Journal
RUSSIAN CHEMICAL BULLETIN
Volume 58, Issue 2, Pages 366-379Publisher
SPRINGER
DOI: 10.1007/s11172-010-0018-2
Keywords
6-aryl-1,5-diazabicyclo[3.1.0]hexanes; carbon disulfide; activated nitriles; ring expansion; 3-aryldihydro-5H-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 center dot Et2O
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Funding
- Russian Academy of Sciences
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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 center dot 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.
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