Refernces
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.
10.1080/00397919308011121
The study presents a practical and convenient two-step synthesis of the title compound, 4,6-dichloro-5-benzylthiopyrimidine (3), starting from 4,6-dihydroxypyrimidine (1). The initial three-step approach involved converting 4,6-dihydroxypyrimidine (1) to 4,6-dihydroxy-5-bromopyrimidine (4) with an 80% yield. Then, compound (4) was reacted with benzylmercaptan and anhydrous potassium carbonate in N,N-dimethylformamide, yielding 4,6-dihydroxy-5-benzylthiopyrimidine (2) with a variable yield, the best being 50%. Finally, compound (2) was converted to the title compound (3) by heating in phosphorus oxychloride, resulting in a 75% yield. An improved method was developed using sulfenyl chloride chemistry, where benzyl sulfenyl chloride was prepared from dibenzyl disulfide and sulfuryl chloride, and reacted with 4,6-dihydroxypyrimidine (1) in N,N-dimethylformamide to obtain compound (2) in quantitative yield. The title compound (3) was then synthesized from compound (2) using phosphorus oxychloride, achieving an overall yield of approximately 72%. The study provides a more efficient and reliable synthesis route for 4,6-dichloro-5-benzylthiopyrimidine, which is a key precursor in the synthesis of various types of 4,6-di-substituted pyrimidine-5-sulfonamides with interesting biological activities.
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.
10.1016/j.bmcl.2005.05.116
The research investigates the impact of lipophilic and hydrogen-bonding interactions in the P3 region on the potency and selectivity of valine aspartyl ketones as inhibitors of caspase 3, an enzyme involved in apoptotic cell death. The study aims to develop more potent and selective caspase 3 inhibitors for potential use in treating degenerative diseases. Key chemicals used include Fmoc-aspartic acid β-t-butyl ester, diazomethane, benzyl mercaptan, and various carboxylic acids for solid-phase synthesis. The researchers found that introducing a hydroxyl group alpha to the P3 carbonyl significantly increased potency and selectivity, suggesting a hydrogen-bonding interaction with the enzyme. They also explored the effects of different substituents on the phenyl ring, concluding that optimal binding required a balance between hydrogen bonding and lipophilic interactions. The most potent compound identified was a mandelic acid derivative with an iodo substituent, which also offered advantages for further development as a cell-permeable radioactive tool.
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