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Russian Chemical Bulletin

, Volume 58, Issue 2, pp 366–379 | Cite as

Insertion of carbon disulfide and the nitrile group into the diaziridine ring of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in ionic liquids catalyzed by BF3 · Et2O

  • Yu. S. Syroeshkina
  • V. V. Kuznetsov
  • K. A. Lyssenko
  • N. N. Makhova
Full Articles

The present study revealed two new reactions resulting in the diaziridine ring expansion, viz., the insertion of the CS2 molecule and the CN group of activated nitriles into the C—N bond of the diaziridine fragment of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes. These reactions can be performed only in ionic liquids in the presence of BF3 · Et2O as the catalyst. Based on these reactions, we developed simple one-pot methods for the synthesis of 3-aryldihydro-5 H-pyrazolo[1,2- c][1,3,4]thiadiazole-1-thiones and 1-aryl-6,7-dihydro-1 H,5H-pyrazolo-[1,2-a][1,2,4]triazoles in high yields. Dipolar intermediates of new reactions, which are direct precursors of the final products, were detected by NMR methods. One of the intermediates was isolated and characterized. The reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with benzoyl cyanide affords (2-benzoyrpyrazolidin-1-yl)(aryl)acetonitriles.

Key words

6-aryl-l,5-diazabicyclo[3.1.0]hexanes carbon disulfide activated nitriles ring expansion 3-aryldihydro-5 H-pyrazolo[1,2-c][1,3,4]thiadiazole-1-thiones 1-aryl-6,7-dihydro-1H,5H-pyrazolo[1,2-a][1,2,4]triazoles (2-benzoylpyrazolidin-1-yl)arylacetonitriles dipolar intermediates ionic liquids BF3 · Et2

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Copyright information

© Springer Science+Business Media, Inc.  2010

Authors and Affiliations

  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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