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Synlett 2011(15): 2200-2202  
DOI: 10.1055/s-0030-1261179
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Solvent-Free Synthesis of Enamines from Alkyl Esters of Propiolic or But-2-yne Dicarboxylic Acid in a Ball Mill

Rico Thorwirth, Achim Stolle*
Institute for Technical Chemistry and Environmental Chemistry (ITUC), Friedrich-Schiller University Jena, Lessingstr. 12, 07743 Jena, Germany
Fax: +49(3641)948402; e-Mail: Achim.Stolle@uni-jena.de;
Further Information

Publication History

Received 8 June 2011
Publication Date:
12 August 2011 (online)

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Abstract

A solvent-free method for the addition of amines to dialkylacetylendicarboxylates or alkylpropiolates using a planetary ball mill was developed. Conversion of educts was quantitative within five minutes without use of any catalyst or base. Beside the E-/Z-isomers, no side products were formed.

Key words

addition - amines - alkynes - enamines - green chemistry

    References

  • 1a Mohri K. Kanie A. Horiguchi Y. Isobe K. Heterocycles  1999,  51:  2377 
    Google Scholar
  • 1b Borisov AA. Rozinov VG. Bozhenkov GV. Larina LI. Russ. J. Gen. Chem.  2004,  74:  1822 
    Google Scholar
  • 1c Al-Saleh B. Makhseed S. Hassaneen HME. Hilmy Elnagdi M. Synthesis  2006,  59 
    Google Scholar
  • 1d Chepyshev SV. Mazurkevich YN. Lebed OS. Prosyanik AV. Chem. Heterocycl. Compd.  2007,  43:  844 
    Google Scholar
  • 1e Zang M. Jiang H.-F. Eur. J. Org Chem.  2008,  3519 
    Google Scholar
  • 1f Shi Z. Zhang C. Li S. Pan D. Ding S. Cui Y. Jiao N. Angew. Chem. Int. Ed.  2009,  48:  4572 
    Google Scholar
  • 1g Matsumoto S. Mori T. Akazome M. Synthesis  2010,  3615 
    Google Scholar
  • 1h Sirijindalert T. Hansuthirakul K. Rashatasakhon P. Sukwattanasinitt M. Ajavakom A. Tetrahedron  2010,  66:  5161 
    Google Scholar
  • 1i Sun J. Xia E.-Y. Wu Q. Yan C.-G. Org. Lett.  2010,  12:  3678 
    Google Scholar
  • 2a Kazi SA. Kelso GF. Harris S. Boysen RI. Chowdhury J. Hearn M. Tetrahedron  2010,  66:  9461 
    Google Scholar
  • 2b Mazzoni O. Esposito G. Diurno MV. Brancaccio D. Carotenuto A. Grieco P. Novellino E. Filippelli W. Arch. Pharm.  2010,  343:  561 
    Google Scholar
  • 3a Huisgen R. Herbig K. Siegl A. Huber H. Chem. Ber.  1966,  99:  2526 
    Google Scholar
  • 3b Cossu S. De Lucchi O. Durr R. Synth. Commun.  1996,  26:  4597 
    Google Scholar
  • 3c Ziyaei-Halimehjani A. Saidi MR. Tetrahedron Lett.  2008,  49:  1244 
    Google Scholar
  • 4 Zhu Q. Jiang H. Li J. Zhang M. Wang X. Qi C. Tetrahedron  2009,  65:  4604 
    CrossrefGoogle Scholar
  • 5a Um I.-H. Yuk S.-M. Yoon S.-I. Bull. Korean Chem. Soc.  2000,  21:  553 
    Google Scholar
  • 5b Nori-Shargh D. Soltani B. Saroogh-Farahani N. Deyhimi F. Int. J. Chem. Kin.  2006,  38:  144 
    Google Scholar
  • For recent reviews, see:
  • 6a Rodriguez B. Bruckmann A. Rantanen T. Bolm C. Adv. Synth. Catal.  2007,  349:  2213 
    Google Scholar
  • 6b Bruckmann A. Krebs A. Bolm C. Green Chem.  2008,  10:  1131 
    Google Scholar
  • 6c Kaupp G. J. Phys. Org. Chem.  2008,  21:  630 
    Google Scholar
  • 6d Tanaka K. Solvent-Free Organic Synthesis   2nd ed.:  Wiley-VCH; Weinheim: 2009. 
    Google Scholar
  • 6e Stolle A. Szuppa T. Leonhardt SES. Ondruschka B. Chem. Soc. Rev.  2011,  40:  2317 
    Google Scholar
  • 7a Feldbæk Nielsen S. Peters D. Axelsson O. Synth. Commun.  2000,  30:  3501 
    Google Scholar
  • 7b Rodriguez B. Bruckmann A. Bolm C. Chem. Eur. J.  2007,  13:  4710 
    Google Scholar
  • 7c Declerck V. Nun P. Martinez J. Lamaty F. Angew. Chem. Int. Ed.  2009,  48:  9318 
    Google Scholar
  • 7d Bruckmann A. Rodriguez B. Bolm C. CrystEngComm  2009,  11:  404 
    Google Scholar
  • 7e Schneider F. Ondruschka B. ChemSusChem  2008,  1:  622 
    Google Scholar
  • 7f Wang G.-W. Gao J. Org. Lett.  2009,  11:  2385 
    Google Scholar
  • 7g Schneider F. Stolle A. Ondruschka B. Hopf H. Org. Process Res. Dev.  2009,  13:  44 
    Google Scholar
  • 7h Fulmer DA. Shearouse WC. Medonza ST. Mack J. Green Chem.  2009,  11:  1821 
    Google Scholar
  • 7i Schneider F. Szuppa T. Stolle A. Ondruschka B. Hopf H. Green Chem.  2009,  11:  1894 
    Google Scholar
  • 7j Waddell DC. Thiel I. Clark TD. Marcum ST. Mack J. Green Chem.  2010,  12:  209 
    Google Scholar
  • 7k Szuppa T. Stolle A. Ondruschka B. Hopfe W. Green Chem.  2010,  12:  1288 
    Google Scholar
  • 7l Thorwirth R. Stolle A. Ondruschka B. Green Chem.  2010,  12:  985 
    Google Scholar
  • 7m Szuppa T. Stolle A. Ondruschka B. Hopfe W. ChemSusChem  2010,  3:  1181 
    Google Scholar
  • 7n Thorwirth R. Stolle A. Ondruschka B. Wild A. Schubert US. Chem. Commun.  2011,  47:  4370 
    Google Scholar
  • 7o Schmidt R. Thorwirth R. Szuppa T. Stolle A. Ondruschka B. Hopf H. Chem. Eur. J.  2011,  17:  8129 
    Google Scholar