Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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An Efficient Solid-phase Parallel Synthesis of 2-Amino and 2-Amidobenzo[d]oxazole Derivatives via Cyclization Reactions of 2-Hydroxyphenylthiourea Resin

  • Jung, Se-Lin (Center for Innovative Drug Library Research, Department of Chemistry, College of Science, Dongguk University) ;
  • Kim, Seul-Gi (Center for Innovative Drug Library Research, Department of Chemistry, College of Science, Dongguk University) ;
  • Lee, Gee-Hyung (Center for Innovative Drug Library Research, Department of Chemistry, College of Science, Dongguk University) ;
  • Gong, Young-Dae (Center for Innovative Drug Library Research, Department of Chemistry, College of Science, Dongguk University)
  • Received : 2012.09.08
  • Accepted : 2012.09.24
  • Published : 2012.12.20
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Abstract

An efficient solid-phase methodology has been developed for the synthesis of 2-amino and 2-amidobenzo[d]-oxazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo-[d]oxazole resins 4 by cyclization reaction of 2-hydroxy-phenylthiourea resin 3. The resin-bound 2-hydroxyphenylthiourea 3 is produced by the addition of 2-aminophenol to the isothiocyanate-terminated resin 2 and serve as a key intermediate for the linker resin. This core skeleton 2-aminobenzo[d]oxazole resin 4 undergoes functionalization reaction with various electrophiles, such as alkylhalides and acid chlorides to generate 2-amino and 2-amidobenzo[d]oxazole resins 5 and 6 respectively. Finally, 2-amino and 2-amidobenzo[d]oxazole derivatives 7 and 8 are then generated in good yields and purities by cleavage of the respective resins 5 and 6 under trifluoroacetic acid (TFA) in dichloromethane ($CH_2Cl_2$).

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References

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