Synthesis 2008(17): 2683-2685  
DOI: 10.1055/s-2008-1067202
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Diethyl Chlorophosphate: A Mild and Versatile Reagent for the One-Pot Preparation of Isothiocyanates from Amines

Babak Kaboudin*, Ehsan Jafari
Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Gava Zang, Zanjan 45195-1159, Iran
Fax: +98(241)4214949; e-Mail: kaboudin@iasbs.ac.ir;
Weitere Informationen

Publikationsverlauf

Received 28 April 2008
Publikationsdatum:
24. Juli 2008 (online)

Preview

Abstract

A simple, efficient, and new method has been developed for the synthesis of isothiocyanates from amines. The reaction of a variety of aromatic and aliphatic amines with carbon disulfide in the presence of diethyl chlorophosphate as an efficient reagent proceeded effectively to afford the corresponding isothiocyanates in moderate yields. This method is easy, rapid, and moderate-yielding for the synthesis of isothiocyanates from amines.

    References

  • 1a The Chemistry of Cyanates and their Thio Derivatives   Patai S., Wiley; Chichester: 1977. 
  • 1b Fernandez JMG. Mellet CO. Blanco JLJ. Mota JF. Gadelle A. Coste-Sarguet A. Depaye J. Carbohydr. Res.  1995,  268:  57 
  • 2a Bones AM. Rossiter JT. Physiol. Plant.  1996,  96:  194 
  • 2b Zhang Y. Li T. Gonzalez V. Mol. Cancer Ther.  2003,  2:  1045 
  • 2c Xiao D. Vogel V. Singh SV. Mol. Cancer Ther.  2006,  5:  2931 
  • 3 Mukerjee AK. Ashare R. Chem. Rev.  1991,  91:  1 ; and references therein
  • 4 Olejniczak B. Zwierzak A. Synthesis  1989,  300 
  • 5 Wadsworth WS. Emmons WD. J. Org. Chem.  1964,  29:  2816 
  • 6 Dyer E. Johnson TB. J. Am. Chem. Soc.  1932,  54:  777 
  • 7a Shibanuma T. Shiono M. Mukaiyama T. Chem. Lett.  1977,  573 
  • 7b Adam W. Bargon RM. Bosio SG. Schenk WA. Stalke D. J. Org. Chem.  2002,  67:  7037 
  • 8a Rathke A. Ber. Dtsch. Chem. Ges.  1872,  5:  799 
  • 8b Dyson GM. George HJ. J. Chem. Soc.  1924,  125:  1702 
  • 8c Kim S. Yi KY. Tetrahedron Lett.  1985,  26:  1661 
  • 9 Molina P. Alajarin M. Tamaiki H. Synthesis  1982,  596 
  • 10a Jochims JC. Seeliger A. Angew. Chem.  1967,  79:  151 
  • 10b Wong R. Dolman SJ. J. Org. Chem.  2007,  72:  3969 
  • 11a Boas U. Pederson MH. J. Chem. Soc., Chem. Commun.  1995,  1995 
  • 11b Boas U. Pederson B. Christensen JB. Synth. Commun.  1998,  28:  1223 
  • 11c Boas U. Gertz H. Christensen J. B. Heegaard P. M. H. Tetrahedron Lett.  2004,  45:  269 
  • 12 Yarovenko VN. Shirokov AV. Zavarzin IV. Krupinova ON. Ignatenko AV. Krayushhkin M. Synthesis  2004,  17 
  • 13a Sardarian AR. Kaboudin B. Tetrahedron Lett.  1997,  38:  2543 
  • 13b Kaboudin B. Chem. Lett.  2001,  880 
  • 13c Kaboudin B. Nazari R. Tetrahedron Lett.  2001,  42:  8211 
  • 13d Kaboudin B. Nazari R. Synth. Commun.  2001,  31:  2245 
  • 13e Kaboudin B. Balakrishna MS. Synth. Commun.  2001,  31:  2773 
  • 13f Kaboudin B. Tetrahedron Lett.  2002,  43:  8713 
  • 13g Kaboudin B. Tetrahedron Lett.  2003,  44:  1051 
  • 13h Kaboudin B. Rahmani A. Synthesis  2003,  2705 
  • 13i Kaboudin B. Saadati F. Synthesis  2004,  1249 
  • 13j Kaboudin B. Rahmani A. Org. Prep. Proced. Int.  2004,  36:  82 
  • 13k Kaboudin B. Moradi K. Tetrahedron Lett.  2005,  46:  2989 
  • 13l Kaboudin B. As-habei N. Tetrahedron Lett.  2003,  44:  4243 
  • 13m Kaboudin B. Karimi M. Bioorg. Med. Chem. Lett.  2006,  16:  5324 
  • 13n Kaboudin B. Farjadian F. Beilstein J. Org. Chem.  2006,  2:  4 
  • 13o Kaboudin B. Moradi K. Synthesis  2006,  2339 
  • 13p Kaboudin B. Jafari E. Synthesis  2006,  3063 
  • 13q Kaboudin B. Elahamifar D. Synthesis  2006,  224 
  • 13r Kaboudin B. Sorbiun M. Tetrahedron Lett.  2007,  48:  9015 
  • 13s Kaboudin B. Jafari E. Synthesis  2007,  1823 
  • 13t Kaboudin B. Saadati F. Tetrahedron Lett.  2007,  48:  2829 
  • 14a Kazemi F. Sharghi H. Naseri MA. Synthesis  2004,  205 
  • 14b Kazemi F. Massah AR. Javaherian M. Tetrahedron  2007,  63:  5083 
  • 14c Massah AR. Kazemi F. Azadi D. Farzaneh S. Aliyan H. Javaherian-Naghash H. Momeni AR. Lett. Org. Chem.  2006,  3:  235 
  • 15 Lukanov LK. Venkov AP. Mollov NM. Synthesis  1985,  971