10.1016/j.jorganchem.2003.10.040
The study presents the synthesis and comprehensive characterization of 4-Me2NC6H4HgOH, the first verified organomercury hydroxide that crystallizes as discrete molecules in the solid state. The researchers detail its preparation from 4-Me2NC6H4HgOAc and discuss the structures of related compounds, including 4-Me2NC6H4HgOAc and (4-Me2NC6H4)2Hg. The study delves into the complex history of organomercury hydroxides, resolving previous conflicting reports and misconceptions about their existence and properties. It also explores the behavior of these compounds in aqueous solution, pointing to pH-dependent equilibria involving various species. The researchers used techniques such as electrospray mass spectrometry, nuclear magnetic resonance, infrared spectroscopy, and X-ray crystallography to characterize the compounds. The results provide a clear structural and spectral signature of 4-Me2NC6H4HgOH, confirming its status as a true organomercury hydroxide and contributing to a better understanding of arylmercury chemistry.
10.1071/CH16710
The study reports on the successful synthesis and characterization of two 28-membered, 2,2'-bipyridine-containing macrocycles in high yield. The first macrocycle was formed through a Williamson ether synthesis, and upon reduction with sodium borohydride, the second macrocycle was produced quantitatively. These macrocycles, which contain a 2,2'-bipyridine unit, are potentially useful components for creating a variety of interlocked architectures, including catenanes, rotaxanes, and molecular machines. The research builds upon previous work by Sauvage, Stoddart, and Feringa, who were awarded the 2016 Nobel Prize in Chemistry for their contributions to the design and synthesis of molecular machines, and it aims to improve upon the yield-limiting macrocyclisation reactions that have historically been a challenge in the field. The study also discusses the use of high-yielding synthetic strategies and the potential for future investigations into the metal-complexation properties of these ligands and their application in forming interlocked structures.
10.1002/cjoc.201100405
The research aimed to develop an efficient and regioselective method for the synthesis of 3,4-diphenylimidazo[1,5-a]pyrimidines, which are important fused heteroaromatic compounds with potential biological activities. The study utilized microwave irradiation to accelerate the cyclocondensation of isoflavones with 5-amino-1H-imidazole-4-carboxamide in the presence of sodium hydroxide, resulting in the formation of the target compounds in good to moderate yields. The optimized conditions involved the use of DMF as a solvent and sodium hydroxide as a base, with a molar ratio of 1a (isoflavone) to 2 (5-amino-1H-imidazole-4-carboxamide) to base of 1:1.6:3. The method was found to be suitable for a variety of structurally divergent isoflavones, leading to the synthesis of 3,4-diphenylimidazo[1,5-a]pyrimidines with yields ranging from 58% to 88%. The research concluded that this approach is an efficient and regioselective method for constructing fused 3,4-diphenylimidazo[1,5-a]pyrimidines derivatives, offering a valuable contribution to the field of pharmaceutical chemistry.
10.1080/00397919108021779
The study presents a method for the synthesis of substituted N-monoalkylaromatic amines under phase-transfer catalysis (PTC) conditions. The researchers used various aromatic amides and amines as starting materials, which were converted to N-monoalkylated products using dimethyl sulphate as the alkylating agent. The reaction was facilitated by the presence of powdered sodium hydroxide, potassium carbonate, and tetrabutylammonium hydrogen sulphate as the PTC. The study found that compounds with ortho electron-withdrawing substituents exclusively yielded monoalkyl amines, while those with electron-donating substituents or no substituents resulted in alkyl amides. The researchers proposed a mechanism for the alkylation and deacylation processes and verified it experimentally. The study provides a simple, economical one-pot synthesis method for producing ortho substituted aromatic monoalkyl amines with electron-withdrawing substituents.
10.1021/jm201332p
The study focuses on the design of inhibitors for β-amyloid (Aβ) aggregation, a key process in Alzheimer's disease (AD). Researchers developed a substituted peptide, [Nle35, D-Pro37]Aβ42, using molecular dynamics simulations to stabilize Aβ structures suitable for NMR analysis. This peptide was found to stabilize Aβ trimers, prevent mature fibril and β-sheet formation, and reduce aggregation when mixed with wild-type Aβ42. Furthermore, a small molecule lead compound was identified through ligand-based drug design, showing similar inhibitory effects to the peptide. The study demonstrates the potential of using molecular dynamics simulation to guide experiments aimed at understanding AD and developing therapeutics.
10.1021/jo00331a016
The study presents a chemical method for converting folic acid to pteroic acid, a valuable intermediate for synthesizing folic acid analogues and derivatives. The process involves treating folic acid with acetic anhydride to form a mixture of acetylated azlactones, which are then cleaved with mild base to yield mainly acetylated pteroic acids. Further treatment with hot base removes the acetyl groups, resulting in pteroic acid with a yield of 55-60% contaminated with folic acid. The study also discusses various side reactions and byproducts, including the formation of a pyrazine derivative from the hydrolysis of the glutamic acid moiety and the opening of the pyrimidine ring. The authors detail the experimental procedures, including HPLC analysis, UV absorption spectra, mass spectrometry, and proton NMR spectra, and provide a method for separating folic and pteroic acids using column chromatography. The research was supported by a grant from the National Cancer Institute, National Institutes of Health.
10.1021/jo00348a046
The main content of the study involves the exploration of the synthesis of (Z)-7-alken-1-ols, which are significant as insect sex attractants, particularly pheromones for various moth species. The researchers utilized organoboranes to achieve a general, one-pot, and stereospecific synthesis of these compounds. The process began with the monohydroboration of 1-alkynes with borepane to produce trans-1-alkenylborepanes. Subsequent treatment of these compounds with iodine in the presence of a base led to a migration of the cycloalkyl chain from boron to the adjacent carbon, forming intermediates with an eight-membered borocane moiety. These intermediates then underwent rapid deiodoboronation to yield (Z)-7-alken-1-boronate esters, which upon oxidation resulted in the desired (Z)-7-alken-1-ols. This method offers a convenient route for the synthesis of specific pheromones, such as (Z)-7-dodecen-1-ol, (2)-7-dodecen-1-yl acetate, and (Z)-7-tetradecen-1-yl acetate, which are crucial for pest control in agriculture.
10.1039/b813890g
The research focuses on the synthesis of novel 5-alkoxymethyl-2-aryl-3-chloropyrroles and 2-aroylpyrroles through the electrophile-induced bromocyclization of N-(1-aryl-2,2-dichloropent-4-enylidene)amines to intermediate 1-pyrrolinium salts. The study investigates the selective conversion of these salts into the target pyrroles by reacting them with alkoxides in the corresponding alcohol or in THF, deviating from the chemistry of c,d-unsaturated a,a-dialkylaldimines. Additionally, the treatment of 5-bromomethyl-1-pyrrolinium bromides with sodium hydroxide in water leads to a new method for synthesizing 2-aroylpyrroles through an unexpected ring transformation of intermediate aziridine derivatives, which can also be isolated. The experiments involved the preparation of N-(1-aryl-2,2-dichloropent-4-enylidene)amines from acetophenone derivatives through a three-step procedure, followed by their cyclization with bromine and subsequent reactions with alkoxides or sodium hydroxide. The analyses used to support the findings include 1H NMR to detect intermediates and crude reaction mixtures, and the yields of the synthesized compounds were reported in a table.
C,
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