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Search for "amine" in Full Text gives 1173 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240

Graphical Abstract
  • -glycoside 11a (Scheme 7) [20]. Debenzylation gave product 11b which was transformed to akashin A (11c) by reduction of the azide to the amine in the presence of propane-1,3-dithiol and subsequent debenzoylation. Akashin A was transformed to akashins B and C by acetylation and reaction with diacetyl
  • -mannose (14) afforded indigo-N-mannoside α-15a, albeit, in low yield (Scheme 11) [21]. Deacetylation afforded product α-15b. Indirubin-N-glycosides (red sugars) In contrast to indigo, indirubin is a non-symmetrical compound containing an amine- and an amide-type nitrogen atom. In our group, we developed a
  • -glycosides containing the carbohydrate moiety located at the amine-type nitrogen atom (Scheme 18) [25]. For this purpose, we decided to react isatins with N-glycosylated indoxyls which were entirely unknown at that time. The reaction of ʟ-rhamnose α/β-4c with indoline afforded α/β-25a (β:α ≈ 4:1
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Published 08 Nov 2024

Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides

  • Baptiste Leroux,
  • Alexis Beaufils,
  • Federico Banchini,
  • Olivier Jackowski,
  • Alejandro Perez-Luna,
  • Fabrice Chemla,
  • Marc Presset and
  • Erwan Le Gall

Beilstein J. Org. Chem. 2024, 20, 2834–2839, doi:10.3762/bjoc.20.239

Graphical Abstract
  • 16 h at 80 °C (Table 1, entry 2). However, its suitability in the multicomponent coupling with an amine and an aldehyde still had to be demonstrated as there was no precedent for such a Mannich multicomponent coupling involving nonstabilized organozinc halides using THF or 2-MeTHF as solvent. To our
  • species 2 were collected using a syringe and allowed to react with an amine 3 and an aldehyde 4 under moderate heating (Scheme 2). The multicomponent couplings proceeded smoothly, with an acceptable yield of the α-branched amine being obtained after 3 h at 50 °C. A range of secondary amines as well as
  • various aromatic aldehydes could be used in the multicomponent coupling. Interestingly, functionalized organozinc reagents gave the multicomponent coupling product, except for the cyanated organozinc compound 2d, which only provided traces of the expected α-branched amine. It can be noted that in sharp
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Published 07 Nov 2024

Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates

  • Kento Iwai,
  • Akari Hikasa,
  • Kotaro Yoshioka,
  • Shinki Tani,
  • Kazuto Umezu and
  • Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2024, 20, 2827–2833, doi:10.3762/bjoc.20.238

Graphical Abstract
  • anhydride, the intermediately formed hemiacetal underwent acetylation, leading to N,O-acetals 1. In this method, an acid amide can be used as an amine masked with an acyl group. Subsequent elimination of acetic acid occurred to afford 2 in situ upon treatment with a base, enabling nucleophilic addition with
  • nucleophiles to synthesize PCPAs, and their ring closures were also investigated. Results and Discussion NAI 2 can be generated by treating N,O-acetal 1 with a base, such as triethylamine. However, the addition of an amine was omitted because lithium acetylide functions both as nucleophile and base. When 1a
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Published 06 Nov 2024

Investigation of a bimetallic terbium(III)/copper(II) chemosensor for the detection of aqueous hydrogen sulfide

  • Parvathy Mini,
  • Michael R. Grace,
  • Genevieve H. Dennison and
  • Kellie L. Tuck

Beilstein J. Org. Chem. 2024, 20, 2818–2826, doi:10.3762/bjoc.20.237

Graphical Abstract
  • , highly sensitive chemosensors via a facile synthetic route/method, we have explored three chelates for lanthanide ions (DO3A, 2,6-pyridinedicarboxylic acid and DO2A), resulting in complexes with different overall charges. Additionally we have explored two copper(II) binding groups (di(2-picolyl)amine and
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Published 05 Nov 2024

Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines

  • Dmitriy Yu. Vandyshev,
  • Daria A. Mangusheva,
  • Khidmet S. Shikhaliev,
  • Kirill A. Scherbakov,
  • Oleg N. Burov,
  • Alexander D. Zagrebaev,
  • Tatiana N. Khmelevskaya,
  • Alexey S. Trenin and
  • Fedor I. Zubkov

Beilstein J. Org. Chem. 2024, 20, 2806–2817, doi:10.3762/bjoc.20.236

Graphical Abstract
  • , it is worth mentioning the work of Li and co-workers (2011) [20], who described a single example of the formation of such structures by carrying out an organocatalytic domino aza-Michael–Mannich reaction between benzylidene-1H-imidazol-2-amine and cinnamaldehyde. Although the imidazo[1,2-a
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Published 05 Nov 2024

Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction

  • Yuta Kabumoto,
  • Eiichiro Yoshimoto,
  • Bing Xiaohuan,
  • Masato Morita,
  • Motohiro Yasui,
  • Shigeyuki Yamada and
  • Tsutomu Konno

Beilstein J. Org. Chem. 2024, 20, 2776–2783, doi:10.3762/bjoc.20.233

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  • amides in moderate three-step yields. Keywords: amine; chirality transfer; [1,3]-proton shift reaction; tetrafluoroethylene fragment; Introduction A fluorine atom has quite peculiar chemical and physical properties compared to others, and hence changes in molecular properties resulting from the
  • 22b could not be completely suppressed. The thus obtained [1,3]-proton shift product (S)-20b was subjected to 2 N HCl aq in Et2O for 2 h, and subsequently 2 N NaOH aq, affording the corresponding free amine (S)-17b. Then, treatment of the amine with CbzCl and pyridine in CH2Cl2 gave the corresponding
  • good yield and a high asymmetric transfer was achieved. As a result, it was found that various optically active amine derivatives could be obtained with high optical purity. Various applications of tetrafluoroethylenated molecules. Precedent synthetic approaches to optically active compounds possessing
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Published 01 Nov 2024

Copper-catalyzed yne-allylic substitutions: concept and recent developments

  • Shuang Yang and
  • Xinqiang Fang

Beilstein J. Org. Chem. 2024, 20, 2739–2775, doi:10.3762/bjoc.20.232

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  • :1 (Scheme 3, 3e). Carbonates with aryl or styryl residue can undergo the reaction smoothly (Scheme 3, 3f–k), but alkyl-substituted substrates showed low yields (Scheme 3, 3l and 3m). Moreover, secondary amines with various substituents, acyclic amines, primary amines, or even the amine moieties in
  • et al. [63][64] reported the first amine-mediated highly enantioselective copper-catalyzed asymmetric yne-allylic substitution, affording 1,4-enynes with up to 98% ee and >20:1 rr. A series of secondary amines can react smoothly and achieve good enantioselectivities and regioselectivities (Scheme 7
  • ). Further control experiments and DFT calculations show that during the catalytic process, tertiary amine directly participates as a nucleophilic reagent to give the ammonium salt, which then releases dimethylaminium to provide the final product (Scheme 12). Chiral allylic sulfone compounds can be easily
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Published 31 Oct 2024

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light

  • Francesco Gambuti,
  • Jacopo Pizzorno,
  • Chiara Lambruschini,
  • Renata Riva and
  • Lisa Moni

Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230

Graphical Abstract
  • Scheme 6. Based on the results reported by Zeitler [28], several mechanisms are involved in the oxidation of N-Ph-THIQ. The most probable involves the photoexcitation of the EDA (Electron Donor-Acceptor) complex promoting an electron transfer from N-Ph-THIQ to BrCCl3 to afford the amine radical cation
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Published 29 Oct 2024

Synthesis of benzo[f]quinazoline-1,3(2H,4H)-diones

  • Ruben Manuel Figueira de Abreu,
  • Peter Ehlers and
  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228

Graphical Abstract
  • when located at position 5 of the uracil ring, which might be due to the protonation of the amine under the employed reaction conditions, making the aryl ring less feasible for the SEAr reaction (Scheme 4b). The same effects may explain the cyclisation of 4f to 5f, while 4c is not converted to the
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Published 28 Oct 2024

Computational design for enantioselective CO2 capture: asymmetric frustrated Lewis pairs in epoxide transformations

  • Maxime Ferrer,
  • Iñigo Iribarren,
  • Tim Renningholtz,
  • Ibon Alkorta and
  • Cristina Trujillo

Beilstein J. Org. Chem. 2024, 20, 2668–2681, doi:10.3762/bjoc.20.224

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  • regioselectivity of the CO2 insertion into PO must be addressed as part of the full mechanistic investigation. The compound 3-boryl-2-propen-1-amine is now considered as the catalyst (Figure 2B). As observed in Figure 2A, the bond length and electron density at the bond critical point (BCP) difference are minimal
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Published 22 Oct 2024

Synthesis and cytotoxicity studies of novel N-arylbenzo[h]quinazolin-2-amines

  • Battini Veeraiah,
  • Kishore Ramineni,
  • Dabbugoddu Brahmaiah,
  • Nangunoori Sampath Kumar,
  • Hélène Solhi,
  • Rémy Le Guevel,
  • Chada Raji Reddy,
  • Frédéric Justaud and
  • René Grée

Beilstein J. Org. Chem. 2024, 20, 2592–2598, doi:10.3762/bjoc.20.218

Graphical Abstract
  • ]quinazolin-2-amine (3): To a stirred solution of guanidinium carbonate (2.0 g, 0.011 mol) in DMA (15 mL) was added compound 2 (1.5 g, 0.008 mol). Then the reaction mixture was heated to stir at 150 °C for 16 h. After completion of the reaction (TLC), the mixture was poured into ice water, a solid was formed
  • ; HRESIMS (m/z): [M + H]+ calcd for C12H10N3,196.0869; found, 196.0872 (1 ppm); mp: 193–195 °C (lit. 194–196 °C [12]). Step 3: Representative procedure for the preparation of compounds 4: To the stirred solution of benzo[h]quinazolin-2-amine (3a, 0.256 mmol, 1.0 equiv) in 1,4-dioxane (4 mL) was added
  • ). Compound 4a: N-phenylbenzo[h]quinazolin-2-amine: 69% yield (off white solid). 1H NMR (400 MHz, DMSO-d6, δ ppm) 10.01 (br s, 1H, NH), 9.29 (s, 1H), 9.03 (dd, J = 7.2, 0.8 Hz, 1H), 8.07–8.01 (m, 3H), 7.84–7.72 (m, 3H), 7.43 (d, J = 2.0 Hz, 1H), 7.41 (t, J = 7.6 Hz, 1H), 7.05 (t, J = 6.8 Hz, 1H); 13C NMR (75
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Published 14 Oct 2024

Base-promoted cascade recyclization of allomaltol derivatives containing an amide fragment into substituted 3-(1-hydroxyethylidene)tetronic acids

  • Andrey N. Komogortsev,
  • Constantine V. Milyutin and
  • Boris V. Lichitsky

Beilstein J. Org. Chem. 2024, 20, 2585–2591, doi:10.3762/bjoc.20.217

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  • refluxing EtOH allowed us to obtain substituted enehydrazine 7 (Scheme 5a). The similar condensation with amine 8 led to enamine derivative 9 (Scheme 5b). Based on the data of X-ray analysis compound 7 has the same configuration of double and hydrogen bonds as in the case of starting tetronic acids 4
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Published 14 Oct 2024

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Graphical Abstract
  • the DDQH• radical to generate a carbocation and DDQH−. In path B, the reaction involves direct hydride transfer to DDQ, forming DDQH− and a carbocation. In both pathways, the amine nucleophile captures the carbocation, resulting in the final amination product after losing a proton. Subsequently, DDQH
  • mediator between the anode and the nickel-chelated enolate intermediate. Simultaneously, the amine substrate is oxidized at the anode and deprotonated to generate a nitrogen-centered radical. The desired product then is generated by the stereoselective cross-coupling of the carbon-centered radical with the
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Published 09 Oct 2024

Asymmetric organocatalytic synthesis of chiral homoallylic amines

  • Nikolay S. Kondratyev and
  • Andrei V. Malkov

Beilstein J. Org. Chem. 2024, 20, 2349–2377, doi:10.3762/bjoc.20.201

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  • as a key methodology in the synthesis of alkaloids and natural products with 4-, 5- and 6-membered cyclic amine motifs. Initially reliant on stoichiometric reagents, synthetic chemists predominantly used N-substituted chiral imines, organometallic chiral reagents and achiral reagents with an
  • directly prepared by combining three readily accessible synthons: an amine, an allyl nucleophile, and a carbonyl compound (Scheme 1) [15][16]. A selection of structural motifs accessible via homoallylic amines is shown in Scheme 1. Despite several reviews on homoallylic amine syntheses being published [17
  • (Scheme 6). The study explored a broad range of p-methoxyphenyl (PMP)imines derived from aryl, heteroaryl and alkyl aldehydes (including ethyl glyoxylate), demonstrating yields of 57–98% and high enantioselectivity of 90–98%. Screening of aldehyde and amine components indicated that the method is
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Published 16 Sep 2024

Improved deconvolution of natural products’ protein targets using diagnostic ions from chemical proteomics linkers

  • Andreas Wiest and
  • Pavel Kielkowski

Beilstein J. Org. Chem. 2024, 20, 2323–2341, doi:10.3762/bjoc.20.199

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  • . The fragmentation of the triazole ring leaving the primary amine and b-ion resulting from the fragmentation of the TEV-recognition peptide sequence. The chemical cleavage of the linker to release probe–peptide conjugates is achieved mainly by the change of the pH or via reducing conditions to release
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Published 12 Sep 2024

Stereoselective mechanochemical synthesis of thiomalonate Michael adducts via iminium catalysis by chiral primary amines

  • Michał Błauciak,
  • Dominika Andrzejczyk,
  • Błażej Dziuk and
  • Rafał Kowalczyk

Beilstein J. Org. Chem. 2024, 20, 2313–2322, doi:10.3762/bjoc.20.198

Graphical Abstract
  • studies by Bolm [12][13], and Juaristi et al. [14]. have significantly advanced chiral secondary amine-catalyzed stereoselective reactions under ball milling conditions, representing a widely explored activation mode in mechanochemical-mediated transformations. However, reports on chiral primary iminium
  • [15][16] or iminium-ion catalysis [17] under ball-mill conditions are scarce, in contrast to the abundance of transformations catalyzed by such covalent catalysis. Among the numerous organocatalytic reactions facilitated by primary amine-based iminium ions, Michael-type additions deserve special
  • by extended reaction times, sometimes up to 168 hours. An intriguing example involves the use of a bifunctional primary amine-sulfonamide catalyst, which activates benzylideneacetone towards dibenzyl malonate, with the presence of water accelerating the reaction [25]. An alternative approach, where
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Published 12 Sep 2024

Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis

  • Stefan P. Schmid,
  • Leon Schlosser,
  • Frank Glorius and
  • Kjell Jorner

Beilstein J. Org. Chem. 2024, 20, 2280–2304, doi:10.3762/bjoc.20.196

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  • including pyrimidines and pyrazines. The importance of mechanistic understanding for model building was underlined by Kuang et al. [126], where the authors considered multi-catalyst enantioselective reactions, where one catalyst was an organocatalyst, either CPA or an amine. The co-catalyst was included in
  • expands the considerable reaction space in organocatalysis. The discussed principle of mechanistic transferability has also been employed outside of CPA catalysis, with a focus on amine-based hydrogen-bond donors, for example imidodiphosphorimidate-type catalysts for the construction of THF and THP rings
  • for this reaction class (ee threshold 80%), even though amine-based catalysts demonstrate a higher average ee. Notably, this strategy is not restricted to literature-extracted examples and can also be applied to enantioselectivities calculated via quantum chemical calculations or predictions from an
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Published 10 Sep 2024

Deuterated reagents in multicomponent reactions to afford deuterium-labeled products

  • Kevin Schofield,
  • Shayna Maddern,
  • Yueteng Zhang,
  • Grace E. Mastin,
  • Rachel Knight,
  • Wei Wang,
  • James Galligan and
  • Christopher Hulme

Beilstein J. Org. Chem. 2024, 20, 2270–2279, doi:10.3762/bjoc.20.195

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  • method to prepare [D1]-formamides (D–C=O) is through a Leuckart–Wallach reaction with an amine and [D1]-methyl/ethyl formate or [D1]-dimethylformamide [19][20]. Stockmann and co-workers produced [D2]-formamides (N–D, D–C=O) via acid-catalyzed nitrile hydrolysis with HCl and D2O [21]. Thus, using the
  • scope of reactivity and determination of deuterium retention using a combination of deuterated aldehydes, [D1]-, and/or [D2]-isocyanides. We began with the venerable Ugi 4-component reaction (Ugi-4CR), first reported by Ivar Ugi in 1959 [28]. The Ugi-4CR utilizes an amine, carbonyl, carboxylic acid, and
  • is comprised of reaction of an isonitrile, amine, and aldehyde/ketone, in the presence of phenylphosphinic acid (PPA), to give α-amino amides [35]. Examples of deuterated Ugi-3CR products are represented in Scheme 4. Like the Ugi 4-CR reaction, there was no deuterium scrambling in the Ugi 3-CR. Using
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Published 06 Sep 2024

Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation

  • Andrey R. Galeev,
  • Maksim V. Dmitriev,
  • Alexander S. Novikov and
  • Andrey N. Maslivets

Beilstein J. Org. Chem. 2024, 20, 2208–2216, doi:10.3762/bjoc.20.188

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  • was released [57] allowing direct comparison of different substituents. On the basis of the calculated Hammett constants, we have selected a model series of 1,3-diketones, bearing heterocyclic substituents with a range of electron-withdrawing ability (Figure 2). For the amine model series, we used
  • amines with different nucleophilicity, namely benzylamine (primary alkylamine), morpholine (secondary alkylamine) and aniline (aromatic amine). We first examined the reaction of 1,2,4-oxadiazole-1,3-diketone 1a (σm/σp 0.463/0.575, which is quite close to the constants of the CO2Me group, so a successful
  • reaction in the presence of molecular sieves and 1.5-fold excess of aniline (conditions B) dramatically reduced the reaction time to 1 d, allowing isolation of diarylamine 3ac in 75% yield (Scheme 2). Next, we started to screen various heterocyclic 1,3-diketones with the model amine series. The reaction of
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Published 02 Sep 2024

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

  • Zsuzsanna Fehér,
  • Dóra Richter,
  • Gyula Dargó and
  • József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

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  • spaces. The confinement of the heterogeneous version of cinchona amine and thiourea catalysts was reported, leading to improved enantioselectivity values in the Michael addition of nitromethane (5) to chalcone (6) through modification of the pore size of mesoporous silica 8 or 9 (Scheme 2) [63]. Thus
  • by azodicarboxylates in a homogeneous phase, as noted by Takemoto [126], it was suggested that this interaction would be significantly impeded by the polymer backbone. Alternatively, it was proposed that this degradation could be due to protonation of the basic tertiary amine unit. It was found that
  • influence of various linkers of cinchona squaramide organocatalysts immobilised on a poly(glycidyl methacrylate) (PGMA) solid support [127]. The support consisted of well-defined monodispersed PGMA microspheres, which were prepared through thorough parameter optimisation. Three amine-functionalised cinchona
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Published 26 Aug 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

Graphical Abstract
  • fluoropyrazoles from fluorinated 1,3-dielectrophiles represents a crucial synthetic pathway. For example, 1,1,2,2-tetrafluoro-N,N-dimethylethan-1-amine (TFEDMA) (82) can be activated using BF3·OEt2 to generate an iminium salt 84 with increased electrophilicity. Subsequently, this intermediate reacts with various
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Published 16 Aug 2024

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

  • Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

Graphical Abstract
  • iodonium through a two-electron process. Subsequent reaction with the hydrazone and deprotonation formed the N-iodo hydrazone intermediate 80, triggering the reaction with the amine 78 through cationic species 81. Final cyclization delivered the desired pyrazole 79 (Scheme 15) [60]. The group of D. Tang
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Published 14 Aug 2024

1,2-Difluoroethylene (HFO-1132): synthesis and chemistry

  • Liubov V. Sokolenko,
  • Taras M. Sokolenko and
  • Yurii L. Yagupolskii

Beilstein J. Org. Chem. 2024, 20, 1955–1966, doi:10.3762/bjoc.20.171

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  • (trifluoromethyl)amine easily reacted with (Z)-1,2-difluoroethylene to form the addition product in high yield (Scheme 11) [89]. However, the stereochemistry of this reaction has not been reported. A similar reaction of (Z)-1,2-difluoroethylene with N-chloroimidobis(sulfonyl fluoride) (Scheme 12) [90] was shown to
  • -Difluoroethylene synthesis from perfluoropropyl vinyl ether. Deuteration reaction of 1,2-difluoroethylene. Halogen addition to 1,2-difluoroethylene. Hypohalite addition to 1,2-difluoroethylene. N-Bromobis(trifluoromethyl)amine addition to 1,2-difluoroethylene. N-Chloroimidobis(sulfonyl fluoride) addition to 1,2
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Published 12 Aug 2024

Negishi-coupling-enabled synthesis of α-heteroaryl-α-amino acid building blocks for DNA-encoded chemical library applications

  • Matteo Gasparetto,
  • Balázs Fődi and
  • Gellért Sipos

Beilstein J. Org. Chem. 2024, 20, 1922–1932, doi:10.3762/bjoc.20.168

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  • and the temperature, all oxime derivatives underwent reduction to yield the corresponding amine. The amino esters were effectively safeguarded against degradation through the immediate formation of the HCl salt or by Boc-protection. This procedure allowed us to obtain all the protected amino acids in
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Published 08 Aug 2024

Novel oxidative routes to N-arylpyridoindazolium salts

  • Oleg A. Levitskiy,
  • Yuri K. Grishin and
  • Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2024, 20, 1906–1913, doi:10.3762/bjoc.20.166

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  • direction of the potential sweep is changed after passing the first reduction peak of salt S2, the new peak appears at the potential of 0.89 V that completely coincides with the first oxidation peak of the amine precursor. The CV curve for the diarylamine, in its turn, exhibited (in the reverse scan after
  • oxidation of the amine) a new reduction peak that coincides to the first reduction peak of the pyridoindazolium salt (one more peak at less negative potential in the reverse scan after amine oxidation corresponds to the reduction of the protonated pyridyl moiety of the diarylamine). Thus, the voltammetry
  • amine oxidation is increased. Electrochemical synthesis of pyridoindazolium salts The results of the voltammetry testing allowed to assume that pyridoindazolium salts can also be obtained using an anodic synthesis. Electric current as a reagent is inherently safe and easily scalable; electrosynthesis is
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Published 07 Aug 2024
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