SYNTHESIS OF DIHETEROARYL SULFIDES VIA CHEMOSELECTIVE REACTION OF 4,6-DIAMINOPYRIMIDINE-2(1<i>H</i>)-THIONE WITH HALOHETEROARYL COMPOUNDS

Authors

  • Tayebeh Davodian Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan 77176
  • Reza Ranjbar-Karimi Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan 77176
  • Hossein Mehrabi Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan 77176

DOI:

https://doi.org/10.1007/3980

Keywords:

perhalo compounds, sulfide, aromatic nucleophilic substitution, chemoselectivity, synthesis

Abstract

A series of substituted diheteroaryl sulfides was synthesized by the reaction of 4,6-diaminopyrimidine-2(1H)-thione with fluoro- and chloroheteroaromatic compounds in the presence of Na2CO3 in acetonitrile under reflux conditions. Our study indicated that 4,6-diaminopyrimidine-2(1H)-thione reacts with fluoro- and chloroheteroaromatic compounds chemoselectively as S- rather than N-nucleophile. The structures of the synthesized compounds were confirmed by IR, 1H, 19F, and 13C NMR spectroscopy, as well as elemental analysis and X-ray structural analysis.

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Published

2017-11-29

Issue

Vol. 53 No. 10 (2017)

Section

Original Papers