10.1002/jhet.625
The research presents the first-time synthesis and X-ray analysis of 7-bromoarbidol hydrochloride, an impurity standard of the antiviral drug Arbidol. The study focuses on the indole scaffold, which is significant in medicinal chemistry for its anti-HIV, antimicrobial, and anti-cytomegalovirus properties. The experiments involve the synthesis of 7-bromoarbidol starting from an indole derivative obtained by the Nenitzescu protocol, followed by bromination, alkylation with thiophenol, and a Mannich reaction to form the final product. Key reactants include benzoquinone, 3-methylamino-but2-enoic acid ethyl ester, bromine, and formaldehyde bisdimethylaminoaminal. Analyses used to characterize the intermediates and final product include high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR), infrared (IR) spectroscopy, and X-ray diffraction. The X-ray analysis confirmed the molecular structure of the final product, which was found to exist as a methanol solvate, with detailed descriptions of the intermolecular hydrogen bond system within the crystal structure.
10.1021/jo026813i
The study focuses on the facile one-pot synthesis of S-alkylthiocarbamates, a class of compounds that have significant biological effects and are useful as herbicides. The study introduces a novel two-step method utilizing trichloroacetyl chloride that is both simple and high-yielding, allowing the incorporation of a wide range of substituents. The process design is simple and uses commercially available reagents, avoiding the use of toxic substances and gaseous reagents. The chemicals used in the synthesis include trichloroacetyl chloride, various thiols (such as alkanethiols, benzyl mercaptan, and benzenethiol), and different amines (including ammonium hydroxide, primary amines, and secondary amines). The conclusions drawn from the study highlight the versatility and efficiency of the method, allowing the production of a range of thiocarbamates in high yields simply by changing the amine used in the reaction. The study also explored alternative routes and found that the traditional order of reagent addition was more successful, although it had certain limitations.
10.1021/ol301383a
The research aims to advance the enantioselective synthesis of (-)-zampanolide, a microtubule-stabilizing agent with significant cytotoxic activity against various cancer cell lines. The study focuses on the construction of the C9-C20 region of the compound, utilizing a series of chemical reactions including ether transfer methodology, intramolecular radical cyclization, cross-metathesis/olefination sequences, Sharpless epoxidation, and selective reduction of a vinyl epoxide. Key chemicals involved in the process include alkoxy ether protected homoallylic alcohols, iodine monochloride (ICl), thiophenol, sulfonyl pyrans, and various other reagents and catalysts necessary for the described synthetic steps. The conclusions of the research detail the successful development of an efficient, enantioselective route to a protected C9-C20 fragment of (-)-zampanolide, with further work underway to couple this intermediate to a previously prepared C1-C8 fragment and complete the synthesis of the full compound.
10.1016/S0040-4020(01)97596-9
The research focuses on the total synthesis of L-hexoses, which are enantiomerically pure polyhydroxylated natural products. The purpose of this study was to demonstrate the power of the "reagent-control" strategy in organic chemistry, which utilizes powerful asymmetric reagents and catalysts to construct any stereochemical combination, including those that are difficult to make using traditional "substrate-control" methods. The researchers employed a reiterative two-carbon extension cycle consisting of four key transformations: conversion of an aldehyde to an allylic alcohol, asymmetric epoxidation, regioselective opening of the epoxy alcohol, and oxidation to generate a bis-homologated aldehyde. Chemicals used in the process include aldehydes, allylic alcohols, L-(+)-diisopropyl tartrate, titanium tetraisopropoxide, t-butylhydroperoxide, benzenethiol, and various Wittig reagents for olefination, among others. The conclusions of the research confirmed the efficiency and generality of the reagent-control methodology in the total synthesis of all eight L-hexoses, showcasing its potential for selective construction of any one of the sixteen hexose stereoisomers.
10.1002/anie.200500443
The research explores a new method for the functionalization of arenes through the addition of nucleophiles to arynes. The purpose of this study is to develop a general procedure for the selective addition of magnesiated thiols and amines to arynes, resulting in the formation of functionalized aryl magnesium species that can be trapped by various electrophiles. Key chemicals used in this research include thiophenol, various substituted thiophenolates (such as 2b-d), magnesium reagents like iPrMgCl, and electrophiles such as iodine, DMF, acid chlorides, and aldehydes. The study concludes that the addition of these nucleophiles to arynes is facilitated by the high reactivity of the arynes, leading to the formation of useful aryl magnesium intermediates that can be efficiently trapped to yield thioethers and arylamines with good yields. The procedure demonstrates excellent functional-group compatibility and regioselectivity, and the researchers are currently exploring extensions using other nucleophiles.
10.1021/ja00244a032
The study investigates the photochemistry of various sulfur-containing ketones, including phenacyl alkyl sulfides, sulfoxides, and sulfones, as well as ring-substituted and a-substituted phenacyl phenyl sulfides. These compounds undergo excited state radical cleavage to form a-keto radicals and sulfur-centered radicals when irradiated. The a-keto radicals are efficiently trapped by benzenethiol, while the sulfur-centered radicals mainly couple. The study finds that the rate of cleavage is influenced by the sulfur oxidation state, with sulfoxides undergoing cleavage at a much higher rate than sulfides and sulfones. The extent of disproportionation to form acetophenone increases with increasing a-alkyl substitution on the ketones. The study also examines the effects of ring substituents on the triplet lifetimes and cleavage rates, concluding that both n,p* and p,p* triplets are intrinsically reactive in these ?-cleavage reactions. The research provides insights into the mechanisms and kinetics of these photochemical reactions, supported by spectroscopic and kinetic data.
10.1039/b814806f
The research focuses on the synthesis and characterization of cationic and neutral NiII complexes containing the non-innocent PNPtBu pincer ligand. The study aims to explore the formation of alkyl and thiolate species using the non-innocent character of the PNPtBu backbone. Starting with the dicationic complex 1, Ni(PNPtBu)(NCMe)2, the researchers prepared a series of dicationic and monocationic NiII complexes. Key chemicals used in the process include tert-butyl isocyanide, azide, benzylmercaptan, thiophenol, and various nickel and phosphorus-containing compounds. The research concludes that complex 1 serves as a versatile building block for the synthesis of well-defined mononuclear NiII species, such as the rare mononuclear monothiolate complexes 7 and 8. The non-innocent nature of the PNPtBu ligand leads to significant electronic changes, which were investigated for both dication 3 and monocation 6, featuring a tert-butyl isocyanide co-ligand. DFT calculations supported the assignment of the deprotonated PN-PtBu ligand as a monoamido fragment, and the study also provided access to new neutral Ni-complexes with Ph, Me, or H as co-ligands, offering potential applications in catalytic reactions.
This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.
T
T+
