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Lewis-Acid-Mediated Benzotriazole Ring Cleavage (BtRC) Strategy for the Synthesis of 2-Aryl Benzoxazoles from N-Acylbenzotriazoles.

ABSTRACT: A Lewis-acid-mediated ring cleavage of acylbenzotriazoles (RCOBt) followed by cyclization to corresponding benzoxazoles was achieved in good to excellent yields. The reaction was found consistent with the milligram to gram scale.

SUBMITTER: Singh AS

PROVIDER: S-EPMC6641914 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Silicon Industry Waste Polymethylhydrosiloxane-Mediated Benzotriazole Ring Cleavage: A Practical and Green Synthesis of Diverse Benzothiazoles.

Project description:A green modification has been introduced to the synthesis of benzothiazoles by using polymethylhydrosiloxane (PMHS) for successive steps of benzotriazole ring cleavage and cyclization, an approach which was previously developed in our lab by the use of n-Bu3SnH. The use of the silicone industry byproduct PMHS makes this protocol a cost-effective and nontoxic one and thus may be considered for the industrial importance.

| S-EPMC6648665 | biostudies-literature

Synthesis of thioethers, arenes and arylated benzoxazoles by transformation of the C(aryl)-C bond of aryl alcohols.

Project description:Transformation of aryl alcohols into high-value functionalized aromatic compounds by selective cleavage and functionalization of the C(aryl)-C(OH) bond is of crucial importance, but very challenging by far. Herein, for the first time, we report a novel and versatile strategy for activation and functionalization of C(aryl)-C(OH) bonds by the cooperation of oxygenation and decarboxylative functionalization. A diverse range of aryl alcohol substrates were employed as arylation reagents via the cleavage of C(aryl)-C(OH) bonds and effectively converted into corresponding thioether, arene, and arylated benzoxazole products in excellent yields, in a Cu based catalytic system using O2 as the oxidant. This study offers a new way for aryl alcohol conversion and potentially offers a new opportunity to produce high-value functionalized aromatics from renewable feedstocks such as lignin which features abundant C(aryl)-C(OH) bonds in its linkages.

| S-EPMC8159426 | biostudies-literature

Lewis acid-promoted [2 + 2] cycloadditions of alkenes with aryl ketenes.

Project description:A method for the [2 + 2] cycloaddition of aryl ketenes and alkenes is presented. The process involves the in situ generation of a ketene in the presence of a Lewis acid. The utility of products is demonstrated towards the synthesis of a common scaffold found in several natural product families.

| S-EPMC4814371 | biostudies-literature

Design, synthesis and evaluation of 2-aryl benzoxazoles as promising hit for the A<sub>2A</sub> receptor.

Project description:The development of adenosine A2A receptor antagonists has received much interest in recent years for the treatment of neurodegenerative diseases. Based on docking studies, a new series of 2-arylbenzoxazoles has been identified as potential A2AR antagonists. Structure-affinity relationship was investigated in position 2, 5 and 6 of the benzoxazole heterocycle leading to compounds with a micromolar affinity towards the A2A receptor. Compound F1, with an affinity of 1 μm, presented good absorption, distribution, metabolism and excretion properties with an excellent aqueous solubility (184 μm) without being cytotoxic at 100 μm. This compound, along with low-molecular weight compound D1 (Ki = 10 μm), can be easily modulated and thus considered as relevant starting points for further hit-to-lead optimisation.

| S-EPMC6445171 | biostudies-literature

An unexpected Lewis acid catalyzed Diels-Alder cycloaddition of aryl allenes and acrylates.

Project description:An unexpected [4+2] cycloaddition of aryl allenes and simple acrylate derivatives is reported. This process functions well with a variety of allenes and acrylates to generate bi- and tricyclic dihydronaphthalene derivatives through a nonconventional bond disconnection.

| S-EPMC5038599 | biostudies-literature

Synthesis and Properties of Magnetic Aryl-Imidazolium Ionic Liquids with Dual Bronsted/Lewis Acidity.

Project description:A series of unique tunable aryl-imidazolium magnetic ionic liquids (MILs) with dual acidity that contain both Brønsted and Lewis acidic sites (abbreviated as B-L MILs) were synthesized and characterized using nuclear magnetic resonance and mass spectrometry. Physical properties, such as thermal properties, magnetic susceptibility, and Brønsted and Lewis acidity, were measured. These properties were found to depend on the cation structure. These B-L MILs had good solubility in many organic solvents, good thermal stability, and low melting points, and exhibited magnet-like behavior. For these B-L MILs, the Brønsted acidity was measured using ultraviolet-visible (UV-Vis), and the Lewis acidity was measured using Fourier transform infrared spectroscopy (FTIR). The results showed that B-L MILs with an electron-withdrawing group in the aryl-imidazolium moiety had higher Brønsted acidity, whereas those with an electron-donating group had higher Lewis acidity. This type of ionic liquid, with both Brønsted and Lewis acidic sites, is expected to be a useful solvent and catalyst for organic reactions.

| S-EPMC6316537 | biostudies-literature

Synthesis of aryl-substituted 2-methoxyphenol derivatives from maltol-derived oxidopyrylium cycloadducts through an acid-mediated ring contraction cascade.

Project description:Oxidopyrylium cycloadducts derived from maltol and aryl acetylenes undergo acid-mediated rearrangements to generate aryl-substituted 2-methoxyphenol (guaiacol) derivatives. Specifically, the cycloadducts react with boron trichloride to form 2-methoxy-5-arylphenol molecules, and with methane sulfonate to form 2-methoxy-4-aryl-6-methylphenol molecules.

| S-EPMC7560963 | biostudies-literature

Lewis acid-assisted Ir(iii) reductive elimination enables construction of seven-membered-ring sulfoxides.

Project description:Iridium has played an important role in the evolution of C-H activation chemistry over the last half century owing to its high reactivity towards stoichiometric C-H bond cleavage; however, the use of Ir(iii) complexes in catalytic C-H functionalization/C-C bond formation appears to have fallen off significantly. The main problem lies in the reductive elimination step, as iridium has a tendency to form stable and catalytically inactive Ir(iii) species. Herein, with a rationally designed Lewis acid assisted oxidatively induced strategy, the sluggish Ir(iii) reductive elimination is successfully facilitated, enabling the facile C-C bond formation. The X-ray crystal structure of a silver salt adduct of iridacycle and DFT calculations demonstrate that the sulfoxide group acts as a key bridge connecting the Ir(iii) metal centre with the silver Lewis acid, which facilitates the reductive elimination of the Ir(iii) metallacycle. Further identification of oxidants was carried out by performing stoichiometric reactions, which enables the development of catalytic construction of various highly functionalized seven-membered-ring sulfoxides, that are of great interest in medicinal chemistry and materials science.

| S-EPMC8162422 | biostudies-literature

Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis.

Project description:The preparation of all possible stereoisomers of a given chiral molecule bearing multiple stereocenters by a simple and unified method is a significant challenge in asymmetric catalysis. We report stereodivergent allylic substitutions with aryl acetic acid esters catalyzed synergistically by a metallacyclic iridium complex and benzotetramisole. Through permutations of the enantiomers of the two chiral catalysts, all four stereoisomers of the products bearing two adjacent stereocenters are accessible with high diastereoselectivity and enantioselectivity. The resulting chiral activated ester products can be converted readily to enantioenriched amides, unactivated esters, and carboxylic acids in a one-pot manner.

| S-EPMC5697981 | biostudies-literature

Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides.

Project description:An efficient room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl bromides is presented. The Pd(OAc)2/NiXantphos-based catalyst enables the introduction of various aryl and heteroaryl groups, via a deprotonative cross-coupling process (DCCP) in good to excellent yields (60-99%).

| S-EPMC4148349 | biostudies-literature

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