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Journal articles on the topic 'Phenylsydnone'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Schmidt, Andreas, Ana-Luiza Lücke, Sascha Wiechmann, and Tyll Freese. "Suzuki–Miyaura Cross-Coupling Reactions in Acetic Acid Employing Sydnone-Derived Catalyst Systems." Synlett 28, no. 15 (2017): 1990–93. http://dx.doi.org/10.1055/s-0036-1589059.

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The catalyst system consisting of lithium N-phenylsydnone-4-carboxylate/Pd(PPh3)4 has proven to be an effective catalyst for the Suzuki–Miyaura reaction of 2,4-dinitrochlorobenzene with boronic acids in acetic acid at pH 5.7, whereas the N-phenylsydnone carbene palladium complex [sydPd(PPh3)2Br] required pH 8.0.

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2

Lücke, Ana-Luiza, Sascha Wiechmann, Tyll Freese, Zong Guan, and Andreas Schmidt. "Palladium complexes of anionic N-heterocyclic carbenes derived from sydnones in catalysis." Zeitschrift für Naturforschung B 71, no. 6 (2016): 643–50. http://dx.doi.org/10.1515/znb-2016-0006.

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AbstractThe anion of N-phenylsydnone, which can be generated on treatment of N-phenylsydnone with cyanomethyllithium without decomposition, can be represented as tripolar zwitterionic and as anionic N-heterocyclic carbene resonance forms. Its palladium complex was prepared from 4-bromo-3-phenylsydnone and tetrakis(triphenylphosphine)palladium and proved to be active as catalyst in Suzuki-Miyaura reactions. Thus, 2,5-dibromo-3,4-dinitrothiophene was effectively converted into 2,5-diaryl-3,4-dinitrothiophenes with 1-naphthyl, (4-trifluoromethoxy)phenyl, [4-(methylsulfanyl)phenyl], and biphenyl-4

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3

Fun, Hoong-Kun, Tze Shyang Chia, Nithinchandra, Balakrishna Kalluraya, and Shobhitha Shetty. "4-Bromoacetyl-3-phenylsydnone." Acta Crystallographica Section E Structure Reports Online 68, no. 7 (2012): o2103. http://dx.doi.org/10.1107/s1600536812026049.

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4

Tullis, S. A., and K. Turnbull. "Acylation and Aroylation of 3-Phenylsydnone." Synthetic Communications 20, no. 20 (1990): 3137–44. http://dx.doi.org/10.1080/00397919008051537.

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5

Jogul, Johnson J., Mohammedshafi A. Phaniband, S. R. Pattan, and B. V. Badami†. "Synthesis and biological evaluation of 3-[p-(heterocyclocarbonyl)]phenylsydnones from the versatile precursor, 3-[p-(hydrazinocarbonyl)]phenylsydnone." Main Group Chemistry 8, no. 4 (2009): 337–47. http://dx.doi.org/10.1080/10241220903377523.

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6

Abdul Ajees, A., S. Karthikeyan, C. V. Yelamaggad, and B. V. Badami. "4-(2-Benzoylhydrazinothiazol-4-yl)-3-phenylsydnone." Acta Crystallographica Section E Structure Reports Online 58, no. 7 (2002): o784—o786. http://dx.doi.org/10.1107/s1600536802010668.

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7

Pruschinski, Lucas, Ana-Luiza Lücke, Tyll Freese, Sean-Ray Kahnert, Sebastian Mummel, and Andreas Schmidt. "Suzuki–Miyaura Cross-Couplings under Acidic Conditions." Synthesis 52, no. 06 (2019): 882–92. http://dx.doi.org/10.1055/s-0039-1691487.

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Suzuki–Miyaura reactions with Pd(PPh3)4 have been carried out using lithium N-phenylsydnone-4-carboxylate as additive, which gave best yields at pH 5.7 in a mixture of acetic acid, water, and sodium carbonate. Reaction parameters such as the Pd source, the solvent, reaction time and temperature, acid, base and carboxylate have been varied and some representative examples of the Suzuki–Miyaura reaction have been examined.

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8

Grossie, D., L. Harrison, and K. Turnbull. "Crystal structure of 4-(2-bromopropionyl)-3-phenylsydnone." Acta Crystallographica Section E Structure Reports Online 70, no. 11 (2014): o1165—o1166. http://dx.doi.org/10.1107/s1600536814022260.

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Sydnones are a class of mesoionic compounds containing a five-membered heterocyclic ring. In general, sydnone compounds are synthesized with an aromatic substutuent at the N3position. This feature, adds to the stability of the heterocyclic ring. In the title compound {systematic name: 4-(2-bromopropanoyl)-3-phenyl-1,2,3λ5-oxadiazol-3-ylium-5-olate}, C11H9BrN2O3, the aromatic substitutent is an unsubstituted phenyl ring. The sydnone ring is almost planar, with a maximum deviation from the mean plane of 0.023 (1) Å, but is not coplanar with the phenyl ring, having a dihedral angle of 40.93 (8)°.

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9

TULLIS, S. A., and K. TURNBULL. "ChemInform Abstract: Acylation and Aroylation of 3-Phenylsydnone." ChemInform 22, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.199115172.

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10

Kawase, Masami, Ryosuke Saijo, Shigeki Mori, and Hidemitsu Uno. "Synthesis and Crystal Structure of 4-Trifluoroacetyl-3-phenylsydnone." HETEROCYCLES 94, no. 11 (2017): 2103. http://dx.doi.org/10.3987/com-17-13802.

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11

Balaguer, Amanda, Ryan Selhorst, and Kenneth Turnbull. "Metal Triflate–Catalyzed Friedel–Crafts Acetylation of 3-Phenylsydnone." Synthetic Communications 43, no. 12 (2013): 1626–32. http://dx.doi.org/10.1080/00397911.2012.657384.

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12

Turnbull, Kenneth, Douglas M. Krein, and Scott A. Tullis. "Alkynylation of 4-Bromo-3-phenylsydnone with Aryl Acetylenes." Synthetic Communications 33, no. 13 (2003): 2209–14. http://dx.doi.org/10.1081/scc-120021499.

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13

Prashant, R. Latthe, and V. Badami Bharati. "Synthesis and tiiological activity of some N-aryl-4-(5-methyl-[1,3,4]-oxadiazolin- 2-one-3-yl) substituted benzamides from 3-(4-carboxy)phenylsydnone." Journal of Indian Chemical Society Vol. 83, Oct 2006 (2006): 1049–51. https://doi.org/10.5281/zenodo.5831392.

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P. G. Department of Chemistry, Karnatak University, Dharwad-580 003, Karnataka. India <em>E-mail </em>: bbadami@rediffmail.com <em>Manuscript received 11 April 2005, revised 8 May 2006, accepted 31 July 2006</em> The title compounds N-aryl-4-(5-methyl-[1,3,4]-oxadiazolin-2-one-3-yl) substituted benzamides (5a-h) were synthesized from 3-(4-carboxy)phenylsydnone (1) by using one-pot ring conversion reaction of sydnone to 1,3,4-oxadiazolin- 2-one. Preliminary antimicrobial screening of these compounds exhibited higher activity for some of them as compared to the reference drugs used.

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14

Cherepanov, I. A., S. N. Lebedev, and V. N. Kalinin. "Functionalised Sydnones Through a Facile Metallation of 3-Methyl-4-Phenylsydnone." Synlett 1998, no. 6 (1998): 667. http://dx.doi.org/10.1055/s-1998-1739.

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15

Balaguer, Amanda, Ryan Selhorst, and Kenneth Turnbull. "ChemInform Abstract: Metal Triflate-Catalyzed Friedel-Crafts Acetylation of 3-Phenylsydnone." ChemInform 44, no. 31 (2013): no. http://dx.doi.org/10.1002/chin.201331141.

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16

NARLA, RAJA SEKHAR, and M. N. A. RAO. "Scavenging of Free-radicals and Inhibition of Lipid Peroxidation by 3-Phenylsydnone." Journal of Pharmacy and Pharmacology 47, no. 8 (1995): 623–25. http://dx.doi.org/10.1111/j.2042-7158.1995.tb05847.x.

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17

Cherepanov, I. A., S. N. Lebedev, and V. N. Kalinin. "3-Lithiomethyl-4-phenylsydnone: A new type of organometallic derivatives of sydnones." Russian Chemical Bulletin 47, no. 9 (1998): 1725–27. http://dx.doi.org/10.1007/bf02495693.

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18

McGowin, A. E., L. Jackson, L. W. Marshall, and K. Tumbull. "1,3-DIPOLAR CYCLOADDITIONS OF 3-PHENYLSYDNONE WITH ACETYLENE DICARBOXYLATES IN SUPERCRITICAL CARBON DIOXIDE." Organic Preparations and Procedures International 33, no. 1 (2001): 100–102. http://dx.doi.org/10.1080/00304940109356581.

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19

CHEREPANOV, I. A., S. N. LEBEDEV, and V. N. KALININ. "ChemInform Abstract: Functionalized Sydnones Through a Facile Metalation of 3-Methyl-4-phenylsydnone." ChemInform 29, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199839133.

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20

Fun, Hoong-Kun, Wan-Sin Loh, Nithinchandra, Balakrishna Kalluraya, and Suresh P. Nayak. "4-[4-Ethoxycarbonyl-5-(3,4-methylenedioxyphenyl)-3-oxocyclohex-1-en-1-yl]-3-phenylsydnone." Acta Crystallographica Section E Structure Reports Online 66, no. 9 (2010): o2367—o2368. http://dx.doi.org/10.1107/s1600536810033106.

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21

CHEREPANOV, I. A., S. N. LEBEDEV, and V. N. KALININ. "ChemInform Abstract: 3-Lithiomethyl-4-phenylsydnone: A New Type of Organometallic Derivatives of Sydnones." ChemInform 29, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199852160.

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22

Fun, Hoong-Kun, Wan-Sin Loh, Nithinchandra, and Balakrishna Kalluraya. "4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenylsydnone." Acta Crystallographica Section E Structure Reports Online 67, no. 5 (2011): o1177—o1178. http://dx.doi.org/10.1107/s1600536811013912.

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23

McGowin, A. E., L. Jackson, L. W. Marshall, and K. Turnbull. "ChemInform Abstract: 1,3-Dipolar Cycloadditions of 3-Phenylsydnone with Acetylene Dicarboxylates in Supercritical Carbon Dioxide." ChemInform 32, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.200126115.

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24

Ueng, C. H., Y. Wang, and M. Y. Yeh. "Structures of 4-acetyl-3-(p-tolyl)sydnone (1) and 4-acetyl-3-phenylsydnone oxime (2)." Acta Crystallographica Section C Crystal Structure Communications 43, no. 6 (1987): 1122–25. http://dx.doi.org/10.1107/s0108270187092801.

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25

Totoe, Harriet, Audrey E. McGowin, and Kenneth Turnbull. "Selectivity of 1,3-dipolar cycloaddition of methyl propiolate to 3-phenylsydnone in near- or supercritical carbon dioxide." Journal of Supercritical Fluids 18, no. 2 (2000): 131–40. http://dx.doi.org/10.1016/s0896-8446(00)00060-7.

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26

Turnbull, Kenneth, and Douglas M. Krein. "The sydnone ring as an ortho-director of lithiation. Dilithiation of 3-phenylsydnone and trapping by electrophiles." Tetrahedron Letters 38, no. 7 (1997): 1165–68. http://dx.doi.org/10.1016/s0040-4039(97)00015-4.

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27

García de la Concepción, Juan, Pedro Cintas, and Rafael Fernando Martínez. "Understanding Bio-Orthogonal Strain-Driven Sydnone Cycloadditions: Data-Assisted Profiles and the Search for Linear Relationships." Molecules 30, no. 13 (2025): 2770. https://doi.org/10.3390/molecules30132770.

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In the realm of click-type reactions and their application to bioorthogonal chemistry in living organisms, metal-free [3+2] cycloadditions involving mesoionic rings and strained cycloalkynes have gained increasing attention and potentiality in recent years. While there has been a significant accretion of experimental data, biological assays, and assessments of reaction mechanisms, some pieces of the tale are still missing. For instance, which structural and/or stereoelectronic effects are actually interlocked and which remain unplugged. With the advent of data-driven methods, including machine

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28

Fun, Hoong-Kun, Madhukar Hemamalini, Nithinchandra, and Balakrishna Kalluraya. "4-({[6-(4-Chlorobenzyl)-4-methyl-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfanyl}acetyl)-3-phenylsydnone." Acta Crystallographica Section E Structure Reports Online 67, no. 4 (2011): o820. http://dx.doi.org/10.1107/s1600536811007689.

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29

Fun, Hoong-Kun, Ching Kheng Quah, Nithinchandra, and Balakrishna Kalluraya. "4-({[4-Amino-6-(p-bromobenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfanyl}acetyl)-3-phenylsydnone." Acta Crystallographica Section E Structure Reports Online 67, no. 4 (2011): o1004. http://dx.doi.org/10.1107/s1600536811010798.

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30

Fun, Hoong-Kun, Mohd Mustaqim Rosli, Nithinchandra, and Balakrishna Kalluraya. "4-(2-{[4-Amino-6-(4-nitrobenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfanyl}acetyl)-3-phenylsydnone." Acta Crystallographica Section E Structure Reports Online 67, no. 5 (2011): o1196. http://dx.doi.org/10.1107/s1600536811014504.

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31

TURNBULL, K., and D. M. KREIN. "ChemInform Abstract: The Sydnone Ring as an ortho-Director of Lithiation. Dilithiation of 3- Phenylsydnone and Trapping by Electrophiles." ChemInform 28, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199723152.

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32

Phaniband, Mohammedshafi A., Shreedhar D. Dhumwad, Johnson J. Jogul, and Prakash Gouda Avaji. "Novel transition complexes of Co(II), Ni(II), Cu(II), and Zn(II) derived from 3-[p-(5-substituted salicylidinehydrazinocarbonyl)]phenylsydnone." Main Group Chemistry 7, no. 4 (2008): 285–99. http://dx.doi.org/10.1080/10241220802688459.

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33

Ueng, C. H., Y. Wang, and M. Y. Yeh. "Structures of bis(3-phenylsydnone) sulfide (1), bis[3-(p-methoxyphenyl)sydnone] sulfide (2), and bis[3-(p-ethoxyphenyl)sydnone] sulfide (3)." Acta Crystallographica Section C Crystal Structure Communications 45, no. 3 (1989): 471–75. http://dx.doi.org/10.1107/s0108270188012132.

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34

Turnbull, Kenneth, Congcong Sun, and Douglas M. Krein. "The sydnone ring as an ortho-director of lithiation. 2.1 Dilithiation of 3-phenylsydnone and regiospecific -aryl acylation using N-methoxy-N-methylamides." Tetrahedron Letters 39, no. 12 (1998): 1509–12. http://dx.doi.org/10.1016/s0040-4039(98)00069-0.

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35

Kalinin, V. N., and She Fan Min. "Synthesis of aryl- and vinyl-sydnones. Cross-coupling of 4-copper-3-phenylsydnone with aryl and vinyl halides catalyzed by palladium(0) complexes." Journal of Organometallic Chemistry 352, no. 1-2 (1988): C34—C36. http://dx.doi.org/10.1016/0022-328x(88)83049-3.

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36

Nan'ya, Seiko, Kaname Katsuraya, Eturǒ Maekawa, Kazumoto Kondo, and Shoji Eguchi. "Synthesis of 2H-indazole-4,7-dione derivatives from 3-phenylsydnone andp-toluquinone. The crystal and molecular structure of 6-bromo-5-methyl-2-phenyl-2H-indazole-4,7-dione." Journal of Heterocyclic Chemistry 24, no. 4 (1987): 971–75. http://dx.doi.org/10.1002/jhet.5570240415.

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37

Marks, Gerald S. "The 1986 Upjohn Award Lecture. Interaction of chemicals with hemoproteins: implications for the mechanism of action of porphyrinogenic drugs and nitroglycerin." Canadian Journal of Physiology and Pharmacology 65, no. 6 (1987): 1111–19. http://dx.doi.org/10.1139/y87-175.

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The ferrochelatase inhibitory activity of a variety of analogues of 3,5-diethoxycarbonyl-1,4-dihydro-2,4,6-trimethylpyridine (DDC) was studied in chick embryo liver cells. The ferrochelatase inhibitory activity of the 4-butyl, 4-pentyl, and 4-hexyl analogues was considered to be due to catalytic activation by cytochrome P-450 leading to heme alkylation and formation of the corresponding N-alkylporphyrins. The relative ferrochelatase inhibitory activity of the DDC analogues has implications for a postulated model of the binding of porphyrins in the ferrochelatase active site. 3-[2-(2,4,6-Trimet

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38

Latthe, P. R., P. S. Shinge, Bharati V. Badami, P. B. Patil, and S. N. Holihosur. "Curtius rearrangement reactions of 3-(4-azidocarbonyl) phenylsydnone. Synthesis of 4-(sydnon-3-yl) phenyl carbamates, N-aryl-N′-[4-(sydnon-3-yl)] phenyl ureas and their antimicrobial and insecticidal activities." Journal of Chemical Sciences 118, no. 3 (2006): 249–56. http://dx.doi.org/10.1007/bf02708284.

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39

HIREMATH, U. S., C. V. YELAMAGGAD, B. V. BADAMI, and G. S. PURANIK. "ChemInform Abstract: Synthetic Utility of 3-(4-(Hydrazinocarbonyl))phenylsydnone: Synthesis and Antimicrobial Activity of 3-(4-(2,5-Dimethylpyrrol-1- ylaminocarbonyl))-, 3-(4-(5-Amino-4-ethoxycarbonyl-3- methylsulfanylpyrazol-1-ylcarbonyl))- and 3-(4-(1,3." ChemInform 26, no. 22 (2010): no. http://dx.doi.org/10.1002/chin.199522154.

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40

Lo, Chok Wah, Wing Lai Chan, Yau Shan Szeto, and Chiu Wing Yip. "Synthesis of a Novel Bismesoionic Phenylsydnonyl-Münchnone System as anin-situIntermediate Intended for the Preparation of Phenylsydnonyl-Heterocycles." Chemistry Letters 28, no. 6 (1999): 513–14. http://dx.doi.org/10.1246/cl.1999.513.

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41

Lo, Chok Wah, Wing Lai Chan, Yau Shan Szeto, and Chiu Wing Yip. "ChemInform Abstract: Synthesis of a Novel Bismesoionic Phenylsydnonyl-Muenchnone System as an in situ Intermediate Intended for the Preparation of Phenylsydnonyl-Heterocycles." ChemInform 30, no. 42 (2010): no. http://dx.doi.org/10.1002/chin.199942141.

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42

Stößer, Reinhard, Christian Csongár, Michael Lieberenz, and Georg Tomaschewski. "Photochemistry of arylsydnones part VI. Peculiarities of the photolysis of N-phenylsydnones." Journal of Photochemistry and Photobiology A: Chemistry 61, no. 2 (1991): 245–52. http://dx.doi.org/10.1016/1010-6030(91)85093-v.

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43

Fun, Hoong-Kun, Madhukar Hemamalini, Nithinchandra, and Balakrishna Kalluraya. "2,3-Dibromo-3-phenyl-1-(3-phenylsydnon-4-yl)propan-1-one." Acta Crystallographica Section E Structure Reports Online 67, no. 4 (2011): o814. http://dx.doi.org/10.1107/s1600536811008026.

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44

Fun, Hoong-Kun, Madhukar Hemamalini, Nithinchandra, and Balakrishna Kalluraya. "2,3-Dibromo-3-(2-bromophenyl)-1-(3-phenylsydnon-4-yl)propan-1-one." Acta Crystallographica Section E Structure Reports Online 66, no. 12 (2010): o3094. http://dx.doi.org/10.1107/s1600536810044776.

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45

Goh, Jia Hao, Hoong-Kun Fun, Nithinchandra, and B. Kalluraya. "2-Bromo-3-phenyl-1-(3-phenylsydnon-4-yl)prop-2-en-1-one." Acta Crystallographica Section E Structure Reports Online 66, no. 5 (2010): o1225—o1226. http://dx.doi.org/10.1107/s1600536810015205.

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46

Turnbull, Kenneth, and Douglas M. Krein. "ortho-(Substituted Silyl)phenylsydnones via a Novel Sydnone to Phenyl Ring, Lithiation-Induced Silicon Migration." Synthetic Communications 33, no. 12 (2003): 2061–67. http://dx.doi.org/10.1081/scc-120021032.

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47

Ding, Mei-Fang, Kai-Feng Cheng, Ying-Nan Chen, and Shaw-Tao Lin. "The Electrophilic Substitution of Sydnones: the Reaction with 3-Aryl-4-Phenylsydnones, 3-Arylmethylsydnones and 3-Phenylethylsydnone." Universal Journal of Chemistry 1, no. 3 (2013): 113–20. http://dx.doi.org/10.13189/ujc.2013.010306.

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48

Morley, John O. "Nonlinear Optical Properties of Organic Molecules. 19. Calculations of the Structure, Electronic Properties, and Hyperpolarizabilities of Phenylsydnones." Journal of Physical Chemistry 99, no. 7 (1995): 1923–27. http://dx.doi.org/10.1021/j100007a022.

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49

SATYANARAYANA, K., and M. N. A. RAO. "ChemInform Abstract: Synthesis of 4-(5-(Substituted aryl)-4,5-dihydro-1H-pyrazol-3-yl)-3- phenylsydnones as Antiinflammatory, Antiarthritic and Analgesic Agents." ChemInform 26, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199548147.

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50

Taj, Tasneem, Ravindra Kamble, T. M. Gireesh, and Ravindra Hunnur. "Facile syntheses of Mannich bases of 3-[p-(5'-aryl-pyrazolin-3'-yl)]-phenylsydnones, as anti-tubercular and anti-microbial agents, under ionic liquid/TBAB catalytic conditions." Journal of the Serbian Chemical Society 76, no. 8 (2011): 1069–79. http://dx.doi.org/10.2298/jsc100708085t.

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% MIC % antitubercular activity KR nema Novel methylene bridged Mannich bases 2(a-j) were synthesized in good to excellent yields from the pyrazoline derivative (1) using various primary/secondary amines, 37 % formalin in presence of ionic liquids/TBas catalyst. The structures of the newly synthesized compounds were confirmed by IR, 1H- and 13C-NMR and GC-MS spectroscopy, as well as elemental analysis. The title compounds were screened for their anti-tubercular and antimicrobial activities. Some of the compounds exhibited very good anti-tubercular, antifungal and antibacterial activities.

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