5767-21-5Relevant articles and documents
Thermal transformations of 7-aryl-1,6-diazabicyclo[4.10]heptanes and 6,13-diarylperhydrodipyridazino-[1,2-a: 1′,2′-d]-1,2,4,5-tetrazines
Koptelov,Ukolov
, p. 852 - 859 (2008)
The thermolysis of 7-aryl-1,6-diazabicyclo[4.1.0]heptanes in the absence of 1,3-dipolarophiles leads to dimers of the initially formed azomethineimines, namely, 6,13-diaryloctahydrodipyridazino[1,2-a:1′,2′.
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
Syroeshkina, Yu. S.,Kuznetsov,Lyssenko,Makhova
experimental part, p. 366 - 379 (2010/07/09)
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.