Studies on the regioselective nucleophilic aromatic substitution (S NAr) reaction of 2-substituted 3,5-dichloropyrazines

  • Scales S
  • Johnson S
  • Hu Q
 et al. 
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Abstract

Differences in regioselectivity were observed during the S(N)Ar reaction of amines with unsymmetrical 3,5-dichloropyrazines. This study revealed that when the 2-position of the pyrazine was occupied with an electron-withdrawing group (EWG), nucleophilic attack occurred preferentially at the 5-position. When the 2-position was substituted with an electron-donating group (EDG), nucleophilic attack occurred preferentially at the 3-position. These results are reported along with a computational rationale for the experimental observations based on the Fukui index at the reacting centers.

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Authors

  • Stephanie Scales

  • Sarah Johnson

  • Qiyue Hu

  • Quyen Quyen Do

  • Paul Richardson

  • Fen Wang

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