Synthesis 2014; 46(06): 781-786
DOI: 10.1055/s-0033-1340616
paper
© Georg Thieme Verlag Stuttgart · New York

An Improved Protocol for the Preparation of 5-Substituted Tetrazoles from Organic Thiocyanates and Nitriles

Svetlana Vorona
Saint Petersburg State University of Technology and Design, ul. Bolshaya Morskaya 18, 191186 Saint Petersburg, Russian Federation   Fax: +7(812)5719584   Email: Myznikov_lv@mail.ru
,
Tatiana Artamonova
Saint Petersburg State University of Technology and Design, ul. Bolshaya Morskaya 18, 191186 Saint Petersburg, Russian Federation   Fax: +7(812)5719584   Email: Myznikov_lv@mail.ru
,
Yuri Zevatskii
Saint Petersburg State University of Technology and Design, ul. Bolshaya Morskaya 18, 191186 Saint Petersburg, Russian Federation   Fax: +7(812)5719584   Email: Myznikov_lv@mail.ru
,
Leonid Myznikov*
Saint Petersburg State University of Technology and Design, ul. Bolshaya Morskaya 18, 191186 Saint Petersburg, Russian Federation   Fax: +7(812)5719584   Email: Myznikov_lv@mail.ru
› Author Affiliations
Further Information

Publication History

Received: 01 November 2013

Accepted after revision: 19 December 2013

Publication Date:
21 January 2014 (online)


Abstract

Organic thiocyanates and nitriles are converted efficiently into the corresponding 5-substituted 1H-tetrazoles by treatment with zinc(II) chloride and sodium azide in aliphatic alcohols. The presented procedure provides mild reaction conditions, short reaction times, and good to excellent yields for a wide range of substrates, including deactivated aliphatic nitriles and thermally unstable thiocyanates.

Supporting Information

 
  • References

  • 1 Finnegan WG, Henry RA, Lofquist R. J. Am. Chem. Soc. 1958; 80: 3908
  • 2 Roh J, Vavrova K, Hrabalek A. Eur. J. Org. Chem. 2012; 31: 6101
  • 3 Demko ZP, Sharpless KB. J. Org. Chem. 2001; 66: 7945
  • 4 Koguro K, Oga T, Mitsui S, Orita R. Synthesis 1998; 910
  • 5 Roh J, Artamonova TV, Vavrova K, Koldobskii GI, Hrabalek A. Synthesis 2009; 2175
  • 6 Akhlaghinia B, Rezazadeh S. J. Braz. Chem. Soc. 2012; 23: 2197
  • 7 Palde PB, Jamison TF. Angew. Chem. Int. Ed. 2011; 50: 3525
  • 8 Amantini D, Beleggia R, Fringuelli F, Pizzo F, Vaccaro L. J. Org. Chem. 2004; 69: 2896
  • 9 Yoneyama H, Usami Y, Komeda S, Harusawa S. Synthesis 2013; 45: 1051
  • 10 Benson FR. Chem. Rev. 1947; 41: 1
  • 11 Beletskaya IP, Sigeev AS, Peregudov AS, Petrovskii PV. Mendeleev Commun. 2006; 16: 250
  • 12 Mahajan US, Akamanchi KG. Synth. Commun. 2009; 39: 2674
  • 13 Shiryaev AK, Moiseev IK. Russ. J. Org. Chem. 2001; 37: 746
  • 14 Lieber E, Enkoji T. J. Org. Chem. 1961; 26: 4472
  • 15 LeBlanc BW, Jursic BS. Synth. Commun. 1998; 28: 3591
  • 16 Zubarev VYu, Trifonov RE, Poborchii VV, Ostrovskii VA. Chem. Heterocycl. Compd. 2006; 42: 469
  • 17 Jin T, Kitahara F, Kamijo S, Yamamoto Y. Tetrahedron Lett. 2008; 49: 2824