2009
DOI: 10.1016/j.mencom.2009.07.014
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Z/E(C=C)-isomerization of coumarin enamines induced by organic solvents

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Cited by 19 publications
(3 citation statements)
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“…According to the 1 H-and 13 C-NMR spectroscopy, they have feature intramolecular hydrogen bonds of O-H/N and N-H/O type, tautomerism between the enol imine and ketoenamine forms, and Z/E-isomerization of the ketoenamine form in respect to the C]C bond. 21 2-Hydroxy-1,4-naphthoquinone, or lawsone, or hennotannic acid, is one of the simplest naturally occurring naphthoquinones and is useful for many applications in various scientic and technological elds. It has been used as the starting material for the synthesis of a variety of biologically active compounds and materials with interesting properties.…”
Section: Introductionmentioning
confidence: 99%
“…According to the 1 H-and 13 C-NMR spectroscopy, they have feature intramolecular hydrogen bonds of O-H/N and N-H/O type, tautomerism between the enol imine and ketoenamine forms, and Z/E-isomerization of the ketoenamine form in respect to the C]C bond. 21 2-Hydroxy-1,4-naphthoquinone, or lawsone, or hennotannic acid, is one of the simplest naturally occurring naphthoquinones and is useful for many applications in various scientic and technological elds. It has been used as the starting material for the synthesis of a variety of biologically active compounds and materials with interesting properties.…”
Section: Introductionmentioning
confidence: 99%
“…This deduction was different from the reported related work. 36 In addition, the calculated heat of formation of the Z isomer of 13 is 0.5 kJ/ mole lower than that for the E isomer, which is too small, thus both configurations Z/E is present in almost equal amount (Fig. 3).…”
Section: Introductionmentioning
confidence: 91%
“…According to the 1 Hand 13 C-NMR spectroscopy, they have feature intramolecular hydrogen bonds of O-H/N and N-H/O type, tautomerism between the enol-imine and keto-enamine forms, and Z/Eisomerization of the keto-enamine form in respect to the C]C bond. 21 In continuation of our interests in synthesis of enolimine and keto-enamine compounds by one-pot, multicomponent reactions, [22][23][24][25][26] herein, we report the one-pot, fourcomponent synthesis of a new series of 6-((arylamino) methylene)benzo[a]phenazin-5(6H)-one derivatives by condensation reaction of 2-hydroxy-1,4-naphthoquinone, 1,2-phenylenediamine, aromatic amines and triethyl orthoformate using formic acid as catalyst under solvent-free conditions and evaluation of antibacterial, antifungal and antibiolm activities of target compounds against some of the tested microorganisms.…”
Section: Introductionmentioning
confidence: 99%