Metal-free C–H/C–H coupling of 1,3-diazines and 1,2,4-triazines with 2-naphthols facilitated by Brønsted acids

Utepova, Irina A.; Nemytov, Alexey I.; Ishkhanian, Victoria A.; Чупахин, О. Н.; Charushin, Valery N.

doi:10.1016/j.tet.2020.131391

Cited by 11 publications

(8 citation statements)

References 46 publications

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“…Based on retrosynthetic analysis of benzofurotriazine ( Scheme 1 d), we assume that 5,6-unsubstituted triazine and α-unsubstituted phenol are the best building blocks for the construction of the desired molecule through a sequence of C-C/C-O cross-coupling reactions. Earlier, our [ 67 , 69 , 70 ] and other [ 70 , 71 ] research groups demonstrated that 5,6-unsubstituted 1,2,4-triazines may be used in a two-step CDC reaction with various aromatic C-nucleophiles via the formation of 1,4-dihydrotriazine derivatives as intermediates, followed by aromatization to bi(het)aryl products. As mentioned above, the prefunctionalized azine is required for C-O cross-coupling reaction [ 53 ].…”

Section: Resultsmentioning

confidence: 99%

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

et al. 2022

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A different type of MnO2-induced oxidative cyclization of dihydrotriazines has been developed. These dihydrotriazines are considered as a “formal” Schiff’s base. This method provided easy access to naphthofuro-fused triazine via the C-C/C-O oxidative coupling reaction. The reaction sequence comprised the nucleophilic addition of 2-naphthol or phenol to 1,2,4-triazine, followed by oxidative cyclization. The scope and limitations of this novel coupling reaction have been investigated. Further application of the synthesized compound has been demonstrated by synthesizing carbazole-substituted benzofuro-fused triazines. The scalability of the reaction was demonstrated at a 40 mmol load. The mechanistic study strongly suggests that this reaction proceeds through the formation of an O-coordinated manganese complex.

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Section: Resultsmentioning

confidence: 99%

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

et al. 2022

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“…Synthesis of diazaperylenes precursor, 4-(2hydroxynaphthalen-1-yl)quinosaline 1, was performed according to the described method by direct introduction of 2-hydroxynaphthalene residue into C2 position of quinazoline 2 by SN H method with using trifluoromethanesulfonic acid as an adduct formation activator [12]. Further alkylation of the hydroxyl group of compound 1 with methyl iodide resulted in the formation of 4-(2-methoxynaphthalene-1-yl)quinazoline 3 (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

New naphtho[1,8-ef]perimidines: synthesis, fluorescence studies and application for detection of nitroanalytes

et al. 2021

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A rational approach to the synthesis of substituted naphtho[1,8-ef]perimidines based on SNH methodology and cyclization reaction in the series of condensed azines with naphthalene substituents was presented. Photophysical properties of the obtained fluorophores were studied, in particular, green fluorescence in the 485–536 nm range with quantum yield up to 32.4% was detected. HOMO-LUMO energy values and distributions for the new compounds were calculated by the DFT method in comparison with nitroanalytes and perylene. Based on the data obtained, as well as on the results of fluorescence titration, the possibility of using the new diazaperylenes as potential chemosensors for the visual detection of nitro-containing explosives was shown.

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“…2020 年 Utepova 课题组 [55] 报道了 Brønsted 酸催化吖嗪类化合物与 β-萘酚的一锅法无金属碳-碳偶联反应 (Scheme 25), 将芳基部分替换为氮杂芳基, 反应可得到包含可合成手性催化剂的 OCCCN 螯合单元的杂联芳基化合物. 此外, 2017 年, 夏吾炯等 [56] 以 Ir(dFCF 3 ppy) BINOL 及衍生物的制备一直以来受到较大关注, 制备光学纯(R)-BINOL 或(S)-BINOL 通常是通过采用酶解或化学拆分的方法, 而通过 β-萘酚不对称氧化偶联反应是制备手性 BINOL 最直接的方法 [57][58] .…”

Section: β-萘酚的芳基化反应unclassified

Recent Advances in the Reactions of β-Naphthol at α-Position

Liu¹,

Chen²,

Liu³

et al. 2023

Chinese Journal of Organic Chemistry

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β-Naphthol is an important synthon in organic synthesis and can participate in various chemical reactions due to its active chemical property at α-site, which has attracted a great attention from chemists. β-Naphthol can undergo various chemical transformations at α-position, such as alkylation, arylation, cyclization, amination, halogenation and so on, which can be used to construct structurally diverse naphthol derivatives with various biological activities. These naphthol derivatives can be used not only as the privileged skeletons of natural active drugs, but also as the building blocks for the preparation of the important intermediates in chemical synthesis. In recent years, chemical reactions based on β-naphthol at α-site have emerged one after another. The reactions of β-naphthol at α-position are reviewed from the aspects of C-

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Metal-free C–H/C–H coupling of 1,3-diazines and 1,2,4-triazines with 2-naphthols facilitated by Brønsted acids

Cited by 11 publications

References 46 publications

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

New naphtho[1,8-ef]perimidines: synthesis, fluorescence studies and application for detection of nitroanalytes

Recent Advances in the Reactions of β-Naphthol at α-Position

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