Solvent-induced E/Z(C=N)-isomerization of imines of some hydroxy-substituted formylcoumarins

被引：0
|
作者：
V. F. Traven’
I. V. Ivanov
A. V. Panov
O. B. Safronova
T. A. Chibisova
机构：
[1] D. I. Mendeleev University of Chemical Technology of Russia,
来源：
Russian Chemical Bulletin | 2008年 / 57卷
关键词：
hydroxyformylcoumarins; imines; solvatochromism; -isomerization;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Aromatic imines, namely, 5-formyl-6-hydroxy-4-methyl- and 8-formyl-7-hydroxy-4-methylcoumarin derivatives, have been synthesized. A dependence of their spectral characteristics (1H NMR spectra, electronic absorption spectra) from the solvent (DMSO, CHCl3, DMF, acetonitrile, MeOH) has been studied. The solvatochromic effects observed for a number of imines, first of all, for 7-hydroxy-4-methyl-8-(4′-nitrophenylimino)methyl-2H-1-benzopyran-2-one, were related to their E/Z-isomerization with respect to the C=N bond based on the quantum chemical calculations by the AM1, PM3, PPP CI methods.
引用
收藏
页码：1989 / 1995
页数：6
相关论文
共 50 条
  • [1] Solvent-induced E/Z(C=N)-isomerization of imines of some hydroxy-substituted formylcoumarins
    Traven', V. F.
    Ivanov, I. V.
    Panov, A. V.
    Safronova, O. B.
    Chibisova, T. A.
    RUSSIAN CHEMICAL BULLETIN, 2008, 57 (09) : 1989 - 1995
  • [2] Z/E (C=C)-isomerization and fluorescence modulation of imines of 7-N,N-dialkylamino-4-hydroxy-3-formylcoumarins in organic solvents
    Traven, Valery F.
    Ivanov, Ivan V.
    Lebedev, Victor S.
    Solov'eva, Natalya P.
    Polshakov, Vladimir I.
    Kazheva, Olga N.
    Alexandrov, Grigorii G.
    Dyachenko, Oleg A.
    HETEROCYCLIC COMMUNICATIONS, 2010, 16 (4-6) : 257 - 260
  • [3] SOLVENT-INDUCED MECHANISM CHANGE IN CHARGE-TRANSFER MOLECULES - INVERSION VERSUS ROTATION PATHS FOR THE Z -] E ISOMERIZATION OF DONOR-ACCEPTOR SUBSTITUTED AZOBENZENES
    SHIN, DM
    WHITTEN, DG
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) : 5206 - 5208
  • [4] Green synthesis of new lawsone enaminones and their Z/E(C=C)-isomerization induced by organic solvent
    Olyaei, Abolfazl
    Mohamadi, Amir
    Rahmani, Nilufar
    RSC ADVANCES, 2021, 11 (21) : 12990 - 12994
  • [5] Solvent-induced E/Z isomerization of 2-(furylmethylidene)-1-hydrazinecarbothioamide: The N-H•••O intramolecular hydrogen bond as promoting factor
    Afonin, Andrei, V
    Pavlov, Dmitry, V
    Albanov, Alexander, V
    Mal'kina, Anastasiya G.
    JOURNAL OF MOLECULAR STRUCTURE, 2020, 1207
  • [6] SOME ANILINOQUINONES AND N-SUBSTITUTED 2-HYDROXY-1-4-NAPHTHAQUINONE IMINES
    BARAKAT, MZ
    SHEHAB, SK
    ELSADR, MM
    JOURNAL OF THE CHEMICAL SOCIETY, 1958, (FEB): : 901 - 902
  • [7] Z/E(C=C)-isomerization of coumarin enamines induced by organic solvents
    Traven, Valery F.
    Ivanov, Ivan V.
    Lebedev, Victor S.
    Milevskii, Boris G.
    Chibisova, Tat'yana A.
    Solov'eva, Natalya P.
    Polshakov, Vladimir I.
    Kazheva, Olga N.
    Alexandrov, Grigorii G.
    Dyachenko, Oleg A.
    MENDELEEV COMMUNICATIONS, 2009, 19 (04) : 214 - 216
  • [8] The (E, Z) Isomerization of C-methoxycarbonyl-N-aryl Chlorohydrazones
    Molteni, Giorgio
    Cargnoni, Fausto
    Soave, Raffaella
    Ponti, Alessandro
    CHEMISTRY-SWITZERLAND, 2022, 4 (04): : 1624 - 1653
  • [9] THE C-13 CHEMICAL-SHIFTS OF 2'-HYDROXY-SUBSTITUTED N-BENZYLIDENE-ANILINES AND SOME N,N-(ORTHO-HYDROXYBENZYLIDENE)DIAMINES
    SALMAN, SR
    ALRAWI, JM
    BEHNAM, GQ
    ORGANIC MAGNETIC RESONANCE, 1984, 22 (08): : 535 - 535
  • [10] MUTAROTATION AND ISOMERIZATION OF IMINES .13. E-Z EQUILIBRIUM IN N-ALKYL-1-ARYLALKANINES
    ARJONA, O
    LOPEZMARDOMINGO, C
    PEREZOSSORIO, R
    PLUMET, J
    ANALES DE QUIMICA SERIE C-QUIMICA ORGANICA Y BIOQUIMICA, 1984, 80 (03): : 304 - 307
12345