Copper-Catalyzed Intramolecular C–H Alkoxylation of Diaryltriazoles: Synthesis of Tricyclic Triazole Benzoxazines

Ma, Xinyuan; Li, Haotian; Hong, Xin; Du, Wenjie; Anderson, Edward A.; Dong, Xian; Jiang, Yubo

doi:10.1021/acs.orglett.0c01517

Cited by 23 publications

(8 citation statements)

References 72 publications

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“…Recently, CuAAC derived triazoles in the presence of Cu(I) catalysis have been reported to undergo C(5)–H activation via intramolecular C–H alkoxylation through a radical route and give high-to-excellent yield of tricyclic triazoles displaying potent antifungal activity . Although, similar C–H activation can also be achieved easily by utilizing the carbohydrate-based triazoles, surprisingly little effort has been made so far in this direction.…”

Section: Cuaac Carbo-click In Sensing Gelation Chelation Glycosylatio...mentioning

confidence: 99%

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

et al. 2021

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Copper(I)-catalyzed 1,3-dipolar cycloaddition between organic azides and terminal alkynes, commonly known as CuAAC or click chemistry, has been identified as one of the most successful, versatile, reliable, and modular strategies for the rapid and regioselective construction of 1,4-disubstituted 1,2,3-triazoles as diversely functionalized molecules. Carbohydrates, an integral part of living cells, have several fascinating features, including their structural diversity, biocompatibility, bioavailability, hydrophilicity, and superior ADME properties with minimal toxicity, which support increased demand to explore them as versatile scaffolds for easy access to diverse glycohybrids and well-defined glycoconjugates for complete chemical, biochemical, and pharmacological investigations. This review highlights the successful development of CuAAC or click chemistry in emerging areas of glycoscience, including the synthesis of triazole appended carbohydrate-containing molecular architectures (mainly glycohybrids, glycoconjugates, glycopolymers, glycopeptides, glycoproteins, glycolipids, glycoclusters, and glycodendrimers through regioselective triazole forming modular and bio-orthogonal coupling protocols). It discusses the widespread applications of these glycoproducts as enzyme inhibitors in drug discovery and development, sensing, gelation, chelation, glycosylation, and catalysis. This review also covers the impact of click chemistry and provides future perspectives on its role in various emerging disciplines of science and technology.

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Section: Cuaac Carbo-click In Sensing Gelation Chelation Glycosylatio...mentioning

confidence: 99%

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

et al. 2021

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“…Notably, 6-endo cyclization was preferred over the 5-exo cyclization irrespective of the substituents present in the alkenes. Later, Jiang and co-workers reported the synthesis of tricyclic triazole-benzoxazines through copper-catalyzed intramolecular triazole C–H alkoxylation (Scheme e) . The antifungal properties of the synthesized compounds were tested against F. oxysporum , F. solani , and C. destructans and showed promising levels of inhibition of F. oxysporum compared to existing antifungal agents…”

Section: Hydroxy-directed C–h Bond Functionalizationsmentioning

confidence: 99%

“…Later, Jiang and coworkers reported the synthesis of tricyclic triazole-benzoxazines through copper-catalyzed intramolecular triazole C−H alkoxylation (Scheme 105e). 207 The antifungal properties of the synthesized compounds were tested against F. oxysporum, F. solani, and C. destructans and showed promising levels of inhibition of F. oxysporum compared to existing antifungal agents In 2015, Wang and co-workers reported a straightforward synthesis of coumarin via carbonylation of vinylphenol using carbon monoxide (Scheme 106). 208 They utilized Cp*Co-(CO)I 2 as catalyst along with Ag 2 CO 3 and Cu(OAc) 2 as oxidant as well as carboxylate source.…”

Section: Ester-directed C−h Bond Functionalizationsmentioning

confidence: 99%

Weak-Coordination in C–H Bond Functionalizations Catalyzed by 3d Metals

2022

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Transition-metal-catalyzed C–H bond functionalizations have had an enormous influence on organic synthesis in recent times. However, the use of low-abundance 4d and 5d metals is almost inevitable, and they are in high demand. This will be a cause of concern, and hence, it is important to develop methods based on 3d metals, which are widely present in the Earth’s crust. In this regard, the use of 3d metal catalysts or their precursors for catalysis, in general, and C–H bond functionalizations, in particular, has gained significant momentum in the recent times. The major development in catalytic C–H bond functionalizations with 3d metals has been achieved predominantly with strongly coordinating directing groups such as pyridyl, pyrimidinyl, pyrazolyl, and 8-amino-quinolinyl groups. Thus, prefunctionalization of substrates with these directing groups is necessary, which contradicts the step- and atom-economy of C–H bond activation. However, commonly available functional groups such as aldehyde, ketone, carboxylic acid, amide, hydroxy, and N-oxides loosely bind to metals through weak-coordination. These weakly coordinating directing groups orient the metal to activate C–H bond regioselectively without the need for preinstalled strongly coordinating directing groups. Although it is challenging, this contemporary topic has been actively pursued by many researchers in recent times. Through this article, we provide a comprehensive overview of 3d metal-catalyzed, weakly coordinating, directing-group-enabled C–H bond functionalizations reported until March 2021.

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“…Li and co-workers synthesized tricyclic triazole-benzoxazines 223 through copper-mediated intramolecular C-H alkoxylation of 1,4-disubstituted 1,2,3-triazoles 224 (Scheme 85). 96 This new methodology has extensive application in the eld of medicinal and agro chemistry. It was observed that the 1,4-disubstituted 1,2,3-triazoles with electron-donating and electron-withdrawing groups were well tolerated in this reaction.…”

Section: C-o Bond Formationmentioning

confidence: 99%