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Search for "amide group" in Full Text gives 92 result(s) in Beilstein Journal of Organic Chemistry.

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

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Published 27 Jun 2025

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

  • Betty A. Kustiana,
  • Galuh Widiyarti and
  • Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

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Published 28 May 2025

Recent total synthesis of natural products leveraging a strategy of enamide cyclization

  • Chun-Yu Mi,
  • Jia-Yuan Zhai and
  • Xiao-Ming Zhang

Beilstein J. Org. Chem. 2025, 21, 999–1009, doi:10.3762/bjoc.21.81

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  • enamides contain an N-acyl group in place of the original alkyl group. The electron-withdrawing effect of the amide group delocalizes the nitrogen lone pair, thereby reducing the electron density and nucleophilicity of the enamide double bond. These features significantly diminish the reactivity of
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Published 22 May 2025

Recent advances in controllable/divergent synthesis

  • Jilei Cao,
  • Leiyang Bai and
  • Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

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  • weakly coordinating OTf− anion synergistically enhanced the electrophilicity of the gold center, enabling coordination with the amide group to form a three-coordinate Au(I)–π-alkyne intermediate Int-12. The umbrella-shaped steric shielding provided by the ligand-stabilized intermediate Int-9, followed by
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Published 07 May 2025

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages

  • Keith G. Andrews

Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30

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  • can incorporate greater bond strain, and therefore the linkers themselves can contribute to cavity shape and symmetry outcomes. For instance, in our cages [38][39][40][41], due to the preference for N-phenylbenzamides to be planar, each amide group can be arranged in two metastable orientations: amide
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Perspective
Published 24 Feb 2025

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

  • Marios Zingiridis,
  • Danae Papachristodoulou,
  • Despoina Menegaki,
  • Konstantinos G. Froudas and
  • Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

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  • installed amino group and a disubstituted amide group at the 2- and 3-positions, respectively, and reacting them with formamide (Scheme 1B). Those synthetic hubs can be rapidly accessed by cyanoacetamide-based MCRs, which is an interesting reaction type that gives access to privileged cores and has been
  • moiety of the amide group resulted in pyrimidone annulation [41]. This was observed for the first time and completed the reported heteroannulation landscape utilizing the Niementowski reaction [25]. In general, the reactions had a rather broad scope as a great range of cyanoacetamides was compatible. The
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Published 24 Jan 2025

Recent advances in organocatalytic atroposelective reactions

  • Henrich Szabados and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

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  • reported. However, the reaction did not tolerate a variety of substitutions on the amide group, probably because of its involvement in hydrogen bonding with the organocatalyst (R)-C23. Expanding on earlier methodologies of Chen et al. [60][61] and Wang et al. [62] utilizing indole derivatives instead of β
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Published 09 Jan 2025

Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds

  • Yuki Nakanishi,
  • Shoichi Sugita,
  • Kentaro Okano and
  • Atsunori Mori

Beilstein J. Org. Chem. 2024, 20, 3256–3262, doi:10.3762/bjoc.20.269

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  • Abstract The C–H arylation of 2-quinolinecarboxyamide bearing a C–Br bond at the N-aryl moiety is carried out with a palladium catalyst. The reaction proceeds at the C–H bond on the pyridine ring adjacent to the amide group in the presence of 10 mol % Pd(OAc)2 at 110 °C to afford the cyclized product in 42
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Published 13 Dec 2024

Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams

  • Valentina Giraldi,
  • Giandomenico Magagnano,
  • Daria Giacomini,
  • Pier Giorgio Cozzi and
  • Andrea Gualandi

Beilstein J. Org. Chem. 2024, 20, 2461–2468, doi:10.3762/bjoc.20.210

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  • their investigation of the hydrofunctionalization reaction of unsaturated amides and thioamides [28]. They have found that the oxygen atom of the amide group, rather than the nitrogen atom, acted as a nucleophile, leading to the formation of 2-oxazolines and 2-thiazolines. Another recent example of
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Published 01 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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  • -substituted substrate 119 and the highest for bulky benzyl substrates. Several reactions showed 94% ee which appears to be an upper limit for this particular (S)-TRIP-catalysed reaction. Screening the amide group revealed, that N-morpholinyl (122), N-piperidinyl (123), N-pyrrolidinyl (124), and N,N-dimethyl
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Published 16 Sep 2024

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

  • Alexander V. Tsygankov,
  • Vladyslav O. Vereshchak,
  • Tetiana O. Savluk,
  • Serhiy M. Desenko,
  • Valeriia V. Ananieva,
  • Oleksandr V. Buravov,
  • Yana I. Sakhno,
  • Svitlana V. Shishkina and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

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  • -called convertible isocyanides [27][28][29][30][31][32][33][34][35][36] in Ugi-4CR makes it possible to obtain carboxylic acids or esters after hydrolysis of the secondary amide group in the Ugi products (Scheme 2) [27][28][29][31][32][34][35][36]. Ugi bisamides modified in this way may be subsequently
  • acid hydrolysis. Similar results were obtained by Dömling and co-workers [27], who used 2-nitrobenzyl isocyanide as a universal convertible isocyanide, and the amide group was also converted into a carboxylic acid under the conditions of acid hydrolysis (Scheme 2). Therefore, taking into account the
  • to drive the process towards the desired hydrolysis of the secondary amide group, we performed the post-Ugi transformation under MW activation in ethanol or acetonitrile (Scheme 3, conditions B or C). However, the application of MW irradiation did not change the course of the reaction, and as under
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Published 26 Jul 2024

Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor

  • Koichi Mitsudo,
  • Atsushi Osaki,
  • Haruka Inoue,
  • Eisuke Sato,
  • Naoki Shida,
  • Mahito Atobe and
  • Seiji Suga

Beilstein J. Org. Chem. 2024, 20, 1560–1571, doi:10.3762/bjoc.20.139

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  • applicable and 2,6-dimethylpiperidine (9g) was obtained in moderate yield. In contrast to quinolines, pyridines bearing an amide group were also applicable and amidylpiperidines 9h and 9i were obtained in high yields. Conclusion We established the electrochemical reduction of cyanoarenes, nitroarenes
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Published 11 Jul 2024

Using the phospha-Michael reaction for making phosphonium phenolate zwitterions

  • Matthias R. Steiner,
  • Max Schmallegger,
  • Larissa Donner,
  • Johann A. Hlina,
  • Christoph Marschner,
  • Judith Baumgartner and
  • Christian Slugovc

Beilstein J. Org. Chem. 2024, 20, 41–51, doi:10.3762/bjoc.20.6

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  • for the conversion of acrylamide, which is probably disturbed when the hydrogen bond donor solvent methanol is interacting with the amide group and/or the hydroxy group. Conclusion The conjugate addition of 2,4-di-tert-butyl-6-(diphenylphosphino)phenol to Michael acceptor molecules allows for a facile
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Published 10 Jan 2024

Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?

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

Beilstein J. Org. Chem. 2023, 19, 808–819, doi:10.3762/bjoc.19.61

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  • (Scheme 6). This means that the cleavage of the amide group that evolves aniline (pKa = 4.6) occurred smoothly after the initial thiazole ring closure (through 12a’ in Scheme 6). The addition of a thiophile (trimethyl phosphite) does not turn the reaction toward ECR and only decreases the yield of 13
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Published 09 Jun 2023

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

  • Artem N. Semakin,
  • Ivan S. Golovanov,
  • Yulia V. Nelyubina and
  • Alexey Yu. Sukhorukov

Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148

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  • -illustrated by Hirshfeld surfaces [41] (Figure 3e and f). The guest molecule (water or methanol) acts as an H-bond acceptor with two axial NH units (distances N···O 2.85–2.93 Å, NHO 166.4–178.0°) and as an H-bond donor for the oxygen atom of the equatorial amide group (distances O···O 2.69–2.78 Å, OHO 163.7
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Published 11 Oct 2022

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

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  • produced a bridged cyclic 2-oxabicyclo[2.2.1]hept-5-ene D. The further hydration of intermediate D gave intermediate E, which was in turn transferred to cyclopentenyl intermediate F by the ring opening of the bridge ring. In the cyclopentenyl intermediate F, the hydroxy group and the amide group clearly
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Published 08 Aug 2022

Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

  • Yasuhiro Igarashi,
  • Yiwei Ge,
  • Tao Zhou,
  • Amit Raj Sharma,
  • Enjuro Harunari,
  • Naoya Oku and
  • Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

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  • -hydroxyamide group (C16: δC 46.7; C27: δC 47.2) were obviously larger than the methylenes adjacent to the amide group (C20: δC 38.52; C31: δC 38.52), consistent with the reported data for avaroferrin [22], bisucaberins [18], and nocardamines [23]. However, this trend is inversed in the hydroxamic acid terminus
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Published 13 Jan 2022

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

  • Li Liu,
  • Yue Li,
  • Tiao Huang,
  • Dulin Kong and
  • Mingshu Wu

Beilstein J. Org. Chem. 2021, 17, 2321–2328, doi:10.3762/bjoc.17.150

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  • has a remarkable structural feature: the phosphate moiety is located at the benzylic position as well as at the position α to an amide group, which makes it a good leaving group for the design and development of new reactions. Accordingly, diethyl (2-oxoindolin-3-yl) phosphates 2 have been used
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Published 07 Sep 2021

(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

  • Luiz Claudio Ferreira Pimentel,
  • Lucas Villas Boas Hoelz,
  • Henayle Fernandes Canzian,
  • Frederico Silva Castelo Branco,
  • Andressa Paula de Oliveira,
  • Vinicius Rangel Campos,
  • Floriano Paes Silva Júnior,
  • Rafael Ferreira Dantas,
  • Jackson Antônio Lamounier Camargos Resende,
  • Anna Claudia Cunha,
  • Nubia Boechat and
  • Mônica Macedo Bastos

Beilstein J. Org. Chem. 2021, 17, 2260–2269, doi:10.3762/bjoc.17.144

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  • ) inherent to this type of treatment [25]. In this regard, Arioli and co-workers developed a series of derivatives (from PAPP) containing the 1,2,3-triazole nucleus in place of the amide group (present in the IMT structure) that showed inhibitory activity of recombinant Abl kinase equivalent to the drug of
  • reference [26]. In this context, the intent is to replace the amide group present in IMT by the 1,2,3-triazole nucleus, similar to compound 3 described in the literature by Li and co-workers, which showed a good inhibition profile of the myelogenous leukemia K562 cell line [27]. Considering the good
  • original work that led to compound 3, and, additionally, they are able to act as acceptors and donors in hydrogen bonds and thus were expected to increase the aqueous solubility of the compounds. Additionally, Kalesh and co-workers demonstrated good results with derivative 4 which contains the amide group
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Published 01 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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Published 30 Jul 2021

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

  • Cansu Esen and
  • Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

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  • primary amide C=O stretching vibration of the amide group. The strong signals at 1558 and 1404 cm−1 are originated from amine N–H bending and scissoring –CH2– vibrations, respectively. At last, the poly(ethylene glycol) methyl ether methacrylate (PEGMEMA)-based network displays O–H stretching from 3106 cm
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Published 21 May 2021

Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study

  • Csilla Hargitai,
  • Györgyi Koványi-Lax,
  • Tamás Nagy,
  • Péter Ábrányi-Balogh,
  • András Dancsó,
  • Gábor Tóth,
  • Judit Halász,
  • Angéla Pandur,
  • Gyula Simig and
  • Balázs Volk

Beilstein J. Org. Chem. 2020, 16, 1636–1648, doi:10.3762/bjoc.16.136

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  • ). According to the single-crystal X-ray experiments of compounds 3b, 8b, and 23a, the solid-phase structures are stabilized by a hydrogen bond between the amide NH and the carbonyl oxygen atom of the other amide group. The H–C–C–H dihedral angles between the two asymmetric centers are not far from 90° as
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Published 13 Jul 2020

Photoredox-catalyzed silyldifluoromethylation of silyl enol ethers

  • Vyacheslav I. Supranovich,
  • Vitalij V. Levin and
  • Alexander D. Dilman

Beilstein J. Org. Chem. 2020, 16, 1550–1553, doi:10.3762/bjoc.16.126

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  • employed in photoredox reactions to scavenge acidic byproducts [28][29], could not be employed. Silane 1 is easily destroyed by bases (even by the amide group [30]) followed by the rapid addition of difluorocarbene to silyl enol ethers [19][20]. Disappointingly, we were unable to isolate ketone 3a using
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Published 29 Jun 2020

The McKenna reaction – avoiding side reactions in phosphonate deprotection

  • Katarzyna Justyna,
  • Joanna Małolepsza,
  • Damian Kusy,
  • Waldemar Maniukiewicz and
  • Katarzyna M. Błażewska

Beilstein J. Org. Chem. 2020, 16, 1436–1446, doi:10.3762/bjoc.16.119

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  • problem. Section 1: Formation of oxazoles from propargylamides One of the most intriguing side reactions was observed when compounds comprising a propargyl amide group were treated with BTMS. Besides the products of addition of HBr, we observed the formation of oxazole. In order to study this process, we
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Published 23 Jun 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

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  • hindrance of the 4-substituted boronic acid. Next, in order to confirm our speculation, the amide group of the aryl bromide was replaced with other functional groups, as shown in Scheme 2. When the amide group was changed into an amine, coupling product 5a was obtained quantitatively but without any
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Published 11 May 2020
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