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Synthesis of new coumarins complemented by quantum chemical studies

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Abstract

New coumarins, namely (E)-N′-(2-methylbenzylidene)-2-((2-oxo-2H-chromen-4-yl)oxy)acetohydrazide 4, N-(4-oxo-2-(o-tolyl)thiazolidin-3-yl)-2-((2-oxo-2H-chromen-4-yl)oxy)acetamide 5, and N-(4,7-dioxo-2-(o-tolyl)-1,3-oxazepin-3(2H,4H,7H)-yl)-2-((2-oxo-2H-chromen-4-yl)oxy)acetamide 6, were synthesized starting from 4-hydroxycoumarin and methyl bromoacetate. They were characterized by different spectroscopic techniques (FT-IR and NMR) and micro-elemental analysis (CHNS). Density Functional Theory calculations of the synthesized coumarins were performed using molecular structures with optimized geometries. Molecular orbital calculations have provided detail description of the orbitals, including spatial characteristics, nodal patterns, and the contributions of individual atoms.

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Acknowledgments

This study was supported by the University of Technology, Baghdad, Iraq, and Universiti Kebangsaan Malaysia under the DIP-2012-02 Grant.

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Authors and Affiliations

  1. University of Technology (UOT), Baghdad, 10001, Iraq

    Ahmed A. Al-Amiery & Yasameen K. Al-Majedy

  2. Department of Chemical and Process Engineering, Universiti Kebangsaan Malaysia (UKM), 43000, Bangi, Selangor, Malaysia

    Ahmed A. Al-Amiery, Yasameen K. Al-Majedy, Abdul Amir H. Kadhum & Abu Bakar Mohamad

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  1. Ahmed A. Al-Amiery
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  2. Yasameen K. Al-Majedy
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  3. Abdul Amir H. Kadhum
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Correspondence to Ahmed A. Al-Amiery or Yasameen K. Al-Majedy.

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Al-Amiery, A.A., Al-Majedy, Y.K., Kadhum, A.A.H. et al. Synthesis of new coumarins complemented by quantum chemical studies. Res Chem Intermed 42, 3905–3918 (2016). https://doi.org/10.1007/s11164-015-2252-6

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  • DOI: https://doi.org/10.1007/s11164-015-2252-6

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