Insertion of carbon disulfide into the diaziridine ring of 6-aryl-1,5-diazabicylo[3.1.0]hexanes assisted by ionic liquids

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

“…8 The structures of all the synthesized compounds were confirmed by elemental analysis and spectroscopic methods. Compounds 7d and 24d were studied also by X ray diffraction.…”

Reaction of 1-arylmethylidenepyrazolidin-1-azomethine imines with aryl ketenes

“…These reactions were success fully accomplished only in ionic liquids, that allowed us to develop simple methods for the preparation of a number of bicyclic structures 7-10 (Scheme 2). [16][17][18][19] The present work is devoted to the study of a possibility of condensation of azomethine imines 1, generated in situ from 6 aryl 1,5 diazabicyclo[3.1.0]hexanes 4 under con ditions found earlier, 15-19 with aryl ketenes 11 in order to obtain 3,4 diaryl(3,3,4 triaryl) 1,5 diazabicyclo[3.3.0] octan 2 ones 12, new γ lactam azaanalogs (Scheme 3).…”

“…[16][17][18][19] Azomethine imine 1a was generated upon the action of BF 3 •Et 2 O in catalyt ic amounts (0.1 mmol) on the starting compound 4a (0.3 mmol) in MeCN or ionic liquid (IL), then phenyl acetyl chloride and Et 3 N were added simultaneously drop wise at reduced temperature. However, in this case too the reaction took similar direction only at considerably higher rate, and 1,2 bis(phenylacetyl)pyrazolidine 19 was isolat ed in low yield as the reaction product independent on the structure of compound 4a-c involved into the reaction.…”

A new reaction of 1,2‐di‐ and 1,2,3‐trialkyldiaziridines: Ring expansion under the action of diethyl acetylenedicarboxylate in ionic liquids

“…These are based on the strained diaziridine ring transformation in readily available [1, 2] 1,2‐dialkyldiaziridines 1 and 1,5‐diazabicyclo[3.1.0]hexanes 2 under the action of electrophilic reagents, in particular, dipolarophiles. Herein, the diaziridine ring is capable of opening on the CN or NN bonds to generate dipolar intermediates prone to cycloaddition reactions (so‐called ring expansion reactions) resulting in other heterocyclic structures [3–10].…”

“…Arylketenes [3–6], aroyliso‐ and aroylisothiocyanates [7, 8], carbon disulfide [9, 10], and activated nitriles [10, 11] were investigated as dipolarophiles. Thus, the reaction of arylketenes with 1,2‐dialkyldiaziridines 1 resulted in 5‐aryl‐1,3‐dialkylimidazolidin‐4‐ones 3 and with 1,5‐diazabicyclo[3.1.0]hexanes 2— in heterocyclic compounds of two kinds—1‐(arylacetyl)pyrazolidines 4 and 1,5‐diazabicyclo[3.3.0]octan‐2‐ones 5 (Scheme ).…”