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Journal articles on the topic 'Nitrone cycloaddition'

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Published: 4 June 2021

Last updated: 8 February 2022

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1

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 (September 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.

2

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 (January 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-nitrone cycloadditions are easily tunable from both the (strained) alkyne and nitrone perspective, both compounds giving the opportunity to modulate the rate of reaction by substituting various positions. Previously, acyclic nitrones have been evaluated in the strain-promoted alkyne-nitrone reactions; however, they were notably prone to hydrolysis. Some five-membered ring endocyclic nitrones developed concomitantly offered the advantage of relatively fast kinetics and better resistance to degradation in aqueous conditions and have been successfully used for labelling of biomolecules in living systems. Herein, we have prepared and studied nitrones inspired by the phenanthridine scaffold that efficiently undergo strain-promoted alkyne-nitrone reactions. Phenanthridine nitrones react fast with strained cyclooctynes with large bimolecular rate constants while maintaining bioorthogonality and resistance to hydrolysis.

3

Jäger, Volker, Wolfgang Frey, Yaser Bathich, Sunitha Shiva, Mohammad Ibrahim, Marco Henneböhle, Pierre-Yves LeRoy, and Mukhtar Imerhasan. "2-Isoxazolinium Salts and 3-Isoxazolines: Exploratory Chemistry and Uses for the Synthesis of Branched Amino Polyols and Amino Acids." Zeitschrift für Naturforschung B 65, no. 7 (July 1, 2010): 821–32. http://dx.doi.org/10.1515/znb-2010-0708.

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2-Isoxazolines represent a well known class of heterocycles, readily accessible in particular by 1,3-dipolar cycloaddition of nitrile oxides to alkenes. 2-Isoxazolines are easily transformed into 2- isoxazolinium salts by N-methylation, and further into 3-isoxazolines by deprotonation. In contrast to the parent system, less is known concerning the chemistry of the derived classes, and potential applications in synthesis. - 2-Isoxazolinium salts, due to their iminium part, are prone to the attack of nucleophiles, and examples for this, addition of hydride (reduction) and C-nucleophiles like methylmagnesium bromide, cyanide, methane nitronate, and malonate are given. With these adducts, syntheses of β - and α-amino acids with OH-containing side chains have been effected. The cyanide products also are useful as precursors of branched, unsymmetrical 1,2-diamino polyols. - On the other hand, 3-isoxazolines due to their oxy-enamine part, represent species with nucleophilic sites and therefore react with electrophilic reagents. Examples given are [3+2] cycloadditions with nitrile oxides, [2+2] cycloadditions with dimethyl acetylenedicarboxylate, and [2+1] cycloaddition in the form of epoxidation which, however, led to a dihydro-1,3-oxazine nitrone by initial attack at the nitrogen atom, in an unprecedented oxidation/N-dealkylation/rearrangement sequence.

4

Parhi, Ajit K., and Richard W. Franck. "A Weinreb Nitrile Oxide and Nitrone for Cycloaddition." Organic Letters 6, no. 18 (September 2004): 3063–65. http://dx.doi.org/10.1021/ol0489752.

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5

Perzanowski, Herman P., Said S. Al-Jaroudi, Mohamed I. M. Wazeer, and Sk Asrof Ali. "Cyclic nitrone-ethene cycloaddition reactions." Tetrahedron 53, no. 34 (August 1997): 11869–80. http://dx.doi.org/10.1016/s0040-4020(97)00760-6.

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6

Toder, Bruce H., George B. Mullen, and Vassil St. Georgiev. "A Novel Nitrone Cycloaddition/Rearrangement." Helvetica Chimica Acta 73, no. 1 (January 31, 1990): 169–73. http://dx.doi.org/10.1002/hlca.19900730119.

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7

Black, DS, PA Keller, and N. Kumar. "Nitrones and Oxaziridines. XLVI. Formation of Pyrrolo[3,2,1-ij]Quinolines by Intramolecular Nitrone Cycloaddition." Australian Journal of Chemistry 46, no. 6 (1993): 843. http://dx.doi.org/10.1071/ch9930843.

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Intramolecular 1,3-dipolar cycloaddition occurs between nitrones derived from indole-7-carbaldehydes and adjacent allylic substituents on the indole nitrogen atoms. The resulting pyrroloquinoline derivatives (4a-i) have been characterized fully. A range of other potential precursors to cycloaddition reactions have been synthesized, but cyclization sequences have not been completed.

8

Grygorenko, Oleksandr O., Viktoriia S. Moskvina, Oleksandr V. Hryshchuk, and Andriy V. Tymtsunik. "Cycloadditions of Alkenylboronic Derivatives." Synthesis 52, no. 19 (June 24, 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 addressed less thoroughly in the previous works.1 Introduction2 [2+1] Cycloaddition2.1 Cyclopropanation2.1.1 With Methylene Synthetic Equivalents2.1.2 With Substituted Carbenoids2.2 Epoxidation2.3 Aziridination3 [2+2] Cycloaddition4 [3+2] Cycloaddition4.1 With Nitrile Oxides4.2 With Diazoalkanes4.3 With Nitrones4.4 With Azomethine Ylides5 [4+2] Cycloaddition6 [4+3] Cycloaddition7 Conclusions and Outlook

9

Paśniczek, Konrad, Dariusz Socha, Margarita Jurczak, Jolanta Solecka, and Marek Chmielewski. "Synthesis of 8-homocastanospermine." Canadian Journal of Chemistry 84, no. 4 (April 1, 2006): 534–39. http://dx.doi.org/10.1139/v06-032.

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The 1,3-dipolar cycloaddition of a five-membered cyclic nitrone derived from malic acid (4) and unsaturated D-threo-hexaldonolactone (1) leads to a single adduct 6, which can be transformed into the 8-homocastanospermine (13) via a sequence involving rearrangement of the six-membered lactone ring into the five-membered one, removal of the terminal carbon atom from the sugar chain, cleavage of the NO bond, and the intramolecular alkylation of the nitrogen atom. The iminosugar (13) does not show any interesting inhibitory activity towards α- and β-glucosidases.Key words: iminosugars, homocastanospermine, nitrones, aldono-1,5-lactone, 1,3-dipolar cycloaddition, glucosidases.

10

Jones, Raymond C. F., Jason N. Martin, and Paul Smith. "Chiral nitrone reagents for cycloaddition reactions." Journal of Heterocyclic Chemistry 37, no. 3 (May 2000): 481–86. http://dx.doi.org/10.1002/jhet.5570370306.

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11

Kang, Han-Young, Yong Seo Cho, Hun Yeong Koh, and Moon Ho Chang. "Intramolecular [3+2] nitrone-alkyne cycloaddition." Tetrahedron Letters 32, no. 24 (June 1991): 2779–82. http://dx.doi.org/10.1016/0040-4039(91)85084-i.

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12

Black, DSC, DC Craig, RB Debdas, N. Kumar, and TA Wright. "Nitrones and Oxaziridines. LXVII. Intermolecular Cycloaddition of Fused Indolyl Nitrone Ring Systems." Australian Journal of Chemistry 46, no. 11 (1993): 1725. http://dx.doi.org/10.1071/ch9931725.

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The two dihydro-β-carboline N-oxides (6) and (18) have been prepared by reductive cyclization of 2-acetyl-3-(β- nitroethyl ) indoles. These cyclic nitrones undergo 1,3-dipolar cycloaddition to alkynes to give the cycloadducts (21)-(25). Thermal rearrangement of the adduct (22) gives the indolizino [8,7-b] indole (27) in high yield. The X-ray crystal structure determination of the adduct (24) is reported.

13

Rawling, M. J., T. E. Storr, W. A. Bawazir, S. J. Cully, W. Lewis, M. S. I. T. Makki, I. R. Strutt, G. Jones, D. Hamza, and R. A. Stockman. "Facile access to a heterocyclic, sp3-rich chemical scaffold via a tandem condensation/intramolecular nitrone–alkene [3+2] cycloaddition strategy." Chemical Communications 51, no. 64 (2015): 12867–70. http://dx.doi.org/10.1039/c5cc05070g.

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A heterocyclic, sp³-rich chemical scaffold was synthesised in just 6 steps via a highly regio- and diastereo-selective tandem nitrone formation/intramolecular nitrone–alkene [3+2] cycloaddition reaction.

14

Acharjee, Nivedita. "Solvent effects on cycloaddition reactions of potent spin-trapping probe N-tert-butylmethanimine N-oxide: A DFT study." Journal of Theoretical and Computational Chemistry 17, no. 04 (June 2018): 1850027. http://dx.doi.org/10.1142/s021963361850027x.

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[Formula: see text]-tert-butylmethanimine [Formula: see text]-oxide is a potent spin-trapping probe for biologically important radicals, and this nitrone undergoes complete regioselective cycloadditions to less electron-deficient monosubstituted olefins. In the present study, solvent effects on the cycloaddition of this nitrone to styrene have been theoretically studied in terms of the global properties of the reactants, electrophilic and nucleophilic Parr function analysis and the activation and reaction energies of located transition states and products. Formation energies of optimized radical adducts were computed to determine their stabilities in different solvents. The cycloaddition is predicted to be completely ortho regioselective which is in complete agreement with experiments and involved earlier C–C bond formation owing to the insufficient depopulation of [Formula: see text]-conjugated carbon atom in styrene and shows varying asymmetry indices in different solvents. Decrease in activation parameters and increase in stability of cycloadducts are predicted with decreasing solvent polarity. Aqueous media destabilize the radical adducts as predicted from the calculated formation energy, enthalpy and free energy of reaction. Hydroxyl as well as methyl radical adducts are predicted to be more stable than superoxide anion radical adducts. These predictions are in complete agreement with the experiments.

15

Ali, Sk Asrof, and Hasan A. Almuallem. "1,3-Dipolar cycloaddition reactions of a heterocyclic nitrone." Tetrahedron 48, no. 25 (1992): 5273–82. http://dx.doi.org/10.1016/s0040-4020(01)89025-6.

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16

de March, Pedro, Marta Figueredo, Josep Font, Sergio Milán, Angel Alvarez-Larena, Juan F. Piniella, and Elies Molins. "First example of a third generation nitrone cycloaddition." Tetrahedron 53, no. 8 (February 1997): 2979–88. http://dx.doi.org/10.1016/s0040-4020(96)01177-5.

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17

KANG, H. Y., Y. S. CHO, H. Y. KOH, and M. H. CHANG. "ChemInform Abstract: Intramolecular (3+2) Nitrone - Alkyne Cycloaddition." ChemInform 23, no. 13 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199213209.

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18

Ning, Xinghai, Rinske P Temming, Jan Dommerholt, Jun Guo, Daniel B Ania, Marjoke F Debets, Margreet A Wolfert, Geert-Jan Boons, and Floris L van Delft. "Protein Modification by Strain-Promoted Alkyne-Nitrone Cycloaddition." Angewandte Chemie 122, no. 17 (March 23, 2010): 3129–32. http://dx.doi.org/10.1002/ange.201000408.

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19

Jones, Raymond C. F., Jason N. Martin, and Paul Smith. "ChemInform Abstract: Chiral Nitrone Reagents for Cycloaddition Reactions." ChemInform 31, no. 39 (September 26, 2000): no. http://dx.doi.org/10.1002/chin.200039249.

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20

Ning, Xinghai, Rinske P Temming, Jan Dommerholt, Jun Guo, Daniel B Ania, Marjoke F Debets, Margreet A Wolfert, Geert-Jan Boons, and Floris L van Delft. "Protein Modification by Strain-Promoted Alkyne-Nitrone Cycloaddition." Angewandte Chemie International Edition 49, no. 17 (March 23, 2010): 3065–68. http://dx.doi.org/10.1002/anie.201000408.

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21

Chiacchio, Ugo, Antonio Rescifina, Francesco Casuscelli, Anna Piperno, Vincenzo Pisani, and Roberto Romeo. "Intramolecular nitrone cycloaddition: Stereoselective synthesis of piperidine systems." Tetrahedron 52, no. 45 (November 1996): 14311–22. http://dx.doi.org/10.1016/0040-4020(96)00883-6.

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22

Black, DS, DC Craig, RB Debdas, and N. Kumar. "Nitrones and Oxaziridines. XLV. Formation of Pyrrolo[1,2-a]indoles by Intramolecular Nitrone Cycloaddition." Australian Journal of Chemistry 46, no. 5 (1993): 603. http://dx.doi.org/10.1071/ch9930603.

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The N-allylindole-2-carbaldehydes (5)-(8) and related methyl ketones (9)-(12) undergo reaction with N- methylhydroxylamine to give the cycloadducts (14)-(17) and (19)-(22), respectively. These adducts contain isoxazolidine rings fused to pyrrolo [1,2-a] indole systems. Corresponding cycloaddition of the N- propargylindole derivatives (24) and (25) could not be effected and the nitrone (26) was isolated. The adducts (14)-(17) underwent hydrogenolysis of the isoxazolidine N-O bond to give the amino alcohols (27)-(30), together with traces of the alcohols (31)-(34). X-Ray crystallographic data for the cycloadducts (15) and (16b) are presented.

23

Aurich, Hans Günter, and Abdellatif Chair. "1,3-DipoIare Cycloaddition von Dinitronen - Bildung tricyclischer Dimerer / 1,3 -Dipolar Cycloaddition of Dinitrones - Formation of Tricyclic Dimers." Zeitschrift für Naturforschung B 49, no. 7 (July 1, 1994): 963–69. http://dx.doi.org/10.1515/znb-1994-0719.

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Abstract Various dialdehydes (1 -5) were formed by addition of dithiols to acrolein. Reaction of these dialdehydes with N-alkylhydroxylamines afforded dinitrones the two nitrone groups of which were joined by an alkylidene chain containing two sulfur atoms (6a,b-10a,b). Cycloaddition of these dinitrones with dimethyl acetylenedicarboxylate proceeded in the usual way giving bis(4-isoxazolines) (11a-15a).However, analogous dinitrones formed by reaction of the dialdehydes with N-(4-tert-butylphenyl)hydroxylamine could not be isolated. Instead tricyclic compounds arose in whichthe central macrocyclic ring is flanked by two isoxazolidine rings (16c-20c). Obviously, thedinitrones formed as intermediates underwent dimerization with formation of the tricycliccompounds by cycloaddition between two nitrone groups and two tautomeric N-hydroxyenaminemoieties.Two of the tricyclic compounds (16c and 20c) formed 1:1 complexes with NiCl2 and FeCl3,respectively.

24

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 (April 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 of benzyl azide with bicyclo[6.1.0]nonyne. We observed that reactions of nitrones with bicyclo[6.1.0]nonyne showed a stronger dependence on substituent effect for the reaction, as evidenced by a larger Hammett ρ value, than that for biaryl-aza-cyclooctanone. We demonstrate the ability to stereoelectronically tune the reactivity of nitrones towards different cyclooctynes in SPANC reactions. This ability to introduce selectivity into different SPANC reactions through substituent provides the opportunity to perform multiple SPANC reactions in one reaction vessel and opens up potential applications in multiplex labeling.

25

Sherratt, Allison R., Mariya Chigrinova, Craig S. McKay, Louis-Philippe B. Beaulieu, Yanouchka Rouleau, and John Paul Pezacki. "Copper-catalysed cycloaddition reactions of nitrones and alkynes for bioorthogonal labelling of living cells." RSC Adv. 4, no. 87 (2014): 46966–69. http://dx.doi.org/10.1039/c4ra07851a.

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26

Tangara, Salia, Alice Kanazawa, Martine Fayolle, Christian Philouze, Jean-François Poisson, Jean-Bernard Behr, and Sandrine Py. "Short synthesis, X-ray and conformational analysis of a cyclic peracetylated l-sorbose-derived nitrone, a useful intermediate towards N–O-containing d-gluco-iminosugars." New Journal of Chemistry 42, no. 20 (2018): 16735–43. http://dx.doi.org/10.1039/c8nj03868f.

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27

Bilodeau, Didier A., Kaitlyn D. Margison, Noreen Ahmed, Miroslava Strmiskova, Allison R. Sherratt, and John Paul Pezacki. "Optimized aqueous Kinugasa reactions for bioorthogonal chemistry applications." Chemical Communications 56, no. 13 (2020): 1988–91. http://dx.doi.org/10.1039/c9cc09473c.

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We present optimized micelle-assisted aqueous copper(i)-catalyzed alkyne–nitrone cycloaddition involving rearrangement (CuANCR) reactions applicable to bioorthogonal applications, namely membrane-associated peptide modification.

28

Ito, Masayuki, and Chihiro Kibayashi. "Total synthesis of (+)-monomorine I via nitrone cycloaddition route." Tetrahedron 47, no. 45 (November 1991): 9329–50. http://dx.doi.org/10.1016/s0040-4020(01)80881-4.

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29

Wang, Yuzhou, André Hennig, Thomas Küttler, Christian Hahn, Anne Jäger, and Peter Metz. "Total Synthesis of (±)-Thebainone A by Intramolecular Nitrone Cycloaddition." Organic Letters 22, no. 8 (April 6, 2020): 3145–48. http://dx.doi.org/10.1021/acs.orglett.0c00905.

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30

de March, Pedni, Maria Escoda, Marta Figueredo, and Josep Font. "Efficient masking of p-benzoquinone in nitrone cycloaddition chemistry." Tetrahedron Letters 36, no. 47 (November 1995): 8665–68. http://dx.doi.org/10.1016/0040-4039(95)01787-i.

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31

Carruthers, William, Peter Coggins, and John B. Weston. "Nitrone cycloaddition: an approach to the cyclophane alkaloid (±)-lythranidine." J. Chem. Soc., Perkin Trans. 1, no. 3 (1991): 611–16. http://dx.doi.org/10.1039/p19910000611.

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32

Ito, Yoshio, Yoshikazu Kimura, and Shiro Terashima. "Nitrone Cycloaddition Route to the 1β-Methylcarbapenem Key Intermediate." Bulletin of the Chemical Society of Japan 60, no. 9 (September 1987): 3337–40. http://dx.doi.org/10.1246/bcsj.60.3337.

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33

Broggini, Gianluigi, Franco Folcio, Nicola Sardone, Milko Sonzogni, and Gaetano Zecchi. "Synthesis of enantiopure 3-hydroxymethylchromanes via intramolecular nitrone cycloaddition." Tetrahedron: Asymmetry 7, no. 3 (March 1996): 797–806. http://dx.doi.org/10.1016/0957-4166(96)00076-6.

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34

Mukherjee, Subhrangshu, Sukhendu B. Mandal, and Anup Bhattacharjya. "Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides." RSC Advances 2, no. 24 (2012): 8969. http://dx.doi.org/10.1039/c2ra20689g.

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35

Said, Awad I., and Talaat I. El-Emary. "Diastereoselective synthesis of atropisomeric pyrazolyl pyrrolo[3,4-d]isoxazolidines via pyrazolyl nitrone cycloaddition to facially divergent maleimides: intensive NMR and DFT studies." RSC Advances 10, no. 2 (2020): 845–50. http://dx.doi.org/10.1039/c9ra10039c.

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Diastereoselective pyrazole-based atropisomeric cycloadducts were formed by cycloaddition of a pyrazole-based nitrone and maleimides with restricted rotation around C–N bond caused by bulk ortho substitution.

36

Bakthadoss, Manickam, and Mohammad Mushaf. "Intramolecular [3 + 2] nitrone cycloaddition reaction: highly regio and diastereoselective synthesis of bicyclo[3.2.1]octane scaffolds." Organic & Biomolecular Chemistry 18, no. 47 (2020): 9653–59. http://dx.doi.org/10.1039/d0ob01960g.

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Development of a regio- and a diastereoselective protocol for the synthesis of bicyclo[3.2.1]octane frameworks from vinylogous carbonates and N-substituted hydroxylamine hydrochlorides via intramolecular 1,3-dipolar nitrone cycloaddition reaction.

37

Giofrè, Salvatore, Matteo Tiecco, Consuelo Celesti, Salvatore Patanè, Claudia Triolo, Antonino Gulino, Luca Spitaleri, Silvia Scalese, Mario Scuderi, and Daniela Iannazzo. "Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent." Nanomaterials 10, no. 12 (December 18, 2020): 2549. http://dx.doi.org/10.3390/nano10122549.

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Due to their outstanding physicochemical properties, the next generation of the graphene family—graphene quantum dots (GQDs)—are at the cutting edge of nanotechnology development. GQDs generally possess many hydrophilic functionalities which allow their dispersibility in water but, on the other hand, could interfere with reactions that are mainly performed in organic solvents, as for cycloaddition reactions. We investigated the 1,3-dipolar cycloaddition (1,3-DCA) reactions of the C-ethoxycarbonyl N-methyl nitrone 1a and the newly synthesized C-diethoxyphosphorylpropilidene N-benzyl nitrone 1b with the surface of GQDs, affording the isoxazolidine cycloadducts isox-GQDs 2a and isox-GQDs 2b. Reactions were performed in mild and eco-friendly conditions, through the use of a natural deep eutectic solvent (NADES), free of chloride or any metal ions in its composition, and formed by the zwitterionic trimethylglycine as the -bond acceptor, and glycolic acid as the hydrogen-bond donor. The results reported in this study have for the first time proved the possibility of performing cycloaddition reactions directly to the p-cloud of the GQDs surface. The use of DES for the cycloaddition reactions on GQDs, other than to improve the solubility of reactants, has been shown to bring additional advantages because of the great affinity of these green solvents with aromatic systems.

38

Liu, Xianfeng, Lue Xiang, Jiayi Li, Ying Wu, and Ke Zhang. "Stoichiometric imbalance-promoted step-growth polymerization based on self-accelerating 1,3-dipolar cycloaddition click reactions." Polymer Chemistry 11, no. 1 (2020): 125–34. http://dx.doi.org/10.1039/c9py01362h.

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A stoichiometric imbalance-promoted step growth polymerization method was developed based on self-accelerating 1,3-dipolar cycloaddition click reactions of Sondheimer diyne and varied 1,3-dipoles, such as diazo, sydnone, and nitrone groups.

39

Bakthadoss, Manickam, and Jayakumar Srinivasan. "A facile synthesis of isoxazolo[3,4-a]pyrrolizine and isoxazolo[4,3-c]pyridine derivatives via intramolecular nitrone cycloaddition reaction." RSC Advances 5, no. 82 (2015): 67206–9. http://dx.doi.org/10.1039/c5ra10371a.

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Isoxazolo [3,4-a]pyrrolizine and isoxazolo[4,3-c]pyridine are formed by a facile and efficient intramolecular [3 + 2] nitrone cycloaddition, forming two new rings and three contiguous stereocentres with high diastereoselectivity and good yields.

40

Jin, Yuan, Yasuhiro Honma, Hisashi Morita, Masamichi Miyagawa, and Takahiko Akiyama. "Enantioselective Synthesis of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines through 1,3-Dipolar Cycloaddition by a Chiral Phosphoric Acid." Synlett 30, no. 13 (June 27, 2019): 1541–45. http://dx.doi.org/10.1055/s-0039-1690108.

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Abstract:

A new approach is described for the asymmetric synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines that is based on the enantioselective 1,3-dipolar cycloaddition reaction of a nitrone and a vinyl ether in the presence of a chiral phosphoric acid that gives the chiral tetrahydroisoquinolines in high yields and with high enantioselectivities. 1H and 31P NMR analyses of the mixture of nitrone and chiral phosphoric acid suggest the formation of a 1:1 complex.

41

Benchouk, Wafaa, and Sidi Mohamed Mekelleche. "Regio- and diastereoselectivity of the 1,3-dipolar cycloaddition of α-aryl nitrone with methacrolein. A theoretical investigation." RSC Advances 5, no. 28 (2015): 22126–34. http://dx.doi.org/10.1039/c4ra17285j.

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Abstract:

The mechanism, regio- and diastereoselectivity of the 1,3-dipolar cycloaddition of N-iso-propyl,α-(4-trifluoromethyl)-phenyl nitrone with methacrolein yielding the isoxazolidine cycloadduct has been studied at the B3LYP/6-31G(d) level of theory.

42

Salehi, Yasser, and Mahshid Hamzehloueian. "The strain-promoted alkyne-nitrone and alkyne-nitrile oxide cycloaddition reactions: A theoretical study." Tetrahedron 73, no. 31 (August 2017): 4634–43. http://dx.doi.org/10.1016/j.tet.2017.06.038.

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43

Zhong, Jiaxin, Haibing He, and Shuanhu Gao. "Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids." Organic Chemistry Frontiers 6, no. 22 (2019): 3781–85. http://dx.doi.org/10.1039/c9qo01111k.

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44

Ríos-Gutiérrez, Mar, Andrea Darù, Tomás Tejero, Luis R. Domingo, and Pedro Merino. "A molecular electron density theory study of the [3 + 2] cycloaddition reaction of nitrones with ketenes." Organic & Biomolecular Chemistry 15, no. 7 (2017): 1618–27. http://dx.doi.org/10.1039/c6ob02768g.

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Abstract:

The zw-type 32CA reactions of nitrones with ketenes are controlled by the nucleophilic character of the nitrone and the electrophilic character of the ketene. They are chemo- and regio-selective and the use of electrophilic ketenes changes the mechanism from one-step to two-step.

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Brandi, Alberto, Silvio Carli, and Andrea Goti. "High Regio- and Stereoselective Cycloaddition of a Nitrone to Alkylidenecyclopropanes." HETEROCYCLES 27, no. 1 (1988): 17. http://dx.doi.org/10.3987/com-87-4312.

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46

Chiacchio, Ugo, Giuseppe Buemi, Francesco Casuscelli, Antonio Procopio, Antonio Rescifina, and Roberto Romeo. "Stereoselective synthesis of fused γ-lactams by intramolecular nitrone cycloaddition." Tetrahedron 50, no. 18 (May 1994): 5503–14. http://dx.doi.org/10.1016/s0040-4020(01)80705-5.

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47

Dugovič, Branislav, Lubor Fišera, Christian Hametner, and Nada Prónayová. "Diastereoselectivity of nitrone 1,3-dipolar cycloaddition to Baylis-Hillman adducts." Arkivoc 2003, no. 14 (December 15, 2003): 162–69. http://dx.doi.org/10.3998/ark.5550190.0004.e15.

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48

Heppt, L. R., J. Bordner, and T. A. Bryson. "Unusual cycloaddition of an unsaturated nitrone to a vinylogous ester." Tetrahedron Letters 26, no. 5 (January 1985): 595–98. http://dx.doi.org/10.1016/s0040-4039(00)89156-x.

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49

Basak, Amit, Hassam M. M. Bdour, and Gautam Bhattacharya. "AN ENANTIOSPECIFIC NITRONE CYCLOADDITION ROUTE TO 3-HYDROXY-2-AZETIDINONES." Tetrahedron Letters 38, no. 14 (April 1997): 2535–38. http://dx.doi.org/10.1016/s0040-4039(97)00394-8.

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50

Annunziata, Rita, Mauro Cinquini, Franco Cozzi, Paola Giaroni, and Laura Raimondi. "The diastereoselectivity of intermolecular nitrone cycloaddition to chiral allyl derivatives." Tetrahedron Letters 32, no. 13 (March 1991): 1659–62. http://dx.doi.org/10.1016/s0040-4039(00)74298-5.

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