Download PDF
Synthesis 2016; 48(11): 1734-1740
DOI: 10.1055/s-0035-1561409
paper
© Georg Thieme Verlag Stuttgart · New York

Three-Component Reaction of 2-Oxoaldehydes, Cyclic 1,3-Dicarbonyl Compounds, and 4-Aminopyridines

Huiping Wei
a   College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P. R. of China   Email: olga@suda.edu.cn   Email: vsevolod@suda.edu.cn
,
Binbin Li
a   College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P. R. of China   Email: olga@suda.edu.cn   Email: vsevolod@suda.edu.cn
,
Gaigai Wang
a   College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P. R. of China   Email: olga@suda.edu.cn   Email: vsevolod@suda.edu.cn
,
Kristof Van Hecke
b   XStruct, Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281S3, 9000 Ghent, Belgium
,
Olga P. Pereshivko*
a   College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P. R. of China   Email: olga@suda.edu.cn   Email: vsevolod@suda.edu.cn
,
Vsevolod A. Peshkov*
a   College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, P. R. of China   Email: olga@suda.edu.cn   Email: vsevolod@suda.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 08 December 2015

Accepted after revision: 15 February 2016

Publication Date:
15 March 2016 (online)

    Permissions and Reprints All articles of this category


Abstract

A novel three-component reaction of 2-oxoaldehydes, cyclic 1,3-dicarbonyl compounds, and 4-aminopyridines leading to the formation of zwitterionic Michael adducts is described.

Key words

2-oxoaldehydes - 1,3-dicarbonyl compounds - 4-aminopyridines - zwitterions - multicomponent reaction

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561409.
  • Supporting Information
 

  • References

  • 1 These authors contributed equally to this work.
    • 2a Bienaymé H, Hulme C, Oddon G, Schmitt P. Chem. Eur. J. 2000; 6: 3321
      CrossrefPubMed
    • 2b Zhu J, Bienaymé H. Multicomponent Reactions . 1st ed. Wiley-VCH; Weinheim: 2005
      CrossrefGoogle Scholar
    • 2c Zhu J, Wang Q, Wang MX. Multicomponent Reactions in Organic Synthesis . Wiley-VCH; Weinheim: 2014
      CrossrefGoogle Scholar
    • 2d Maes BU. W, Orru RV. A, Ruijter E. Synthesis of Heterocycles via Multicomponent Reaction I & II . Springer; Heidelberg: 2010
      Google Scholar
    • 2e Jiang B, Rajale T, Wever W, Tu S.-J, Li G. Chem. Asian J. 2010; 5: 2318
      Crossref
    • 2f Sunderhaus JD, Martin SF. Chem. Eur. J. 2009; 15: 1300
      CrossrefPubMed
  • 3 For a focused review on synthetic applications of 2-oxoaldehydes, see: Eftekhari-Sis B, Zirak M, Akbari A. Chem. Rev. 2013; 113: 2958
    Crossref
  • 4 For a focused review on the use of 1,3-dicarbonyl compounds in multicomponent reactions, see: Bugaut X, Constantieux T, Coquerel Y, Rodriguez J. In Multicomponent Reactions in Organic Synthesis . Zhu J, Wang Q, Wang MX. Wiley-VCH; Weinheim: 2014. Chap. 5, 109–15
    Google Scholar

      • For recent representative examples, see:
    • 5a Wang H.-Y, Shi D.-Q. ACS Comb. Sci. 2013; 15: 261
      Crossref
    • 5b Gozalishvili LL, Beryozkina TV, Omelchenko IV, Zubatyuk RI, Shishkin OV, Kolos NN. Tetrahedron 2008; 64: 8759
      Crossref
    • 5c Quiroga J, Acosta PA, Cruz S, Abonía R, Insuasty B, Nogueras M, Cobo J. Tetrahedron Lett. 2010; 51: 5443
      Crossref
    • 5d Khalafy J, Rimaz M, Ezzati M, Prager RH. Bull. Korean Chem. Soc. 2012; 33: 2890
      Crossref
    • 5e Rimaz M, Rabiei H, Khalili B, Prager RH. Aust. J. Chem. 2013; 67: 283
    • 5f Kolos NN, Zamigaylo LL, Musatov VI. Chem. Heterocycl. Compd. 2009; 45: 970
      Crossref

      For related multicomponent processes utilizing 2-oxoaldehydes and enaminones of cyclic 1,3-dicarbonyl compounds, see:
    • 6a Fu L.-P, Shi Q.-Q, Shi Y, Jiang B, Tu S.-J. ACS Comb. Sci. 2013; 15: 135
      Crossref
    • 6b Jiang B, Yi M.-S, Shi F, Tu S.-J, Pindi S, McDowell P, Li G. Chem. Commun. 2012; 48: 808
      CrossrefPubMed
    • 6c Tu X.-C, Fan W, Jiang B, Wang S.-L, Tu S.-J. Tetrahedron 2013; 69: 6100
      Crossref
    • 6d Jiang B, Yi M.-S, Tu M.-S, Wang S.-L, Tu S.-J. Adv. Synth. Catal. 2012; 354: 2504
      Crossref
  • 7 Peshkov VA, Peshkov AA, Pereshivko OP, Van Hecke K, Zamigaylo LL, Van der Eycken EV, Gorobets NYu. ACS Comb. Sci. 2014; 16: 535
    Crossref

      • For the synthesis and X-ray crystallographic analysis of related zwitterionic Michael-type adducts, see:
    • 8a O’Leary J, Formosa X, Skranc W, Wallis JD. Org. Biomol. Chem. 2005; 3: 3273
      Crossref
    • 8b Lari A, Pitak MB, Coles SJ, Rees GJ, Day SP, Smith ME, Hanna JV, Wallis JD. Org. Biomol. Chem. 2012; 10: 7763
      Crossref
    • 8c O’Leary J, Wallis JD. Org. Biomol. Chem. 2009; 7: 225
      Crossref
    • 8d Földi AA, Ludányi K, Bényei AC, Mátyus P. Synlett 2010; 2109
      Article in Thieme Connect
    • 8e Polonka-Bálint A, Saraceno C, Ludányi K, Bényei AC, Mátyus P. Synlett 2008; 2846
      Article in Thieme Connect
  • 9 The isolated yields were checked directly after drying the prepared products 6 in vacuo as we have noticed that many of them tend to acquire water from the air during storage resulting in a weight increase and in an appearance of a strong water signal in 1H NMR spectra (see Supporting Information). Likewise, the obtained single crystal of 6{4,1,1} contains 2 equivalents of water acquired during crystallization from a CDCl3/CH2Cl2 (~1:5) solution.
  • 10 See Supporting Information.
  • 11 CCDC 1440885 contains the supplementary crystallographic data for this paper and can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html.