Regio-selective synthesis of 5-substituted 1H-tetrazoles using ionic liquid [BMIM]N3 in solvent-free conditions: a click reaction

Abstract

A multi-component, one pot and regio-selective synthesis of different 5-substituted 1H-tetrazoles was successfully accomplished via a click reaction. In this respect, we have performed the reaction of either isatins or various aromatic aldehydes with malononitrile and ionic liquid, 1-butyl-3-methylimidazolium azide ([BMIM]N3), as a relatively green source of azide mediated by o-phthalimide-N-sulfonic acid (OPNSA). The calculated thermodynamic results demonstrate a reliable agreement with our experimentally observed regio-selectivity. From the electronic viewpoint, we have also assessed the nature of regio-selectivity via quantum theory of atoms in molecule analysis.

Graphical Abstract

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Abbreviations

T :

Temperature (°C)

t :

Time (t)

ρ b :

Values of electron density

2 ρ b :

Laplacian of ρ b

G b :

Electronic kinetic energy density

V b :

Electronic potential energy density

H b :

Total electronic energy density

ΔE e,r :

The reaction energy from the total electronic energies

ΔE 0,r :

The reaction energy with zero-point energies

ΔH r :

Reaction enthalpy

ΔG r :

Free energy

ΔS r :

Entropy change

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Acknowledgments

M. M. Heravi is thankful to the Reaearch Council of Alzahra University for partial financial assistance.

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Correspondence to Majid M. Heravi.

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Khaghaninejad, S., Heravi, M.M., Hosseinnejad, T. et al. Regio-selective synthesis of 5-substituted 1H-tetrazoles using ionic liquid [BMIM]N3 in solvent-free conditions: a click reaction. Res Chem Intermed 42, 1593–1610 (2016). https://doi.org/10.1007/s11164-015-2105-3

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Keywords

  • Click reaction
  • Ionic liquid: 1-butyl-3-methylimidazolium azide
  • 5-Substituted 1H-tetrazoles
  • Density functional theory
  • Quantum theory of atoms in molecule
  • Regio-selectivity