Download PDF
Synthesis 2002(1): 0075-0078
DOI: 10.1055/s-2002-19308
PAPER
© Georg Thieme Verlag Stuttgart · New York

Microwave Assisted Synthesis of 1,5-Disubstituted Hydantoins and Thiohydantoins in Solvent-Free Conditions

Satya Paul*a, Mukta Guptaa, Rajive Guptaa, André Loupyb
a Department of Chemistry, University of Jammu, Jammu-180 006, India
Fax: +91(191)505086; e-Mail: paul7@rediffmail.com;
b Laboratoire des Réactions Sélectives sur Supports, CNRS UMR 8615, Université Paris-Sud, 91405, Orsay, France
Fax: +33(169)154679; e-Mail: aloupy@icmo.u-psud.fr;
Further Information

Publication History

Received 28 June 2001
Publication Date:
04 August 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

1,5-Disubstituted hydantoins/thiohydantoins 3a-p have been synthesized in 81-95% yield by a microwave-promoted solvent-free condensation of arylglyoxals 1 and phenylurea/thiourea 2 using PPE as a reaction mediator. This method can be extended towards the parallel synthesis of 3. The workup is simple and involves treatment with ice-cold water.

Key words

arylglyoxals - solvent-free conditions - polyphosphoric ester (PPE) - microwave activation - hydantoins

    References

  • 1 Havera HJ, and Stryeker WG. inventors; US Patent  3835151.  ; Chem. Abstr. 1974, 81, 152224m
  • 2 Havera HJ, and Stryeker WG. inventors; US Patent  3994904.  ; Chem. Abstr. 1977, 86, 106586m
  • 3 El-Kerdawy MM. Tantawy AS. Abououf AA. Egypt. J. Chem.  1974,  17:  845 
    Google Scholar
  • 4 Dziedzic B. Szadowska A. Kaminska A. Acta Pol. Pharm.  1978,  35:  423 
    Google Scholar
  • 5 Rodgers TR. Lamontagne MP. Markovc A. Ash AB. J. Med. Chem.  1977,  20:  591 
    CrossrefGoogle Scholar
  • 6 Valavicient J. Blyum RA. Lutsenko VV. Poliskilzuch, Portivoopukholevykh, Protivovospalitelmykh Mutagennykh Veshchestv  1977,  44 ; Chem. Abstr. 1978, 88, 105221t
    Google Scholar
  • 7 Sarges R, and Sehnur R. inventors; US Patent  4127665.  ; Chem. Abstr. 1979, 90, 87464j
  • 8 Schulte KE. Von WV. Eur. J. Med. Chem.-Chim. Ther.  1978,  13:  25 
    Google Scholar
  • 9 Claussuer A, Goubet F, and Teutsch J.-J. inventors; PCT Int. Appl. WO 97  19064.  ; Chem. Abstr. 1997, 127, 50640v
  • 10 Hussain I. Nasir M. J. Ind. Chem. Soc.  1979,  56:  177 
    Google Scholar
  • 11 Seki T. inventors; Jpn. Kokai Tokkyo Koho JP  09278645.  ; Chem. Abstr. 1997, 127, 362483q
  • 12 Elokdah HM, Chai S.-Y, Sulkowski TS, and Strike DP. inventors; PCT Int. Appl. WO 97  19932.  ; Chem. Abstr. 1997, 127, 81453r
  • 13 Moloney GP. Martin GR. Mathews N. Milne A. Hobbs H. Dudsworth S. Sang PY. Knigh C. Williams M. Maxwell M. Glen RC. J. Med. Chem.  1999,  42:  2504 
    CrossrefGoogle Scholar
  • 14 Joshi KC. Pathak VN. Goyal MK. J. Heterocycl. Chem.  1981,  18:  1651 
    CrossrefGoogle Scholar
  • For recent reviews on microwave-assisted organic reactions:
  • 15a Deshayes S. Liagre M. Loupy A. Luche J.-L. Petit A. Tetrahedron  1999,  55:  10851 
    Google Scholar
  • 15b Varma S. Green Chemistry  1999,  1:  43 
    Google Scholar
  • 15c Loupy A. Petit A. Hamelin J. Texier-Boullet F. Jacquault P. Mathe D. Synthesis  1998,  1213 
    Google Scholar
  • 15d Bose AK. Banik BK. Lavlinskaia N. Jayaraman M. Manhas MS. Chemtech  1997,  27:  18 
    Google Scholar
  • 15e Majetich G. Hicks R. J. Microwave Power  1995,  30:  27 
    Google Scholar
  • 15f Abramovitch RA. Org. Prep. Proced. Int.  1991,  2:  683 
    Google Scholar
  • 16 Loupy A. Topics of Current Chemistry: Modern Solvents in Organic Synthesis   Vol. 206:  Knochel P. Springer Verlag; New York: 1999.  p.153 
    Google Scholar
  • 17 Cleophax J. Liagre M. Loupy A. Petit A. Org. Process Res. Dev.  2000,  6:  498 
    Google Scholar
  • 18a Loupy A. Perreux L. Liagre M. Burle K. Moneuse M. Pure Appl. Chem.  2001,  73:  161 
    Google Scholar
  • 18b

    Perreux, L.; Loupy, A. Tetrahedron, in press.
  • 19 Arnold K, and Moebius G. inventors; Ger. Patent (East)  89846DD.  ; Chem. Abstr., 1972, 77, 126634
  • 20 Pentassuglia G. Araldi GL. Donati D. Feriani A. Oliosi B. Pasquarello A. Ursini A. Farmaco  1997,  52:  573 
    Google Scholar