First catalytic hetero-Diels-Alder reaction of imidazole-2-thiones and in silico biological evaluation of the cycloadducts

Nikolaos Eleftheriadis, Evanthia Samatidou, Constantinos G. Neochoritis

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4 Citations (Scopus)

Abstract

The Lewis acid-catalyzed Diels-Alder reactions of suitably substituted imidazole-2-thiones with dienes were studied. It was found that the electron density of the imidazole core influenced the reaction, since electron withdrawing groups led to the novel spiro-derivatives 2 whereas electron donating groups gave rise to the sulfur substituted imidazole derivatives 6. The reaction conditions were optimized and full assignment of all1H and13C NMR chemical shifts has been unambiguously achieved. In silico evaluation of the cycloadducts by means of molecular modeling in three different proteins and calculation of ADME-Tox properties was performed.
Original languageEnglish
Pages (from-to)1742-1748
Number of pages7
JournalTetrahedron
Volume72
Issue number14
DOIs
Publication statusPublished - Apr-2016

Keywords

  • In silico evaluation
  • 1,3-Dimethylbutadiene
  • Diels-Alder addition
  • Imidazolethiones
  • Microwave irradiation
  • calculation
  • catalysis
  • Diels Alder reaction
  • molecular model

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