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Synthesis 2011(19): 3133-3137  
DOI: 10.1055/s-0030-1260184
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Unexpected Rearrangement; A Novel Route to 3-Thiazoline

Yingrui Liu, Baoxiang Zhao*, Yonghai Li, Liangwen Zheng, Jinting Liu
Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China
Fax: +86(531)88564464; e-Mail: bxzhao@sdu.edu.cn;
Further Information

Publication History

Received 29 April 2011
Publication Date:
24 August 2011 (online)

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Abstract

An unexpected and novel rearrangement was discovered and used to synthesize a series of 3-thiazoline derivatives. The structures of the new compounds were determined by HRMS, IR, NMR and X-ray analyses.

Key words

rearrangement - amino acids - synthesis - thiazoline - X-ray

    References

  • 1a Wipf P. Venkatraman S. Synlett  1997,  1 
    Google Scholar
  • 1b White JD. Kim T.-S. Nambu M. J. Am. Chem. Soc.  1997,  119:  103 
    Google Scholar
  • 1c Numajiri Y. Takahashi T. Doi T. Chem. Asian J.  2009,  4:  111 
    Google Scholar
  • 2a Wipf P. Reeves JT. Balanchandran R. Day BW. J. Med. Chem.  2002,  45:  1901 
    Google Scholar
  • 2b Hussein MA. Kafafy A.-H. Abdel-Moty SG. Abou-Ghadir OM. Acta Pharm. (Zagreb, Croatia)  2009,  59:  365 
    Google Scholar
  • 2c Kim E.-A. Hahn H.-G. Kim K.-S. Kim TU. Choi SY. Cho S.-W. Cell Mol. Neurobiol.  2010,  30:  807 
    Google Scholar
  • 2d Nagasawa HT. Goon DJW. Crankshaw DL. Vince R. Patterson SE. J. Med. Chem.  2007,  50:  6462 
    Google Scholar
  • 3a Boyce RJ. Mulqueen GC. Pattenden G. Tetrahedron Lett.  1994,  35:  5705 
    Google Scholar
  • 3b Havrylyuk D. Zimenkovsky B. Vasylenko O. Zaprutko L. Gzella A. Lesyk R. Eur. J. Med. Chem.  2009,  44:  1396 
    Google Scholar
  • 3c Wipf P. Xu W.-J. J. Org. Chem.  1996,  61:  6556 
    Google Scholar
  • 3d Zarantonello P. Leslie CP. Ferritto R. Kazmierski WM. Bioorg. Med. Chem. Lett.  2002,  12:  561 
    Google Scholar
  • 4a Seijas JA. Vázquez-Tato MP. Crecente-Campo J. Tetrahedron  2008,  64:  9280 
    Google Scholar
  • 4b Guirado A. Andreu R. Martiz B. Pérez-Ballester S. Tetrahedron  2006,  62:  9688 
    Google Scholar
  • 4c Chen J.-H. Forsyth CJ. Org. Lett.  2003,  5:  1281 
    Google Scholar
  • 5a Endres T. Fendt M. J. Exp. Biol.  2009,  212:  2324 
    Google Scholar
  • 5b Fendt M. Endres T. Lowry CA. Apfelbach R. McGregor IS. Neurosci. Biobehav. Rev.  2005,  29:  1145 
    Google Scholar
  • 5c Fendt M. Endres T. Neurosci. Biobehav. Rev.  2008,  32:  1259 
    Google Scholar
  • 6a Asinger F. Thiel M. Dathe W. Hampel O. Mittag E. Plaschil E. Schröder CC. Liebigs Ann. Chem.  1961,  639:  146 
    Google Scholar
  • 6b Martens J. Offermanns H. Scherberich P. Angew. Chem., Int. Ed. Engl.  1981,  20:  668 
    Google Scholar
  • 6c Schlemminger I. Janknecht H.-H. Maison W. Saak W. Martens J. Tetrahedron Lett.  2000,  41:  7289 
    Google Scholar
  • 7a Fernandez X. Fellous R. Lizzani-Cuvelier L. Loiseau M. Duñach E. Tetrahedron Lett.  2001,  42:  1519 
    Google Scholar
  • 7b Fernandez X. Duñach E. Fellous R. Lizzani-Cuvelier L. Loiseau M. Flavour Fragr. J.  2002,  17:  432 
    Google Scholar
  • 7c Fernandez X. Duñach E. Tetrahedron: Asymmetry  2001,  12:  1279 
    Google Scholar
  • 7d Vedejs E. Fields S. J. Org. Chem.  1988,  53:  4663 
    Google Scholar
  • 8a Fan C.-D. Su H. Zhao J. Zhao B.-X. Zhang S.-L. Miao J.-Y. Eur. J. Med. Chem.  2010,  45:  1438 
    Google Scholar
  • 8b Lian S. Su H. Zhao B.-X. Liu W.-Y. Zheng L.-W. Miao J.-Y. Bioorg. Med. Chem.  2009,  17:  7085 
    Google Scholar
  • 8c Zheng L.-W. Wu L.-L. Zhao B.-X. Dong W.-L. Miao J.-Y. Bioorg. Med. Chem.  2009,  17:  1957 
    Google Scholar
  • 8d Ding X.-L. Zhang H.-Y. Qi L. Zhao B.-X. Lian S. Lv H.-S. Miao J.-Y. Bioorg. Med. Chem. Lett.  2009,  19:  5325 
    Google Scholar
  • 8e Zhang J.-H. Fan C.-D. Zhao B.-X. Shin D.-S. Dong W.-L. Xie Y.-S. Miao J.-Y. Bioorg. Med. Chem.  2008,  16:  10165 
    Google Scholar
  • 8f Zhao B.-X. Zhang L. Zhu X.-S. Wan M.-S. Zhao J. Zhang Y. Zhang S.-L. Miao J.-Y. Bioorg. Med. Chem.  2008,  16:  5171 
    Google Scholar
  • 9 Xie Y.-S. Zhao B.-X. Lv H.-S. Li J.-K. Wang B.-S. Shin D.-S. J. Mol. Struct.  2009,  930:  83 
    CrossrefGoogle Scholar
  • 10a Sakai K. Yoneda N. Chem. Pharm. Bull.  1981,  29:  1554 
    Google Scholar
  • 10b Suzuki T. Nagaoka H. Kondo Y. Takahashi T. T akeuchi M. Hara H. Saito M. Yamada T. Tomioka K. Hamada M. Mase T. Chem. Pharm. Bull.  1998,  46:  1468 
    Google Scholar
  • 12 Platonov AYu. Evdokimov AN. Kurzin AV. Maiyorova HD. J. Chem. Eng. Data  2002,  47:  1175 
    CrossrefGoogle Scholar
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X-ray crystallography: CCDC-779249 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at http://www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or e-mail: deposit@ccdc.cam.ac.uk].