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Synthesis of diheteroaryl sulfides via chemoselective reaction of 4,6-diaminopyrimidine-2(1H)-thione with haloheteroaryl compounds

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Chemistry of Heterocyclic Compounds Aims and scope

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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The authors wish to thank Vali-e-Asr University of Rafsanjan for partially funding this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan, 77176, Islamic Republic of Iran

    Tayebeh Davodian, Reza Ranjbar-Karimi & Hossein Mehrabi

Authors
  1. Tayebeh Davodian
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  2. Reza Ranjbar-Karimi
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  3. Hossein Mehrabi
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Correspondence to Reza Ranjbar-Karimi.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(10), 1120–1123

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Davodian, T., Ranjbar-Karimi, R. & Mehrabi, H. Synthesis of diheteroaryl sulfides via chemoselective reaction of 4,6-diaminopyrimidine-2(1H)-thione with haloheteroaryl compounds. Chem Heterocycl Comp 53, 1120–1123 (2017). https://doi.org/10.1007/s10593-017-2181-y

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  • DOI: https://doi.org/10.1007/s10593-017-2181-y

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