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Synthesis of 2-amino-3-cyano 4-H-chromenes containing quinoline in water: computational study on substituent effects

Abstract

An efficient, high yielding and environmentally benign strategy to the synthesis of new 2-amino-3-cyano-4-H-chromene derivatives, via one-pot three-component reaction involving malononitrile, various α- or β-naphthol and appropriate aromatic aldehydes including 2-chloroquinoline-3-carbaldehydes in the presence of morpholine in water, was achieved. During the development of the synthesis five new chromene derivatives were fruitfully synthesized. It was found that employing this approach, aromatic aldehydes bearing electron-withdrawing groups give higher yields of the corresponding products in shorter reaction times. This observation was in agreement with topological analysis of calculated electron density functions using density functional theory and quantum theory of atoms in molecules approaches.

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Acknowledgements

The authors gratefully acknowledge the financial support received from the research council of Alzahra University. MMH is also thankful to Iran National Science Foundation (INSF) for the grant allocated based on awarded individual research chair.

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Correspondence to Majid M. Heravi or Tayebeh Hosseinnejad.

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Heravi, M.M., Hosseinnejad, T., Faghihi, Z. et al. Synthesis of 2-amino-3-cyano 4-H-chromenes containing quinoline in water: computational study on substituent effects. J IRAN CHEM SOC 14, 823–832 (2017). https://doi.org/10.1007/s13738-016-1032-6

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  • DOI: https://doi.org/10.1007/s13738-016-1032-6

Keywords

  • Chromene
  • 2-Chloroquinoline-3-carbaldehyde
  • Water
  • Density functional theory
  • Electron density properties
  • Quantum theory of atoms in molecules