Azabrendanes. I. Synthesis, structure and spectral parameters of N-(arylsulfonyl)-exo-2-hydroxy-4-azatricyclo[4.2.1.03,7]nonanes

Spectral investigations, DFT computations and molecular docking studies of 1,7,8,9-tetrachloro-10,10-dimethoxy-4-{3-[4-(2-methylphenyl)piperazin-1-yl]propyl}-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

“…The double bonds C 16 ]O 17 and C 13 ]O 18 are conjugated with the psystem of the imido fragment of RingI, with the torsion angles O 17 eC 16 eN 15 eC 13 , C 16 eN 15 eC 13 eC 4 being À175.9 , À6.3 and O 18 eC 13 eN 15 eC 16 , C 13 eN 15 eC 16 eC 5 being 178.7 , 8.1 respectively as reported by Kasyan et al [57]. At N 15 position, the bond angles C 16 eN 15 eC 19 eN 15 eC 13 ¼ 113.8 and this asymmetry of angles reveal the steric repulsion of the atoms H 26 , H 25 and O 17 , O 18[57].For the piperazine ring, El-Emam et al[46] reported the bond lengths N38 eC 40 ¼ 1.465 Å, N 38 eC 39 ¼ 1.463 Å, C 39 eC 46 ¼ 1.514 Å, N 47 eC 45 ¼ 1.458 Å, N 47 eC 46 ¼ 1.471 Å, C 40 eC 45 ¼ 1.511 Å and the corresponding bond lengths of the title compound are 1.488 Å, 1.485 Å, 1.535 Å, 1.488 Å, 1.477 Å, 1.547 Å respectively. The B3LYP calculation gives the bond angles within the piperazine ring N 38 eC 39 eC 46 ¼ 110.4 , N 38 eC 40 eC 45 ¼ 113.1 , N 47 eC 45 eC 40 ¼ 110.7 , N 47 eC 46 eC 39 ¼ 109.7 , C 45 eN 47 eC 46 ¼ 114.8 .…”

Azabrendanes V. Synthesis and reactions of stereoisomeric exo- and endo-5-aminomethylbicyclo[2.2.1]hept-2-ene-based ureas

“…The 1 H and 13 C NMR spectra of exo-and endo-ureas were found to be very similar to those of sulfonamides [15,16,[18][19][20], carboxamides [21,22], and previously studied ureas of the norbornene series [12]. The signals were assigned by comparison with the 1 H NMR spectrum of initial amine 2a, for which a two-dimensional (COSY) spectrum was obtained.…”

“…The IR spectra are not substantially informative for structural confirmation of compounds (18)(19)(20)(21)(22)(23)(24)(25)(26) as both characteristic absorption bands (860-850 cm -1 , ν C-O, 3040-3020 cm -1 , ν C-H of the epoxynorbornane fragment) occupy the same regions as the benzenering bonds vibrations. However, the signals of the H 2 and H 3 protons of the epoxide cycle, in the 2.9-3.1 ppm region of the 1 H NMR spectra, are characteristic of epoxy compounds [23,24,29,30].…”

Cage-like amino alcohols. synthesis, reactions, and application

“…The latter procedure was successfully used previously to perform reactions of stereoisomeric 5-aminomethylbicyclo[2.2.1]hept-2-enes 45a and 45b with arenelsulfonyl chlorides [113,117]; however, amino alcohols 128a and 128b gave rise to only 30-40% of sulfonamides 131a and 131b (Scheme 58). Following alternative procedure, the same sulfonamides were obtained in 65-70% yield.…”