Electrochemical electrophilic bromination/spirocyclization of N-benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes

Green Chemistry, Год журнала: 2023, Номер 25(9), С. 3543 - 3548

Опубликована: Янв. 1, 2023

An electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes with 2-bromoethan-1-ol as the brominating reagent has been developed.

Язык: Английский

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Indole derivatives as agrochemicals: An overview

Chinese Chemical Letters, Год журнала: 2023, Номер 35(7), С. 109005 - 109005

Опубликована: Авг. 29, 2023

Язык: Английский

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Dual Copper/Photoredox Catalysis for Radical-Mediated Arylation and Alkylation of Sulfenamides

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 4007 - 4016

Опубликована: Фев. 20, 2025

Язык: Английский

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Dearomative 1,4-Difunctionalization of Non-Activated Arenes Enabled by Boryl Radical-Mediated Halogen-Atom Transfer

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 1294 - 1304

Опубликована: Янв. 7, 2025

Given the widespread presence of spirocyclic scaffolds in natural products and pharmacologically relevant synthetic compounds, development efficient methodologies for their construction holds great importance medicinal chemistry pharmaceutical research. In this study, a general photochemical dearomative spirocyclization nonactivated arenes has been established. The key to method lies ability amine-borane radicals activate aryl bromides iodides via halogen-atom transfer, thereby allowing conversion halides into corresponding subsequent chemodivergent transformations. remarkable compatibility versatility 1,4-difunctionalization is showed by rapid assembly structurally diverse 1,4-cyclohexadiene-based spirocycles incorporating oxindole, indoline, or dihydrobenzofuran subunits. Moreover, potential utility protocol exemplified formal total synthesis vasopressin V2 receptor antagonist Satavaptan.

Язык: Английский

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Chemodivergent and Enantioselective Synthesis of Spirobi[dihydrophenalene] Structures

Organic Letters, Год журнала: 2025, Номер 27(3), С. 869 - 873

Опубликована: Янв. 10, 2025

The development and enantioselective synthesis of two types C2-symmetric spirobi[dihydrophenalene] structures is reported. reaction proceeds via rhodium-catalyzed 2-fold asymmetric conjugate arylation dienones followed by BF3·OEt2-promoted spirocyclization to give the enantiopure spiro products. Additive-dependent chemodivergent 3,3'-diarylated 2,2',3,3'-tetrahydro-1,1'-spirobi[phenalene]-9,9'-diols (3,3'-Ar2-SPHENOLs) corresponding diary ethers from same intermediate achieved. structural properties 3,3'-Ph2-SPHENOL are analyzed, its application in catalysis has been preliminarily demonstrated.

Язык: Английский

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Decarboxylative Radical Sulfilimination via Photoredox, Copper, and Brønsted Base Catalysis

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(6)

Опубликована: Дек. 21, 2023

Sulfilimines, the aza-variants of sulfoxides, are key structural motifs in natural products, pharmaceuticals, and agrochemicals; sulfilimine synthesis is therefore important organic chemistry. However, methods for radical sulfilimination remain elusive, as a result, diversity currently available sulfilimines limited. Herein, we report first protocol decarboxylative reactions between sulfenamides N-hydroxyphthalimide esters primary, secondary, tertiary alkyl carboxylic acids, which were achieved via combination photoredox, copper, Brønsted base catalysis. This novel provided wide variety sulfilimines, addition to serving an efficient route S-alkyl/S-aryl homocysteine S-(4-methylphenyl) sulfoximine. Moreover, it could be used late-stage introduction group into structurally complex molecules, thereby avoiding need preserve labile organosulfur moieties through multistep synthetic sequences. A mechanism involving photocatalytic substrate transformation copper-mediated C(sp

Язык: Английский

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Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110094 - 110094

Опубликована: Июнь 1, 2024

Язык: Английский

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Synthesis, toxicological and in silico evaluation of novel spiro pyrimidines against Culex pipiens L. referring to chitinase enzyme

Scientific Reports, Год журнала: 2024, Номер 14(1)

Опубликована: Янв. 17, 2024

Abstract The exponential development of resistance to conventional chemical insecticides adds another important motive for the creation novel insecticidal active agents. One keys meeting this challenge is exploration classes molecules with different modes action. Herein, a series spiro pyrimidine derivatives was prepared using some green synthetic methodologies such as microwave irradiation, and sonication under ultrasound waves. Spiro aminonitrile 1 key starting material synthesis targets 2–9 by reaction carbon electrophiles nitrogen nucleophiles. structures all newly synthesized compounds were approved spectral data. toxicological efficiency biological impacts assessed against Culex pipiens L. larvae. toxicity showed remarkable variations C. Where, 3 , 4 2 most efficient LC 50 values 12.43, 16.29 21.73 µg/mL, respectively. While least potent compound an value 95.18 µg/mL. As well, other arranged according follows 5 > 7 6 9 8 . In addition, exhibited significant prolongation developmental duration greatly inhibited adult emergence. Moreover, many morphological deformities observed in stages. Furthermore, cytotoxicity effective normal human cells (WI-38) non-target organisms, where weak non-toxic effects. study binding affinity correlation between structure reactivity carried out molecular docking DFT calculations investigate their mode This shed light on promising larvicidal activity life cycle.

Язык: Английский

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Spiro-materials with aggregation-induced emission

Matter, Год журнала: 2024, Номер 7(10), С. 3390 - 3421

Опубликована: Окт. 1, 2024

Язык: Английский

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Design, synthesis, and biological activity of novel spiro‐pyrazolo[1,5‐a]quinazolines derivatives as potential insecticides

Pest Management Science, Год журнала: 2022, Номер 79(3), С. 1164 - 1174

Опубликована: Ноя. 13, 2022

Arylpyrazole insecticides display broad-spectrum insecticidal activity against insect pests. However, the high toxicity toward honeybees associated with fipronil prohibits its agronomic utility. To explore reducing of aryl pyrazole analogs to bees, a series new spiro-pyrazolo[1,5-a]quinazoline derivatives were designed and synthesized.Bioassay results showed that these compounds exhibited good activity. In particular, compound 5f Plutella xylostella larvae (median lethal contentration, LC50 = 1.43 mg L-1 ) was equivalent fipronil. Moreover, some also Solenopsis invicta. Importantly, bee study confirmed had much lower acute oral toxicity, median dose (LD50 1.15 μg bee-1 three four orders magnitude greater than (0.0012 ). Electrophysiological studies conducted using honeybee γ-aminobutyric acid receptor heterologously expressed in Xenopus oocytes explain reduced 5f. The inhibitory effect (16.29 μmol determined be approximately 700-fold (0.023 ).These could potential candidates lead structures for discovery novel low toxicity. © 2022 Society Chemical Industry.

Язык: Английский

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