Refernces
10.1007/s11172-007-0243-5
The research presents a novel method for synthesizing 6-R-3-arylazo-1H-pyridazin-4-ones from difluoroboron chelates of 1,3-diketones. The study is based on the reactivity of the methyl group in these chelates with two equivalents of a diazonium salt. The synthesis involves a two-step process: first, the reaction of difluoroboron complexes of ?-diketones with diazonium salts at low temperatures to form dark red crystalline intermediates, followed by their decomposition upon refluxing in a pyridine-butanol mixture to yield the final 3-arylazo-1H-pyridazin-4-one derivatives. Acetylacetone and aroylacetones as the starting 1,3-diketones. Boron trifluoride etherate and tributyl borate for the preparation of difluoroboron chelates. The researchers utilized various spectroscopic techniques, including 1H and 13C NMR, IR, and mass spectrometry, to identify and analyze the structures of the synthesized compounds. The study also explored the possibility of structural isomers and confirmed the formation of the desired compounds through 2D NMR spectroscopy.
10.3762/bjoc.8.81
The research focuses on the synthesis and coordination behavior of axially chiral oxazoline-carbene ligands with an N-naphthyl framework, specifically their interaction with AuCl·SMe2 to form Au(I) complexes. The main reactants used in the synthesis include methyl 1-hydroxy-2-naphthoate, trifluoromethylation reagents, 2-nitroaniline, Pd/C for reduction, triethyl orthoformate, TsOH for cyclization, and (S)-2-amino-2-phenylethanol, among others. The synthesis process involved several steps, including trifluoromethylation, coupling reactions, reduction, cyclization, and amide formation, leading to the formation of axially chiral ligands. The coordination study with AuCl·SMe2 was conducted using NaOAc in acetonitrile, and the Au(I) complexes were isolated by flash column chromatography. The analysis of the complexes was performed using 1H NMR spectroscopy to compare the chemical shifts of protons on the oxazoline ring before and after complexation, and single-crystal X-ray diffraction studies were employed to confirm the structure of the complexes, revealing a nearly linear coordination geometry around the gold(I) center. The study found that the geometry of the chiral N-naphthyl axis significantly influenced the yields of the Au(I) complexes, with (Sa,S)-7 yielding higher complex yields than (Ra,S)-7.
10.1007/s10593-006-0272-2
The research discusses the oxidation-reduction reactions of 1,3-dithioles and their ions, focusing on the transfer of hydrogen from the C-H group of organic compounds to electrophilic substrates as a model for fermentation processes. The study explores the reduction potential of 1,3-benzodithiole and its derivatives, comparing their hydride-ion donating abilities. Experiments involved the reduction of dibenzopyrilium perchlorate by 1,3-benzodithiole to form dibenzopyran, and the subsequent reduction of 1,3-benzodithiolium cation by dibenzothiopyran. The reactions were carried out in tetrahydrofuran (THF) at 80°C, and the products were analyzed using 1H NMR spectroscopy and mass spectrometry. Key reactants included 1,3-benzodithiole, dibenzopyrilium perchlorate, and dibenzothiopyran, along with various 4-aryl-1,3-dithiolium perchlorates and 10-methyl-9,10-dihydroacridine. The analyses confirmed the formation of the expected products, such as 4-aryl-1,3-dithioles, and provided insights into the relative hydride-donating abilities of the compounds involved.