Bulletin of the Korean Chemical Society

  • 제35권12호
  • /
  • Pages.3609-3617
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  • 2014
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Microwave Assisted Synthesis of 1,3,4-Oxadiazole/Thiohydantoin Hybrid Derivatives via Dehydrative Cycliztion of Semicarbazide

  • Yang, Seung-Ju (Innovative Drug Library Research Center, Department of Chemistry, College of Science, Dongguk University) ;
  • Lee, Jae-Min (Innovative Drug Library Research Center, Department of Chemistry, College of Science, Dongguk University) ;
  • Lee, Gee-Hyung (Innovative Drug Library Research Center, Department of Chemistry, College of Science, Dongguk University) ;
  • Kim, NaYeon (Innovative Drug Library Research Center, Department of Chemistry, College of Science, Dongguk University) ;
  • Kim, Yong-Sang (Innovative Drug Library Research Center, Department of Chemistry, College of Science, Dongguk University) ;
  • Gong, Young-Dae (Innovative Drug Library Research Center, Department of Chemistry, College of Science, Dongguk University)
  • 투고 : 2014.07.29
  • 심사 : 2014.09.16
  • 발행 : 2014.12.20
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초록

A series of compounds containing both 1,3,4-oxadiazole and thiohydantoin were synthesized as a promising scaffold for application in medicinal chemistry. The key step of the synthesis is a microwave-assisted cyclization of semicarbazides possessing a thiohydantoin moiety at one of the acyl termini using $POCl_3$ as a dehydrating reagent. A wide range of semicarbazides were prepared through the substitution of hydrazides with an N-acylated thiohydantoin derived from the cyclization of the corresponding isothiocyanate with an amino acid and subsequent N-acylation of the resultant thiohydrantion. Consequently, the 58 number of 1,3,4-oxadiazole derivatives having a thiohydantoin substituent were prepared in good overall yields.

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  1. ]imidazoles via a Phase-Based, Chemoselective Reaction pp.2156-8944, 2017, https://doi.org/10.1021/acscombsci.7b00106