Synlett 2004(7): 1323-1324  
DOI: 10.1055/s-2004-825608
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Phenyl Isothiocyanate: A Very Useful Reagent in Heterocyclic Synthesis

Geoffroy Sommen*
Department of Chemistry, University of Florida, Gainesville, FL 32611, USA.
e-Mail: sommen@chem.ufl.edu;
Further Information

Publication History

Publication Date:
19 May 2004 (online)

Introduction

Naturally occurring isothiocyanates are limited in number. There is, however, a large number of synthetic isothiocyanates which constitute an important class of compounds. Thus, it is apparent that the chemistry of and from isothiocyanates has burgeoned over the years, [1] and it continues to be a blossoming field. The attraction of isothiocyanates as synthons is due to their ready availability. The most important isothiocyanate which is easily synthesized from aniline and carbon disulfide is phenyl isothiocyanate. Several heterocycles, such as thiophenes, pyrroles, pyrimidines [2] or imidazoles, [3] can be constructed from this starting material.

Figure 1

    References

  • 1a Sharma S. Sulfur Reports  1989,  8:  327 
  • 1b Mukerjee AK. Ashare R. Chem. Rev.  1991,  91:  1 
  • 2 Srirastava SK. Haq W. Chauhan PMS. Bioorg. Med. Chem. Lett.  1999,  9:  965 
  • 3 Boeijen A. Likamp MJ. Tetrahedron Lett.  1998,  39:  3589 
  • 4a Sommen G. Comel A. Kirsch G. Tetrahederon Lett.  2002,  43:  257 
  • 4b Lozinskii MO. Shelyakin VV. Chem. Heterocycl. Cmpd.  2002,  38:  1077 
  • 5a Sommen G. Comel A. Kirsch G. Synlett  2001,  1731 
  • 5b Sommen G. Comel A. Kirsch G. Tetrahedron  2003,  59:  1557 
  • 6 Krylsky DV. Shikhaliev KS. Solovyev AS. Chem. Heterocycl. Cmpd.  2001,  37:  524 
  • 7 El-Sayed AM. Abdel-Ghany H. J. Heterocycl. Chem.  2000,  37:  1233 
  • 8a Nedolya NA. Brandsma L. Verkruijsse HD. Van der Kerk A. Trofimov BA. Tetrahedron Lett.  1998,  39:  2631 
  • 8b Brandsma L. Nedolya NA. Tarasova OA. Trofimov BA. Chem. Heterocycl. Cmpd.  2000,  36:  1241 
  • 9 Cocco M. T., Congiu C., Onnis V., Piras R.; Il Farmaco; 2001, 56: 741
  • 10a Katritzky AR. Wang X. Maimait R. J. Org. Chem.  2000,  65:  8077 
  • 10b Jackson B. Gakis N. Marky M. Hansen H.-J. von Philipsborn W. Schmid H. Helv. Chim. Acta  1972,  55:  916 
  • 11 Katritzky AR. Wang X. Denisenko A. J. Org. Chem.  2001,  66:  2850