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Search for "anilines" in Full Text gives 205 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

α-Ketol and α-iminol rearrangements in synthetic organic and biosynthetic reactions

  • Scott Benz and
  • Andrew S. Murkin

Beilstein J. Org. Chem. 2021, 17, 2570–2584, doi:10.3762/bjoc.17.172

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  • equivalent of aniline in the presence of a Brønsted acid undergoes a multistep rearrangement to form the indole group as part of the target tryptamine 110 (Figure 20). The one-pot conversions occurred successfully over a wide range of monosubstituted anilines, including various para-alkyl groups (65–72
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Published 15 Oct 2021

Copper-catalyzed monoselective C–H amination of ferrocenes with alkylamines

  • Zhen-Sheng Jia,
  • Qiang Yue,
  • Ya Li,
  • Xue-Tao Xu,
  • Kun Zhang and
  • Bing-Feng Shi

Beilstein J. Org. Chem. 2021, 17, 2488–2495, doi:10.3762/bjoc.17.165

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  • also reported the Co-catalyzed C–H alkoxylation of ferrocenes under nearly room temperature [38]. In comparison, despite the direct C–H amination of arenes with alkylamines has emerged as an efficient strategy to prepare substituted anilines [39][40][41][42][43][44][45][46][47][48][49], the application
  • %), largely due to the poison of copper catalyst by thioether. Acyclic amines were also tested and the amination products were obtained in low yields (4n, 18%; 4o, 15%). Unfortunately, primary amines and anilines were completely inert. Encouraged by the above results, we further tried to synthesize ferrocene
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Published 28 Sep 2021

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

  • Yi Liu,
  • Puying Luo,
  • Yang Fu,
  • Tianxin Hao,
  • Xuan Liu,
  • Qiuping Ding and
  • Yiyuan Peng

Beilstein J. Org. Chem. 2021, 17, 2462–2476, doi:10.3762/bjoc.17.163

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  • trifluoromethylated coumarins [59], we recently developed a Rh-catalyzed approach to trifluoromethyl-substituted pyrroles using the Togni reagent II as trifluoromethyl source. It involves a three-component cascade reaction of 1,3-enynes, anilines, and Togni reagent II to afford fully substituted pyrrole derivatives
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Published 22 Sep 2021

A visible-light-induced, metal-free bis-arylation of 2,5-dichlorobenzoquinone

  • Pieterjan Winant and
  • Wim Dehaen

Beilstein J. Org. Chem. 2021, 17, 2315–2320, doi:10.3762/bjoc.17.149

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  • conditions, different anilines were applied to explore the scope of the reaction (Scheme 1). The procedure is tolerant towards a range of different substituents. Both 4- and 3-substituted anilines readily functionalized the quinone (3a–n), and the halogens and other functional groups present are providing
  • , explaining the lowered yield. The reaction also required six equivalents and 72 h of reaction time to produce the product. ortho-Substituted anilines are interesting substrates as the product enables several possibilities for post-functionalization. Despite the inherent steric hindrance originating from the
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Published 06 Sep 2021

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

  • Renato L. Carvalho,
  • Amanda S. de Miranda,
  • Mateus P. Nunes,
  • Roberto S. Gomes,
  • Guilherme A. M. Jardim and
  • Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

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  • authors used a bulky titanium catalyst, by which a desirable regioselectivity could be achieved (Scheme 7B and C). The obtained N-substituted anilines resemble some important compounds already known for their biological activities, such as antimalarial (17) [69] and anticancer (18) [70][71] properties
  •  30C). A straightforward method for an α-amino C−H bond functionalization was described by Kang et al. in 2020 to promote the synthesis of tetrahydroquinolines from tertiary anilines (Scheme 31B and C) [163]. Tetrahydroquinolines are a class of compounds already known to present varied biological
  • anilines afforded α-aminoalkyl radicals that could be coupled with a wide range of electrophilic partners to afford the products in moderate to good yields. The new reaction was also used in the first step of the total synthesis of a caspase-3 inhibitor (90), and mechanistic investigations showed that O2
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Published 30 Jul 2021

Substituted nitrogen-bridged diazocines

  • Pascal Lentes,
  • Jeremy Rudtke,
  • Thomas Griebenow and
  • Rainer Herges

Beilstein J. Org. Chem. 2021, 17, 1503–1508, doi:10.3762/bjoc.17.107

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  • . In contrast to previous approaches, the azo cyclization (ring closure) was achieved via the oxidation of the bis-anilines 7 with mCPBA (≈60% yield). Among the nitrogen-bridged diazocines compounds 10a and 11c are water soluble and retained their high switching efficiency (≈70%) also in water. The
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Published 25 Jun 2021

Synthetic accesses to biguanide compounds

  • Oleksandr Grytsai,
  • Cyril Ronco and
  • Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

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  • heterocyclic biguanides found applications as new solid energetic materials [28]. ”Biguanide-like” molecules: Similar conditions were reported with ortho-substituted anilines. The addition of these compounds to cyanoguanidine usually results in a cyclization by subsequent ammonia or water condensation to form
  • N1,N5-substituted biguanides, that shows little variation in reactivity. By adapting these conditions, other reactants can be used such as nitrogen-containing heterocycles, other aminated nucleophiles, or ortho-substituted anilines, extending the scope of this reaction to a broader diversity of
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Published 05 May 2021

Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues

  • Rashmi Singh,
  • Tomas Horsten,
  • Rashmi Prakash,
  • Swapan Dey and
  • Wim Dehaen

Beilstein J. Org. Chem. 2021, 17, 977–982, doi:10.3762/bjoc.17.79

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  • -radical mechanism [29]. Similar reaction intermediates can be prepared using precursors such as organoboron reagents [30]. However, due to the accessibility, aryldiazonium salts are the reagents of choice. They can be prepared starting from the commercially available corresponding anilines. The present
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Published 30 Apr 2021

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

  • Zhonglie Yang,
  • Yutong Liu,
  • Kun Cao,
  • Xiaobin Zhang,
  • Hezhong Jiang and
  • Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

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  • electron-withdrawing groups, the scope of the reaction comprises anilines including electron-withdrawing or electron-donating substituents in the arene, except N-acetylated or ortho-halogenated anilines. In 2017, Chen and colleagues [21] reported a method that promoted the formation of an alkoxy radical
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Published 06 Apr 2021

Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction

  • Lukáš Marek,
  • Lukáš Kolman,
  • Jiří Váňa,
  • Jan Svoboda and
  • Jiří Hanusek

Beilstein J. Org. Chem. 2021, 17, 527–539, doi:10.3762/bjoc.17.47

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  • of the oxindole skeleton were also described starting from 2-alkynylphenyl isocyanates and their precursors [21][22][23], or from N-phenylpropiolamides [24][25][26]. The newest method of synthesis, starting from 3-bromo-3-[bromo(phenyl)methyl]oxindole and substituted anilines [27], is similar to a
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Published 23 Feb 2021

Novel library synthesis of 3,4-disubstituted pyridin-2(1H)-ones via cleavage of pyridine-2-oxy-7-azabenzotriazole ethers under ionic hydrogenation conditions at room temperature

  • Romain Pierre,
  • Anne Brethon,
  • Sylvain A. Jacques,
  • Aurélie Blond,
  • Sandrine Chambon,
  • Sandrine Talano,
  • Catherine Raffin,
  • Branislav Musicki,
  • Claire Bouix-Peter,
  • Loic Tomas,
  • Gilles Ouvry,
  • Rémy Morgentin,
  • Laurent F. Hennequin and
  • Craig S. Harris

Beilstein J. Org. Chem. 2021, 17, 156–165, doi:10.3762/bjoc.17.16

Graphical Abstract
  • compounds 24. In practice, the process was very efficient affording 60 final compounds with a median yield of 47%. Best results were obtained with electron-rich anilines (e.g., compounds 24a–d) and aliphatic amines (e.g., compounds 24k–l). For electron-deficient anilines (e.g., compounds 24e–g), the
  • reaction mixtures were heated to 65 °C to complete the amide coupling reaction. For the least reactive anilines (e.g., compounds 24h,i), HATU only afforded trace quantities of the amide even at 65 °C. However, satisfactory results were obtained by generating the acid chloride in situ by adding a 3 fold
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Published 18 Jan 2021

Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access N-(hetero)aryl-4,5-unsubstituted pyrroles

  • Wenbo Huang,
  • Kaimei Wang,
  • Ping Liu,
  • Minghao Li,
  • Shaoyong Ke and
  • Yanlong Gu

Beilstein J. Org. Chem. 2020, 16, 2920–2928, doi:10.3762/bjoc.16.241

Graphical Abstract
  • was reflected by the tolerance of a broad range of functional groups attached to the aromatic amine. For example, anilines bearing methyl (in 4f), phenyl (in 4g), and halo functionalities (in 4h–m) were readily compatible with the AlCl3 and 1,4-dioxane system. In these cases, the pyrrole products were
  • isolated in moderate to good yield. The presence of an electron-donating group in the phenyl ring facilitated the progress of the reaction to some extent, resulting in 4n. Anilines with electron-withdrawing groups, such as an acetyl or carboxy group, can also be used in the reaction, but the yields
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Published 30 Nov 2020

A novel and robust heterogeneous Cu catalyst using modified lignosulfonate as support for the synthesis of nitrogen-containing heterocycles

  • Bingbing Lai,
  • Meng Ye,
  • Ping Liu,
  • Minghao Li,
  • Rongxian Bai and
  • Yanlong Gu

Beilstein J. Org. Chem. 2020, 16, 2888–2902, doi:10.3762/bjoc.16.238

Graphical Abstract
  • investigation, the LS-FAS-Cu was also found to be an efficient catalyst for the synthesis of aminonaphthalene derivatives (Table 5). The substituent effect of aniline was examined systematically, and the results showed that anilines bearing electron-donating groups such as Me, OMe and t-Bu at the para-position
  • could convert smoothly and give the corresponding products in excellent yields (10a–c). The anilines with electron-withdrawing substituents such as 4-bromoaniline (9d) worked sluggishly and only a moderate yield of 10d was obtained. Disubstituted anilines also tolerated the catalytic system, generating
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Published 26 Nov 2020

Synthesis of purines and adenines containing the hexafluoroisopropyl group

  • Viacheslav Petrov,
  • Rebecca J. Dooley,
  • Alexander A. Marchione,
  • Elizabeth L. Diaz,
  • Brittany S. Clem and
  • William Marshall

Beilstein J. Org. Chem. 2020, 16, 2739–2748, doi:10.3762/bjoc.16.224

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  • report by Ishikawa and Kitazume that the reaction of anilines with tetrakis(trifluoromethyl)-1,3-dithietane (1) results in the formation of the corresponding imines of hexafluoroacetone [18]. Unfortunately, we were not able to confirm the structures by X-ray diffraction, and the structural assignment for
  • of the reaction of tetrakis(trifluoromethyl)-1,3-dithietane (1) with the azoles 2–7 is not entirely clear. Although there are two similar reactions reported in the literature (the reaction of 1 with anilines [18] and azoles [17]), no satisfactory mechanism was suggested for these reactions. Recently
  • into the final product, with extrusion of elemental sulfur) is not well understood and may be more complex, involving additional steps. The mechanism clarification of the reaction of tetrakis(trifluoromethyl)-1,3-dithietane (1) with azoles (and anilines) does require further investigation. As was
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Published 11 Nov 2020

Recent developments in enantioselective photocatalysis

  • Callum Prentice,
  • James Morrisson,
  • Andrew D. Smith and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

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Published 29 Sep 2020

The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization

  • Sharna-kay Daley and
  • Nadale Downer-Riley

Beilstein J. Org. Chem. 2020, 16, 2026–2031, doi:10.3762/bjoc.16.169

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  • Ullman coupling, Suzuki–Miyaura coupling and Stille coupling have dominated the field for the synthesis of biaryls [1][4]. Throughout the years, the exploration of oxidative dimerization reactions of electron-rich aromatic compounds, such as thiophenes, anilines and alkoxyarenes, in an attempt to
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Published 18 Aug 2020

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

  • Alessandra Del Tito,
  • Havall Othman Abdulla,
  • Davide Ravelli,
  • Stefano Protti and
  • Maurizio Fagnoni

Beilstein J. Org. Chem. 2020, 16, 1476–1488, doi:10.3762/bjoc.16.123

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  • the synthesis of 6-(trifluoromethyl)phenanthridines 10.3a–e. Synthesis of phenanthridines via aryl–aryl-bond formation. Oxidative conversion of N-biarylglycine esters to phenanthridine-6-carboxylates. Photocatalytic synthesis of benzo[f]quinolines from 2-heteroaryl-substituted anilines and
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Published 25 Jun 2020

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

  • Rodrigo Costa e Silva,
  • Luely Oliveira da Silva,
  • Aloisio de Andrade Bartolomeu,
  • Timothy John Brocksom and
  • Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

Graphical Abstract
  • % yields). Mixtures of regioisomers were obtained when a m-substituted N,N-dimethylaniline was used. The authors have proposed a reductive quenching pathway mechanism for this protocol (Scheme 8). The use of NiTPP as photoreductant was also exploited in the selenylation and thiolation reactions of anilines
  • the aryldiazonium salt leads to the other aryl radical species (path b, Scheme 9). The thio- and selenoethers were obtained after solvolysis. Excellent yields (up to 94%) were reported for both selenylation and thiolation of anilines with electron-withdrawing and electron-donating groups in the ortho
  • chemoselective manner. Regarding porphyrin-mediated reduction reactions, we have selected one representative example reported by Nagaraja and co-workers. They have shown a heterogeneous photocatalytic reduction of nitroaromatic compounds to the corresponding anilines using a Ni(II)-MOF, [Ni3(Ni-TCPP)2(µ2-H2O)2
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Published 06 May 2020

Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in RhII-catalyzed X–H insertion reactions

  • Maria Eremeyeva,
  • Daniil Zhukovsky,
  • Dmitry Dar’in and
  • Mikhail Krasavin

Beilstein J. Org. Chem. 2020, 16, 607–610, doi:10.3762/bjoc.16.55

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  • found to be unstable and to undergo unproductive dimerization to bishydrazones, were successfully converted immediately to various X–H insertion products with alcohols, aromatic amines and thiols via an in situ RhII-catalyzed reaction. With aliphatic amines or unreactive, sterically hindered anilines
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Published 02 Apr 2020

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

  • Pezhman Shiri and
  • Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

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  • solution of Cu(OAc)2, and the mixture was heated at reflux for 12 h. Finally, the material Cu@ImPy–SBA-15 (69) was collected, washed with ethanol, and dried. The catalyst was applied in the synthesis of triazole products via the reaction of in situ-prepared arylazides from anilines with aryl-/alkyl-alkynes
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Published 01 Apr 2020

Recent advances in photocatalyzed reactions using well-defined copper(I) complexes

  • Mingbing Zhong,
  • Xavier Pannecoucke,
  • Philippe Jubault and
  • Thomas Poisson

Beilstein J. Org. Chem. 2020, 16, 451–481, doi:10.3762/bjoc.16.42

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  • under air, N,N-dialkylated aniline derivatives were reacted with various N-substituted maleimides and benzylidenemalonitrile to provide polysubstituted tetrahydroquinolines in moderate to good yields. When N-aryltetrahydroisoquinoline was used instead of N,N-dialkylated anilines, octahydroisoquinolo[2,1
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Published 23 Mar 2020

Architecture and synthesis of P,N-heterocyclic phosphine ligands

  • Wisdom A. Munzeiwa,
  • Bernard Omondi and
  • Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

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  • phosphorus can be adjusted by changing the bulkiness of substituents around both, the N and P centers [99]. When reacting anilines and chlorophosphines under basic conditions they undergo P–N bond formation affording conventional aminophosphines [100][101]. A facile alternative method replaces the aniline
  • imines and the reaction rates were low for anilines and analogous compounds. However, using dichloromethane proved to be a more suitable solvent because of higher product solubility and the reactions could be followed using 31P NMR spectroscopy [98][102]. The addition of four molar equivalents of Ph2PCl
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Published 12 Mar 2020

Copper-promoted/copper-catalyzed trifluoromethylselenolation reactions

  • Clément Ghiazza and
  • Anis Tlili

Beilstein J. Org. Chem. 2020, 16, 305–316, doi:10.3762/bjoc.16.30

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  • heteroaromatic species. More recently, the same group reported the synthesis of 2-trifluoromethylselenylated benzofused heterocycles (Scheme 7) [24]. This tandem process consisted in a first Pd-catalyzed cyclization of 2-(2,2-dibromovinyl)phenols/-thiophenols/-anilines, leading to the corresponding 2-brominated
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Published 03 Mar 2020

Ultrasonic-assisted unusual four-component synthesis of 7-azolylamino-4,5,6,7-tetrahydroazolo[1,5-a]pyrimidines

  • Yana I. Sakhno,
  • Maryna V. Murlykina,
  • Oleksandr I. Zbruyev,
  • Anton V. Kozyryev,
  • Svetlana V. Shishkina,
  • Dmytro Sysoiev,
  • Vladimir I. Musatov,
  • Sergey M. Desenko and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2020, 16, 281–289, doi:10.3762/bjoc.16.27

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  • OH group in the tetrahydropyrimidine moiety (e.g., Scheme 2, VI and VIII), the formation of heterocycles that are amino-substituted in a similar position is also possible and has been described [31][32]. In particular, the reaction of methyl pyruvate and anilines led to the formation of 4-arylamino
  • -substituted tetrahydroquinolines (Scheme 3). To the best of our knowledge, an analogous reaction has not been described for aminoazoles. We were interested to study reactions similar to the ones shown in Scheme 3, involving aromatic aldehydes and pyruvic acid but using aminoazoles instead of anilines
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Published 27 Feb 2020

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

  • Rafia Siddiqui and
  • Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

Graphical Abstract
  • assembled using this strategy, as displayed in Scheme 15, and a plausible mechanism for the reaction is shown in Figure 16. C–H nitration of protected anilines Nitroanilines are an important class of compounds and found in many drugs and dyes [144]. Therefore, recently, König and co-worker reported the
  • synthesis of protected anilines by employing organic photoredox catalyst 4 with sodium nitrite as a cost-efficient source of NO2 at room temperature (Scheme 16) [145]. They also tried to perform the same reaction in the absence of light and photocatalyst, but no reaction progress was observed. As reported
  • purines via dual photoredox catalysis. Arylation of substituted arenes with an organic photoredox catalyst. C–H trifluoromethylation. Synthesis of benzo-3,4-coumarin derivatives. Oxidant-free oxidative phosphonylation. Nitration of anilines. Synthesis of carbazoles via intramolecular amination. Synthesis
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Published 26 Feb 2020
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