Theoretical study on the reaction mechanism and regioselectivity of [3+2] cycloaddition of azomethine imines for preparation of pyrazolo[1,2-a]pyrazolones

Document Type : Original Article

Authors

Department of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar, Iran

Abstract

The mechanism and regioselectivity of the [3+2] cycloaddition reaction of an azomethine imine for preparation of pyrazolo[1,2-a]pyrazolones, have been investigated at B3LYP/6-31G(d,p) and M06-2X levels of theory. The regiochemistry of the reaction has been studied based on the potential energy surface analysis and global reactivity indices of the reactants. In the case of M06-2X, as the reactants approached to each other, a van der Waals pre-complexes is generated which is energetically more stable than the separated reactants due the dispersion effects. These pre-complexes have been optimized and the activation energies of the possible reaction pathways were calculated with respect to these van der Waals pre-complexes instead of the separated reactants. This reaction is highly regioselective with a low stereoselectivity, leading to the formation of a mixture of pyrrolidines exo3 and endo3. However, based on the computational results, major product obtained under thermodynamic control. These results are in agreement with the experimental observation and the other theoretical studies. The ELF analysis indicate a one-step two-stage mechanism for the reactions in which the formation of C-N single bonds takes place after the formation of C-C bond. In this context, the parr indices are used to study the role of the electronic factors.

Graphical Abstract

Theoretical study on the reaction mechanism and regioselectivity of [3+2] cycloaddition of azomethine imines for preparation of pyrazolo[1,2-a]pyrazolones

Keywords

Main Subjects

References

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Iranian Journal of Chemistry
Volume 1, Issue 1 - Serial Number 1
January 2019
Pages 21-31

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History

  • Receive Date: 29 April 2018
  • Revise Date: 27 July 2018
  • Accept Date: 25 September 2018

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