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Journal articles on the topic 'Pyridinium Ylides'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Pidlypnyi, Nazar, Sandra Kaul, Sebastian Wolf, Martin H. H. Drafz, and Andreas Schmidt. "Syntheses and Characterization of N-(Indolyl)pyridinium Salts and of Their Ylides." Zeitschrift für Naturforschung B 69, no. 5 (2014): 605–14. http://dx.doi.org/10.5560/znb.2014-3324.

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3-Methylindole reacts with pyridines in the presence of NBS to give indol-2-yl-pyridinium salts which were converted into their ylides by an anion exchange resin in its hydroxide form. Indol-3- amine was subjected to a nucleophilic ring transformation with pyrylium salts which resulted in the formation of indol-3-yl-pyridinium salts, the 2,4,6-trimethylpyridinium derivative of which proved to be unstable. The 2,4,6-triphenylpyridinium derivate was deprotonated to the corresponding ylide. The isomeric indol-2-yl and indol-3-yl derivatives are cycloimmonium ylides which are members of the compou

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2

Theato, Patrick, and Daniel Klinger. "Synthesis of Photoreactive Block Copolymers Based on 1-Iminopyridinium Ylides." Australian Journal of Chemistry 63, no. 8 (2010): 1164. http://dx.doi.org/10.1071/ch10079.

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Two photoreactive pyridinium ylide containing monomers, {[2-(metacryloyloxy)ethoxy]carbonyl}(pyridinium-1-yl)azanide (M1) and pyridinium-1-yl-(4-vinylbenzoyl)azanide (M2), were synthesized. Both monomers were polymerized under controlled radical polymerization conditions, i.e. reversible addition–fragmentation chain transfer polymerization (M1 and M2) and nitroxide-mediated polymerization (M2). Further block copolymers PMMA-b-PM1 and PS-b-PM2 were successfully synthesized and their molecular weight, Mn, and block ratio could be determined by 1H NMR analysis, thereby opening the synthetic possi

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3

Shustov, Gennady V., Michael TH Liu, and K. N. Houk. "Facile formation of azines from reactions of singlet methylene and dimethylcarbene with precursor diazirines: theoretical explorations." Canadian Journal of Chemistry 77, no. 5-6 (1999): 540–49. http://dx.doi.org/10.1139/v99-012.

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The reactions of the singlet methylene (1a) and dimethylcarbene (1b), with their diazirine precursors, diazirine (2a), and dimethyldiazirine (2b), have been studied theoretically using ab initio and density functional theory. The reaction has no activation barriers for the parent system (1a + 2a) and proceeds via a reactive complex and a transition state with a small negative enthalpy of activation Δ Hnot =298 = -1.1 kcal mol-1, ΔSnot =298 = -34.4 cal mol-1 K-1, ΔG°298 = 9.2 kcal mol-1) for the dimethyl derivatives (1b + 2b). The formation of N-methylene diazirinium ylides (3a,b) is exothermic

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4

Seifi, Mohammad, S. Yousef Ebrahimipour, Jim Simpson, Michal Dusek, Vaclav Eigner, and Hassan Sheibani. "Combination of Pyridinium and Isoquinolinium Ylides with Phenylisocyanate and Isothiocyanates: Synthesis, Characterisation, and X-Ray Crystal Structures of Mesoionic Monosubstituted 3-Oxo-Propanamides or Thioamides." Australian Journal of Chemistry 68, no. 10 (2015): 1577. http://dx.doi.org/10.1071/ch15113.

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Pyridinium ylides derived from 2-bromoacetophenone or methyl bromoacetate have been reacted with phenylisocyanate, phenyl- or methylisothiocyanate to afford mesoionic monosubstituted 3-oxo-propanamides or thioamides, via self-protonation of the intermediate N-anion. A similar reaction under the same conditions of isoquinolinium ylides with phenylisocyanate or phenyisothiocyante also produced the corresponding mesoionic compounds. In order to establish the exact structure of the mesoionic compounds, single crystal X-ray structures were obtained for three of the pyridinium ylides.

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5

Liao, Fan, Wenhuan Huang, Biao Chen, et al. "Are pyridinium ylides radicals?" Chemical Communications 56, no. 76 (2020): 11287–90. http://dx.doi.org/10.1039/d0cc04604c.

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6

Grünefeld, Johann, Wolfgang Kliegel, Steven J. Rettig, and James Trotter. "Reaction of diphenylborinic acid with pyridinium and phosphonium bisacyl methylides. Crystal and molecular structures of resulting B,N- and B,P-betaines." Canadian Journal of Chemistry 77, no. 4 (1999): 439–50. http://dx.doi.org/10.1139/v99-067.

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Reaction of pyridinium and phosphonium 2-carboxy-1-formyl-2-oxoethylides with oxybis(diphenylborane) yields 5-(2-oxo-1-(pyridinio or phosphonio)ethylidene)-2,2-diphenyl-1,3-dioxa-2-borata-4-cyclopentanones, which represent novel types of boron nitrogen and boron phosphorus betaines, respectively. Crystals of 5-(2-oxo-1-pyridinioethylidene)-2,2-diphenyl-1,3-dioxa-2-borata-4-cyclopentanone,1a, are monoclinic, a = 15.589(3), b = 12.366(2), c = 20.1869(11) Å, β = 111.227(2)°, Z = 8 (two independent molecules), space group P21/a; and those of 5-[2-oxo-1-(triphenylphosphonio)ethylidene]-2,2-diphenyl

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7

Motornov, Vladimir A., Andrey A. Tabolin, Yulia V. Nelyubina, Valentine G. Nenajdenko, and Sema L. Ioffe. "Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines." Organic & Biomolecular Chemistry 17, no. 6 (2019): 1442–54. http://dx.doi.org/10.1039/c8ob03126f.

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8

Popa, Marcel Mirel, Emilian Georgescu, Mino R. Caira, et al. "Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively." Beilstein Journal of Organic Chemistry 11 (June 26, 2015): 1079–88. http://dx.doi.org/10.3762/bjoc.11.121.

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The three possible structural isomers of 4-(pyridyl)pyrimidine were employed for the synthesis of new pyrrolo[1,2-c]pyrimidines and new indolizines, by 1,3-dipolar cycloaddition reaction of their corresponding N-ylides generated in situ from their corresponding cycloimmonium bromides. In the case of 4-(3-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine the quaternization reactions occur as expected at the pyridine nitrogen atom leading to pyridinium bromides and consequently to new indolizines via the corresponding pyridinium N-ylides. However, in the case of 4-(2-pyridyl)pyrimidine the steric h

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9

Choyal, Manisha. "Structural parameters of N-heterocyclic pyridinium methylides - A DFT study." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 35, no. 02 (2025): 342. https://doi.org/10.59467/ijhc.2025.35.342.

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The present communication includes an investigation of the structural parameters of nitrogen ylides present in differently substituted pyridine rings generated as a chemical intermediate during the formation of functionalized indolizine derivatives via [3+2]/1,3-dipolar cycloaddition. Remarkable experimental observations such as hydrogen bonding and delocalization of charge density have been made through computational calculation based on geometry optimization of ylides.. KEYWORDS :Cycloaddition reactions, Density functional theory, N-Heterocyclic ylides, Stereoelectronic effects.

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10

Cui, Zhaohui, Kuan Zhang, Lijie Gu, Zhanwei Bu, Junwei Zhao, and Qilin Wang. "Diastereoselective trifunctionalization of pyridinium salts to access structurally crowded azaheteropolycycles." Chemical Communications 57, no. 74 (2021): 9402–5. http://dx.doi.org/10.1039/d1cc03478b.

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A highly diastereoselective dearomative trifunctionalization of pyridinium salts with multifunctional o-hydroxy aromatic azomethine ylides has been established to assemble challenging and architecturally crowded fused pentacycles.

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11

Aksenov, Alexander V., Nikolai A. Arutiunov, Nikita K. Kirilov, et al. "[3 + 2]-Annulation of pyridinium ylides with 1-chloro-2-nitrostyrenes unveils a tubulin polymerization inhibitor." Organic & Biomolecular Chemistry 19, no. 33 (2021): 7234–45. http://dx.doi.org/10.1039/d1ob01141c.

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12

Quan, Bao-Xue, Jun-Rui Zhuo, Jian-Qiang Zhao, et al. "[4 + 1] annulation reaction of cyclic pyridinium ylides with in situ generated azoalkenes for the construction of spirocyclic skeletons." Organic & Biomolecular Chemistry 18, no. 10 (2020): 1886–91. http://dx.doi.org/10.1039/c9ob02733e.

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13

LITVINOV, V. P. "ChemInform Abstract: Pyridinium Ylides in Organic Synthesis. Part 3. Pyridinium Ylides as Dipoles in Cycloaddition Reactions." ChemInform 27, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.199632319.

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14

Kakehi, Akikazu. "Reactions of Pyridinium N-Ylides and Their Related Pyridinium Salts." HETEROCYCLES 85, no. 7 (2012): 1529. http://dx.doi.org/10.3987/rev-12-735.

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15

Bayazit, Mustafa Kemal, Nihat Celebi, Selcuk Gumus, and Lemi Turker. "An experimental and theoretical approach to synthesis of novel indolizine type heterocycles." Celal Bayar Üniversitesi Fen Bilimleri Dergisi 16, no. 2 (2020): 129–34. https://doi.org/10.18466/cbayarfbe.457856.

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1,3-Dipolar cycloaddition reactions of certain pyridinium ylides with various dipolarophiles were studied. Synthesis of new indolizine heterocycles was achieved. The new indolizine systems were characterized spectroscopically. A theoretical study of the reactions was accomplished at FMO level (PM3-RHF calculations).

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16

Sliwa, Wanda. "Cycloaddition Reactions of Pyridinium Ylides and Oxidopyridiniums." HETEROCYCLES 43, no. 9 (1996): 2005. http://dx.doi.org/10.3987/rev-96-478.

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17

Tomilov, Yu V., D. N. Platonov, D. V. Dorokhov, and O. M. Nefedov. "Reactions of alkyl diazoacetates with pyridinium ylides." Russian Chemical Bulletin 54, no. 4 (2005): 1008–12. http://dx.doi.org/10.1007/s11172-005-0349-6.

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18

Jacobs, Jan, Eva Van Hende, Sven Claessens, and Norbert De Kimpe. "ChemInform Abstract: Pyridinium Ylides in Heterocyclic Synthesis." ChemInform 42, no. 40 (2011): no. http://dx.doi.org/10.1002/chin.201140236.

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19

LITVINOV, V. P., and A. M. SHESTOPALOV. "ChemInform Abstract: Pyridinium Ylides in Organic Synthesis. Part 4. Pyridinium Ylides in Nucleophilic Addition-Elimination (AdN-E) Reactions." ChemInform 29, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199838335.

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20

Zhou, Jian, Yuefei Hu, and Hongwen Hu. "Synthesis of 5-(2-Phenylethenyl)indolizines by Selective Intermolecular 1,3-Dipolar Cycloaddition of 2-(2-Phenylethenyl)pyridinium N-Ylide with Alkenes Promoted by Tetrakis-pyridine Cobalt(II) Dichromate." Journal of Chemical Research 23, no. 2 (1999): 136–37. http://dx.doi.org/10.1177/174751989902300235.

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Intermolecular 1,3-dipolar cycloadditions of 2-(2-phenylethenyl)pyridinium N-ylides (3a–d) with electron-deficient alkenes (5a–d) were carried out selectively in the presence of tetrakis-pyridine cobalt(II) dichromate to yield 5-(2-phenylethenyl)indolizines (6a–j) in moderate yields (48–63%).

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21

Kakehi, Akikazu. "ChemInform Abstract: Reactions of Pyridinium N-Ylides and Their Related Pyridinium Salts." ChemInform 43, no. 41 (2012): no. http://dx.doi.org/10.1002/chin.201241224.

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22

Funt, Liya D., Mikhail S. Novikov, and Alexander F. Khlebnikov. "New applications of pyridinium ylides toward heterocyclic synthesis." Tetrahedron 76, no. 35 (2020): 131415. http://dx.doi.org/10.1016/j.tet.2020.131415.

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23

Kokkinidis, George, Evangelia Hatzigrigoriou, Dimitra Sazou, and Anastasios Varvoglis. "Electrochemical reduction of some pyridinium and sulfonium ylides." Electrochimica Acta 36, no. 1 (1991): 101–7. http://dx.doi.org/10.1016/0013-4686(91)85186-b.

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24

Padwa, Albert, David J. Austin, Laura Precedo, and Lin Zhi. "Cycloaddition reactions of pyridinium and related azomethine ylides." Journal of Organic Chemistry 58, no. 5 (1993): 1144–50. http://dx.doi.org/10.1021/jo00057a029.

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25

Chuang, Che-Ping, and An-I. Tsai. "Pyridinium Ylides in the Synthesis of 2,3-Dihydrofurans." Synthesis 2006, no. 04 (2006): 675–79. http://dx.doi.org/10.1055/s-2006-926300.

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26

Alvarez-Builla, J., E. Gálvez, A. M. Cuadro, F. Florencio, and S. Garcia Blanco. "Synthesis and structure of dithioester stabilised pyridinium ylides." Journal of Heterocyclic Chemistry 24, no. 4 (1987): 917–26. http://dx.doi.org/10.1002/jhet.5570240406.

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27

Kakehi, Akikazu. "Preparation of New Nitrogen-Bridged Heterocycles Using Pyridinium N-Ylides and Pyridinium Salts." Journal of Synthetic Organic Chemistry, Japan 63, no. 3 (2005): 222–31. http://dx.doi.org/10.5059/yukigoseikyokaishi.63.222.

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28

Ma, Yangyang, Hua Zhang, Xiaoxiao Du та ін. "β,β-Difluoro Peroxides as Fluorinated C2-Building Blocks for the Construction of Functionalized Indolizines". Molecules 29, № 24 (2024): 5927. https://doi.org/10.3390/molecules29245927.

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An effective method for the construction of functionalized indolizines has been developed in which β,β-difluoro peroxides act as novel C2-building blocks to implement [3+2] annulation with pyridinium ylides under base-mediated conditions. With this protocol, a broad range of multisubstituted indolizines were prepared in moderate to good yields under mild conditions, and many useful functional groups were tolerated.

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29

Ballesteros, Rafael, Belen Abarca, and Gurnos Jones. "Triazolopyrideines. 15. Reaction between Triazolo-pyridinium Ylides and Alkenes." HETEROCYCLES 35, no. 2 (1993): 851. http://dx.doi.org/10.3987/com-92-s(t)68.

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30

Jung, Young-Sik, and Jae-Yun Jaung. "Halochromism of pyridinium azomethine ylides stabilized by dicyanopyrazine group." Dyes and Pigments 65, no. 3 (2005): 205–9. http://dx.doi.org/10.1016/j.dyepig.2004.07.020.

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31

SLIWA, W. "ChemInform Abstract: Cycloaddition Reactions of Pyridinium Ylides and Oxidopyridiniums." ChemInform 28, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199706313.

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32

Belguedj, Roumaissa, Abdelmalek Bouraiou, Sofiane Bouacida, Hocine Merazig, and Aissa Chibani. "Pyridinium ylides in the one-pot synthesis of a new quinoline/indolizine hybrid." Zeitschrift für Naturforschung B 70, no. 12 (2015): 885–87. http://dx.doi.org/10.1515/znb-2015-0118.

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AbstractThe reaction of 1-(quinolin-2-ylmethyl)pyridinium ylide with dimethyl acetylenedicarboxylate was investigated. The X-ray crystallographic characterization of the new dimethyl 3-(quinolin-2-yl)indolizine-1,2-dicarboxylate (2) shows the formation of a five-membered ring between the pyridine ring and the methylene group.

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33

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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34

K., C. GUPTA, and MANGLUM P. "Synthesis of 2-Arylindoles via Aza-ring Closure of Sulphonium Salts." Journal of Indian Chemical Society Vol. 65, Mar 1988 (1988): 223–25. https://doi.org/10.5281/zenodo.6090178.

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Department of Chemistry, D. V. (P. G.) College, Orai-285 001 <em>Manuscript received 23 September 1987, revised 6 January 1988, accepted 13 January 1988</em> MANY routes have been devised to synthesise 2- arylindoles, but the methods are not versatile because the reactions involve drastic reaction conditions. Hirroze <em>et al.</em><sup>1</sup> reported the reaction of <em>N</em>-phenacylpyridinium bromide with anilines to furnish 2-phenylindoles. Junjappa<sup>2 </sup>extended this reaction using phenacyldimethylsulphonium bromide. Bansal <em>et al</em>. <sup>3,4</sup>  reported the synth

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35

LaVilla, Joseph A., and Joshua L. Goodman. "The thermodynamics of the formation of pyridinium ylides from carbienes." Tetrahedron Letters 31, no. 44 (1990): 6287–90. http://dx.doi.org/10.1016/s0040-4039(00)97044-8.

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36

Zhang, Xue-chun, and Wei-yuan Huang. "Cycloaddition reactions of N-(cyanomethyl)pyridinium ylides with 2,2-dihydropolyfluoroalkanoates." Journal of Fluorine Chemistry 92, no. 1 (1998): 13–16. http://dx.doi.org/10.1016/s0022-1139(98)00241-3.

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37

Shestopalov, A. M., Yu A. Sharanin, I. A. Aitov, V. N. Nesterov, Yu T. Struchkov, and V. P. Litvinov. "Electronic regioselectivity in the reactions of pyridinium ylides with tetracyanoethylene." Chemistry of Heterocyclic Compounds 27, no. 8 (1991): 872–78. http://dx.doi.org/10.1007/bf00472289.

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38

Shestopalov, A. M., Yu A. Sharanin, and V. P. Litvinov. "Stereochemistry of the reaction of pyridinium ylides with ?,?-unsaturated nitriles." Chemistry of Heterocyclic Compounds 26, no. 3 (1990): 311–17. http://dx.doi.org/10.1007/bf00472552.

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39

SHESTOPALOV, A. M., YU A. SHARANIN, I. A. AITOV, et al. "ChemInform Abstract: Electron Regioselective Reaction of Pyridinium Ylides with Tetracyanoethylene." ChemInform 24, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199311216.

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40

PADWA, A., D. J. AUSTIN, L. PRECEDO, and L. ZHI. "ChemInform Abstract: Cycloaddition Reactions of Pyridinium and Related Azomethine Ylides." ChemInform 24, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199323089.

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41

Bucher, Götz. "Sulfene−Pyridine Adducts: Lewis Acid/Base Complexes, Ylides, Pyridinium Sulfinate Zwitterions, or Carbene Ylide/SO2 Complexes?" European Journal of Organic Chemistry 2003, no. 19 (2003): 3868–74. http://dx.doi.org/10.1002/ejoc.200300292.

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42

Dawood, Kamal M., Eman A. Ragab, and Sanaa N. Mohamed. "Synthesis of Some New Indolizine and Pyrrolo[1,2-a]quinoline Derivatives via Nitrogen Ylides." Zeitschrift für Naturforschung B 64, no. 4 (2009): 434–38. http://dx.doi.org/10.1515/znb-2009-0413.

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Pyridine and quinoline react with 3-bromoacetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile (2) in dry benzene to give the corresponding pyridinium and quinolinium salts 3 and 9. The latter salts undergo [3+2] 1,3-dipolar cycloaddition with some acetylene and ethylene derivatives to give the corresponding indolizine and pyrrolo[1,2-a]quinoline derivatives

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43

Hori, Mikio, Tadashi Kataoka, Hiroshi Shimizu, et al. "Ylide-induced Ylide Formation: A Thermal Reaction and a Double Cycloaddition Reaction of [1,2,4]Triazolo[1,5-a]pyridinium Ylides." HETEROCYCLES 24, no. 9 (1986): 2563. http://dx.doi.org/10.3987/r-1986-09-2563.

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44

Yokoe, Ichiro, Shunsuke Matsumoto, Yoshiaki Shirataki, and Manki Komatsu. "1,3-Dipolar Cycloaddition Reaction of Chromones and Coumarin with Pyridinium Ylides." HETEROCYCLES 23, no. 6 (1985): 1395. http://dx.doi.org/10.3987/r-1985-06-1395.

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45

Matsuda, Yoshiro, Makoto Yamashita, Kimitoshi Takahashi, et al. "Studies on Pyridinium N-Ylides: One Step Synthesis of Heteropolycycles, Indolizinoquinolizines." HETEROCYCLES 34, no. 5 (1992): 899. http://dx.doi.org/10.3987/com-92-5992.

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46

Allgäuer, Dominik S., Peter Mayer, and Herbert Mayr. "Nucleophilicity Parameters of Pyridinium Ylides and Their Use in Mechanistic Analyses." Journal of the American Chemical Society 135, no. 40 (2013): 15216–24. http://dx.doi.org/10.1021/ja407885h.

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47

Gololobov, Yu G., O. V. Dovgan, I. Yu Krasnova, P. V. Petrovskii, and I. A. Garbuzova. "Reversible C→N migration of the ethoxycarbonyl group in pyridinium ylides." Russian Chemical Bulletin 49, no. 8 (2000): 1490. http://dx.doi.org/10.1007/bf02495109.

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48

Albrecht, Marcel, Maxim Yulikov, Thomas Kohn, Gunnar Jeschke, Jörg Adams, and Andreas Schmidt. "Pyridinium salts and ylides as partial structures of photoresponsive Merrifield resins." Journal of Materials Chemistry 20, no. 15 (2010): 3025. http://dx.doi.org/10.1039/b919862h.

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49

Day, Jonathan, Maliha Uroos, Richard A. Castledine, William Lewis, Ben McKeever-Abbas, and James Dowden. "Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides." Organic & Biomolecular Chemistry 11, no. 38 (2013): 6502. http://dx.doi.org/10.1039/c3ob41415a.

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50

Dega-Szafran, Z., G. Schroeder, M. Szafran, A. Szwajca, B. Łęska, and M. Lewandowska. "Experimental and quantum chemical evidences for C–H⋯N hydrogen bonds involving quaternary pyridinium salts and pyridinium ylides." Journal of Molecular Structure 555, no. 1-3 (2000): 31–42. http://dx.doi.org/10.1016/s0022-2860(00)00585-8.

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