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Chemistry of Heterocyclic Compounds

, Volume 50, Issue 5, pp 634–646 | Cite as

Synthesis and Transformations of Nitrogen Heterocycles in Ionic Liquids (Review)

  • N. N. Makhova
  • M. I. Pleshchev
  • M. A. Epishina
  • A. S. Kulikov
Article

A review is given for our work in the Nitrogen Compound Laboratory of the Institute of Organic Chemistry of the Russian Academy of Sciences over the past 10 years on the use of ionic liquids as reaction media and catalysts in the 1,3-dipolar cycloaddition of various 1,3-dipoles, such as azomethine imines, azides, and nitrile oxides, including domino reactions for the expansion of the three-membered diaziridine ring in monocyclic diaziridine derivatives and condensation reactions such as the synthesis of aminothiadiazoles and dihydroisoquinolines. The Schmidt rearrangement and Henry and Mannich reactions of polynitroalkanes in ionic liquids are also discussed.

Keywords

ionic liquids nitrogen heterocycles polynitroalkanes Bischler–Napieralski reaction 1,3-dipolar cycloaddition domino reaction Henry reaction Mannich reaction metathesis regioselectivity ring expansion Schmidt rearrangement stereoselectivity 

Notes

This work was partially supported by the Russian Foundation for Basic Research (grant No. 13-03-00153a) and by Merck KGaA.

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • N. N. Makhova
    • 1
  • M. I. Pleshchev
    • 1
  • M. A. Epishina
    • 1
  • A. S. Kulikov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia

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