Aziridination of naphthalene by 3-acetoxyaminoquinazolin-4(3H)-ones

Synthesis and photolysis of N-phthalimidoaziridines with electron-withdrawing substituents

“…Aziridine 1 (775 mg, 85%) was obtained, the analytical characteristics of which agreed completely with the literature data of [13]. 13 C NMR spectrum (CDCl 3 ), δ, ppm: 43.45 (C (2,8) ); 46.59 (CH 2 ); 50.85 (C (1, 9) and C (4,6) ); 123.83 (C (b) ); 129.89 (C (a) ); 134.87 (C (c) ); 137.14 (C (10,11) (2,7) , and C (9,11) ); 123.39 (C (b) ); 130.63 (C (a) ); 134.46 (C (c) ); 142.48 (C (4,5) 13 C NMR spectrum (mixture of DMSO-d 6 -CCl 4 , ~1:2), δ, ppm: 24.72 (CH 2 ); 37.49 (C (1, 9) ); 41.39 (C (2,8) ); 49.22 (C (4,6) ); 52.36 (C (10,12) ); 122.28 and 122.89 (C (b,b') ); 129.53 and 129.82 (C (a,a') ); 133.69 and 134. N-Aminophthalimide (486 mg, 3 mmol) and lead tetraacetate (1.33 g, 3 mmol) were added alternately in 10-15 mg portions during 40 min to a suspension of anhydrous potassium carbonate (1.3 g, 9.4 mmol) in a mixture of ethyl cinnamate (792 mg, 4.5 mmol) and methylene chloride (40 ml) cooled to 0°C.…”

“…Oxidative addition of N-aminophthalimide and related N-aminoheterocycles to a conjugated multiple bond goes, as a rule, far more readily than to an unconjugated bond [10][11][12][13]. However in dienedione 6 the reactivity of the C (9) -C (10) bond is increased due to its inclusion in a strained structure of the norbornene type.…”

Copper Complexes with N-Alkylated NS2-Macrocyclic Ligands: Synthesis, Characterization, and Capabilities as Aziridination Precatalysts

“…These results suggest that at the conclusion of the reaction the ligands were associated with the copper ion and were unchanged by the catalytic process; i.e., ligand sulfur oxidation and naphthyl group aziridination did not occur (assuming that any reaction product of the ligand either survives the copper ion removal process or is converted to a different species than the starting ligand; for instance, sulfilimines are stable to hydrolysis in basic solutions but are hydrolyzed under forcing acidic conditions to give sulfoxides). Although naphthyl groups have not been found to react under these aziridination conditions, naphthalene aziridination has been reported under different conditions . In addition, PhINTs has been reported to oxidize DMSO 12 and cause multiple nitrene insertions to generate a tetraamido complex from a Cu(I) bis(dithiocarbamate) complex .…”

“…Although naphthyl groups have not been found to react under these aziridination conditions, naphthalene aziridination has been reported under different conditions. 52 In addition, PhINTs has been reported to oxidize DMSO 12 and cause multiple nitrene insertions to generate a tetraamido complex from a Cu(I) bis(dithiocarbamate) complex. 48 In contrast to the results with L nap and L Me , the acac ligands from Cu(acac) 2 may be liberated or modified during the aziridination reaction, as IR spectra of the postcatalytic copper-containing product(s) do not contain strong, distinctive acetoacetonate C-O bands.…”