx.doi.org/10.3762/bjoc.15.209.

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The unusual electronic properties and unique reactivity of fulvenes have interested researchers for over a century. The propensity to form dipolar structures at relatively low temperatures and to participate as various components in cycloaddition reactions, often highly selectively, makes them ideal for the synthesis of complex polycyclic carbon scaffolds. As a result, fulvene cycloaddition chemistry has been employed extensively for the synthesis of natural products. More recently, fulvene cycloaddition chemistry has also found application to other areas including materials chemistry and dyna

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31

Charmier, Marie-Odile Januário, Najat Moussalli, Josette Chanet-Ray, and Sithan Chou. "1,3-Dipolar Cycloaddition Reactions of Nitrones with Unsaturated Methylsulfones and Substituted Crotonic Esters." Journal of Chemical Research 23, no. 9 (1999): 566–67. http://dx.doi.org/10.1177/174751989902300924.

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The cycloaddition reaction of nitrones to unsaturated methylsulfones and substituted crotonic esters gives a sole product or a mixture of tri- or tetra-substituted isoxazolidines, such that with disubstituted dipolarophiles the regiochemistry is dependent upon the nitrone and the vicinal electron-withdrawing group (CN or CO2Me) but with trisubstituted olefins, regiospecific cycloadditions are observed.

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32

Sosnovskikh, Vyacheslav Y. "Synthesis and Reactivity of Electron-Deficient 3-Vinylchromones." SynOpen 05, no. 03 (2021): 255–77. http://dx.doi.org/10.1055/a-1589-9556.

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AbstractThe reported methods and data for the synthesis and reactivity of electron-deficient 3-vinylchromones containing electron-withdrawing groups at the exo-cyclic double bond are summarized and systematized for the first time. The main methods for obtaining these compounds are Knoevenagel condensation, Wittig reaction, and palladium-catalyzed cross-couplings. The most important chemical properties are transformations under the action of mono- and dinucleophiles, ambiphilic cyclizations, and cycloaddition reactions. The cross-conjugated and polyelectrophilic dienone system in 3-vinylchromo

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Krafft, Marie E., James A. Wright, and Llorente VR Boñaga. "PausonKhand reactions in water." Canadian Journal of Chemistry 83, no. 6-7 (2005): 1006–16. http://dx.doi.org/10.1139/v05-112.

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We have investigated the cobalt mediated PausonKhand (PK) reaction in water. In the presence of detergents and surfactants, Co2(CO)8 and Co4(CO)12 are effective under aqueous-phase, thermal PK reactions. In a waterTriton®X-100 medium, Co4(CO)12 is catalytically active. Further, dicobalthexacarbonyl complexes of alkynes and enynes undergo effective cyclization under thermal (70 °C) and NMO-promoted conditions. The oxidative nature of the latter conditions inhibits the reductive PK reaction. In all protocols, moderate to excellent yields of the cycloadducts are obtained. Substrates that are pr

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Li, Dan, Wei Gao, and Xiaochao Chen. "Asymmetric Synthesis of C1-Chiral THIQs with Imines in Isoquinoline Rings." Synthesis 52, no. 22 (2020): 3337–55. http://dx.doi.org/10.1055/s-0040-1707206.

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Tetrahydroisoquinoline (THIQ) scaffolds are important structural units that widely exist in a variety of natural alkaloids and synthetic analogues. Asymmetric synthesis of C1-chiral THIQ is of particular importance due to its significant pharmaceutical, agrochemical, and other biological activities, and the usually distinct bioactivities exhibited by the two enantiomers. In this review, we highlight the significant advances achieved in this field, present recent asymmetric synthesis with imines in isoquinoline rings ordered according to the sequence of various substrate types. New strategies c

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Choi, Cheol Ho, and Mark S. Gordon. "Cycloaddition Reactions of Dienes on the SI(100)-2 × 1 Surface." International Journal of Modern Physics B 17, no. 08n09 (2003): 1205–10. http://dx.doi.org/10.1142/s0217979203018752.

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Quantum mechanical methods were adopted to study the surface reaction mechanisms of 1, 3-cyclohexadiene and acrylonitrile on the Si(100)-2x1 surface. According to the computed potential energy surfaces, both ⌊4+2⌋ and ⌊2+2⌋ cycloaddition products resulting from the reactions of surface dimers are possible due to the negligible activation barriers at the surface. Isomerization reactions among the surface products are very unlikely due to the predicted large activation barriers preventing thermal redistributions of the surface products. As a result, the distribution of the final surface products

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Antoci, Vasilichia, Costel Moldoveanu, Ramona Danac, Violeta Mangalagiu, and Gheorghita Zbancioc. "Huisgen [3 + 2] Dipolar Cycloadditions of Phthalazinium Ylides to Activated Symmetric and Non-Symmetric Alkynes." Molecules 25, no. 19 (2020): 4416. http://dx.doi.org/10.3390/molecules25194416.

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We present herein a straightforward and efficient pathway for the synthesis of pyrrolophthalazine cycloadducts via Huisgen [3 + 2] dipolar cycloaddition reactions of phthalazinium ylides to methyl propiolate or dimethyl acetylenedicarboxylate (DMAD). A thoroughly comparative study concerning the efficiency of synthesis, conventional thermal heating (TH) versus microwave (MW) and ultrasound (US) irradiation, has been performed. The cycloaddition reactions of phthalazinium ylides to methyl propiolate occur regiospecific, with a single regioisomer being obtained. Under conventional TH, the cycloa

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Denis, Pablo A., C. Pereyra Huelmo, and Federico Iribarne. "Cycloaddition reactions on epitaxial graphene." New Journal of Chemistry 43, no. 28 (2019): 11251–57. http://dx.doi.org/10.1039/c9nj02528f.

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By means of first principles calculations we studied the occurrence of cycloaddition reactions on the buffer layer of silicon carbide. Interestingly, the presence of the substrate favors the 1,3 cycloaddition instead of the [2+2] or [4+2] ones.

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Bakhouch, Mohamed, Bouchra Es-Sounni, Ayoub Ouaddi, et al. "Highly Regioselective 1,3-Dipolar Cycloaddition of Nitrilimines and Thioaurones Towards Spiro-2-Pyrazolines: Synthesis, Characterization, and Mechanistic Study." Reactions 5, no. 4 (2024): 1066–79. https://doi.org/10.3390/reactions5040056.

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In this paper, we report a regiospecific 1,3-dipolar cycloaddition (1,3-DC) reaction of nitrilimines with thioaurone derivatives that afforded the hitherto unreported spiropyrazolines. Spectroscopic and spectrometric data were utilized to confirm the structure of all products and elucidate the reaction’s regiochemistry. A mechanistic study was performed within the Molecular Electron Density Theory (MEDT) at the B3LYP/6-311G(d,p) computational level to explain the regioselectivity observed. The electron localization function (ELF) topological analysis confirms the carbenoid-type (cb-type) mecha

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Strmiskova, Miroslava, Didier A. Bilodeau, Mariya Chigrinova, and John Paul Pezacki. "Phenanthridine-based nitrones as substrates for strain-promoted alkyne-nitrone cycloadditions." Canadian Journal of Chemistry 97, no. 1 (2019): 1–6. http://dx.doi.org/10.1139/cjc-2018-0253.

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Over the past decade, bioorthogonal chemistry that facilitates the efficient conjugation of biomolecules has expanded from the copper-catalyzed alkyne-azide cycloadditions to a multitude of diverse reactions, varying additives and reactional partners, and most often offering better alternatives with faster rates and lower toxicity of employed reactants. Among these, the copper-free strain-promoted cycloaddition reactions have been demonstrated to be more promising, offering a reaction without toxic metal catalysts and with faster inherent kinetic rate constants. The strain-promoted alkyne-nitr

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Sikervar, Vikas, Ravindra Sonawane, Raghuramaiah Mandadapu, Amol Satish Dehade, Shrikant Abhiman Shete, and Mark Montgomery. "Lewis Acid Mediated [3+2] and [3+3] Annulations of an Azomethine Imine with Donor–Acceptor Cyclopropanes." Synthesis 53, no. 16 (2021): 2865–73. http://dx.doi.org/10.1055/a-1503-8068.

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AbstractTwo different Lewis acids were used for developing [3+2] and [3+3] regioselective cycloaddition reactions of an azomethine imine with activated cyclopropanes. Scandium(III) triflate catalyzes a [3+2] cycloaddition reaction of the azomethine imine with cyclopropanes to form tetrahydropyrazolone derivatives and tricyclic tetrahydrofuran derivatives in moderate yields. Complementary to this, a novel [3+3] cycloaddition reaction of the azomethine imine with activated cyclopropanes was developed by using EtAlCl2 as a Lewis acid to form hexahydropyridazinone derivatives in high regioselectiv

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Gulías, Moisés, Fernando López, and José L. Mascareñas. "Development of transition-metal-catalyzed cycloaddition reactions leading to polycarbocyclic systems." Pure and Applied Chemistry 83, no. 3 (2011): 495–506. http://dx.doi.org/10.1351/pac-con-10-10-23.

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We present a compilation of methodologies developed in our laboratories to assemble polycyclic structures containing small- and medium-sized cycles, relying on the use of transition-metal-catalyzed (TMC) cycloadditions. First, we discuss the use of alkylidenecyclopropanes (ACPs) as 3C-atom partners, in particular in their Pd-catalyzed (3 + 2) cycloadditions with alkynes, alkenes, and allenes, reactions that lead to cyclopentane-containing polycyclic products in excellent yields. Then, we present the expansion of this chemistry to a (4 + 3) annulation with conjugated dienes, and to inter- and i

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Chen, Jing-Biao, and Yi-Xia Jia. "Recent progress in transition-metal-catalyzed enantioselective indole functionalizations." Organic & Biomolecular Chemistry 15, no. 17 (2017): 3550–67. http://dx.doi.org/10.1039/c7ob00413c.

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Recent progress on the transition-metal-catalyzed enantioselective functionalization reaction of indoles is reviewed, which is mainly focused on asymmetric indole alkylations, arylations, cycloaddition reactions, and other reactions.

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WANG, JING-FANG, DONG-QING WEI, CHUN-FANG WANG, et al. "A THEORETICAL STUDY ON THE MECHANISM OF 2:1 1, 3 DIPOLAR CYCLOADDITION REACTIONS." Journal of Theoretical and Computational Chemistry 06, no. 04 (2007): 861–67. http://dx.doi.org/10.1142/s0219633607003489.

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The reactions between nitrile oxides and alkenes are of considerable interest in organic synthesis as the resulting heterocycles are versatile intermediates for the synthesis of natural products and biologically active compounds. In this paper, we design a series of reactions of phosphonyl nitrile oxides with acrylonnitrile, which can give 2:1 cycloaddition products with no crystal structure released so far, and present a detailed theoretical study on the mechanism of the 2:1 1, 3-dipolar cycloaddition reaction, which has been explored with density functional theory calculations at B3LYP/6-31G

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Winne, Johan, Jan Hullaert, Bram Denoo, Mien Christiaens, and Brenda Callebaut. "Heterocycles as Moderators of Allyl Cation Cycloaddition Reactivity." Synlett 28, no. 18 (2017): 2345–52. http://dx.doi.org/10.1055/s-0036-1588511.

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For the rapid elaboration of polycarbocyclic scaffolds, prevalent in many important families of terpenoid natural products, allyl cations derived from simple heterocyclic alcohols can be used as versatile reaction partners in both (4+3) and (3+2) cycloaddition pathways. Our recent progress in this area is outlined, pointing towards the untapped potential of heterocycles to act as reagents in novel or known but challenging organic transformations.1 Heterocyclic Reagents2 Cycloadditions and Allyl Cations3 Furfuryl Cations in Cycloadditions4 Heterocycle-Substituted Cations in Cycloadditions5 Mech

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Maiuolo, Loredana, Vincenzo Algieri, Fabrizio Olivito, and Antonio De Nino. "Recent Developments on 1,3-Dipolar Cycloaddition Reactions by Catalysis in Green Solvents." Catalysts 10, no. 1 (2020): 65. http://dx.doi.org/10.3390/catal10010065.

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The use of eco-compatible synthetic procedures in organic reactions and, in particular, in 1,3-dipolar cycloaddition reactions, has recently received a great deal of attention and considerable progress has been achieved in this area in the last years. This review summarizes the approaches currently employed to synthesize heterocyclic compounds by catalyzed 1,3-dipolar cycloadditions in green solvents in the last six years. Our choice to do a selection of the literature from 2014 to 2019 was made considering the absence of a recent review about this period, to our knowledge. Several examples to

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Dunstan, James B. F., Gordon M. Elsey, Richard A. Russell, G. Paul Savage, Gregory W. Simpson, and Edward R. T. Tiekink. "Dipolar Cycloaddition Reactions of Nitrilimines." Australian Journal of Chemistry 51, no. 6 (1998): 499. http://dx.doi.org/10.1071/c97157.

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A series of γ-substituted α-methylidene-γ-butyrolactone derivatives underwent regiospecific 1,3-dipolar cycloaddition with N-methyl-C-phenylnitrilimine. These reactions proceeded regiospecifically and with high diastereoselectivity, generally favouring the anti diastereomer as determined by n.m.r. spectroscopy and semiempirical molecular orbital calculations. The assignment for one product was confirmed by X-ray crystallography. N-Methyl-C-phenylnitrilimine underwent regiospecific cycloaddition with a range of C=S-containing dipolarophiles. Substituted thioureas were generally unreactive as di

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Sleziak, Róbert, and Alžbeta Krutošíková. "Cycloaddition Reactions of Furo[2,3-b]pyrroles." Collection of Czechoslovak Chemical Communications 64, no. 2 (1999): 321–28. http://dx.doi.org/10.1135/cccc19990321.

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Reactions of furo[2,3-b]pyrroles with dimethyl butynedioate and ethyl propynoate were investigated. The reaction course is influenced by the substituents on the fused system. Products of [4+2]cycloaddition to the furan ring leading to indole derivatives have been observed. In the case of the reaction of methyl 6H-furo[2,3-b]pyrrole-5-carboxylate (1a) with dimethyl butynedioate, products of [4+2]cycloaddition to the furan ring as well as of Michael addition to the pyrrole ring leading to N-substituted indole derivative 3 have been observed.

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Yoon, Hyo Jae, Sangmin Jung, and Seo Yeon Kim. "Force-Induced Cycloaddition of Aziridine: Can We Force a New Route?" Synlett 31, no. 14 (2020): 1343–48. http://dx.doi.org/10.1055/s-0040-1707145.

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Cycloaddition reactions of aziridines with dipolarophiles under traditional thermal or photochemical conditions entail destructive routes to form reactive intermediates such as an azomethine ylide. This article highlights a recent study that demonstrates a cycloaddition reaction of aziridine induced by mechanical force. Experimental results suggest that the force-induced cycloaddition of aziridine with dimethyl acetylenedicarboxylate as a dipolarophile does not seem to involve an ylide, with implications for a possible new reaction route.1 Rivalry between Aziridine and Epoxide2 Mechanochemical

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Sokolova, Ekaterina A., Alexey A. Festa, Karthikeyan Subramani, et al. "Microwave-Assisted Synthesis of Fluorescent Pyrido[2,3-b]indolizines from Alkylpyridinium Salts and Enaminones." Molecules 25, no. 18 (2020): 4059. http://dx.doi.org/10.3390/molecules25184059.

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Pyridinium ylides are well recognized as dipoles for cycloaddition reactions. In its turn, the microwave-assisted interaction of N-(cyanomethyl)-2-alkylpyridinium salts with enaminones unexpectedly proceeds as a domino sequence of cycloisomerization and cyclocondensation reactions, instead of a 1,3-dipolar cycloaddition. The reaction takes place in the presence of sodium acetate as base and employs benign solvents. The optical properties of the resulting pyrido[2,3-b]indolizines were studied, showing green light emission with high fluorescence quantum yields.

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Cavaleiro, José A. S., Maria G. P. M. S. Neves, and Augusto C. Tomé. "Cycloaddition reactions of porphyrins." Arkivoc 2003, no. 14 (2003): 107–30. http://dx.doi.org/10.3998/ark.5550190.0004.e11.

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