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Mendeleev Communications, 2009, Volume 19, Issue 4, Pages 214–216
DOI: https://doi.org/10.1016/j.mencom.2009.07.014
(Mi mendc3174)
 

This article is cited in 19 scientific papers (total in 19 papers)

Z/E(C=C)-isomerization of coumarin enamines induced by organic solvents

V. F. Traven'a, I. V. Ivanova, V. S. Lebedeva, B. G. Milevskiia, T. A. Chibisovaa, N. P. Solov'evab, V. I. Polshakovb, O. N. Kazhevac, G. G. Alexandrovd, O. A. Dyachenkoc

a D.Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation
b Center for Drug Chemistry, Moscow, Russian Federation
c Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation
d N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: Imines of 3-formyl-4-hydroxycoumarin have been found to exist in E- and Z-ketoenamine forms in a crystal state and undergo Z/E-isomerization around the C=C bond in organic solvents (e.g., CHCl3).
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (145.5 Kb)


Citation: V. F. Traven', I. V. Ivanov, V. S. Lebedev, B. G. Milevskii, T. A. Chibisova, N. P. Solov'eva, V. I. Polshakov, O. N. Kazheva, G. G. Alexandrov, O. A. Dyachenko, “Z/E(C=C)-isomerization of coumarin enamines induced by organic solvents”, Mendeleev Commun., 19:4 (2009), 214–216
Linking options:
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  • https://www.mathnet.ru/eng/mendc/v19/i4/p214
  • This publication is cited in the following 19 articles:
    1. Vigneshkumar Ganesan, Chandramohan Govindasamy, Esakkimuthu Shanmugasundaram, Kannan Vellaisamy, Nithesh Kumar Krishnan, Murali Krishnan Mani, Selvam Kaliyamoorthy, Bo‐Tau Liu, Stalin Thambusamy, “2‐Hydroxybenzaldehyde Azine and γ‐Cyclodextrin Based Colorimetric/Fluorescent Probe for Highly Sensitive and Selective Detection of Cu2+”, ChemPhotoChem, 8:12 (2024)  crossref
    2. Abolfazl Olyaei, Nooshin Ghaleghovandi, Foozieh Moghadami, Mahdieh Sadeghpour, Shohreh Abediha, “Design, synthesis, antimicrobial, antibiofilm evaluation and Z/E-isomerization of novel 6-((arylamino)methylene)benzo[a] phenazin-5(6H)-ones induced by organic solvent”, RSC Adv., 13:42 (2023), 29393  crossref
    3. S. N. Adamovich, I. A. Ushakov, A. V. Afonin, N. V. Vchislo, E. N. Oborina, D. V. Pavlov, “O- and S-containing 1-azadiene derivatives of 3-aminopropylsilatrane”, Russ Chem Bull, 70:2 (2021), 406  crossref
    4. Abolfazl Olyaei, Amir Mohamadi, Nilufar Rahmani, “Green synthesis of new lawsone enaminones and theirZ/E(CC)-isomerization induced by organic solvent”, RSC Adv., 11:21 (2021), 12990  crossref
    5. Andrei V. Afonin, Dmitry V. Pavlov, Alexander V. Albanov, Anastasiya G. Mal'kina, “Solvent-induced E/Z isomerization of 2-(furylmethylidene)-1-hydrazinecarbothioamide: The N–H⋅⋅⋅O intramolecular hydrogen bond as promoting factor”, Journal of Molecular Structure, 1207 (2020), 127782  crossref
    6. Abolfazl Olyaei, Soheila Javarsineh, Mahdieh Sadeghpour, “Green Synthesis and Z/E-Isomerization of Novel Coumarin Enamines Induced by Organic Solvents”, Chem Heterocycl Comp, 54:10 (2018), 934  crossref
    7. B. G. Milevskii, T. A. Chibisova, N. P. Solov´eva, A. Yu. Sukhorukov, V. F. Traven, “Synthesis of 3-aminomethyl-4-hydroxycoumarins and their retro-Mannich reaction in dimethyl sulfoxide”, Russ Chem Bull, 64:2 (2015), 423  crossref
    8. Islam H. El Azab, Mohamed R. E. Aly, “Synthesis of Some New Isoindoline-1,3-dione Based Heterocycles”, HETEROCYCLES, 91:2 (2015), 287  crossref
    9. I. N. Shcherbakov, S. I. Levchenkov, L. D. Popov, G. G. Aleksandrov, L. N. Etmetchenko, V. A. Kogan, “Binuclear copper(II) complex with bis(azomethine) based on 1,3-diaminopropan-2-ol and 4-hydroxy-3-formylcoumarin: Crystal structure and magnetic properties”, Russ J Coord Chem, 41:2 (2015), 69  crossref
    10. V. S. Lebedev, B. G. Milevskii, N. P. Solov'eva, T. A. Chibisova, O. N. Kazheva, O. A. Dyachenko, G. G. Alexandrov, V. F. Traven, “Tautomeric Forms of 3-Formyl- 4-Hydroxycoumarin Arylhydrazones”, Chem Heterocycl Comp, 50:8 (2014), 1081  crossref
    11. B. G. Milevskii, T. A. Chibisova, N. P. Solov'eva, O. S. Anisimova, V. S. Lebedev, I. V. Ivanov, V. F. Traven, “Synthesis and structure of Schiff bases derived from 3-formyl-4-hydroxycoumarin and diamines”, Chem Heterocycl Comp, 48:12 (2013), 1781  crossref
    12. Jiun-Han Lin, Chi-Hui Lin, Ding-Yah Yang, “Synthesis of 4-hydroxy-7-dimethylamino-3-pyrazolinylcoumarins and their polarity-sensitive properties”, Tetrahedron Letters, 53:7 (2012), 778  crossref
    13. Gregory K. Pierens, T. K. Venkatachalam, Paul V. Bernhardt, Mark J. Riley, David C. Reutens, “A Solid State Study of Keto-enol Tautomerismin Three Naphthaledene Schiff Bases”, Aust. J. Chem., 65:5 (2012), 552  crossref
    14. V. F. Traven, A. V. Manaev, A. Yu. Bochkov, T. A. Chibisova, I. V. Ivanov, “New reactions, functional compounds, and materials in the series of coumarin and its analogs”, Russ Chem Bull, 61:7 (2012), 1342  crossref
    15. T. K. Venkatachalam, Gregory K. Pierens, Paul V. Bernhardt, Luke Hammond, David C. Reutens, “Synthesis and Structural Characterization of (Z)-3-[(4-Chlorophenylamino) Methylene] Naphthalene-2(3H)-One: An Enol, Keto or Zwitterionic Tautomer?”, J Chem Crystallogr, 41:7 (2011), 944  crossref
    16. Valery F. Traven, Ivan V. Ivanov, Victor S. Lebedev, Natalya P. Solov'eva, Vladimir I. Polshakov, Olga N. Kazheva, Grigorii G. Alexandrov, Oleg A. Dyachenko, “Z/E(C=C)-isomerization and fluorescence modulation of imines of 7-N,N-dialkylamino-4-hydroxy-3-formylcoumarins in organic solvents”, Heterocyclic Communications, 2011, -  crossref
    17. Valery F. Traven, Ivan V. Ivanov, Victor S. Lebedev, Natalya P. Solov'eva, Vladimir I. Polshakov, Olga N. Kazheva, Grigorii G. Alexandrov, Oleg A. Dyachenko, “Z/E (C=C)-isomerization and fluorescence modulation of imines of 7-N,N-dialkylamino-4-hydroxy-3-formylcoumarins in organic solvents”, Heterocyclic Communications, 16:4-6 (2010)  crossref
    18. T. K. Venkatachalam, Gregory K. Pierens, David Reutens, “Synthesis and Characterization of Anils Exhibiting Thermochromism”, Aust. J. Chem., 63:8 (2010), 1272  crossref
    19. N. A. Kondratova, N. P. Solov'eva, V. F. Traven, “Dihydrofuran ring opening in the reactions of 2,3- dihydrofuro[3,2-c]coumarin-3-one with arylhydrazines”, Russ Chem Bull, 59:8 (2010), 1612  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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