Download PDF
Synthesis 2009(12): 2035-2039  
DOI: 10.1055/s-0029-1216805
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Strecker-Type Reaction Catalyzed by Carboxylic Acids in Aqueous Media

Zhengfeng Xiea,b, Guilong Lic, Gang Zhao*c, Jide Wang*a,b
a School of Sciences, Xi’an Jiaotong University, Xi’an 710049, P. R. of China
b College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, P. R. of China
Fax: +86(991)8582807; e-Mail: awangjd@xju.edu.cn ;
c Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: Zhaog@mail.sioc.ac.cn;
Further Information

Publication History

Received 16 December 2008
Publication Date:
12 May 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Carboxylic acid catalyzed Strecker-type reactions were successfully carried out by simply mixing aldehydes, amines, tributyltin cyanide and carboxylic acid in aqueous media at room temperature, to afford α-aminonitriles in high yields.

Key words

Strecker reaction - α-aminonitriles - tributyltin cyanide - carboxylic acid - aqueous media

    References

  • 1 Strecker A. Ann. Chem. Pharm.  1850,  75:  27 
    CrossrefGoogle Scholar
  • 2a Ishitani H. Komiyama S. Kobayashi S. Angew. Chem. Int. Ed.  1998,  37:  3186 
    Google Scholar
  • 2b Kobayashi S. Busujima T. Nagayama S. Chem. Commun.  1998,  981 
    Google Scholar
  • 2c Surendra K. Krishnaveni NS. Mahesh A. Rao KR. J. Org. Chem.  2006,  71:  2532 
    Google Scholar
  • 2d De S K. J. Mol. Catal. A: Chem.  2005,  225:  167 
    Google Scholar
  • 3a Kobayashi S. Nagayama S. Busujima T. Tetrahedron Lett.  1996,  37:  9221 
    Google Scholar
  • 3b De S K. Gibbs RA. Tetrahedron Lett.  2004,  45:  7407 
    Google Scholar
  • 3c De S K. Synth. Commun.  2005,  35:  653 
    Google Scholar
  • 3d De S K. Gibbs RA. Synth. Commun.  2005,  35:  961 
    Google Scholar
  • 3e Kobayashi S. Ishitani H. Ueno M. Synlett  1997,  115 
    Google Scholar
  • 3f Chen W.-Y. Lu J. Synlett  2005,  2993 
    Google Scholar
  • 3g Fetterly BM. Jana NK. Verkade JG. Tetrahedron  2006,  62:  440 
    Google Scholar
  • 4a Keith JM. Jacobsen EN. Org. Lett.  2004,  6:  153 
    Google Scholar
  • 4b Jiao Z. Feng X. Liu B. Chen F. Zhang G. Jiang Y. Eur. J. Org. Chem.  2003,  3818 
    Google Scholar
  • 4c Kim SS. Kwak JM. Tetrahedron  2006,  62:  49 
    Google Scholar
  • 4d Royer L. De S. K. Gibbs RA. Tetrahedron Lett.  2005,  46:  4595 
    Google Scholar
  • 4e Martinez R. Ramon DJ. Yus M. Tetrahedron Lett.  2005,  46:  8471 
    Google Scholar
  • 4f Yadav JS. Reddy BVS. Eshwaraiah B. Srinivas M. Tetrahedron  2004,  60:  1767 
    Google Scholar
  • 5 Yadav JS. Reddy BVS. Eshwaraiah B. Srinivas M. Vishnumurthy P. New J. Chem.  2003,  27:  462 
    CrossrefGoogle Scholar
  • 6a Nagayama S. Kobayashi S. Angew. Chem. Int. Ed.  2000,  39:  567 
    Google Scholar
  • 6b Obora Y. Baleta AS. Tokunaga M. Tsuji Y. J. Organomet. Chem.  2002,  660:  173 
    Google Scholar
  • 6c Ishitani H. Komiyama S. Hasegawa Y. Kobayashi S. J. Am. Chem. Soc.  2000,  122:  762 
    Google Scholar
  • 7a Li G.-l. Zhao G. J. Org. Chem.  2005,  70:  4272 
    Google Scholar
  • 7b Li G.-l. Zhao G. Synlett  2005,  2540 
    Google Scholar
  • 7c Li G.-l. Zhao G. Org. Lett.  2006,  8:  633 
    Google Scholar
  • 8 Bordwell FG. Acc. Chem. Res.  1998,  21:  456 
    Google Scholar
  • 9 St-Denis Y. Chan TH. Can. J. Chem.  2000,  78:  776 
    CrossrefGoogle Scholar
  • 10 Formanovskii AA. Mikhura IB. Sokolovskii SA. Murakhovskaya AS. Terent’ev PB. Sharbatyan PA. Chem. Heterocycl. Compd. (Engl. Transl.)  1988,  24:  930 
    CrossrefGoogle Scholar
  • 11a McEwen WE. Grossi AV. MacDonald RJ. Stamegna AP. J. Org. Chem.  1980,  45:  1301 
    Google Scholar
  • 11b Neelakantan L. Hartung WH. J. Org. Chem.  1959,  24:  1943 
    Google Scholar
  • 11c Barnikow G. Hagen A. Hagen V. Goeres E. Richter D. Fichtner K. Pharmazie  1983,  38:  449 
    Google Scholar
  • 11d El-Ahl A.-AS. Synth. Commun.  2003,  33:  989 
    Google Scholar
  • 11e Lee BS. Mahajan S. Janda KD. Tetrahedron Lett.  2005,  46:  807 
    Google Scholar
  • 11f Van Daele G. inventors; Patent US 4246429  .  , 63
  • 12 Brown JM. Chapman AC. Harper R. Mowthorpe DJ. Davies AG. Smith PJ. J. Chem. Soc., Dalton Trans.  1972,  338 
    CrossrefGoogle Scholar