Refernces
10.1016/S0040-4039(02)01731-8
The research focuses on the synthesis of isocoumarins and α-pyrones, which are important intermediates in the synthesis of various carbocyclic and heterocyclic compounds with diverse biological activities. The study introduces a method for synthesizing these compounds using electrophilic cyclization with iodocyclization agents, specifically ICl, on o-(1-alkynyl)benzoates and (Z)-2-alken-4-ynoates. The experiments involved the reaction of these substrates with ICl under mild conditions, leading to the formation of 3-substituted 4-iodoisocoumarins and 6-substituted 5-iodo-2(2H)-pyranones in excellent yields. The scope of the reaction was tested with various functional groups, and the products were further elaborated using palladium-catalyzed coupling reactions like Sonogashira, Heck, and Suzuki reactions. The analyses used to characterize the products included techniques such as NMR spectroscopy, infrared spectroscopy, and high-resolution mass spectrometry.
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.
10.1139/v82-082
The study investigates the iodination and chlorination of uracil bases and protected nucleosides. Iodine monochloride (ICl) is used to iodinate uracil compounds, yielding 5-iodouracil derivatives with over 95% purified yields. Iodobenzene dichloride (PhICl?) is employed for chlorination, resulting in 5-chlorouracil products. The nucleosides are protected as p-toluyl esters, which enhance their solubility in organic solvents and facilitate high-yield crystallization. The study provides a convenient and efficient method for synthesizing 5-substituted uracil derivatives, which have potential applications in the treatment of neoplastic and viral diseases.
10.1002/jhet.5570220112
The research aimed to develop new organ-specific radiopharmaceuticals by synthesizing compounds containing the 4-phenylpiperazine moiety, which is known for its selective mechanisms of action and ability to undergo electrophilic substitution reactions. The study successfully synthesized 4(4-iodophenyl)piperazine (2) with a 70% yield and characterized it. This compound was then converted to its 1-carboxamidino derivative (4) with a 61% yield, using S-methylthiouronium sulfate. The researchers chose a milder reaction condition to avoid separation problems and complex mixtures that resulted from higher temperatures. The study concluded that the synthesized compounds could be potential candidates for myocardial imaging radiopharmaceuticals, as the 1-carboxamidino derivative showed identical properties to the radioiodinated material previously evaluated for this purpose. Key chemicals used in the research included 4-phenylpiperazine, iodine monochloride, S-methylthiouronium sulfate, and various solvents such as acetic acid-water mixture and dimethyl sulfoxide.
10.1080/00397911.2015.1005630
The research investigates the use of iodine monochloride (ICl) as a highly efficient and green oxidant for converting alcohols to corresponding carbonyl compounds, aiming to find a cheap, mild, and high-yield oxidizing method for large-scale synthesis. The study optimizes reaction conditions using 2,3,4,6-tetra-O-benzyl-D-glucopyranose as the substrate, finding that 1.5 equivalents of ICl added dropwise in CH2Cl2 solution at 0°C to room temperature, with 3 equivalents of Cs2CO3 as the base in CH2Cl2 solvent, yields the best results. The optimized ICl/Cs2CO3 system is then tested on various alcohol substrates, successfully oxidizing aldose hemiacetals, diarylmethanols, arylalkylmethanols, and dialkylmethanols to their corresponding carbonyl compounds with short reaction times and high yields, but failing with olefin-bearing and primary alcohols. The research concludes that ICl is a superior alternative to the I2/K2CO3 system, offering less oxidant quantity, shorter reaction times, and higher yields, thus providing a greener and more efficient oxidation method for the studied alcohol substrates.
10.1016/S0022-328X(99)00709-3
The study in the Journal of Organometallic Chemistry focuses on the direct nucleophilic displacement of halides (chlorine or iodine) in compounds with the formula (Me3Si)3CSiRRX, where R and R represent various organic groups. The researchers investigated the reactions of these compounds with nucleophiles such as KOCN, KSCN, KCN, or NaN3 in different solvents like CH3CN, MeOH, and DMSO, or CH3CN mixed with H2O. The study explores the influence of steric hindrance on the reactivity of silicon centers bearing the bulky trisyl group (Tsi). It was found that by reducing the steric hindrance or using linear nucleophiles, direct bimolecular displacement reactions occur without the observation of rearrangement. The study also successfully synthesized new compounds with different groups and examined their reactivity with the mentioned nucleophiles, providing insights into the ease of reactions on silicon centers bearing the bulky trisyl group.
10.1021/jo102060j
The study presents an efficient method for synthesizing iodoisoquinoline-fused benzimidazole derivatives, which are significant for their potential biological activities such as anti-HIV-1, anticancer, antimicrobial, and antifungal properties. The researchers developed a tandem cyclization strategy using CuI/I2 to promote the electrophilic tandem cyclization of 2-ethynylbenzaldehydes with ortho-benzenediamines. This approach led to the formation of the desired iodoisoquinoline-fused benzimidazoles in moderate to good yields. The study also explored the scope of the reaction with various substrates and demonstrated the potential of the synthesized products for further functionalization through cross-coupling reactions, highlighting the importance of this method for drug discovery and the development of heterocyclic compounds with diverse biological activities.