Bulletin of the Korean Chemical Society

  • 제33권1호
  • /
  • Pages.55-59
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  • 2012
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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)
  • 투고 : 2011.10.16
  • 심사 : 2011.10.28
  • 발행 : 2012.01.20
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초록

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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참고문헌

  1. Koldobskii, G. I.; Kharbash, R. B. Russ. J. Org. Chem. 2003, 39, 453.
  2. Koldobskii, G. I.; Harbalek, A.; Esikov, K. A. Russ. J. Org. Chem. 2004, 40, 447. https://doi.org/10.1023/B:RUJO.0000036061.40446.49
  3. Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett, 1998, 1, 26.
  4. Hennesian, S.; Focken, T.; Oza, R. Org. Lett. 2010, 12, 3172. https://doi.org/10.1021/ol101103q
  5. Trost, B. M.; Chisoim, J. D.; Wrobleski, S. T.; Jung, M. J. Am. Chem. Soc. 2002, 124, 12420. https://doi.org/10.1021/ja027883+
  6. Lieber, E. C.; Pillai, N.; Hites, R. D. Can. J. Chem. 1957, 35, 832. https://doi.org/10.1139/v57-116
  7. Lieber, E.; Ramachandran, J. Can. J. Chem. 1959, 37, 101. https://doi.org/10.1139/v59-015
  8. Altland, H. W. J. Org. Chem. 1976, 41, 3395. https://doi.org/10.1021/jo00883a013
  9. Elguelo, J.; Marzin, C.; Katrithzky, A. R.; Linda, P. The Tautomerism of Heterocycles; Academic, New York, 1976.
  10. Borjaska-lejnik, E.; Stefaniak, L.; Witanowski, M.; Webb, G. A. Bull. Chem. Soc. Jpn. 1986, 59, 3263. https://doi.org/10.1246/bcsj.59.3263
  11. Koldovski, G. I.; Ostrovskii, V. A. Usp. Khim. 1994, 63, 847.
  12. Poplavskaya, Y. V.; Trifonov, R. E.; Shcherbinin, M. B.; Koldobskii, G. I. Russ. J. Org. Chem. 2000, 36, 1788.
  13. Blakemore, P. R. J. Chem. Soc., Perkin Trans. 2002, 1, 2563.
  14. Orth, R. E. J. Pharm. Sci. 1963, 52, 909. https://doi.org/10.1002/jps.2600520923
  15. Cowper, A. J.; Astik, R. R.; Thaker, K. A. J. Indian Chem. Soc. 1981, 58, 1087.
  16. Postovskii, I. Y. Zhur. Obshchei Khim. 1964, 34, 2517.
  17. Tochtermann, W. Chem. Ber. 1978, 111, 566. https://doi.org/10.1002/cber.19781110216
  18. Sheldrick, G. M. SADABS, Program for Absorption Correction, University of Gottingen, 1996.
  19. Bruker, SHELXTL, Structure Determination Software Programs, Bruker, Analytical X-ray Instruments Inc., Madison, Wisconsin, U.S., 1997.

피인용 문헌

  1. Synthesis of Mono-substituted 5-Aminothiatriazoles and Their Conversion to Tetrazole-5-thiones vol.33, pp.7, 2012, https://doi.org/10.5012/bkcs.2012.33.7.2385
  2. -tetrazole-5-thiol vol.16, pp.17, 2014, https://doi.org/10.1021/ol5020416
  3. Reactions of dimethyl 2-chloroethynylphosphonate with 1-substituted 5-oxo-1H-1,2,3,4-tetrazoles vol.84, pp.11, 2014, https://doi.org/10.1134/S107036321411019X
  4. Coumarin heterocyclic derivatives: chemical synthesis and biological activity vol.32, pp.10, 2015, https://doi.org/10.1039/C4NP00162A
  5. Tetrazolethiones: synthesis and S-functionalization reactions (microreview) vol.52, pp.6, 2016, https://doi.org/10.1007/s10593-016-1894-7
  6. ][1,3]thiazines vol.17, pp.9, 2019, https://doi.org/10.1039/C8OB03220C
  7. A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles employing CeCl3·7H2O in PEG-400 vol.4, pp.65, 2014, https://doi.org/10.1039/c4ra05625f
  8. Synthesis of Some Derivatives of Pyrimido[5,4-e]Tetrazolo[5,1-c][1,2,4]triazine; a Novel Heterocyclic System vol.39, pp.10, 2012, https://doi.org/10.3184/174751915x14428472915706
  9. Molecular and Crystal Structure of 1-(4-Fluorophenyl)-1,4-Dihydro-1H-Tetrazole-5-Thione and Its Complex with Cadmium(II) vol.59, pp.7, 2018, https://doi.org/10.1134/s0022476618070193
  10. Synthesis of some new organotellurium compounds based on 1-substituted tetrazole vol.1853, pp.1, 2021, https://doi.org/10.1088/1742-6596/1853/1/012034