Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A Facile One-Pot Synthesis of 1-Substituted Tetrazole-5-thiones and 1-Substituted 5-Alkyl(aryl)sulfanyltetrazoles from Organic Isothiocyanates

  • Han, Sam-Yong (Department of Chemistry, Gangneung-Wonju National University) ;
  • Lee, Je-Woo (Department of Chemistry, Gangneung-Wonju National University) ;
  • Kim, Hee-Jung (Department of Chemistry, Gangneung-Wonju National University) ;
  • Kim, Yong-Joo (Department of Chemistry, Gangneung-Wonju National University) ;
  • Lee, Soon-W. (Department of Chemistry, Sungkyunkwan University, Natural Science Campus) ;
  • Gyoung, Young-Soo (Department of Chemistry, Gangneung-Wonju National University)
  • Received : 2011.10.16
  • Accepted : 2011.10.28
  • Published : 2012.01.20
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Abstract

Treatments of organic isothiocyanates (R-NCS) with $NaN_3$ in the presence of pyridine in water at room temperature gave corresponding various organic tetrazole-thiones, [$S=CN_4(R)$] (R = alkyl or aryl). Isolated products are obtained as white or yellow solids in good yields (76-97%). The molecular structure by X-ray diffraction study for one of products shows the proposed formation. In addition, one-pot synthesis of 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles has been demonstrated. Addition of alkyl or aryl halides into the mixture of organic isothiocyanates, $NaN_3$, and pyridine in water at room temperature exclusively formed 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles (S-derivatives) in high yields.

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References

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