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Search for "functionality" in Full Text gives 613 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide

  • Noble Brako,
  • Sreerag Moorkkannur Narayanan,
  • Amber Burns,
  • Layla Auter,
  • Valentino Cesiliano,
  • Rajeev Prabhakar and
  • Norito Takenaka

Beilstein J. Org. Chem. 2024, 20, 3069–3076, doi:10.3762/bjoc.20.255

Graphical Abstract
  • ; Introduction Enantioenriched α-allenic alcohols are an important class of chiral building blocks used for the chemical synthesis of biologically relevant molecules [1][2][3][4][5]. Their strength comes from the rich synthetic versatility [6][7][8][9] and biological relevance [10] of the allene functionality
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Letter
Published 25 Nov 2024

Advances in radical peroxidation with hydroperoxides

  • Oleg V. Bityukov,
  • Pavel Yu. Serdyuchenko,
  • Andrey S. Kirillov,
  • Gennady I. Nikishin,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

Graphical Abstract
  • development of efficient synthetic approaches to implement organic peroxide functionality in various substrates is a timely task. From the synthetic point of view, organic peroxides are one of the best sources of oxygen atoms for a variety of oxygenation reactions [6]. Hydroperoxides (especially TBHP), acyl
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Review
Published 18 Nov 2024

Structure and thermal stability of phosphorus-iodonium ylids

  • Andrew Greener,
  • Stephen P. Argent,
  • Coby J. Clarke and
  • Miriam L. O’Duill

Beilstein J. Org. Chem. 2024, 20, 2931–2939, doi:10.3762/bjoc.20.245

Graphical Abstract
  • enable access to chemical motifs that are difficult to synthesise using traditional approaches. However, gaps remain in the functionality they can transfer. Specifically, unstabilised alkyl groups are still underrepresented. For the development of new hypervalent iodine reagents to bridge this gap, it is
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Published 14 Nov 2024

The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives

  • Sondos A. J. Almahmoud,
  • Joseph Cameron,
  • Dylan Wilkinson,
  • Michele Cariello,
  • Claire Wilson,
  • Alan A. Wiles,
  • Peter J. Skabara and
  • Graeme Cooke

Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244

Graphical Abstract
  • , and a λmax at 701 nm with ε of 4.69 × 104 L mol−1 cm−1 which might lead to the contribution of 3b to the photocurrent. All previous studies suggested that violanthrone and its derivatives display electronic functionality and could be potentially used in organic electronics. Nevertheless, to the best
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Published 13 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
  • proposed to function by Cu2+ sequestration. The remaining report is of a terbium(III) complex [Tb(DPA-N3)3]3− (Figure 7), which contains an aryl azide-functionalized ligand. In this system the azide functionality prohibits the energy transfer to the lanthanide ion, effectively quenching luminescence. In
  • the presence of gaseous hydrogen sulfide, the aryl azide is reduced to an aniline functionality and luminescence is restored [11]. Drawing our previous findings and insights from the work of Hou, Wu, and co-workers [21], we postulate that gaseous H2S is interacting with the [Tb.1·3Cu]3+ complex as it
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Published 05 Nov 2024

Applications of microscopy and small angle scattering techniques for the characterisation of supramolecular gels

  • Connor R. M. MacDonald and
  • Emily R. Draper

Beilstein J. Org. Chem. 2024, 20, 2608–2634, doi:10.3762/bjoc.20.220

Graphical Abstract
  • -assembly across many length scales (Figure 1), allowing for the control of properties through not only chemical modifications on the monomer, but also changes to the gelation process [2]. Whilst this tunability is advantageous in that it allows for a wide range of functionality and applications, this also
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Published 16 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

Graphical Abstract
  • , that the 2-aminophenol functionality in the substrates is a prerequisite for attaining high enantioselectivity in the allylation. Interestingly, the aldimines synthesised from 2-hydroxy-4-methylaniline produced inferior yields. While the N-aryl homoallylic amines 66 can be useful intermediates in total
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Published 16 Sep 2024

Tandem diazotization/cyclization approach for the synthesis of a fused 1,2,3-triazinone-furazan/furoxan heterocyclic system

  • Yuri A. Sidunets,
  • Valeriya G. Melekhina and
  • Leonid L. Fershtat

Beilstein J. Org. Chem. 2024, 20, 2342–2348, doi:10.3762/bjoc.20.200

Graphical Abstract
  • , whether isolated or generated in situ, may undergo various controlled transformations [42]. However, previously, we failed to introduce amino-1,2,5-oxadiazoles bearing an amide functionality into the diazotization protocol, arguably due to an increased electron-withdrawing effect and elevated instability
  • and straightforward approach for the synthesis of previously unknown [1,2,5]oxadiazolo[3,4-d][1,2,3]triazin-7(6H)-one derivatives based on tandem diazotization/azo coupling reactions of readily available (1,2,5-oxadiazolyl)carboxamides containing an amino functionality. The developed protocol was
  • ). NO release data. Tandem diazotization/azo coupling reactions of (1,2,5-oxadiazolyl)carboxamides containing an amino functionality. Synthesis of target furoxanotriazinones 1a–h. The synthesis of furazanotriazinones 7a–h. Control experiment with Na15NO2. Optimization of the diazotization of amide 2aa
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Published 16 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

Graphical Abstract
  • condensation by introducing additional functional groups into the amine moiety (Figure 3). Substituted arylamines bearing alcohol (3ae), phenol (3ad), alkene (3bi), dimethyl acetal (3bj) functionality can be accessed in good yields. Reaction of 1,3-diketone 1a with a non-amidine type heterocyclic amine, 3
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Published 02 Sep 2024

Computational toolbox for the analysis of protein–glycan interactions

  • Ferran Nieto-Fabregat,
  • Maria Pia Lenza,
  • Angela Marseglia,
  • Cristina Di Carluccio,
  • Antonio Molinaro,
  • Alba Silipo and
  • Roberta Marchetti

Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180

Graphical Abstract
  • docking software (unfortunately not free) designed to predict the conformations of small molecules in protein binding sites, thus facilitating the discovery of new drugs. Within SeeSAR, its functionality allows ligands to be placed in binding sites using an incremental construction algorithm that splits
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Published 22 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
  • gives access to polyfunctional ynedione 129 [147]. In contrast to Sonogashira alkynylation, where glyoxyl substrates furnish ynones with concomitant decarbonylation [145], Stephens–Castro alkynylation preserves the dicarbonyl functionality in the product [148]. Embedded within a consecutive four
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Published 16 Aug 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

Graphical Abstract
  • the tolerability of a wide range of aldehydes, starting from one of the most used, benzaldehyde, passing through heteroaromatic and aliphatic structures with different substituents. In this context, some examples where the aldehyde functionality is incorporated into sugar derivatives, natural
  • economy (water was the only byproduct) and thermal stability as well as remarkable fluorescence properties. Multicomponent reaction can be also employed to prepare crystalline porous materials namely covalent organic frameworks (COFs). The structural diversity and functionality of COFs were assembled from
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Published 01 Aug 2024

Hetero-polycyclic aromatic systems: A data-driven investigation of structure–property relationships

  • Sabyasachi Chakraborty,
  • Eduardo Mayo Yanes and
  • Renana Gershoni-Poranne

Beilstein J. Org. Chem. 2024, 20, 1817–1830, doi:10.3762/bjoc.20.160

Graphical Abstract
  • have also been incorporated into larger structures such as nano-hoops, in order to tune and expand their functionality [26]. Herein, we perform an in-depth analysis of the data contained within COMPAS-2, aiming to elucidate the effects of electron count, geometry, atomic composition, and aromatic
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Published 31 Jul 2024

Syntheses and medicinal chemistry of spiro heterocyclic steroids

  • Laura L. Romero-Hernández,
  • Ana Isabel Ahuja-Casarín,
  • Penélope Merino-Montiel,
  • Sara Montiel-Smith,
  • José Luis Vega-Báez and
  • Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

Graphical Abstract
  • androgenic activity. Poirier’s group reported two methodologies to prepare spiromorpholin-3-ones from a β-amino alcohol functionality [39]. Spiro compounds were synthesized starting from estrone, in which the phenol group was protected as a methoxymethyl ether. Then, the protected compound was subjected to
  • peroxide–hydrochloric acid. A subsequent reaction of the resulting compound with simple ketones in the presence of sulfuric acid produced steroidal 1,2,4,5-tetraoxanes 170 possessing an ester functionality. The unsubstituted ketones gave a single product as expected, while those with substituted precursors
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Published 24 Jul 2024

Tetrabutylammonium iodide-catalyzed oxidative α-azidation of β-ketocarbonyl compounds using sodium azide

  • Christopher Mairhofer,
  • David Naderer and
  • Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1510–1517, doi:10.3762/bjoc.20.135

Graphical Abstract
  • . Keywords: azidation; nitration; organocatalysis; oxidation; quaternary ammonium iodides; Introduction Organic compounds containing an azide functionality are highly valuable synthesis targets that offer considerable potential for various applications and further manipulations [1][2][3][4][5][6][7][8][9
  • in the presence of Bu4NHSO4 (Table 1, entry 9) and the use of Bu4NCl (Table 1, entry 8) was not satisfying either. On the other hand, the beneficial effect of the quaternary ammonium functionality was clearly underscored by employing KI instead of Bu4NI (compare Table 1, entries 10 and 5). While
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Published 05 Jul 2024

Synthetic applications of the Cannizzaro reaction

  • Bhaskar Chatterjee,
  • Dhananjoy Mondal and
  • Smritilekha Bera

Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120

Graphical Abstract
  • synthetic tool for the construction of functionalized molecules. Dating back to the 19th century, this reaction, though initially used for the synthesis of an alcohol and acid functionality from aldehydes, has henceforth proven useful to generate diverse molecular entities using both intermolecular and
  • Cannizzaro reaction commencing from 68. The primary hydroxymethyl functionality in 69 was oxidized to the corresponding aldehyde 70, which was subsequently treated with 37% aqueous formaldehyde and NaOH, to result in a mixture of the gem-hydroxymethyl derivative 72 and the carbamate 71 which led to the spiro
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Published 19 Jun 2024
Graphical Abstract
  • ] cycloaddition between maleic anhydride and secondary amine occurs first, followed by the corresponding amidation (Figure 3, path II) [110]. Although IMDAF reactions involving furan systems bearing amide functionality are generally reversible [134], the formation of the addition products in high yields in this
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Published 06 Jun 2024

Stability trends in carbocation intermediates stemming from germacrene A and hedycaryol

  • Naziha Tarannam,
  • Prashant Kumar Gupta,
  • Shani Zev and
  • Dan Thomas Major

Beilstein J. Org. Chem. 2024, 20, 1189–1197, doi:10.3762/bjoc.20.101

Graphical Abstract
  • from the NCI plots. In general, stabilization of some 5-7 bicyclic carbocations (e.g., F-OH and H-OH) are via C+···OH interactions, which are facilitated by the carbocation and hydroxyl functionality being located in the relatively flexible 7-membered ring. This type of interaction is absent in case of
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Published 23 May 2024

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

  • Mohd Farhan Ansari,
  • Atul Kumar Maurya,
  • Abhishek Kumar and
  • Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

Graphical Abstract
  • alcohols as an alkylating agent using the protic functionality on a naphthyridine‑N‑oxide manganese complex [68]. The reaction conditions were optimized using acetophenone and benzyl alcohol as model substrates. After optimizing various reaction parameters, 2 mol % of Mn14 and 20 mol % of KOH in toluene
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Published 21 May 2024

Synthesis of 1,4-azaphosphinine nucleosides and evaluation as inhibitors of human cytidine deaminase and APOBEC3A

  • Maksim V. Kvach,
  • Stefan Harjes,
  • Harikrishnan M. Kurup,
  • Geoffrey B. Jameson,
  • Elena Harjes and
  • Vyacheslav V. Filichev

Beilstein J. Org. Chem. 2024, 20, 1088–1098, doi:10.3762/bjoc.20.96

Graphical Abstract
  • used. There are two obvious choices based on the literature on CDA inhibitors, THU (Ia) and phosphapyrimidine nucleoside IV (Figure 1). However, the hemiaminal functionality in the nucleobase and the fast transformation into pyranose in THU (Ia) along with instability of nucleoside IV in water prevent
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Published 15 May 2024

Light on the sustainable preparation of aryl-cored dibromides

  • Fabrizio Roncaglia,
  • Alberto Ughetti,
  • Nicola Porcelli,
  • Biagio Anderlini,
  • Andrea Severini and
  • Luca Rigamonti

Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95

Graphical Abstract
  • molecular wires or extended structures – either linear or cyclic – with enhanced functionality. Consequently, they play a crucial role in the fabrication of polymers [4][5][6][7], cyclophanes [8], photoactive materials [9][10][11], membranes [12], and other architectures. The synthetic potential of aryl
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Published 14 May 2024

Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines

  • Vladislav V. Nikol’skiy,
  • Mikhail E. Minyaev,
  • Maxim A. Bastrakov and
  • Alexey M. Starosotnikov

Beilstein J. Org. Chem. 2024, 20, 1069–1075, doi:10.3762/bjoc.20.94

Graphical Abstract
  • either annulation of an isoxazole fragment to a pyridine cycle or vice versa formation of a pyridine ring based on appropriately substituted isoxazoles. In the first case (Scheme 1A) 3-halo- [11][15][16][17][18][19] or 3-hydroxypyridines [8][20] bearing a suitable functionality in position 2 were used
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Published 14 May 2024

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

  • Tural N. Akhmedov,
  • Ajeet Kumar,
  • Daken J. Starkenburg,
  • Kyle J. Chesney,
  • Khalil A. Abboud,
  • Novruz G. Akhmedov,
  • Jiangeng Xue and
  • Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

Graphical Abstract
  • dicyanopyrazinoquinoxalines (DCPQs) 1a–7a and subsequent mild one-step synthesis of hydrogen-bonding dihydropyrazinoquinoxalinedione (DPQDs) 1b–7b. The structure–property relationships have been established within and between the two families using optical measurements. Moreover, the incorporation of H-bonding functionality
  • functionality as well as Buchwald–Hartwig amination involving aryl halides. Thermal studies Thermal stabilities of DCPQs 1a–6a and DPQDs 1b–7b were evaluated using thermogravimetric analysis (TGA; Figure 2 and Table S4 in Supporting Information File 1). The thermal stability of the DCPQs is attributed to their
  • DCPQs and DPQDs in this context. Overall, this work contributes to our overarching objective to investigate the influence of hydrogen-bonding functionality on optoelectronic material organization and next-generation organic semiconductor device performance. Experimental General methods Reagents and
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Published 08 May 2024

Innovative synthesis of drug-like molecules using tetrazole as core building blocks

  • Jingyao Li,
  • Ajay L. Chandgude,
  • Qiang Zheng and
  • Alexander Dömling

Beilstein J. Org. Chem. 2024, 20, 950–958, doi:10.3762/bjoc.20.85

Graphical Abstract
  • of tetrazole building blocks which provides the handle of alcohol functionality and further oxidation serves as an oxo component in subsequent MCRs (Figure 1d). The synthesis of oxo-tetrazoles was targeted because of the prevalence of the aldehyde substrate in MCRs and their use in medicinal
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Published 29 Apr 2024

Monitoring carbohydrate 3D structure quality with the Privateer database

  • Jordan S. Dialpuri,
  • Haroldas Bagdonas,
  • Lucy C. Schofield,
  • Phuong Thao Pham,
  • Lou Holland and
  • Jon Agirre

Beilstein J. Org. Chem. 2024, 20, 931–939, doi:10.3762/bjoc.20.83

Graphical Abstract
  • unlikeliness for a human to read and understand the WURCS code. It is much more likely that the WURCS code would be copied and searched for in a glycomics database, hence we provide that functionality in a streamlined way. The final section of the validation report includes all of the validation metrics
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Published 24 Apr 2024
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