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Synthesis 2011(1): 30-32  
DOI: 10.1055/s-0030-1258343
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Preparation of Thioflavones via Thiophosphoryl Chloride Mediated Cyclodehydration and Thionation of 1-(2-Hydroxyphenyl)-3-arylpropane-1,3-diones

Manorama Vimal, Uma Pathak*, Lokesh Kumar Pandey, Malladi V. S. Suryanarayana
Synthetic Chemistry Division, Defence Research & Development Establishment, Gwalior (MP) 474 002, India
Fax: +91(751)2341148; e-Mail: sc_drde@rediffmail.com;
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Publication History

Received 30 September 2010
Publication Date:
30 November 2010 (online)

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Abstract

A simple and convenient one-pot strategy for the preparation of thioflavones from 1,3-diketones is described. Cyclodehydration of a range of β-diketones and thionation of the resulting flavones was achieved using thiophosphoryl chloride (PSCl3) which serves as both a catalyst and thionating agent.

Key words

β-diketones - flavones - thioflavones - thiophosphoryl chloride

    References

  • 1a Razdan RK. Bruni RJ. Mehta AC. Weinhardt KK. Papanastassiou ZB. J. Med. Chem.  1978,  21:  643 
    Search in Google Scholar
  • 1b Mughal EU. Ayaz M. Hussain Z. Hasan A. Sadiq A. Riaz M. Malik A. Hussain S. Choudhary MI. Bioorg. Med. Chem.  2006,  14:  4704 
    Search in Google Scholar
  • 1c Ba LT. Seth MC. Chem. Commun.  2006,  203 
  • 1d Dao TT. Tuyen TN. Park H. Arch. Pharm. Res.  2005,  28:  652 
    Search in Google Scholar
  • 2a Schonberg A. Nickel S. Ber. Dtsch. Chem. Ges.  1931,  64:  2323 
    Search in Google Scholar
  • 2b Baker W. Harborne JB. Ollis W. J. Chem. Soc.  1952,  1303 
  • 2c Baker W. Clarke GG. Harborne JB. J. Chem. Soc.  1954,  998 
  • 2d Levai A. Heterocycl. Commun.  1999,  5:  419 
    Search in Google Scholar
  • 2e Mughal EU. Hasan A. Rashid L. Heterocycl. Commun.  2005,  11:  445 
    Search in Google Scholar
  • 2f Dudley KH. Miller H. Corley RC. Wall ME. J. Med. Chem.  1967,  10:  985 
    Search in Google Scholar
  • 2g Witczak Z. Krolikowska M. Pol. J. Chem.  1981,  55:  763 
    Search in Google Scholar
  • 2h Briggs MT. Duncan GLS. Thornber CW. J. Chem. Res.  1982,  9:  2461 
    Search in Google Scholar
  • 3a Balint J. Bognar R. Rakosi M. In Organic Sulfur Chemistry   Bernadi F. Csizmadia IG. Magini A. Elsevier; Amsterdam: 1985. 
  • 3b The Chemistry of Flavonoid Compounds   Geisman TA. Pergamon Press; London: 1952. 
  • 3c Wagner H. Farkas L. In The Flavonoids   Harborne J. Mabry TJ. Mabry H. Academic Press; New York: 1975. 
  • 3d Allan J. Robinson R. J. Chem. Soc.  1924,  20:  2192 
    Search in Google Scholar
  • 4a Baker W. J. Chem. Soc.  1933,  1381 
  • 4b Mahal HS. Venkataraman K. Curr. Sci.  1933,  4:  214 
    Search in Google Scholar
  • 4c Mahal HS. Venkataraman K. J. Chem. Soc.  1934,  1767 
  • 5 A literature survey revealed a report in which the direct preparation of 2-methylchromone-4-thione from the corresponding β-diketone by refluxing in P2S5-pyridine was described, see: Coombers RC. Fenton DE. Phosphorus, Sulfur Silicon Relat. Elem.  1983,  14:  139.  For comparison with our protocol, this system was utilized for the preparation of 2-phenyl-4H-chromene-4-thione from 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-dione (1a), as a model substrate. The reaction was monitored by TLC and GC-MS, but only formation of the corresponding flavone was observed, even after stirring for 4 h
    CrossrefSearch in Google Scholar
  • 6a Pathak U. Pandey LK. Tank R. J. Org. Chem.  2008,  73:  2890 
    Search in Google Scholar
  • 6b Pathak U. Pandey LK. Mathur S. Suryanarayana MVS. Chem. Commun.  2009,  5409