Biologically Oriented Hybrids of Indole and Hydantoin Derivatives

Indoles and hydantoins are important heterocycles scaffolds which present in numerous bioactive compounds which possess various biological activities. Moreover, they are essential building blocks in organic synthesis, particularly for the preparation of important hybrid molecules. The series of hybrid compounds containing indoles and imidazolidin-2-one moiety with direct C–C bond were synthesized using an amidoalkylation one-pot reaction. All compounds were investigated as a growth regulator for germination, growth and development of wheat seeds (Triticum aestivum L). Their effect on drought resistance at very low concentrations (4 × 10−5 M) was evaluated. The study highlighted identified the leading compounds, 3a and 3e, with higher growth-regulating activity than the indole-auxin analogues

When Applying the Mercury Poisoning Test to Palladacycle-Catalyzed Reactions, One Should Not Consider the Common Misconception of Mercury(0) Selectivity

The aim of this study was to demonstrate the absolute necessity of control experiments for a correct interpretation of mercury drop test results when applied to mechanistic studies of palladacycle-catalyzed reactions. It was shown that the interaction of diverse azapalladacycles with metallic mercury leads to the formation of organomercuric chlorides during the redox-transmetalation process. The structure of these organomercurials was confirmed by elemental analysis, ¹H, ¹³C­{¹H}, and ¹⁹⁹Hg­{¹H} NMR spectra, X-ray diffraction analysis, and DFT calculations. The behavior and properties of <i>C</i>,<i>N</i>-mercuracycles bearing the weak and labile N···Hg bond are discussed on the basis of the temperature dependence of the NMR spectra and calculated thermodynamic parameters of the dechelation process

Determination of the Absolute Configuration of <i>CN</i>-Palladacycles by ³¹P{¹H} NMR Spectroscopy Using (1<i>R</i>,2<i>S</i>,5<i>R</i>)‑Menthyloxydiphenylphosphine as the Chiral Derivatizing Agent: Efficient Chirality Transfer in Phosphinite Adducts

A series of (1<i>R</i>)-MenOPPh₂ phosphinite derivatives of α-arylalkylaminate <i>CN</i>-palladacycles of known absolute configuration was prepared. Their structure and stereochemistry were determined using different experimental (NMR spectroscopy and X-ray diffraction) and theoretical (density functional theory calculation) methods. Despite the conformational mobility of the phosphinite reagent and the highly remote position of its stereocenters from those of the cyclopalladated amine, efficient chirality transfer in the phosphinite cyclopalladated complexes was established. On the basis of these results, a new method for the determination of the absolute configuration of chiral <i>CN</i>-palladacycles was elaborated using the (1<i>R</i>)-MenOPPh₂ phosphinite as a highly sensitive referee ligand and <i>in situ</i> ³¹P­{¹H} NMR spectroscopy as a control method. The proposed approach is a remarkable addition to the classical NMR techniques, increasing their versatility and excluding the isolation of the phosphinite derivatives

When Applying the Mercury Poisoning Test to Palladacycle-Catalyzed Reactions, One Should Not Consider the Common Misconception of Mercury(0) Selectivity

The aim of this study was to demonstrate the absolute necessity of control experiments for a correct interpretation of mercury drop test results when applied to mechanistic studies of palladacycle-catalyzed reactions. It was shown that the interaction of diverse azapalladacycles with metallic mercury leads to the formation of organomercuric chlorides during the redox-transmetalation process. The structure of these organomercurials was confirmed by elemental analysis, ¹H, ¹³C­{¹H}, and ¹⁹⁹Hg­{¹H} NMR spectra, X-ray diffraction analysis, and DFT calculations. The behavior and properties of <i>C</i>,<i>N</i>-mercuracycles bearing the weak and labile N···Hg bond are discussed on the basis of the temperature dependence of the NMR spectra and calculated thermodynamic parameters of the dechelation process