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Synthesis 2009(2): 205-210  
DOI: 10.1055/s-0028-1083289
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 1,4-Benzodiazepine-2,5-diones Using an Ionic Liquid as a Soluble Support

Hongwei Xie, Cuifen Lu, Guichun Yang*, Zuxing Chen
Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, School of Chemistry and Chemical Engineering, Hubei University, Wuhan, Hubei, 430062, P. R. of China
e-Mail: yangguichun@hubu.edu.cn;
Further Information

Publication History

Received 31 July 2008
Publication Date:
19 December 2008 (online)

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Abstract

The first report of the use of an ionic liquid as a soluble support for the synthesis of 1,4-benzodiazepine-2,5-diones is reported in this paper. This synthetic method is simple and efficient and the products are obtained in good yields. All of the products were characterized by IR, ¹H NMR, and ¹³C NMR.

Key words

ionic liquid - synthesis - 1,4-benzodiazepine-2,5-diones - soluble support

    References

  • For recent articles on the syntheses and bioactivities of 1,4-benzodiazepine-2,5-diones, see:
  • 1a Kamal A. Reddy KL. Devaiah V. Synlett  2004,  2533 
    Google Scholar
  • 1b Kamal A. Ramana AV. Reddy KS. Tetrahedron Lett.  2004,  45:  818 
    Google Scholar
  • 1c Sabb AL. Vogel RL. Welmaker GS. Sabalski JE. Coupet J. Dunlop J. Rosenzweig-Lipson S. Harrison B. Bioorg. Med. Chem. Lett.  2004,  14:  2603 
    Google Scholar
  • 1d Li XY. Cao H. Zhang CC. Fuchs K. J. Med. Chem.  2003,  46:  5567 
    Google Scholar
  • 1e Parks DJ. LaFrance LV. Calvo RR. Milkiewicz KL. Gupta V. Lattanze J. Ramachandren K. Carver TE. Petrella EC. Cummings MD. Maguire D. Grasberger BL. Lu T. B. Bioorg. Med. Chem. Lett.  2005,  15:  765 
    Google Scholar
  • For solid-phase synthesis of 1,4-benzodiazepine-2,5-diones, see:
  • 2a Boojamra CG. Burow KM. Thompson LA. Ellman JA. J. Org. Chem.  1997,  62:  1240 
    Google Scholar
  • 2b Mayer JP. Zhang J. Bjergarde K. Lenz DM. Gaudino JJ. Tetrahedron Lett.  1996,  37:  8081 
    Google Scholar
  • 2c Hulme C. Peng J. Morton G. Salvino JM. Herpin T. Labaudiniere R. Tetrahedron Lett.  1998,  39:  7227 
    Google Scholar
  • 2d Kennedy AL. Fryer AM. Josey JA. Org. Lett.  2002,  4:  1167 
    Google Scholar
  • For recent reviews, see:
  • 3a Hermkens PHH. Ottenheijm HCJ. Rees D. Tetrahedron  1996,  52:  4527 
    Google Scholar
  • 3b Booth S. Hermkens PHH. Ottenheijm HCJ. Rees DC. Tetrahedron  1998,  54:  15385 
    Google Scholar
  • 3c Lorsbach BA. Kurth MJ. Chem. Rev.  1999,  99:  1549 
    Google Scholar
  • 3d Guillier F. Orain D. Bradley M. Chem. Rev.  2000,  100:  2091 
    Google Scholar
  • 3e Sammelson R. Kurth MJ. Chem. Rev.  2001,  101:  137 
    Google Scholar
  • 3f Krchòák V. Holladay W. Chem. Rev.  2002,  102:  61 
    Google Scholar
  • 3g Blaney P. Grigg R. Sridharan V. Chem. Rev.  2002,  102:  2607 
    Google Scholar
  • 4a Gravert DJ. Janda KD. Chem. Rev.  1997,  97:  489 
    Google Scholar
  • 4b Wentworth PJ. Janda KD. Chem. Commun.  1999,  1917 
    Google Scholar
  • 5a Toy PH. Janda KM. Acc. Chem. Res.  2000,  33:  546 
    Google Scholar
  • 5b Fishman A. Farrah ME. Zhong JH. Paramanantham S. Carrera C. Lee-Ruff E. J. Org.Chem.  2003,  68:  9843 
    Google Scholar
  • 5c Sauvagnat B. Kulig K. Lamaty F. Lazaro R. Martinez J. J. Comb. Chem.  2000,  2:  134 
    Google Scholar
  • 5d Chen S. Janda KD. J. Am. Chem. Soc.  1997,  119:  8724 
    Google Scholar
  • 5e Lin XF. Zhang J. Wang YG. Tetrahedron Lett.  2003,  44:  4113 
    Google Scholar
  • 5f Wang YG. Lin XF. Cui SL. Synlett  2004,  1175 
    Google Scholar
  • 6 For a recent review, see: Davis JHJ. Chem. Lett.  2004,  33:  1072 
    CrossrefGoogle Scholar
  • 7a Fraga-Dubreuil J. Bazureau JP. Tetrahedron Lett.  2001,  42:  6097 
    Google Scholar
  • 7b Miao W. Chan TH. Org. Lett.  2003,  5:  5003 
    Google Scholar
  • 7c Fraga-Dubreuil J. Famelart MH. Bazureau JP. Org. Process Res. Dev.  2002,  6:  374 
    Google Scholar
  • 7d Fraga-Dubreuil J. Bazureau JP. Tetrahedron  2003,  59:  6121 
    Google Scholar
  • 8a Peng HD. Huang YL. Yang JH. Chen ZX. Yang GC. Comb. Chem. High Throughput Screening  2007,  10:  257 
    Google Scholar
  • 8b Zhang HQ. Yang GC. Chen JN. Chen ZX. Synthesis  2004,  3055 
    Google Scholar
  • 8c Rao Z. Peng HD. Yang GC. Chen ZX. Comb. Chem. High Throughput Screening  2006,  9:  1743 
    Google Scholar
  • 8d Chen ZX. Yue GZ. Lu CF. Yang GC. Synlett  2004,  1231 
    Google Scholar
  • 8e Yue GZ. Wan YD. Song SJ. Yang GC. Chen ZX. Bioorg. Med. Chem. Lett.  2005,  15:  453 
    Google Scholar