Synthesis and Properties of 1,3-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: X. 1-[1-(4-Isobutylphenyl)ethyl]-3-R-ureas

Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XI. 1-[(Adamantan-1 yl)alkyl]-3-arylselenoureas

“…The structure of 4a-4g and 5a-5g was confirmed by 1 H and 13 C (for 4a) NMR spectra and elemental analyses. The 1 H NMR spectra of 4a-4g characteristically showed a signal at δ 7.48-7.96 ppm due to NH proton nearest to the adamantane fragment and a signal at δ 9.60-10.04 ppm due to NH group linked to the benzene ring.…”

“…The ratio of phenyl isoselenocyanate and N,N′-diphenylcarbodiimide was 1:2. We found that the catalyst can be readily removed by filtration of the reaction mixture through a thin bed (2 mm) of silica gel on a glass filter; the filtrate contained only phenyl isoselenocyanate (1) and N,N′-diphenylcarbodiimide (1a). Despite significant difference in the boiling points of 1 and 1a, attempted purification of phenyl isoselenocyanate by vacuum distillation at 180-185°C (p = 25 mbar) did not result in acceptable separation of the products; in contrast, increased tar formation was observed, while the yield decreased.…”

“…Yield 7.64 g (42%). 1 H NMR spectrum, δ, ppm: 7.30-7.33 m (2H, 2-H, 6-H), 7.34-7.37 m (1H, 4-H), 7.38-7.41 m (2H, 3-H, 5-H). 13 C NMR spectrum (APT), δ C , ppm: 126.12 (C 3 , C 5 ), 128.11 (C 4 ), 129.60 (C 2 , C 6 ).…”

“…Yield 0.168 g (45%), mp 202-203°C. 1 H NMR spectrum, δ, ppm: 1.61-1.68 m (6H, Ad), 1.89 d (3H, Ad, J = 2.7 Hz), 2.08 d (3H, Ad, J = 14.1 Hz), 2.29 s (3H, Ad), 7.08-7.10 m (1H, H arom ), 7.13-7.17 m (1H, H arom ), 7.31-7.38 m (3H, H arom ), 7.48 s (1H, AdNH), 9.60 s (1H, NHPh). 13…”

“…was synthesized in a similar way from 0.2 g (1.1 mmol) of 1 and 0.182 g (1.1 mmol) of (adamantan-1-yl)methanamine (3b) using 0.111 g (1.1 mmol) of Et 3 N. Yield 0.223 g (58%), mp 197-198°C. 1 H NMR spectrum, δ, ppm: 1.51 s (6H, Ad), 1.61 d (3H, Ad, J = 12.2 Hz), 1.68 d (3H, Ad, J = 11.9 Hz), 1.95 s (3H, Ad), 3.38 N-[1-(Adamantan-1-yl)ethyl]-N′-phenylselenourea (4c) was synthesized in a similar way from 0.12 g (0.66 mmol) of 1 and 0.119 g (0.66 mmol) of 1-(adamantan-1-yl)ethan-1-amine (3c) using 0.067 g (0.66 mmol) of Et 3 N. Yield 0.101 g (42%). 1…”