Synthesis and antioxidant activity of 1-R-3-(2-fluorophenyl)selenoureas containing polycyclic fragments

1-(3-Isoselenocyanatopropyl)adamantane

“…However, in some cases, due to the low concentration of isonitriles, this effect may be weak or not observed at all [14,15]. In the 13 C NMR spectrum, CH2-NC is a singlet at 69.16 ppm. Compound 5 was washed with water to separate tert-butyl alcohol and NaOH, and with 1 N HCl to remove unreacted amine 4.…”

“…We investigated a range of alcohols, methanol, ethanol, isopropanol, tert-butanol, and 1-octanol, as replacements for the Aliquat 336 phase transfer catalyst. The best results have been achieved with tert-butanol [13]. By excluding water from the reaction, and using dry alkali, it was possible to increase the yield of isonitrile up to 88% (Table 1).…”

“…1 H and 13 C NMR spectra were taken with a Bruker DPX 300 machine (Bruker AXS Handheld Inc., Kennewick, WA, USA) (at frequencies of 300 and 75 MHz) in CDCl 3 solution with TMS as the standard. J values are given in Hz.…”

“…The organic layer was separated, washed with 1 N HCl, and dried with Na 2 SO 4 . Solvent was removed in vacuo to give 338 mg (88% yield) of crude 1-(3-isocyanopropyl)adamantane (5, Figure 2 6 , H 10 , H 12 ), 1.88-1.99 (m, 3H, H 3 , H 5 , H 7 ), 3.36 (tt, J = 6.8, 1.9 Hz, 2H, H 13 ). 13 could then be isolated with 84% yield (GC-MS) by filtration of the excess of selenium and evaporation of the solvent.…”

“…%): 202 (50% [M − 1] + ), 188 (41% [M-CSe] + ), 175 (48% [M-NCSe] + ), 160 (19% [M-CH2NCSe] + ), 146 (30% [Ad − CH2] + ), 135 (100% [Ad] + ), retention time = 13.583 min. 1 H NMR (300 MHz, CDCl3), δ, ppm: 1.15-1.21 (m, 2H, H 11 ), 1.46 (d, J = 2.9 Hz, 6H, H 2 , H 8 , H 9 ), 1.60-1.76 (m, 8H, H 4 , H6 , H 10 , H12 ), 1.88-1.99 (m, 3H, H 3 , H 5 , H 7 ), 3.36 (tt, J = 6.8, 1.9 Hz, 2H, H13 ) 13. C NMR (75 MHz, CDCl3), δ, ppm: 22.85 (C 12 ), 28.61 (C 3 , C 5 , C 7 ), 31.94 (C 1 ), 37.09 (C 4 , C 6 , C 10 ), 41.13 (C 11 ), 42.31 (C 2 , C 8 , C 9 ), 69.16 (C 13 ).…”