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Journal articles on the topic '3-dipolar cycloaddition reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

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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2

Nallamala, Sirisha, Srikumar Mannem, and Raghunathan Raghavachary. "Highly Efficient Construction of Sugar-Fused Spirochromanono Pyrrolidines/Pyrrolizidines/Thiolizidines via 1,3-Dipolar Cycloaddition of Azomethine Ylides." SynOpen 01, no. 01 (2017): 0063–67. http://dx.doi.org/10.1055/s-0036-1588520.

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A variety of sugar-fused chromanono pyrrolidines/pyrrolizidines/thiolizidines have been synthesized by intermolecular 1,3-dipolar cycloaddition reaction of azomethine ylides (generated from glucose aldehyde and different secondary amino acids) with various 3-arylidene chroman-4-ones as dipolarophiles. The solvent effect on the 1,3-dipolar cycloaddition reaction is also studied.

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3

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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4

Ogurtsov, Vladimir A., and Oleg A. Rakitin. "New Cycloadditon Reaction of 2-Chloroprop-2-enethioamides with Dialkyl Acetylenedicarboxylates: Synthesis of Dialkyl 2-[4,5-Bis(alkoxycarbonyl)-2-(aryl{alkyl}imino)-3(2H)-thienylidene]-1,3-dithiole-4,5-dicarboxylates." Molecules 27, no. 20 (2022): 6887. http://dx.doi.org/10.3390/molecules27206887.

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The 1,3-dipolar cycloaddition of 1,2-dithiole-3-thiones with alkynes to form 1,3-dithioles is one of the most studied reactions in this class of polysulfur-containing heterocycles. Nucleophilic substitution of chlorine atoms in dimethyl 2-(1,2-dichloro-2-thioxoethylidene)-1,3-dithiole-4,5-dicarboxylate, which was obtained by addition one molecules of DMAD to 4,5-dichloro-3H-1,2-dithiole-3-thione, led to a series of 2-chloro-2-(1,3-dithiol-2-ylidene)ethanethioamides. Cycloaddition reaction of 2-chloro-2-(1,3-dithiol-2-ylidene)ethanethioamides with activated alkynes led to the unexpected formati

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5

Nallamala, Sirisha, and Raghavachary Raghunathan. "Efficient Synthesis of Dispiropyrrolidines Linked to Sugars." International Journal of Carbohydrate Chemistry 2013 (November 10, 2013): 1–7. http://dx.doi.org/10.1155/2013/340546.

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An expedient method for the synthesis of glyco-dispiropyrrolidines is reported through 1,3-dipolar cycloaddition reaction (1,3 DC reaction). The novel glycosyl dipolarophiles derived from D-glucose underwent neat [3+2] cycloaddition reaction with the azomethine ylides generated from 1,2-diketones and sarcosine to give the corresponding glycosidic heterocycles in good yields.

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6

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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7

Nakamura, Masaharu, Motoki Toganoh, Xio Qun Wang, Shigeru Yamago, and Eiichi Nakamura. "Intramolecular [3 + 2]Cycloaddition Reaction of Dipolar Trimethylenemethane." Chemistry Letters 29, no. 6 (2000): 664–65. http://dx.doi.org/10.1246/cl.2000.664.

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8

Vale, Luís S. H. P., Joana F. B. Barata, Carla I. M. Santos, et al. "Corroles in 1,3-dipolar cycloaddition reactions." Journal of Porphyrins and Phthalocyanines 13, no. 03 (2009): 358–68. http://dx.doi.org/10.1142/s1088424609000371.

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The azomethine ylide generated from the reaction of a corrole-3-carbaldehyde and N-methylglycine was trapped with dimethyl fumarate, dimethyl acetylenedicarboxylate and fullerene C60 in 1,3-dipolar cycloadditions. A similar azomethine ylide generated from a corrole-2-carbaldehyde was trapped with 1,4-naphthoquinone, yielding the expected dehydrogenated 1,3-dipolar cycloadduct and a quinone-fused corrole derivative. A detailed synchrotron single-crystal X-ray diffraction analysis of the gallium(III)(pyridine) complex of 5,10,15-tris(pentafluorophenyl)corrole-3-carbaldehyde is also presented.

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9

Salem, Mohammed A., Moustafa A. Gouda, and Ghada G. El-Bana. "Chemistry of 2-(Piperazin-1-yl) Quinoline-3-Carbaldehydes." Mini-Reviews in Organic Chemistry 19, no. 4 (2022): 480–95. http://dx.doi.org/10.2174/1570193x18666211001124510.

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Abstract: This review described the preparation of 2- chloroquinoline-3-carbaldehyde derivatives 18 through Vilsmeier-Haack formylation of N-arylacetamides and the use of them as a key intermediate for the preparation of 2-(piperazin-1-yl) quinoline-3-carbaldehydes. The synthesis of the 2- (piperazin-1-yl) quinolines derivatives was explained through the following chemical reactions: acylation, sulfonylation, Claisen-Schmidt condensation, 1, 3-dipolar cycloaddition, one-pot multicomponent reactions (MCRs), reductive amination, Grignard reaction and Kabachnik-Field’s reaction.

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10

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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11

Huang, Ying, Yi-Xin Huang, Jing Sun, and Chao-Guo Yan. "Diastereoselective synthesis of dispirooxindoles via [3+2] cycloaddition of azomethine ylides to 3-phenacylideneoxindoles and evaluation of their cytotoxicity." RSC Advances 8, no. 42 (2018): 23990–95. http://dx.doi.org/10.1039/c8ra04375b.

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The three-component reaction of 1,2,3,4-tetrahydroisoquinoline, isatins and 3-phenacylideneoxindoles in refluxing ethanol afforded dispiro[indoline-3,1′-pyrrolo[2,1-a]isoquinoline-3′,3′-indolines] (4a–4x) in good yields via 1,3-dipolar cycloaddition.

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12

Wanapun, D., K. A. Van Gorp, N. J. Mosey, M. A. Kerr, and T. K. Woo. "The mechanism of 1,3-dipolar cycloaddition reactions of cyclopropanes and nitrones A theoretical study." Canadian Journal of Chemistry 83, no. 10 (2005): 1752–67. http://dx.doi.org/10.1139/v05-182.

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The 1,3-dipolar cycloaddition reaction of cyclopropanes and nitrones to give tetrahydro-1,2-oxazine has been studied with density functional theory calculations at the B3LYP/6-31+G(d,p) level of theory. Realistic substituents were modelled including those at the 2-, 3-, 4-, and 6-positions of the final oxazine ring product. The strained σ bond of the cyclopropane was found to play the role of an alkene in a conventional [3+2] dipolar cycloaddition. Two distinct, but similar, reaction mechanisms were found an asymmetric concerted pathway and a stepwise zwitterionic pathway. The reaction barri

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13

Belaissaoui, Abdelhak, Sandrine Jacquot, Claude Morpain, Gérard Schmitt, Joël Vebrel, and Bernard Laude. "Réactivité dipolaire-1,3 du 4,4,4-trichiloro-3-éthoxycarbonylamino-2-diazobutyrate d'éthyle issu de l'action du diazoacétate d'éthyle sur la N-éthoxycarbonyl-N-(2,2,2-trichloroéthylidène)amine." Canadian Journal of Chemistry 75, no. 5 (1997): 523–30. http://dx.doi.org/10.1139/v97-061.

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The reaction of ethyl diazoacetate with the N-ethoxycarbonyl-N-(2,2,2-trichloroethylidene)amine yields, by a nucleophilic addition, a new diazo compound that gives 1,3-dipolar cycloaddition reactions with acetylenic esters and maleimides. With acetylenic esters, the cycloadduct leads to substituted pyrazoles by [1,5] sigmatropic rearrangements. With maleimides, we observe a diastereospecific cycloaddition reaction. The intermediary cycloadduct evolves by nitrogen elimination to give a maleimidocyclopropane. The diastereospecificity was explained by an endo-anti approach of the reactants. Keywo

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14

Cardoso, Ana L., and Maria I. L. Soares. "1,3-Dipolar Cycloadditions Involving Allenes: Synthesis of Five-Membered Rings." Current Organic Chemistry 23, no. 27 (2020): 3064–134. http://dx.doi.org/10.2174/1385272823666191203122959.

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The 1,3-dipolar cycloaddition reaction is a powerful and versatile strategy for the synthesis of carbocyclic and heterocyclic five-membered rings. Herein, the most recent developments on the [3+2] cycloaddition reactions using allenes acting either as dipolarophiles or 1,3-dipole precursors, are highlighted. The recent contributions on the phosphine- and transition metal-catalyzed [3+2] annulations involving allenes as substrates are also covered, with the exception of those in which the formation of a 1,3-dipole (or synthetic equivalent) is not invoked. This review summarizes the most relevan

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15

Santos, Hugo, Amy Distiller, Asha M. D'Souza, et al. "1,3-Dipolar cycloaddition reactions of phthalic anhydrides with an azomethine ylide." Organic Chemistry Frontiers 2, no. 6 (2015): 705–12. http://dx.doi.org/10.1039/c5qo00062a.

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A series of phthalic anhydrides underwent a 1,3-dipolar cycloaddition reaction with N-benzylazomethine ylide to produce unstable spiro(isobenzofuran-1,5′-oxazolidin)-3-ones, which underwent a subsequent reductive ring-opening reaction to afford 1(3H)-isobenzofuranones.

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16

Caraculacu, Adrian A., Elena Scorţanu, and Georgeta Caraculacu. "New Parabanate Products by 1, 3-Dipolar Cycloaddition Reaction (‘Criss-Cross’ Cycloaddition)." High Performance Polymers 11, no. 4 (1999): 477–82. http://dx.doi.org/10.1088/0954-0083/11/4/311.

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17

Wang, Kai-Kai, Yan-Xin Xie, Yan-Li Li, Rongxiang Chen, and Zhan-Yong Wang. "Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides." RSC Advances 10, no. 48 (2020): 28720–24. http://dx.doi.org/10.1039/d0ra05687a.

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A simple and efficient method for the synthesis of benzo[4,5]thieno[2,3-c]pyrroles via dearomative [3 + 2] 1,3-dipolar cycloaddition reaction of nitrobenzothiophenes with an in situ-generated nonstabilized azomethine ylides have been developed.

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18

Boudriga, Sarra, Saoussen Haddad, Moheddine Askri, et al. "Highly diastereoselective construction of novel dispiropyrrolo[2,1-a]isoquinoline derivativesviamulticomponent 1,3-dipolar cycloaddition of cyclic diketones-based tetrahydroisoquinoliniumN-ylides." RSC Advances 9, no. 20 (2019): 11082–91. http://dx.doi.org/10.1039/c8ra09884k.

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A new series of dispiropyrrolo[2,1-a]isoquinoline derivatives was synthesized by multicomponent 1,3-dipolar cycloaddition reaction of tetrahydroisoquinoliniumN-ylides and (E)-3-arylidene-1-phenyl-pyrrolidine-2,5-diones.

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19

El-Sayed, Wael A., and Adel A. H. Abdel-Rahman. "Copper-catalyzed Synthesis and Antimicrobial Activity of Disubstituted 1,2,3-Triazoles Starting from 1-Propargyluracils and Ethyl (4-Azido- 1,2,3-trihydroxybutyl)furan-3-carboxylate." Zeitschrift für Naturforschung B 65, no. 1 (2010): 57–66. http://dx.doi.org/10.1515/znb-2010-0110.

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1,3-Dipolar cycloaddition reactions of 1-propargyluracils 2a - h with the azido derivative 3 afforded the corresponding 1,2,3-triazoles 4a - h. Hydrazinolysis of the esters 4a - h gave the corresponding acid hydrazides 5a - h. Reaction of 5a - h with carbon disulfide in ethanol afforded 6a - h. The antimicrobial activity of compounds 4 - 6 was determined

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20

Hunnur, Raveendra K., Prashant R. Latthe, and Bharati V. Badami. "1,3-Dipolar Cycloaddition Reactions in Heterocyclic Synthesis. Synthesis of [1-[4-(thiazolyl/imidazothiazolyl/triazolyl)phenyl]-1H-pyrazole-3,4-dicarboxylate esters from 3-(4-acetylphenyl)sydnone." Journal of Chemical Research 2005, no. 9 (2005): 592–94. http://dx.doi.org/10.3184/030823405774308907.

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Cycloaddition of 3-(4-acetylphenyl)sydnone (1) with DMAD gave dimethyl 1-(4-acetylphenyl)-1H-pyrazole-3,4-dicarboxylate (2), which on bromination yielded the corresponding monobromoacetyl (3) and dibromoacetyl (4) derivatives. Both compounds 3 and 4 on reaction with thiourea and thioacetamide afforded the 2-amino- (5) and the 2-methyl- (6) thiazole derivatives respectively, while compound 3 on reaction with 2-aminothiazole gave the imidazothiazole 7. Compound 3 was converted into its azide (8), which on 1,3-dipolar cycloaddition with DMAD afforded the 1,2,3-triazole-4,5-dicarboxylate (9).

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21

Nakamura, Masaharu, Naohiko Yoshikai, Motoki Toganoh, and Eiichi Nakamura. "[3 + 3] Cycloaddition Reaction of Dipolar Trimethylenemethane with Active Methylene Compound." Synlett 2001, Special Issue (2001): 1030–33. http://dx.doi.org/10.1055/s-2001-14653.

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22

Filatov, Alexander S., Olesya V. Khoroshilova, Anna G. Larina, Vitali M. Boitsov, and Alexander V. Stepakov. "Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple." Beilstein Journal of Organic Chemistry 18 (June 29, 2022): 769–80. http://dx.doi.org/10.3762/bjoc.18.77.

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A reliable method for the synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexanes through the 1,3-dipolar cycloaddition (1,3-DC) reactions of cyclopropenes to the stable azomethine ylide – protonated form of Ruhemann's purple (PRP) has been developed. Both 3-substituted and 3,3-disubstituted cyclopropenes reacted with PRP, affording the corresponding bis-spirocyclic 3-azabicyclo[3.1.0]hexane cycloadducts in moderate to good yields with high diastereofacial selectivity. Moreover, several unstable 1,2-disubstituted cyclopropenes were successfully trapped by the stable 1,3-dipole u

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23

Mawhinney, Robert C., Heidi M. Muchall, and Gilles H. Peslherbe. "A computational study of the 1,3-dipolar cycloaddition reaction mechanism for nitrilimines." Canadian Journal of Chemistry 83, no. 9 (2005): 1615–25. http://dx.doi.org/10.1139/v05-179.

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The [3+2] and [1+2] cycloaddition pathways between ethene and a series of 13 nitrilimines (R1CNNR2) have been examined by density functional theory [PBE0/6-311++G(2df,pd)] calculations. All reactions have low barriers ranging from 14.14 (R1 = CH3, R2 = H) to 1.01 (R1 = R2 = F) kcal mol1, and large reaction exothermicities consistent with the transient nature of nitrilimines. The [3+2] and [1+2] transition-state structures are very similar, mainly differing in the relative orientation of their fragments and the newly forming CC bond distance, and exhibit only minor deviations from the structu

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24

Fišera, Lubor, Libuše Jarošková, Werner Schroth, Michael Gäbler, and Peter Oravec. "Cycloaddition of arylnitrile oxides to 2H,5H-1,6-benzodioxocine and related compounds." Collection of Czechoslovak Chemical Communications 53, no. 5 (1988): 1060–67. http://dx.doi.org/10.1135/cccc19881060.

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3-Aryl-3a,4,11,11a-tetrahydroisoxazolo[5,4c]-1,6-benzodioxocines VIII were formed by a 1,3-dipolar cycloaddition of arylnitrile oxides to 2H,5H-1,6-benzodioxocine (III). The heterocycle VII afforded monoadducts IX, whereas dipolarophiles IV-VI do not yield cycloaddition products with nitrile oxides under the same reaction conditions. Irradiation of isoxazolines VIII, IX with UV light led to tarry products.

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25

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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26

Bazgir, Ayoob, and Hossein Yazdani. "Lewis Acid Catalyzed Regio- and Diastereoselective Synthesis of Spiroisoxazolines via One-Pot Sequential Knoevenagel Condensation/1,3-Dipolar Cycloaddition Reaction." Synthesis 51, no. 07 (2019): 1669–79. http://dx.doi.org/10.1055/s-0037-1610676.

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A ZnCl2-catalyzed regio- and diastereoselective one-pot sequential Knoevenagel condensation/1,3-dipolar cycloaddition reaction of CH acids (oxindole, 1,3-indandione, and 3H-pyrazol-3-one), aldehydes, and dibromoformaldoxime has been established. The method allows the synthesis of diversely functionalized spiroisoxazolines in good isolated yields under mild reaction conditions. Moreover, the preparation of spiroindene-isoxazole-1,3-diones containing benzoimidazole or benzothiazole moieties as new ligands for the metal-catalyzed coupling reactions and C–H activation is demonstrated.

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27

Nakamura, Masaharu, Motoki Toganoh, Xio Qun Wang, Shigeru Yamago, and Eiichi Nakamura. "ChemInform Abstract: Intramolecular [3 + 2] Cycloaddition Reaction of Dipolar Trimethylenemethane." ChemInform 31, no. 43 (2000): no. http://dx.doi.org/10.1002/chin.200043039.

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28

Zhou, Xiao, Xianhong Xu, Zhenyan Shi, Kun Liu, Hua Gao та Wenjun Li. "Enolate-mediated 1,3-dipolar cycloaddition reaction of β-functionalized ketones with nitrile oxides: direct access to 3,4,5-trisubstituted isoxazoles". Organic & Biomolecular Chemistry 14, № 23 (2016): 5246–50. http://dx.doi.org/10.1039/c6ob00717a.

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Enolate-mediated [3 + 2] organocatalytic 1,3-dipolar cycloaddition reactions of β-functionalized ketones with nitrile oxides have been developed. This strategy could generate 3,4,5-trisubstituted isoxazole in high yields and regioselectivities.

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29

Uroosa Aslam, Uroosa Aslam, Imran Ali Hashmi Imran Ali Hashmi, Muhammad Naveed Javed Muhammad Naveed Javed, Shoaib Muhammad Shoaib Muhammad, Muhammad Nabeel Muhammad Nabeel, and Ahmed Bari and Firdous Imran Al Ahmed Bari and Firdous Imran Al. "Chromatography Free Synthesis of Reversed N-Triazole Nucleosides Starting from D-Galactopyranose using 1,3-Dipolar Cycloaddition Reactions." Journal of the chemical society of pakistan 46, no. 2 (2024): 185. http://dx.doi.org/10.52568/001436/jcsp/46.02.2024.

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A chromatography free, four-step strategy has been developed to synthesize reversed N- nucleosides (4A-D) starting from -D-galactopyranose. The triaozle moiety served as heterocyclic part of nucleoside was created via 1,3 dipolar cycloaddition reaction between sugar azide (1,2:3,4-di-O-isopropylidene-6-deoxy-6-azido- -Dgalactopyranoside, 3) and terminal alkyne. Sugar azide 3 was obtained from 1,2:3,4-di-O-isopropylidene-6-tosyl- -Dgalactopyranoside (2). Purification of products was carried out through solvent-solvent extraction and/or crystallization techniques. This is an example of click

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30

Petrov, A. O., Georgiy V. Malkov, Sergei V. Karpov, A. V. Shastin, and A. V. Bakeshko. "Kinetic Study of the Polyaddition of Azide-Alkyne AB₂ Monomers in Nonisotermic Conditions." Key Engineering Materials 816 (August 2019): 151–56. http://dx.doi.org/10.4028/www.scientific.net/kem.816.151.

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Nowadays, hyperbranched polymers (HBP) are obtained by different polycondensation and polyaddition reactions [1]. Almost interest is the reaction of 1,3-dipolar cycloaddition of azides to alkynes (1,3-DCA) [2, 3]. There is a series of papers dedicated to the preparation of triazine-triazole HBPs [4, 5, 6]. These polymers were obtained by the reaction of azido-acetylene AB2 monomers polyaddition: 2-azido-4,6-bis (propyne-2-yloxy) -1,3,5-triazine (ABPOT) and 2,4-diazido-6- (propine-2-yloxy) -1,3,5-triazine (DAPOT) (Fig. 1).

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31

Zhou, Feng-Ji, Bao-Lei Zhu, Zhen-Hui Huang, Ning Lin, and Zhen-Wei Zhang. "DBU-catalyzed diastereoselective 1,3-dipolar [3+2] cycloaddition of trifluoroethyl amine-derived isatin ketimines with chalcones: synthesis of 5′-CF₃-substituted 3,2′-pyrrolidinyl spirooxindoles." RSC Advances 14, no. 1 (2024): 548–51. http://dx.doi.org/10.1039/d3ra08127c.

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32

Xu, Xianhong, Zhenyan Shi, and Wenjun Li. "Organocatalytic 1,3-dipolar [3+3] cycloaddition reaction of 1,2-cyclohexanedione with azides: direct access to highly substituted 1,2,3-triazoles." New Journal of Chemistry 40, no. 8 (2016): 6559–63. http://dx.doi.org/10.1039/c6nj01083k.

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Enamine-mediated 1,3-dipolar [3+3] cycloaddition reactions of 1,2-cyclohexanedione with azides have been developed. This strategy could generate highly substituted 1,2,3-triazoles in high yields and high levels of regioselectivities. It is demonstrated that various types of products could be obtained with different organocatalysts and substrates.

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33

Julino, Markus, Philip R. Lowe, and Malcolm F. G. Stevens. "Structural Studies on Bioactive Compounds. Part 31. Interaction of 9-azidoacridine and 1-morpholinocyclohexene: Formation, Decomposition and Rearrangement of the Intermediate 1,2,3-triazoline." Journal of Chemical Research 2000, no. 2 (2000): 74–75. http://dx.doi.org/10.3184/030823400103166418.

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9-Azidoacridine 1 and the cyclic enamine 2 undergo a selective 1,3-dipolar cycloaddition reaction to give the 1,2,3-triazoline 3 with the expected regiochemistry. Exposure of the triazoline 3 to methanol induces the extrusion of nitrogen accompanied by a ring contraction to furnish the amidino-acridine 5 in high yield.

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34

Belguedj, Roumaissa, Sofiane Bouacida, Hocine Merazig, Ali Belfaitah, and Abdelmalek Bouraiou. "1-(2′-Benzimidazolylmethyl)-pyridinium ylide in the one-pot synthesis of indolizine and benzimidazo[1,2-a]pyridine derivatives." Zeitschrift für Naturforschung B 70, no. 8 (2015): 555–61. http://dx.doi.org/10.1515/znb-2015-0016.

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AbstractFour indolizine derivatives were obtained via 1,3-dipolar cycloaddition reaction of 1-(2′-benzimidazolylmethyl)pyridinium ylide with various electron-deficient alkynes. The reaction of this pyridinium N-ylide with dimethyl maleate gave an unexpected methyl 1-oxo-benzimidazo[1,2-a]pyridine-3-carboxylate. The structures of all reported compounds have been examined by X-ray crystallography and NMR spectroscopy.

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35

Gucma, Mirosław, Marek Gołębiewski, Krzysztof Żelechowski, and Maria Krawczyk. "Studies on the [2+3] cycloaddition reaction of nitrile oxides to abietic acid esters." Journal of the Serbian Chemical Society 84, no. 10 (2019): 1073–81. http://dx.doi.org/10.2298/jsc180517018g.

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[2+3] Dipolar cycloadditions of aromatic nitrile oxides to abietic acid esters were investigated. The reactions showed complete site selectivity and regioselectivity, while the stereoselectivity depended on the structures of the dipolarophiles.

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36

M., Abd Al-Hakim Badawi, and Aziz Baddour Noura. "Theoretical study of 1, 3-Dipolar Cycloaddition Reaction of Benzyl Azide and its Derivatives with Cinnamic Acid M062X/6-31 g(d)." Chemistry Research Journal 5, no. 1 (2020): 1–8. https://doi.org/10.5281/zenodo.12165990.

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<strong>Abstract </strong>The 1,3-dipolar cycloaddition of the Benzyl azide and its derivatives( -H, 2-CI, 3-CI, 3-OCH<sub>3</sub>, 4-OCH<sub>3</sub>, 4-NO<sub>2</sub>, 2,6-Cl ) with Cinnamic acid was studied theoretically using  Density Functional Theory (DFT) MO62X with the basic set 6-31g(d) with solvents: water, dimethyl sulfoxide(DMSO), Acetonitrile, Ethanol, Tetrahydrofuran (THF), Dimethyl Ether and Heptane. We have identified thermodynamic properties and kinetic factors using Polarization Continuous Method PCM in the level of theory M062X/6-31 g (d). The results of the level of the

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37

Gao, Lingfeng, Kai Fu, and Gengxiu Zheng. "Quickly FeCl3-catalyzed highly chemo- and stereo-selective [3 + 2] dipolar cycloaddition of aziridines with isothiocyanates." RSC Advances 6, no. 53 (2016): 47192–95. http://dx.doi.org/10.1039/c6ra04923k.

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38

Boitsov, Vitali M., Alexander V. Stepakov, Siqi Wang, et al. "Construction of Spiro[3-azabicyclo[3.1.0]hexanes] via 1,3-Dipolar Cycloaddition of 1,2-Diphenylcyclopropenes to Ninhydrin-Derived Azomethine Ylides." Synthesis 53, no. 12 (2021): 2114–32. http://dx.doi.org/10.1055/a-1360-9716.

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AbstractThe multi-component 1,3-dipolar cycloaddition of ninhydrin, α-amino acids (or peptides), and cyclopropenes for the synthesis of spirocyclic heterocycles containing both 3-azabicyclo[3.1.0]hexane and 2H-indene-1,3-dione motifs has been developed. This method provides easy access to 3-azabicyclo[3.1.0]hexane-2,2′-indenes with complete stereoselectivity and a high degree of atom economy under mild reaction conditions. A broad range of cyclopropenes and α-amino acids have been found to be compatible with the present protocol, which offers an opportunity to create a new library of biologica

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39

Tao, Hongwen, Yinan Yuan, Jian Chen, Xianyong Yu, and Pinggui Yi. "Synthesis of Cholestan -3-One Derivatives Possessing a C-2 Spiro-Oxindole Substituent." Journal of Chemical Research 42, no. 1 (2018): 15–19. http://dx.doi.org/10.3184/174751918x15161933697781.

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A series of C-2 cholestan-3-one spiro-oxindole derivatives were prepared by the 1:3 dipolar cycloaddition reaction between the cholestan-3-one substituted by a C-2 arylidene and the azomethine ylid derived from isatin and sarcosine. The dipolarophiles were efficiently obtained by a Claisen-Schmidt reaction of cholestan-3-one and aromatic aldehydes. The structures of the products were established by a combination of NMR, high-resolution mass spectrometry (HRMS) and X-ray data analysis.

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40

Chaouni, Wafaâ, Mina Aadil, Ahmed Djellal, and Gilbert Kirsch. "Synthesis of Methyl 3-Azidothieno[2,3-b]pyridine-2-carboxylates and Application of the Huisgen Reaction." Zeitschrift für Naturforschung B 69, no. 5 (2014): 509–18. http://dx.doi.org/10.5560/znb.2014-3320.

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The preparation of new substituted methyl 3-azidothieno[2,3-b]pyridine carboxylates by azotization of methyl 3-aminothieno[2,3-b]pyridine and subsequent treatment with sodium azide is described. Via Huisgen’s 1,3-dipolar cycloaddition between substituted alkynes and the prepared azides, methyl 1,2,3-triazolo-thieno[2,3-b]pyridine carboxylates have been obtained.

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41

Girgis, Adel S. "Facile Regioselective Synthesis of 1,2,6,8-Tetraazaspiro[4.4]nona-2,6-dien-9-ones." Zeitschrift für Naturforschung B 55, no. 2 (2000): 222–26. http://dx.doi.org/10.1515/znb-2000-0215.

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1,3-Dipolar cycloaddition reaction of nitrilimines to a variety of 3-aryl-5-arylmethylidene- 3,5-dihydro-2-phenyl-4H-imidazol-4-ones (3) afforded the corresponding 1,3,4,7,8-pentaaryl -1,2,6,8-tetraazaspiro[4.4]-nona-2,6-dien-9-ones (4) and not the regio-isomers 2,3,6,8,9-pentaaryl- 1,3,7,8-tetraazaspiro[4.4]nona-1,6-dien-4-ones (5) in high regioselectivity.

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42

Choi, Anthony, Rebecca M. Morley, and Iain Coldham. "Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts." Beilstein Journal of Organic Chemistry 15 (July 3, 2019): 1480–84. http://dx.doi.org/10.3762/bjoc.15.149.

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Quinolinium salts, Q+-CH2-CO2Me Br− and Q+-CH2-CONMe2 Br− (where Q = quinoline), were prepared from quinolines. Deprotonation of these salts with triethylamine promoted the reaction of the resulting quinolinium ylides (formally azomethine ylides) with electron-poor alkenes by conjugate addition followed by cyclization or by [3 + 2] dipolar cycloaddition. The pyrroloquinoline products were formed as single regio- and stereoisomers. These could be converted to other derivatives by Suzuki–Miyaura coupling, reduction or oxidation reactions.

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43

Zhang, Zhenhua, Xiaowei Wang, Song Tao, and Shizheng Zhu. "1,3-Dipolar cycloaddition reaction of 3-trifluoromethyl-4-diazopyrazolinones with acetylenedicarboxylates." Tetrahedron 68, no. 30 (2012): 5969–78. http://dx.doi.org/10.1016/j.tet.2012.05.062.

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44

Booth, Ceri A., and Douglas Philp. "Efficient recognition-induced acceleration of a [3+2] dipolar cycloaddition reaction." Tetrahedron Letters 39, no. 38 (1998): 6987–90. http://dx.doi.org/10.1016/s0040-4039(98)01483-x.

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45

Sivakumar, Krishnamoorthy, Fang Xie, Brandon M. Cash, Su Long, Hannah N. Barnhill, and Qian Wang. "A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes†." Organic Letters 6, no. 24 (2004): 4603–6. http://dx.doi.org/10.1021/ol047955x.

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46

Lukevics, E., P. Arsenyan, I. Shestakova, et al. "Cytotoxic Activity of Silyl- and Germyl-Substituted 4,4-Dioxo-3a,6a-Dihydrothieno[2,3−d]isoxazolines-2." Metal-Based Drugs 7, no. 2 (2000): 63–66. http://dx.doi.org/10.1155/mbd.2000.63.

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The [2+3] dipolar cycloaddition of nitrile oxides to the double C = C bonds of thiophene-1, 1-dioxides leads to formation of the fused isoxazolines-2 (1, 2). Tumor growth inhibition of these compounds strongly depends on the nature of group IV A element increasing from slightly active tert-butyl derivatives to silicon and germanium containing analogues. The products of benzonitrile oxide cycloaddition have greater cytotoxic effect than the compounds obtained from the cycloaddition reaction of 2, 5-disubstituted thiophene-1, 1-dioxides with acetonitrile oxide. Fused silyl substituted isoxazolin

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47

Bhaskar, Chakraborty, and Kumar Sharma Prawin. "Microwave assisted one pot 1 ,3-dipolar cycloaddition reactions of novel dihydropyran derived nitrone." Journal of Indian Chemical Society Vol. 89, Jun 2012 (2012): 841–47. https://doi.org/10.5281/zenodo.5763900.

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Organic Chemistry Labor~ tory, Sikkim Government College, Gangtok-737 102, Sikkim, India <em>E-mail</em> : bchakraborty42@gmail.com <em>Manuscript received 20 April 2011, revised 19 September. 2011, accepted 17 October 2011</em> Microwave assisted 1,3-dipolar cycloaddition reactions of novel dihydropyran derived nitrone with various dipolarophiles have been studied<em> in situ</em> and found to afford novel isoxazolidine derivatives with high selectivity and synthetic potentials.

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48

Nakamura, Masaharu, Naohiko Yoshikai, Motoki Toganoh, and Eiichi Nakamura. "ChemInform Abstract: [3 + 3] Cycloaddition Reaction of Dipolar Trimethylenemethane with Active Methylene Compounds." ChemInform 32, no. 42 (2010): no. http://dx.doi.org/10.1002/chin.200142173.

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49

Kidou, Chihiro, Haruki Mizoguchi, Tatsuo Nehira та Akira Sakakura. "Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α-(Acyloxy)acroleins Catalyzed by Dipeptide-Derived Chiral Tri- or Diammonium Salts". Synlett 30, № 15 (2019): 1835–39. http://dx.doi.org/10.1055/s-0039-1690133.

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Organoammonium salts of dipeptide-derived chiral triamines or diamines with TfOH catalyzed the enantioselective 1,3-dipolar cycloaddition reactions of α-acyloxyacroleins with nitrones to give the corresponding adducts in good yields (up to 96%) and with high diastereo- and enantioselectivities (up to 89% ee). Although α-(p-methoxybenzoyloxy)acrolein is rather unstable under the reaction conditions, α-(3-pyrroline-1-carbonyloxy)acrolein is stable enough to be smoothly converted into the corresponding adducts with the aid of the chiral organoammonium salt catalysts.

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50

Nguyen, Duy Trinh, Nguyen Phu Thuong Nhan, Tran Thien Hien, Nguyen Dai Hai, Dai Viet N. Vo, and Long Giang Bach. "A Simple Approach for Immobilization of Fe-Core/Au-Shell Magnetic Nanoparticles on Multi-Walled Carbon Nanotubes via Cu(I) Huisgen Cycloaddition: Preparation and Characterization." Solid State Phenomena 279 (August 2018): 187–91. http://dx.doi.org/10.4028/www.scientific.net/ssp.279.187.

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In this report, we demonstrated a novel efficient a simple strategy route for the preparation of smart hybrid Fe-core/Au-shell magnetic onto multi-walled carbon nanotubes (CNT) sidewalls via Cu (I)-catalyzed 1, 3-dipolar cycloaddition (“click” coupling). The fabrication of gold-coated iron nanoparticles (Fe@AuNPs) is initially achieved by employing a two-step reverse micelle process. A new azide terminated ligand was first synthesized to change Fe@AuNPs by ligand exchange reaction. The Fe@Au NPs decorated MWNTs (MWNTs-Fe@Au) nanohybrids were synthesized by the reaction of an azide-containing F

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