33924-49-1Relevant articles and documents
Structure and absolute configuration of some 5-chloro-2-methoxy-N-phenylbenzamide derivatives
Galal, Alaaeldin M F,Shalaby, Elsayed M.,Abouelsayed, Ahmed,Ibrahim, Medhat A.,Al-Ashkar, Emad,Hanna, Atef G
, p. 213 - 221 (2018)
The absolute configuration of 5-chloro-2-methoxy-N-phenylbenzamide single crystal [compound (1)] and the effect of introducing –[CH2]n–, n?=?1,2 group adjacent to the amide group [compounds (2) and (3)], were studied. Furthermore, the replacement of the methoxy group with a hydroxy group [compound (4)] was defined. Proton and carbon-13 NMR spectrometer were used to record the structural information of the prepared compounds. X-ray single crystal diffractometer were used to elucidate the 3D structural configurations. Intensity data for the studied compounds were collected at room temperature. The X-ray data prove that compound (1) is almost planar, with maximum r.m.s. deviations of 0.210(3)?? corresponds to C13. This planarity starts to disturb by adding –[CH2]n–, n?=?1,2 groups between the NH group and the phenyl ring in compounds (2) and (3), respectively. By replacing the OCH3 group by an OH group in compound (4), the plane of the chlorophenyl moiety is nearly perpendicular to that of the phenyl ring. Such new structural configurations were further illustrated by the infrared, and ultraviolet-visible spectroscopy measurements in the frequency range 400–4000?cm??1 and 190–1100?nm, respectively. Spectroscopic analyses were verified with the help of molecular modeling using density functional theory. The estimated total dipole moment for the prepared compounds reflects its ability to interact with its surrounding molecules. The higher dipole moment for a given structures is combined with the higher reactivity for potential use in medicinal applications.
Intermolecular C-H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis
Gu, Zheng-Yang,Wu, Yang,Jin, Feng,Bao, Xiaoguang,Xia, Ji-Bao
supporting information, p. 3361 - 3371 (2021/04/09)
An atom- and step-economic intermolecular multi-component palladium-catalyzed C-H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho -directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.
Metal-Free Thermal Activation of Molecular Oxygen Enabled Direct α-CH2-Oxygenation of Free Amines
Ghosh, Santanu,Jana, Chandan K.
, p. 260 - 266 (2018/02/19)
Direct oxidation of α-CH2 group of free amines is hard to achieve due to the higher reactivity of amine moiety. Therefore, oxidation of amines involves the use of sophisticated metallic reagents/catalyst in the presence or absence of hazardous oxidants under sensitive reaction conditions. A novel method for direct C-H oxygenation of aliphatic amines through a metal-free activation of molecular oxygen has been developed. Both activated and unactivated free amines were oxygenated efficiently to provide a wide variety of amides (primary, secondary) and lactams under operationally simple conditions without the aid of metallic reagents and toxic oxidants. The method has been applied to the synthesis of highly functionalized amide-containing medicinal drugs, such as O-Me-alibendol and -buclosamide.
