Synlett 2010(3): 501-502  
DOI: 10.1055/s-0029-1219338
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Ethyl 2-Cyano-3,3-bis(methylthio)acrylate

Mohan Balasaheb Kalyankar*
Department of Organic Chemistry, North Maharashtra University, Jalgaon-425001, India
e-Mail: kalyankar.mb@rediffmail.com;
Further Information

Publication History

Publication Date:
25 January 2010 (online)

Introduction

Ethyl 2-cyano-3,3-bis(methylthio)acrylate (Figure  [¹] ) was prepared by the reaction of ethyl cyanoacetate, carbon di­sulfide and dimethyl sufate in the presence of a base. [¹] Gommper and co-workers studied this reaction thoroughly. The electron-attracting groups on C2 makes it a very useful reagent for the preparation of heterocyclic compounds. [²] Moreover, Ethyl 2-cyano-3,3-bis(methyl­thio)acrylate can also be prepared efficiently using sodium ethoxide as a base. [³] In the literature numerous reports appeared highlighting its chemistry and use.

Figure 1 Ethyl 2-Cyano-3,3-bis(methylthio)acrylate

    References

  • 1 Gompper R. Topfl W. Chem. Ber.  1962,  95:  2861 
  • 2a Chauhan SMS. Junjappa H. Tetrahedron  1976,  32:  1779 
  • 2b Chauhan SMS. Junjappa H. Tetrahedron  1976,  32:  1911 
  • 2c Potts KT. Cipullo MJ. Ralli P. Theodoridis G. J. Am. Chem. Soc.  1981,  103:  3584 
  • 2d Kumar A. Mhatra S. Ila H. Junjappa H. J. Chem. Soc. Chem. Commun.  1976,  592 
  • 3 Kumar A. Malhotra S. Vats A. . Singh SK. Sharma SK. Prasad AK. Errington W. Olsen CE. Jain SC. Parmar VS. Indian J. Chem.  2002,  41B:  360 
  • 4 Tominaga Y. Ushirogochi A. Matsuda Y. Kobayashi G. Chem. Pharm. Bull.  1984,  32:  3384 
  • 5a Ram VJ. Verma M. Indian J. Chem.  1990,  29B:  624 
  • 5b Pratap R. Kumar B. Ram VJ. Tetrahedron  2007,  63:  10300 
  • 5c Singh FV. Vatsyayan R. Roy U. Goel A. Bioorg. Med. Chem. Lett.  2006,  16:  2734 
  • 6 Baheti KG. Kuberkar SV. Indian J. Heterocycl. Chem.  2003,  12:  343 
  • 7a Pratap R. Ram VJ. Tetrahedron Lett.  2007,  48:  4715 
  • 7b Pratap R. Ram VJ. J. Org. Chem.  2007,  72:  7402 
  • 8 Ram VJ. Goel A. Shukla PK. Kapil A. Bioorg. Med. Chem. Lett.  1997,  7:  3101 
  • 9a Agarwal N. Raghuwanshi SK. Upadhyay DN. Shukla PK. Ram VJ. Bioorg. Med. Chem. Lett.  2000,  10:  703 
  • 9b Kohra S. Tominaga Y. Hosomi AJ. Heterocycl. Chem.  1988,  25:  959 
  • 10 Mukherjee-Singh O. Farooque MA. Indian J. Chem.  2004,  43B:  1561 
  • 11 Omran OA. Amer AA. Khodairy A. Synth. Commun.  2006,  36:  3647 
  • 12 Liu H. Yang G. Chen K. Yang H. Synth. Commun.  1999,  29:  3143 
  • 13 Liu H. Lu R. Yang H. Synth. Commun.  1998,  28:  3965 
  • 14 Metwally MA. Desoky EI. Fawzy R. Etman HA. Chem. Heterocycl. Compd.  2007,  43:  382