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Synlett 2012(1): 80-84  
DOI: 10.1055/s-0031-1290087
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Imidazolidine-2-(thi)ones via C2-Selective Oxidation and Thionation of 2-Imidazolinium Halides

Maurice Mooijman, Robin S. Bon, Nanda E. Sprenkels, Hugo N. van Oosterhout, Frans J. J. de Kanter, Marinus B. Groen, Eelco Ruijter*, Romano V. A. Orru*
Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands
Fax: +31(20)5987488; e-Mail: r.v.a.orru@vu.nl; e-Mail: e.ruijter@vu.nl;
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Publication History

Received 11 October 2011
Publication Date:
05 December 2011 (online)

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Abstract

This article describes a scope study for the synthesis of imidazolidine-2-(thi)ones by selective oxidation or thionation of 2-imidazolinium halides, which in turn are synthesized by alkylation of 2-imidazolines obtained from an initial multicomponent reaction.

Key words

alkylation - cyclization - heterocycles - imines - multicomponent reactions

    References

  • 1 Shue H.-J. Chen X. Shih N.-Y. Blythin DJ. Paliwal S. Lin L. Gu D. Schwerdt JH. Shah S. Reichard GA. Piwinski JJ. Duffy RA. Lachowicz JE. Coffin VL. Liu F. Nomeir AA. Morgan CA. Varty GB. Bioorg. Med. Chem. Lett.  2005,  15:  3896 
    Search in Google Scholar
  • 2 Goodacre CJ. Bromidge SM. Clapham D. King FD. Lovell PJ. Allen M. Campbell LP. Holland V. Riley GJ. Starr KR. Trail BK. Wood MD. Bioorg. Med. Chem. Lett.  2005,  15:  4989 
    Search in Google Scholar
  • 3 Park H. Min K. Kwak H.-S. Koo KD. Lim D. Seo S.-W. Choi J.-U. Platt B. Choi D.-Y. Bioorg. Med. Chem. Lett.  2008,  18:  2900 
    Search in Google Scholar
  • 4 Kurihara M. Rouf ASS. Kansui H. Kagechika H. Okuda H. Miyata N. Bioorg. Med. Chem. Lett.  2004,  14:  4131 
    Search in Google Scholar
  • 5a Cardillo G. Orena M. Romero M. Sandri S. Tetrahedron  1989,  45:  1501 
    Search in Google Scholar
  • 5b Scheid G. Ruijter E. Konarzycka-Bessler M. Bornscheuer UT. Wessjohann LA. Tetrahedron: Asymmetry  2004,  15:  2861 
    Search in Google Scholar
  • 5c Kim TH. Lee G.-J. Tetrahedron Lett.  2000,  41:  1505 
    Search in Google Scholar
  • 6 Sztanke K. Pasternak K. Sidor-Wójtowicz A. Truchlinska J. Józwiak K. Bioorg. Med. Chem.  2006,  14:  3635 
    Search in Google Scholar
  • 7 Vassilev LT. Vu BT. Graves B. Carvajal D. Podlaski F. Filipovic Z. Kong N. Kammlott U. Lukacs C. Klein C. Fotouhi N. Liu EA. Science  2004,  303:  844 
    Search in Google Scholar
  • 8a Isobe T. Fukuda K. Ishikawa T. J. Org. Chem.  2000,  65:  7770 
    Search in Google Scholar
  • 8b Isobe T. Fukuda K. Tokunaga T. Seki H. Yamaguchi K. Ishikawa T. J. Org. Chem.  2000,  65:  7774 
    Search in Google Scholar
  • 8c Isobe T. Fukuda K. Yamaguchi K. Seki H. Tokunaga T. Ishikawa T. J. Org. Chem.  2000,  65:  7779 
    Search in Google Scholar
  • 9a Chen W. Li R. Wu Y. Ding L.-S. Chen Y.-C. Synthesis  2006,  3058 
  • 9b Dai M. Liang B. Wang C. Chen J. Yang Z. Org. Lett.  2003,  6:  221 
    Search in Google Scholar
  • 9c Li R. Chen W. Shi J. Chen L. Chen Y. Ding L. Wei Y. J. Mass Spectrom.  2008,  43:  542 
    Search in Google Scholar
  • 10 Bon RS. Sprenkels NE. Koningstein MM. Schmitz RF. de Kanter FJJ. Dömling A. Groen MB. Orru RVA. Org. Biomol. Chem.  2008,  6:  130 
    Search in Google Scholar
  • 11a Cava MP. Levinson MI. Tetrahedron  1985,  41:  5061 
    Search in Google Scholar
  • 11b Pederson BS. Scheibye S. Nilsson NH. Lawesson S.-O. Bull. Soc. Chim. Belg.  1978,  87:  223 
    Search in Google Scholar
  • 12 Bon RS. de Kanter FJJ. Lutz M. Spek AL. Jahnke MC. Hahn FE. Groen MB. Orru RVA. Organometallics  2007,  3639 
  • 13a Bon RS. Hong C. Bouma MJ. Schmitz RF. de Kanter FJJ. Lutz M. Spek AL. Orru RVA. Org. Lett.  2003,  5:  3759 
    Search in Google Scholar
  • 13b Elders N. Schmitz RF. de Kanter FJJ. Ruijter E. Groen MB. Orru RVA. J. Org. Chem.  2007,  72:  6135 
    Search in Google Scholar
  • For other applications of this versatile MCR, see:
  • 14a Elders N. Ruijter E. de Kanter FJJ. Groen MB. Orru RVA. Chem. Eur. J.  2008,  14:  4961 
    Search in Google Scholar
  • 14b Elders N. van der Born D. Hendrickx LJD. Timmer BJJ. Krause A. Janssen E. de Kanter FJJ. Ruijter E. Orru RVA. Angew. Chem. Int. Ed.  2009,  48:  5856 
    Search in Google Scholar
  • 14c Strassberger Z. Mooijman M. Ruijter E. Alberts AH. de Graaff C. Orru RVA. Rothenberg G. Appl. Organomet. Chem.  2010,  24:  142 
    Search in Google Scholar
  • 14d Strassberger Z. Mooijman M. Ruijter E. Alberts AH. Maldonado A. Orru RVA. Rothenberg G. Adv. Synth. Catal.  2010,  352:  2201 
    Search in Google Scholar
  • 15 Bon RS. van Vliet B. Sprenkels NE. Schmitz RF. de Kanter FJJ. Stevens CV. Swart M. Bickelhaupt FM. Groen MB. Orru RVA. J. Org. Chem.  2005,  70:  3542 
    Search in Google Scholar
  • 16a Marshall C. Ward MF. Harrison WTA.
    J. Organomet. Chem.  2005,  690:  3970 
    Search in Google Scholar
  • 16b Karkhanis DW. Field L. Phosphorous Sulfur Relat. Elem.  1985,  22:  49 
    Search in Google Scholar