Search results

Search for "arylamines" in Full Text gives 71 result(s) in Beilstein Journal of Organic Chemistry.

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

  • Lucas Guillemard and
  • Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

Graphical Abstract
PDF
Album
Review
Published 21 Jul 2020

Pd-catalyzed asymmetric Suzuki–Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position

  • Yongsu Li,
  • Bendu Pan,
  • Xuefeng He,
  • Wang Xia,
  • Yaqi Zhang,
  • Hao Liang,
  • Chitreddy V. Subba Reddy,
  • Rihui Cao and
  • Liqin Qiu

Beilstein J. Org. Chem. 2020, 16, 966–973, doi:10.3762/bjoc.16.85

Graphical Abstract
  • benzoic acid (monitored by TLC), the corresponding arylamines (1.5 equiv) were added, followed by the addition of triethylamine (2.0 equiv) in DCM (10 mL). After that the resulting reaction mixture was stirred for 20 h at room temperature and checked by TLC for reaction completion. The reaction mixture
  • rotary evaporator. Then, the corresponding arylamines (1.2 equiv) were added to the acyl chlorides, triethylamine (1.5 equiv) and DMAP (5 mol %) in DCM (20 mL). The resulting reaction mixture was stirred for 20 h at room temperature. The completion of the reaction was monitored by TLC. After completion
PDF
Album
Supp Info
Full Research Paper
Published 11 May 2020

The use of isoxazoline and isoxazole scaffolding in the design of novel thiourea and amide liquid-crystalline compounds

  • Itamar L. Gonçalves,
  • Rafaela R. da Rosa,
  • Vera L. Eifler-Lima and
  • Aloir A. Merlo

Beilstein J. Org. Chem. 2020, 16, 175–184, doi:10.3762/bjoc.16.20

Graphical Abstract
  • were synthetized and the liquid crystal properties studied. Thioureas were obtained using a condensation reaction of benzoyl chlorides, arylamines and ammonium thiocyanate. The amides, on the other hand, were the byproduct of a quantitative reaction which used potassium cyanate as the starting material
PDF
Album
Supp Info
Full Research Paper
Published 06 Feb 2020

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

  • Xiaowei Li,
  • Xiaolin Shi,
  • Xiangqian Li and
  • Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

Graphical Abstract
PDF
Album
Review
Published 23 Sep 2019

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

  • Gagandeep Kour Reen,
  • Ashok Kumar and
  • Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

Graphical Abstract
PDF
Album
Review
Published 19 Jul 2019

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

  • Edorta Martínez de Marigorta,
  • Jesús M. de Los Santos,
  • Ana M. Ochoa de Retana,
  • Javier Vicario and
  • Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

Graphical Abstract
  • also been performed by using scandium catalyst (Sc(OTf)3, 2.5 mol %) and starting from ester 29. Under these conditions, not only benzyl or alkyl, but also a wide range or ortho-, meta- and para-arylamines 2 can be used at room temperature to make 3-oxoisoindolinone-1-carbonitriles 53a in very good
PDF
Album
Review
Published 08 May 2019

Azologization of serotonin 5-HT3 receptor antagonists

  • Karin Rustler,
  • Galyna Maleeva,
  • Piotr Bregestovski and
  • Burkhard König

Beilstein J. Org. Chem. 2019, 15, 780–788, doi:10.3762/bjoc.15.74

Graphical Abstract
  • photochromic derivatives with varying electronic and thus photochromic properties. The respective arylamines 13a–c were converted into their corresponding hydrazines 14a–c via diazonium-salt formation using sodium nitrite and subsequent reduction using tin(II) chloride [70]. The following nucleophilic
PDF
Album
Supp Info
Full Research Paper
Published 25 Mar 2019

An efficient and concise access to 2-amino-4H-benzothiopyran-4-one derivatives

  • Peng Li,
  • Yongqi Wu,
  • Tingting Zhang,
  • Chen Ma,
  • Ziyun Lin,
  • Gang Li and
  • Haihong Huang

Beilstein J. Org. Chem. 2019, 15, 703–709, doi:10.3762/bjoc.15.65

Graphical Abstract
  • group to afford the desired 2-amino-4H-benzothiopyran-4-ones through conjugated addition–elimination by nucleophiles. Subsequently, substrates 2a and 3a were reacted with a variety of alkyl/arylamines in the optimized solvent isopropanol (Table 2). Substrate 2a having an ethylsulfinyl group in general
  • amines such as arylamines successfully afforded the targeted compounds 4r,s albeit in only about 50% yield. The results indicated that the nucleophilicity of the amine exerts a more pronounced effect on the reactivity (i.e., aliphatic amines vs aromatic amines) under the above optimal conditions
PDF
Album
Supp Info
Full Research Paper
Published 18 Mar 2019

The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX

  • Md Toufique Alam,
  • Saikat Maiti and
  • Prasenjit Mal

Beilstein J. Org. Chem. 2018, 14, 2396–2403, doi:10.3762/bjoc.14.216

Graphical Abstract
  • using several arylamines and hypervalent iodine(V) reagents by direct mixing is unrealistic because of the high exothermic reaction or explosion. Herein we demonstrate, when anilines were substituted with an amide group at the ortho-position, successful chemical reactions could be performed due to
  • ]. During the reaction with the stronger oxidant PIDA, the basicity of the amine was regulated using an externally added acid salt, NaHSO4 (Figure 2a). In Figure 2b, a comparison in the reactivities of arylamines in the presence of non-iodine-based oxidant oxone [32] and IBX (iodine-based oxidant) is shown
  • IBA (6). Arylamines caused explosion and benzamide was found to be unreactive with IBX. However, the reaction was found to be successful with 2-aminobenzamide under similar conditions (Figure 1). 2-Aminobenzamide having one highly reactive amine part and another unreactive part, can be considered an
PDF
Album
Supp Info
Full Research Paper
Published 12 Sep 2018

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

  • Michael K. Bogdos,
  • Emmanuel Pinard and
  • John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

Graphical Abstract
  • electron-poor heterocycles under the current conditions. However, the aniline coupling partner opens up a huge variety of opportunities, as arylamines and heteroarylamines are widely available. Scaffolds such as 7b have lots of potential for further elaboration. In addition, the presence of electron-poor
PDF
Album
Review
Published 03 Aug 2018

Functionalization of graphene: does the organic chemistry matter?

  • Artur Kasprzak,
  • Agnieszka Zuchowska and
  • Magdalena Poplawska

Beilstein J. Org. Chem. 2018, 14, 2018–2026, doi:10.3762/bjoc.14.177

Graphical Abstract
  • desirable due to the commercial accessibility of the reactants (aromatic amines). The diazotization reaction is also a versatile approach, as a wide range of arylamines (bearing various substituents) can be subjected to the process [9]. This reaction’s mechanism is not fully understood, but several
PDF
Album
Review
Published 02 Aug 2018

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

  • Fateh V. Singh,
  • Priyanka B. Kole,
  • Saeesh R. Mangaonkar and
  • Samata E. Shetgaonkar

Beilstein J. Org. Chem. 2018, 14, 1778–1805, doi:10.3762/bjoc.14.152

Graphical Abstract
  • co-workers [95] investigated an efficient approach for the synthesis of a spirocyclic-skeleton-containing dieniminium moiety. Herein, arylamines 67 were cyclized to spirocyclic dieniminium salts 68 using PIFA (31) as an electrophilic species in nitromethane (Scheme 23). All the reactions were
  • oxidative cyclization of anilide 60 to bis-spirobisoxindole 61. PIDA-mediated spirocyclization of phenylacetamides 65 to spirocyclic lactams 66. Oxidative dearomatization of arylamines 67 with PIFA (31) to give dieniminium salts 68. PIFA-mediated oxidative spirocarbocyclization of 4-methoxybenzamide 69 with
PDF
Album
Review
Published 17 Jul 2018

An amine protecting group deprotectable under nearly neutral oxidative conditions

  • Shahien Shahsavari,
  • Chase McNamara,
  • Mark Sylvester,
  • Emily Bromley,
  • Savannah Joslin,
  • Bao-Yuan Lu and
  • Shiyue Fang

Beilstein J. Org. Chem. 2018, 14, 1750–1757, doi:10.3762/bjoc.14.149

Graphical Abstract
  • 10.3762/bjoc.14.149 Abstract The 1,3-dithiane-based dM-Dmoc group was studied for the protection of amino groups. Protection was achieved under mild conditions for aliphatic amines, and under highly reactive conditions for the less reactive arylamines. Moderate to excellent yields were obtained
  • with 4 and heating excess amine with 4 without any solvent but failed to identify one that could afford useful yields. We also tried to use the optimized conditions for the protection of aliphatic primary amines to protect arylamines, but found that arylamines were not reactive enough for the reaction
  • . Therefore, for protecting arylamines, we used conditions for the formation of hindered O-tert-alkyl N-arylcarbamates we reported earlier [20]. Treating one equivalent 3e with two equivalents LDA and one equivalent 4 in THF gave the desired arylamine dM-Dmoc carbamate 5e in synthetically useful yield (Table
PDF
Album
Supp Info
Full Research Paper
Published 13 Jul 2018

Diels–Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts

  • Huangguan Chen,
  • Jianwei Han and
  • Limin Wang

Beilstein J. Org. Chem. 2018, 14, 354–363, doi:10.3762/bjoc.14.23

Graphical Abstract
  • products under thermal conditions to afford arylamines [22]. Inspired by the pioneering work of Stuart and Wang [12][13], herein we reported the usage of diaryliodonium salts as aryne precursor for Diels–Alder cycloadditions of N-arylpyrroles (Scheme 1d). Results and Discussion We initially started the
PDF
Album
Supp Info
Letter
Published 06 Feb 2018

Progress in copper-catalyzed trifluoromethylation

  • Guan-bao Li,
  • Chao Zhang,
  • Chun Song and
  • Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

Graphical Abstract
  • was conducted under mild conditions using Umemoto’s reagent as the trifluoromethylation agent in the presence of isoamyl nitrite (iAmONO). The reaction proceeded smoothly with various arylamines under these conditions to give the corresponding products in modest to good yields. The reaction exhibits
PDF
Album
Review
Published 17 Jan 2018

From dipivaloylketene to tetraoxaadamantanes

  • Gert Kollenz and
  • Curt Wentrup

Beilstein J. Org. Chem. 2018, 14, 1–10, doi:10.3762/bjoc.14.1

Graphical Abstract
  • ]nonadienes (bisdioxines) 4. When arylamines are used as the nucleophiles under neutral conditions, decarboxylation occurs during the formation of bisdioxines 8. However, when water or alcohols are added to 3 under acidic conditions, bisdioxine-carboxylic acids and esters 10 and 11 are obtained. Acid
  • Scheme 4. The amides 8, formed by the addition of arylamines are invariably decarboxylated. We interpret this in terms of the sequence 3 → 14 → 15 → 16, which in the absence of an acid decarboxylates. In contrast, the addition of water and alcohols to 3 requires the addition of acid (p-TsOH) and results
  • need for acid catalysis. As in the case of the addition of arylamines, monodecarboxylation takes place, and in the presence of a strong acid, they are converted to the tetraoxaadamantanes 28 and 29 (65–93%) [35]. Several bisdioxine derivatives of aromatic di- and triamines as well as crown-ether
PDF
Album
Review
Published 02 Jan 2018

Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis

  • Raju Cheerlavancha,
  • Ahmed Ahmed,
  • Yun Cheuk Leung,
  • Aggie Lawer,
  • Qing-Quan Liu,
  • Marina Cagnes,
  • Hee-Chan Jang,
  • Xiang-Guo Hu and
  • Luke Hunter

Beilstein J. Org. Chem. 2017, 13, 2316–2325, doi:10.3762/bjoc.13.228

Graphical Abstract
  • reductions to arylamines were successful, an alternative approach was investigated in which the nitroarene group would be converted into the corresponding acetanilide 43. If this approach were successful, it was envisaged that the acetanilide 43 could be directly oxidised to carboxylic acid 44, thereby
PDF
Album
Supp Info
Full Research Paper
Published 01 Nov 2017

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

  • Nikolay V. Lukashev,
  • Gennadii A. Grabovyi,
  • Dmitry A. Erzunov,
  • Alexey V. Kazantsev,
  • Gennadij V. Latyshev,
  • Alexei D. Averin and
  • Irina P. Beletskaya.

Beilstein J. Org. Chem. 2017, 13, 564–570, doi:10.3762/bjoc.13.55

Graphical Abstract
  • ). Consequently, this system was used for the synthesis of bis-steroidal arylamines 5a and 5b starting from 24-aminocholanol 3a. Activated chlorinated substrates, such as 1,8- and 1,5-dichloroanthraquinones, are very promising substrates for nucleophilic substitution. For instance, 1,8-dichloro-9,10-anthraquinone
PDF
Album
Supp Info
Full Research Paper
Published 20 Mar 2017

Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides

  • Yi Lai,
  • Zhijian Zong,
  • Yujie Tang,
  • Weimin Mo,
  • Nan Sun,
  • Baoxiang Hu,
  • Zhenlu Shen,
  • Liqun Jin,
  • Wen-hua Sun and
  • Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 213–221, doi:10.3762/bjoc.13.24

Graphical Abstract
  • quantitative yield. With compounds 1, 2, 3 and 4 in hand, further condensations with different arylamines and direct coordination to PdCl2 in one pot smoothly in the presence of TsOH. For this transformation, we found that vigorous stirring during the reaction was very important, which increased the yields
PDF
Album
Supp Info
Full Research Paper
Published 03 Feb 2017

Microwave-assisted cyclizations promoted by polyphosphoric acid esters: a general method for 1-aryl-2-iminoazacycloalkanes

  • Jimena E. Díaz,
  • María C. Mollo and
  • Liliana R. Orelli

Beilstein J. Org. Chem. 2016, 12, 2026–2031, doi:10.3762/bjoc.12.190

Graphical Abstract
  • sensitive substrates. Results and Discussion The ω-arylaminonitrile precursors were obtained by reaction of the corresponding ω-halonitrile and arylamines, as previously reported by our group [44]. We examined first the cyclization of 4-(p-tolylamino)butyronitrile (1a) with PPE under microwave irradiation
PDF
Album
Supp Info
Full Research Paper
Published 14 Sep 2016

Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

  • Lucie Brulíková,
  • Aidan Harrison,
  • Marvin J. Miller and
  • Jan Hlaváč

Beilstein J. Org. Chem. 2016, 12, 1949–1980, doi:10.3762/bjoc.12.184

Graphical Abstract
  • Scheme 5). More recently, the method was extended to the mild copper-catalyzed aerobic oxidation of hydroxylamines [48][49][50]. In 2014, the Lykakis group reported the selective oxidation of various arylamines into the corresponding nitrosoarenes through polyoxometalate anions supported on mesoporous
PDF
Album
Review
Published 01 Sep 2016

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

  • Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

Graphical Abstract
  • arylamines were found to be effective in this reaction. Eventually, the biological evaluation of the (2H-isoindol-1-yl)phosphonates 74 revealed their potential as HCT-116 inhibitors. 2.2.4 Pyrazolyl- and oxazolylphosphonates: A series of modified Kabachnik–Fields condensations based on the reaction of 6
PDF
Album
Review
Published 21 Jun 2016

Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C–H and sp3 C–H bonds

  • Nivesh Kumar,
  • Santanu Ghosh,
  • Subhajit Bhunia and
  • Alakesh Bisai

Beilstein J. Org. Chem. 2016, 12, 1153–1169, doi:10.3762/bjoc.12.111

Graphical Abstract
  • reaction of N-methyl arylamines and monoalkyl malonates/cyanoacetic acids. Under optimized conditions A and B, various β-N-arylamido esters and nitriles (3) were subjected to a one-pot alkylations using 1.2 equivalents of KOt-Bu to produce C-alkylated intermediate 5 followed by oxidative coupling using 1.2
PDF
Album
Supp Info
Full Research Paper
Published 08 Jun 2016

Opportunities and challenges for direct C–H functionalization of piperazines

  • Zhishi Ye,
  • Kristen E. Gettys and
  • Mingji Dai

Beilstein J. Org. Chem. 2016, 12, 702–715, doi:10.3762/bjoc.12.70

Graphical Abstract
  • -throughput and automated workflow platform, they have discovered a photoredox-catalyzed C–H arylation of N-arylamines with 1,4-dicyanobenzene (88) to produce pharmaceutically important benzylic amines. This reaction works well with piperazine substrate 87 to synthesize the α-arylated piperazine 89 in 95
PDF
Album
Review
Published 13 Apr 2016

Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines with aryl iodides

  • Svetlana P. Panchenko,
  • Alexei D. Averin,
  • Maksim V. Anokhin,
  • Olga A. Maloshitskaya and
  • Irina P. Beletskaya

Beilstein J. Org. Chem. 2015, 11, 2297–2305, doi:10.3762/bjoc.11.250

Graphical Abstract
  • the literature. One of them employs an iridium-based catalyst with amidophosphonate as the ligand which allows to convert aminoalcohols into N-monoaryl-substituted diamines by the reaction with arylamines [20]. Another method uses a bimetallic catalyst (Pt–Sn/γ-Al2O3) in the reactions of diols with
PDF
Album
Supp Info
Full Research Paper
Published 24 Nov 2015
Other Beilstein-Institut Open Science Activities