Cyclopropanation reactions on α-cis-himachalene and a β-himachalene

New enaminone sesquiterpenic: TiCl4-catalyzed synthesis, spectral characterization, crystal structure, Hirshfeld surface analysis, DFT studies and cytotoxic activity

“…The C⎯Cl bond lengths average 1.766(3) Å, are in good agreement with the Cl---C bond length of 1.764(6) Å reported for the related compound [44][45][46][47]. In the amino-α-ester function, the C⎯N bond length range from 1.359(4) -1.440(4) Å are similar for the structure of similar compound [47].…”

“…In the amino-α-ester function, the C⎯N bond length range from 1.359(4) -1.440(4) Å are similar for the structure of similar compound [47]. The main difference between the conformations of these molecules is observed for the cyclohexene ring (between envelope and half-chair for [44], half-chair for [45], screwboat for and envelope for [46].…”

Hybrid of the 1,2,3‐triazole nucleus and sesquiterpene skeleton as a potential antitumor agent: Hemisynthesis, molecular structure, Hirshfeld surface analysis, density functional theory, and in vitro cytotoxic and apoptotic effects

“…The obtained compounds were purified by silica gel column chromatography and elucidated by their 1 H and 13 C NMR spectroscopic analyses. One should mention here that products 2 and 3 were identified according to the reported method [24,25]. On the 1 H NMR spectrum (Figure S1) of the newly prepared product 4, we note the disappearance of the ethylenic proton which appears at δ 5.88 ppm and the appearance of an AB system (J = 20.1 Hz) centered at 5.01 ppm characterizing the methylene proton H-14 as well as the presence of signals between δ 7.23 and 7.40 ppm attributed to aromatic protons, and a signal as a singlet at δ 3.28 ppm assigned to the proton at position 10.…”

Hemisynthesis, crystal structure and inhibitory effect of sesquiterpenic thiosemicarbazones and thiazolidin-4-ones on the corrosion behaviour of stainless steel in 1 M H2SO4 solution

“…Thus, treatment of thiosemicarbazone 1 (Auhmani et al, 1999(Auhmani et al, , 2002Ourhriss et al, 2005) or thiosemicarbazone 2 with an equivalent of ethyl 2-bromoacetate in the presence of sodium acetate afforded the nonsubstituted thiazolidinones (Z)-2-{(Z)-[(1aR,5aR,9aS)-1,1-dichloro-1a,5,5,7-tetramethyl-1a,2,3,4,5,5a,8,9-octahydro-1H-benzo[a]cyclopropa[b][7]annulen-8-ylidene]hydrazono}thiazolidin-4-one, 3, and (Z)-2-{(Z)-[(1aR,5aR,9aS)-1,1-dibromo-1a,5,5,7-tetramethyl-1a,2,3,4,5,5a,-8,9-octahydro-1H-benzo[a]cyclopropa[b][7]annulen-8-ylidene]-hydrazono}thiazolidin-4-one, 4. They were purified by flash chromatography with hexane as eluent and isolated as yellow liquids.…”

“…Another point of interest is the comparison of the molecular structure of 5 with that of parent compound a (Auhmani et al, 1999) and also with b (Benharref et al, 2016) and c (Ourhriss et al, 2005) (see Scheme 2). The C-Cl bond lengths [average 1.767 (3) Å ] are in good agreement with the Cl-C bond length of 1.764 (6) Å reported for the related compounds (Table 2 and Scheme 2).…”