Synthesis of functionized N-arylbenzotriazoles via palladium catalyzed intramolecular amination

Wang, Dachao; Gan, Xiaoting; Zhou, Lewei; Shu, Hanyu; Zhou, Jun

doi:10.1016/j.tetlet.2021.153587

Cited by 4 publications

(2 citation statements)

References 56 publications

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“…The use of benzotriazole also afforded a C4-adduct (6d), and CH 2 Cl 2 was found to be a better solvent than THF. Although the reason for the behavior of the nucleophilic positions of indazole [17][18][19][20][21][22][23][24][25] and benzotriazole [26][27][28][29][30][31][32][33][34][35] is unclear, it is noteworthy that the nucleophilic positions were perfectly controlled. N-Methylaniline was also compatible in this reaction, furnishing C4-adduct 6e.…”

Section: Resultsmentioning

confidence: 99%

Oxidative Functionalization of Catechol Derivatives Substituted with Electron-Withdrawing Groups

Sawama,

Shimizu,

Aijima

et al. 2023

CHEMICAL & PHARMACEUTICAL BULLETIN

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Catechols possessing electron-withdrawing groups at the C3 position effectively underwent oxidative functionalization at the C4 position in the presence of phenyliodine(III) diacetate (PIDA) and heteroarene nucleophiles (e.g., indole, indazole, and benzotriazole) to produce the corresponding biaryl products. The PIDA-mediated oxidation of catechol derivatives afforded the ortho-benzoquinone intermediate, which subsequently underwent regioselective nucleophilic addition to the α,β-unsaturated carbonyl moiety of ortho-benzoquinone using indole, indazole, and benzotriazole to give 4-substituted catechol derivatives in a one-pot manner. Notably, the nucleophilic substitution positions of indazole and benzotriazole were perfectly controlled. Additionally, the reaction using N-methylaniline as the nucleophile afforded a tertiary amine product.

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Section: Resultsmentioning

confidence: 99%

Oxidative Functionalization of Catechol Derivatives Substituted with Electron-Withdrawing Groups

Sawama,

Shimizu,

Aijima

et al. 2023

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…1 [1,2,3]triazole (14b). 72,73 Yellow oil (purified by silica gel column chromatography using 10/1 hexane/ ethyl acetate). Product yield: isolated as a diastereo-mixture in 41% (19 mg, 0.08 mmol).…”

Section: -Bromo-5-methyl-1-phenyl-1h-pyrazole (9b)mentioning

confidence: 99%

Arene C–H Amination with N-Heteroarenes by Catalytic DDQ Photocatalysis

Nakayama

Okada

2023

J. Org. Chem.

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Arene C−H aminations using catalytic amounts of a 2,3-dichloro-5,6-dicyanop-benzoquinone (DDQ) photocatalyst are described. Benzene, which has an oxidation potential of 2.48 V (vs SCE), was functionalized by pyrazoles, triazoles, tetrazoles, purines, and tert-butoxycarbonyl amine. Arenes underwent amination via a combination of ultraviolet (UV) light and a DDQ photocatalyst without a typical co-oxidant. Although the mechanism remains an open question, DDQH 2 , which is generated from DDQ after oxidation, is reactivated to DDQ under UV light irradiation conditions, possibly with the assistance of adventitious O 2 and/or a solvent as the terminal oxidant(s) in this system.

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Five-membered ring systems: with more than one N atom

Yet

2023

Progress in Heterocyclic Chemistry

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Synthesis of functionized N-arylbenzotriazoles via palladium catalyzed intramolecular amination

Cited by 4 publications

References 56 publications

Oxidative Functionalization of Catechol Derivatives Substituted with Electron-Withdrawing Groups

Oxidative Functionalization of Catechol Derivatives Substituted with Electron-Withdrawing Groups

Arene C–H Amination with N-Heteroarenes by Catalytic DDQ Photocatalysis

Five-membered ring systems: with more than one N atom

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