PDF herunterladen
Synlett 2011(9): 1281-1284  
DOI: 10.1055/s-0030-1260548
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of Sulfonyl Amidines and β-Amino Sulfonyl Enamines under Transition-Metal-Free Conditions

Tingting Gao, Mingming Zhao, Xu Meng, Chuanbin Li, Baohua Chen*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Gansu Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: chbh@lzu.edu.cn;
Weitere Informationen

Publikationsverlauf

Received 15 March 2011
Publikationsdatum:
29. April 2011 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

Treatment of enamine and azide resulted in the formation of either sulfonyl amidine or β-amino sulfonyl enamine derivative in moderate to good yields. The reaction could proceed under catalyst-free conditions.

Key words

enamine - azide - amidine - catalyst-free

    References and Notes

  • 1 Foley SR. Bensimon C. Richeson DS. J. Am. Chem. Soc.  1997,  119:  10359 
    CrossrefSuche in Google Scholar
  • 2a Sienkiewich P. Bielawski K. Bielawska A. Palka J. Environ. Toxicol. Pharmacol.  2005,  20:  118 
    Suche in Google Scholar
  • 2b Greenhill JV. Lue P. Prog. Med. Chem.  1993,  30:  203 
    Suche in Google Scholar
  • 2c Barker J. Kilner M. Coord. Chem. Rev.  1994,  133:  219 
    Suche in Google Scholar
  • 3a Dunn PJ. In Comprehensive Organic Functional Group Transformations   Vol. 5:  Katritzky AR. Meth-Cohn O. Rees CW. Pergamon Press; Amsterdam: 1995.  p.741-782  
    Suche in Google Scholar
  • 3b Boyd GV. In The Chemistry of Amidines and Imidates   Vol. 2:  Patai S. Rappoport Z. Wiley; New York: 1991.  Chap. 8.
    Suche in Google Scholar
  • 4a Chang S. Lee M. Jung DY. Yoo EJ. Cho SH. Han SK. J. Am. Chem. Soc.  2006,  128:  12366 
    Suche in Google Scholar
  • 4b Bae I. Han H. Chang S. J. Am. Chem. Soc.  2005,  127:  2038 
    Suche in Google Scholar
  • 5a Takuwa T. Minowa T. Onishi JY. Mukaiyama T. Bull. Chem. Soc. Jpn.  2004,  77:  1717 
    Suche in Google Scholar
  • 5b Kumagai N. Matsunaga S. Shibasaki M. Angew. Chem. Int. Ed.  2004,  43:  478 
    Suche in Google Scholar
  • 5c Lange UEW. Schäfer B. Baucke D. Buschmann E. Mack H. Tetrahedron Lett.  1999,  40:  7067 
    Suche in Google Scholar
  • 6a Xu X. Ge Z. Cheng D. Ma L. Lu C. Zhang Q. Yao N. Li X. Org. Lett.  2010,  12:  897 
    Suche in Google Scholar
  • 6b Li Z. Yu R. Li H. Angew. Chem. Int. Ed.  2008,  47:  7497 
    Suche in Google Scholar
  • 6c Li Z. Li H. Guo X. Cao L. Yu R. Li H. Pan S. Org. Lett.  2008,  10:  803 
    Suche in Google Scholar
  • 6d Cho SH. Hwang SJ. Chang S. J. Am. Chem. Soc.  2008,  130:  9254 
    Suche in Google Scholar
  • 6e Cheng D. Bao W. J. Org. Chem.  2008,  73:  6881 
    Suche in Google Scholar
  • 6f Cheng D. Bao W. Adv. Synth. Catal.  2008,  350:  1263 
    Suche in Google Scholar
  • 6g Murahashi S.-I. Nakae T. Terai H. Komiya N. J. Am. Chem. Soc.  2008,  130:  11005 
    Suche in Google Scholar
  • 6h Niu M. Yin Z. Fu H. Jiang Y. Zhao Y. J. Org. Chem.  2008,  73:  3961 
    Suche in Google Scholar
  • 6i Liu X. Zhang Y. Wang L. Fu H. Jiang Y. Zhao Y. J. Org. Chem.  2008,  73:  6207 
    Suche in Google Scholar
  • 6j Zhang Y. Fu H. Jiang Y. Zhao Y. Org. Lett.  2007,  9:  3813 
    Suche in Google Scholar
  • 6k Li Z. Bohle DS. Li C.-J. Proc. Natl. Acad. Sci. U.S.A.  2006,  103:  8928 
    Suche in Google Scholar
  • 6l Doye S. Angew. Chem. Int. Ed.  2001,  40:  3351 
    Suche in Google Scholar
  • 6m Murahashi S.-I. Pure Appl. Chem.  1992,  64:  403 
    Suche in Google Scholar
  • 7a Xu X. Li X. Org. Lett.  2009,  11:  1027 
    Suche in Google Scholar
  • 7b Xu X. Li X. Ma L. Ye N. Weng B. J. Am. Chem. Soc.  2008,  130:  14048 
    Suche in Google Scholar
  • 7c Liu N. Tang B. Chen Y. He L. Eur. J. Org. Chem.  2009,  2059 
  • 8 Wang S. Wang Z. Zheng X. Chem. Commun.  2009,  7372 
  • 9a Fan J. Wang Z. Chem. Commun.  2008,  5381 
  • 9b Anilkumar G. Bitterlich B. Gelalcha FG. Tse MK. Beller M. Chem. Commun.  2007,  289 
10

Typical Procedure for the Preparation of 4-Methyl- N -[morpholino(phenyl)methylene]benzenesulfonamide (3): To a stirred solution of 4-(1-phenylvinyl)morpholine (0.1 mmol) and CH2Cl2 (0.1 mL), p-toluenesulfonyl azide (0.15 mmol) was added successively. The mixture was kept at r.t. under air and stirred for 20 min. The mixture was then extracted with EtOAc, dried over MgSO4 and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chroma-tography (PE-EtOAc, 1:1) to give the product 3 as a white solid. ¹H NMR (400 MHz, CDCl3): δ = 2.36 (s, 3 H), 3.11-3.13 (m, 2 H), 3.53-3.56 (m, 2 H), 3.76-3.78 (m, 2 H), 3.92-3.95 (m, 2 H), 7.12-7.16 (m, 4 H), 7.34-7.45 (m, 3 H), 7.49-7.51 (m, 2 H). ¹³C NMR (100 MHz, CDCl3): δ = 21.4, 45.0, 48.2, 66.3, 66.7, 126.5, 127.3, 128.4, 128.8, 130.0, 131.3, 140.6, 141.7, 165.8.