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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
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Further Information

Publication History

Received: 08 December 2015

Accepted after revision: 15 February 2016

Publication Date:
15 March 2016 (online)

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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.
  • 3 For a focused review on synthetic applications of 2-oxoaldehydes, see: Eftekhari-Sis B, Zirak M, Akbari A. Chem. Rev. 2013; 113: 2958
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  • 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
    Search in Google Scholar
  • 7 Peshkov VA, Peshkov AA, Pereshivko OP, Van Hecke K, Zamigaylo LL, Van der Eycken EV, Gorobets NYu. ACS Comb. Sci. 2014; 16: 535
    CrossrefSearch in Google Scholar
  • 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.