Refernces
10.1016/S0040-4039(01)01178-9
The research focuses on the synthesis of 5-(ω-sulfhydrylalkyl)salicylaldehydes, which are precursors for the preparation of alkanethiol-modified metal salens. These compounds are of interest for their potential use in modifying the surfaces of gold electrodes. The experiments involved multistep syntheses to obtain two specific alkanethiol-modified salicylaldehydes: 5-(2-sulfhydrylethyl)salicylaldehyde and 5-(6-sulfhydrylhexyl)salicylaldehyde. Key reactants included 4-methoxyphenethyl alcohol, hydriodic acid, Grignard reagent, paraformaldehyde, triethylamine, and thiourea, among others. The synthesis procedures involved refluxing, formation of Grignard reagents, column chromatography for purification, and treatment with base. The synthesized compounds were characterized using gas chromatography-mass spectrometry (GC–MS) and nuclear magnetic resonance (NMR) spectrometry to confirm their structures and purity.
10.1007/BF00766679
The research focused on the synthesis and evaluation of the antitumor and antibacterial activity of a series of substituted acrylophenones, specifically 1,3-bis-(p-alkoxybenzoyl)-1-bis-(2-chloroethyl)aminomethylbut-3-ene hydrochlorides (II-IX). The purpose of the study was to investigate the impact of different substituents on the benzene ring of these compounds on their toxicity and antitumor efficacy. The chemicals used in the synthesis process included 1,5-bis-(p-alkoxyphenyl)-1,5-pentanediones (I), bis-(2-chloroethyl)amine hydrochloride, paraformaldehyde, and dioxane as a solvent. The researchers found that the compounds' toxicities varied widely, with some showing high antitumor activity against certain tumor strains, such as sarcoma 45 and Walker's carcinoma, without observable toxic effects. Notably, compound (II), which is unsubstituted in the benzene ring, was the most active. However, none of the compounds showed significant antibacterial activity. The study concluded that the novel acrylophenone derivatives warrant further investigation as potential antitumor drugs.
10.1021/acs.orglett.9b00357
The study presents an efficient and regioselective method for the C3-alkoxymethylation of indoles using aldehydes and alcohols through a three-component cascade reaction under transition-metal-free conditions. The researchers optimized the reaction conditions, finding that indole, paraformaldehyde, and methanol in the presence of NaOH under air at 120 °C for 2 hours provided the best yields. The study explored the scope of various indoles and aldehydes, demonstrating good tolerance for both electron-donating and -withdrawing groups, and achieving yields up to 98%. The products are valuable building blocks in organic synthesis, particularly for creating biologically active molecules. The method is notable for its simplicity, efficiency, and environmental benignity, avoiding the use of transition metals and harsh conditions.
10.1039/c2dt30448a
The research focuses on the utilization of a bifunctional frustrated Lewis pair (FLP), specifically 1-[bis(pentafluorophenyl)boryl]-3,5-di-tert-butyl-1H-pyrazole (1), for the fixation of carbon dioxide (CO2) and related small molecules. The study explores the reactivity of this FLP with CO2, paraformaldehyde, tert-butyl isocyanate, tert-butyl isothiocyanate, methyl isothiocyanate, benzonitrile, and phenylacetylene, resulting in the formation of zwitterionic, bicyclic boraheterocycles (adducts 3–8) and other complexes (adducts 9 and 10). The experiments involved treating the FLP with these reactants in toluene solutions, followed by stirring, solvent evaporation, and in some cases, washing with pentane to isolate the products. The molecular structures of the products were established using X-ray diffraction analyses, and Density Functional Theory (DFT) calculations at the M06-2X/6-311++G(d,p) level of theory were performed to understand the energetics of the CO2 fixation process. The analyses included NMR (1H, 13C, 11B, and 19F), IR spectroscopy, and elemental analysis to characterize the products and confirm the fixation of the small molecules.
10.1023/A:1013172730470
The study investigates the stereochemical characteristics of the reactions between a series of 2,4,5-substituted 1,3,2-dioxaborinanes (I-III) and paraformaldehyde, which are cyclic boronic acid esters and an aldehyde, respectively. The purpose of these reactions is to form 4,5-disubstituted 1,3-dioxanes (IV-VI). The reactions are catalyzed by anhydrous ZnCl2, and the products are identified by comparing them with authentic samples. The study aims to understand the influence of substituent and configuration on the reactivity of these cyclic boronic esters, particularly in processes involving the cleavage of the B-O bond. The results indicate that the reaction rates differ between stereoisomers, with trans-esters reacting faster than their cis counterparts, and that the reaction is stereospecific, not involving bond rupture at chiral centers. The chemicals used in the study include the 1,3,2-dioxaborinanes (I-III), paraformaldehyde, anhydrous ZnCl2 as a catalyst, and 1,3-dioxanes (IV-VI) as the products of the reaction.
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