ChemInform Abstract: REACTIONS OF AZINES AND IMINES (AZOMETHINES, SCHIFF BASES) WITH DIENOPHILES

Jauregg, Th. Wagner

doi:10.1002/chin.197638213

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“…These compounds have pharmacological and biological properties and close relationships with their structures, which act as anti-inflammatory, analgesic, antibacterial, antifungal, antitumor, anti-HIV and antimicrobial agents [15][16][17][18][19]. Azines are also important for drug design, organocatalysis and synthesis of heterocyclic compounds [20][21] by undergoing different types of cyclo-addition reactions [21][22]. In recent years, computational studies on azines have been conducted to study their molecular properties, which involves the theoretical and experimental characterization of their electronic structure [23][24][25][26], including their conformational equilibrium structure, their tautomerism, their NMR spectra and potential energy distribution (PED) vibration frequencies [27][28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

Yahyaoui

Bouchama²,

Anak³

et al. 2019

Journal of Molecular Structure

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In this paper, we report the synthesis of new unsymmetrical azines Schiff bases. These compounds were prepared by condensation of hydrazine with different aldehydes and ketones to give (E) -2-hydroxynaphthalene-1-carbaldehyde [(1E) -2-thienylmethylene] hydrazone compound (I) and (Z) -2 -[(E) -1-(2-hydroxyphenyl) ethylidenehydrazin-1-ylidene] -1,2diphenylethanone compound (II). The method adopted consists in reacting the two different carbonyl compounds simultaneously in one step in a stepwise manner reported which is practical and cost-effective. The reaction with a minor modification in operating conditions proceeded efficiently and with excellent performance. The structure of each of the two compounds (I) and (II) was determined by the X-ray diffraction technique performed on single crystals. The asymmetric unity of the two molecules consists of one asymmetry-independent molecule. In addition, hydrogen bonds C-H ... π are observed in the compound (II). We then present a detailed DFT study based on B3LYP / 6-31G (d, p) geometric structures of compounds (I); (II) and another compound (III) also another asymmetric azine (Z) -2 -[(E) -2-benzylidenehydrazine-1-ylidene] -1,2diphenylethanone whose crystal structure is reported. The fundamental vibration wave numbers are calculated and a good agreement between the observed and calculated wave numbers is obtained. The study was extended to the HOMO-LUMO analysis to calculate the energy gap. The calculated HOMO and LUMO energy reveals that the charge is transferred into the molecule.

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Section: Introductionmentioning

confidence: 99%

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

Yahyaoui

Bouchama²,

Anak³

et al. 2019

Journal of Molecular Structure

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ChemInform Abstract: REACTIONS OF AZINES AND IMINES (AZOMETHINES, SCHIFF BASES) WITH DIENOPHILES

Abstract: In diesem Übersichtsartikel wird die Herstellung von Heterocyclen durch Umsetzung von Azinen und Iminen mit Dienophilen beschrieben.

Cited by 1 publication

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Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

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