Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

• Beatriz Dedeiras,
• Catarina S. Caldeira,
• José C. Cunha,
• Clara S. B. Gomes and
• M. Manuel B. Marques

Beilstein J. Org. Chem. 2024, 20, 3281–3289, doi:10.3762/bjoc.20.272

• benziodoxolone, 2d) were obtained with quantitative yields, as white solids on the gram-scale, easy to manipulate and long-term stable below 0 °C. Crystals of compound 2d were successfully obtained and its molecular structure was confirmed through single-crystal X-ray diffraction. The X-ray analysis revealed a

• the electrophilic amination of tert-butyl 3-(p-tolylsulfinyl)propanoate (4a) with BBX 2a (0.23 mmol of limitant in 2 mL of solvent). Supporting Information Supporting Information File 54: Experimental procedures, characterization data, NMR spectra, and X-ray diffraction data. Funding The authors

Synthesis of 2H-azirine-2,2-dicarboxylic acids and their derivatives

• Anastasiya V. Agafonova,
• Mikhail S. Novikov and
• Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2024, 20, 3191–3197, doi:10.3762/bjoc.20.264

• single-crystal X-ray diffraction analysis. The reaction of azetidine with diacyl chloride 2a gave a complex mixture of products, and O-methyl hydroxylamine did not react. Diacyl chloride 2a reacts with methanol and ethanol to give diesters 11a,b (Scheme 5). An experiment with isoxazole 1a and methanol on

• research was carried out using resources of the Centre for Magnetic Resonance, the Research Centre for X-ray Diffraction Studies, the Centre for Chemical Analysis and Materials, and the Computer Centre of the Science Park of St. Petersburg State University. Funding This work was supported by Russian

Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold

• Thierry Milcent,
• Pascal Retailleau,
• Benoit Crousse and
• Sandrine Ongeri

Beilstein J. Org. Chem. 2024, 20, 3174–3181, doi:10.3762/bjoc.20.262

• trifluoro/difluoromethylated tetrahydropyridazine acids. Synthetic strategy to obtain fluorinated tetrahydropyridazines from difluoro- or trifluoromethylated hydrazones. X-ray diffraction of compound 8f. Reported syntheses of tetrahydropyridazine ester derivatives. Synthesis of fluorinated hydrazones 3a–f

Controlled oligomerization of [1.1.1]propellane through radical polarity matching: selective synthesis of SF₅- and CF₃SF₄-containing [2]staffanes

• Jón Atiba Buldt,
• Wang-Yeuk Kong,
• Yannick Kraemer,
• Masiel M. Belsuzarri,
• Ansh Hiten Patel,
• James C. Fettinger,
• Dean J. Tantillo and
• Cody Ross Pitts

Beilstein J. Org. Chem. 2024, 20, 3134–3143, doi:10.3762/bjoc.20.259

• truncated after incorporation of two bicyclopentane (BCP) units. Synthetic and computational studies suggest this phenomenon can be attributed to alternating radical polarity matching. In addition, single-crystal X-ray diffraction (SC-XRD) data reveal structurally interesting features of the CF3SF4

• for the first time created an opportunity for structural analysis. We previously reported and contextualized single-crystal X-ray diffraction (SC-XRD) data on 2 [36]; thus, we proceeded to grow crystals of 3 suitable for X-ray analysis through slow evaporation of ethyl acetate. To our surprise, an

4,6-Diaryl-5,5-difluoro-1,3-dioxanes as chiral dopants for liquid crystal compositions

• Maurice Médebielle,
• Peer Kirsch,
• Jérémy Merad,
• Carolina von Essen,
• Clemens Kühn and
• Andreas Ruhl

Beilstein J. Org. Chem. 2024, 20, 2940–2945, doi:10.3762/bjoc.20.246

• enantiomers (R,R)-3/(S,S)-3, (R,R)-4/(S,S)-4 were obtained by slow evaporation from n-heptane solution and structures were determined by X-ray diffraction, which allowed the correlation of the chiroptical properties with the configuration (Figure 2 and Figure 3). The HTP of all enantiomers were measured with

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

• functionalities they can transfer. In this study, a fundamental understanding of the thermal stability of phosphorus-iodonium ylids is obtained through X-ray diffraction, differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Insights into the structural factors affecting thermal stability

• ][26][27] and the mechanisms by which they decompose when heated through a systematic investigation of structural data from X-ray diffraction (XRD) and thermal stability data from differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The insights from this study will galvanise

• the rational design and synthesis of novel, unstabilised hypervalent iodine(III) compounds and expand the application of these powerful reagents in organic synthesis. Results and Discussion Structural data Twelve phosphorus-iodonium ylids were synthesised (Figure 2). X-ray diffraction data (XRD) of

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

• otherwise. The absence of transition states was confirmed by the absence of imaginary frequencies in vibrational frequency calculations. The long side chains were replaced by methyl units to aid the convergence of the geometry optimisations. Crystallography Single crystal X-ray diffraction data for 3b were

Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

• Marzieh Norouzi,
• Mohammad Taghi Nazeri,
• Ahmad Shaabani and
• Behrouz Notash

Beilstein J. Org. Chem. 2024, 20, 2870–2882, doi:10.3762/bjoc.20.241

• studied by X-ray diffraction analysis, and the crystal structure is illustrated in Figure 2 (detailed information can be found in the Supporting Information File 1). The 1H NMR spectrum of product 6f obtained through the I-MCR was investigated and some unexpected chemical shifts were observed at room

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

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

• fragment in the region δ = 2.5–2.4 ppm and methylene unit at δ = 2.7–2.5 ppm. The remaining signals are also in good agreement with the presented structure. Besides that, compound 4 has been analyzed using X-ray diffraction (Figure 1). It is important to emphasize that based on X-ray data the structure of

Anion-dependent ion-pairing assemblies of triazatriangulenium cation that interferes with stacking structures

• Yohei Haketa,
• Takuma Matsuda and
• Hiromitsu Maeda

Beilstein J. Org. Chem. 2024, 20, 2567–2576, doi:10.3762/bjoc.20.215

• (100), 595.3 (40), 596.3 (10), [M − BF4]+ calcd for C43H36N3, 594.29; (negative) 86.0 (20), 87.0 (100); [M – C43H36N3]− calcd for BF4, 87.00. This compound was further characterized by single-crystal X-ray diffraction analysis. 4,8,12-Tris(2,6-dimethylphenyl)-4,8,12-triazatriangulenium as a PF6− ion

• (0.21); MALDI–TOF MS (m/z) (% intensity): (positive) 594.3 (100), 595.3 (40), 596.3 (10), [M − F6P]+ calcd for C43H36N3, 594.29; (negative) 145.1 (100), [M − C49H30N3]− calcd for F6P, 144.96. This compound was further characterized by single-crystal X-ray diffraction analysis. 4,8,12-Tris(2,6

• –TOF MS (m/z) (% intensity): (positive) 594.3 (100), 595.3 (40), 596.3 (10), [M − C24BF20]+ calcd for C43H36N3, 594.29; (negative) 678.0 (20), 679.0 (100), 680.0 (20), [M – C43H36N3]– calcd for C24BF20, 678.98. This compound was further characterized by single-crystal X-ray diffraction analysis. 4,8,12

HFIP as a versatile solvent in resorcin[n]arene synthesis

• Hormoz Khosravi,
• Valeria Stevens and
• Raúl Hernández Sánchez

Beilstein J. Org. Chem. 2024, 20, 2469–2475, doi:10.3762/bjoc.20.211

• compounds. Acknowledgements This research was supported through instrumentation made available through the Shared Instrumentation Authority at Rice University. We thank Dr. Christopher L. Pennington for assistance with HRMS data collection and Dr. Hong-Lei Xu for help with single-crystal X-ray diffraction

Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

• Daria A. Burmistrova,
• Andrey Galustyan,
• Nadezhda P. Pomortseva,
• Kristina D. Pashaeva,
• Maxim V. Arsenyev,
• Oleg P. Demidov,
• Mikhail A. Kiskin,
• Andrey I. Poddel’sky,
• Nadezhda T. Berberova and
• Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

• catechols with a 2-pyridine or 1,3,4-oxadiazole-2-thione ring in the crystalline state were studied by X-ray diffraction. It has been established that the number of heteroatoms in the cycle which are bonded to the catechol ring through a sulfur atom and/or methylene bridge as well as the presence of

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

• additionally confirmed by X-ray diffraction (see Supporting Information File 1 for details) (Figure 2). To confirm the reaction mechanism, we performed diazotization followed by azo coupling of amide 2a using labeled Na15NO2 as the nitrosating reagent (Scheme 4). As a result, 15N-labeled triazinone 8 was

Understanding X-ray-induced isomerisation in photoswitchable surfactant assemblies

• Beatrice E. Jones,
• Camille Blayo,
• Jake L. Greenfield,
• Matthew J. Fuchter,
• Nathan Cowieson and
• Rachel C. Evans

Beilstein J. Org. Chem. 2024, 20, 2005–2015, doi:10.3762/bjoc.20.176

• , depending on the X-ray energy available from laboratory or synchrotron sources. Moreover, this effect may have significant consequences when measuring any light-responsive materials using X-rays, from self-assembled PS systems (using SAXS) to crystalline or powder samples (using X-ray diffraction) [28][29

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations

• Pengcheng Lu,
• Luis Juarez,
• Paul A. Wiget,
• Weihe Zhang,
• Krishnan Raman and
• Pravin L. Kotian

Beilstein J. Org. Chem. 2024, 20, 1940–1954, doi:10.3762/bjoc.20.170

• Texas A&M University for X-ray diffraction analysis. Funding All studies were funded by BioCryst Pharmaceuticals Inc. Conflict of Interest The authors declare the following competing financial interest(s): All authors are employees/former employees of BioCryst Pharmaceuticals Inc. and may hold stock in

Access to 2-oxoazetidine-3-carboxylic acid derivatives via thermal microwave-assisted Wolff rearrangement of 3-diazotetramic acids in the presence of nucleophiles

• Ivan Lyutin,
• Vasilisa Krivovicheva,
• Grigory Kantin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 1894–1899, doi:10.3762/bjoc.20.164

• information, X-ray crystallographic data, synthetic procedures, analytical data and NMR spectra for the reported compounds. Acknowledgements We thank the Research Center for Magnetic Resonance, the Center for Chemical Analysis and Materials Research, and the Center for X-ray Diffraction Methods of Saint

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

• reaction step for the synthesis and purification of the starting azomethines 9, we cannot propose the Ugi-3CR approach as more suitable compared to the Ugi-4CR approach. The structure of the Ugi bisamides 5–8 were proved by X-ray diffraction study on the example of substance 8c (Figure 2), according to

• conventional thermal heating, amide 10a was isolated, albeit in a lower yield and accompanied with tar formation. In addition to the 1H, 13C NMR spectra and mass spectrometry data, the structure of compound 10d was established by X-ray diffraction analysis (Figure 3). It was also found that the substituents at

• case of bisamides 5d, 6a, 6c, 7b, 8a, and 8c (Table 2), additional transformation products were also isolated from the reaction mixture. According to 1H and 13C NMR, MS, and X-ray diffraction studies these were the corresponding ketobisamides 12, which are products of a nucleophilic substitution of the

Synthesis and characterization of 1,2,3,4-naphthalene and anthracene diimides

• Adam D. Bass,
• Daniela Castellanos,
• Xavier A. Calicdan and
• Dennis D. Cao

Beilstein J. Org. Chem. 2024, 20, 1767–1772, doi:10.3762/bjoc.20.155

• information file for compound 8-Ph. Acknowledgements We thank Victor G. Young, Jr. of the University of Minnesota X-Ray Crystallographic Laboratory for acquiring X-ray diffraction data and solving crystal structures. Funding The Bruker-AXS D8 Venture diffractometer was purchased through a grant from NSF/MRI

Harnessing unprotected deactivated amines and arylglyoxals in the Ugi reaction for the synthesis of fused complex nitrogen heterocycles

• Javier Gómez-Ayuso,
• Pablo Pertejo,
• Tomás Hermosilla,
• Israel Carreira-Barral,
• Roberto Quesada and
• María García-Valverde

Beilstein J. Org. Chem. 2024, 20, 1758–1766, doi:10.3762/bjoc.20.154

• single diastereomer (Scheme 5, Table 3), while N-phenylglycine afforded the enamine derivative 10 (Scheme 6, Table 4). Both structures were confirmed by single-crystal X-ray diffraction of compounds 9a and 10a (Figure 2). The diastereoselectivity observed in the hemiaminals and their stability can be

• further confirmed by single-crystal X-ray diffraction of compound 12c (Figure 3). Conclusion In this work, we have demonstrated the straightforward access to a variety of complex nitrogen heterocycles by using unprotected deactivated amines tethered to carboxylic acids combined with arylglyoxals in the

• functional group in the resulting Ugi adduct can be exploited in different post-condensation strategies to generate multiple fused nitrogen heterocycles in an easy manner. Fused heterocycles containing the piperazine and diazepine core. X-ray diffraction structures of pyrrolopiperazinones 9a (left) and 10a

Supramolecular assemblies of amphiphilic donor–acceptor Stenhouse adducts as macroscopic soft scaffolds

• Ka-Lung Hung,
• Leong-Hung Cheung,
• Yikun Ren,
• Ming-Hin Chau,
• Yan-Yi Lam,
• Takashi Kajitani and
• Franco King-Chi Leung

Beilstein J. Org. Chem. 2024, 20, 1590–1603, doi:10.3762/bjoc.20.142

• revealed by X-ray diffraction analysis. Upon visible-light irradiation, significant transformations of the DA geometry enabled transformations of the supramolecular assemblies on a microscopic scale, subsequently disassembling macroscopic soft scaffolds of DAs. The current work shows promising use for the

• investigated with through-view wide-angle X-ray diffraction (WAXD). The 2D WAXD image of the macroscopic soft scaffold of DA11 showed a diffraction ring in the region of q = 0.5–5.0 nm−1 (Figure 4c), which was similar to that of DA10 [37]. A low degree of angular dependency was observed in the macroscopic soft

• his generous support and help with X-ray diffraction measurements and for his helpful suggestions. Funding This work was financially supported by the National Natural Science Foundation of China (22001223), the Hong Kong Research Grants Council, General Research Fund (GRF 15300521 and GRF 15305822

Towards an asymmetric β-selective addition of azlactones to allenoates

• Behzad Nasiri,
• Ghaffar Pasdar,
• Paul Zebrowski,
• Katharina Röser,
• David Naderer and
• Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1504–1509, doi:10.3762/bjoc.20.134

• residual water during column chromatography. Unfortunately, attempts to assign the absolute configuration of products 5 failed, as we have not been able to obtain any crystals suited for single crystal X-ray diffraction analysis. Finally, we also tested the suitability of products 5 to access acyclic α-AA

Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction

• Xiu-Yu Chen,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2024, 20, 1436–1443, doi:10.3762/bjoc.20.126

• produced in the reaction, while the other diastereomers were not detected. In order to elucidate the relative configuration of the obtained compounds, the molecular structure of the compound 4a was determined by single crystal X-ray diffraction (Figure 1). From Figure 1, it can be seen that the fused

• can be performed with a wide variety of substrates. The molecular structure of the compound 6g was determined by single crystal X-ray diffraction method (Figure 2). The o-methoxyphenyl group exists on the trans-position of the fused pyrrolidine unit. The methoxycarbonyl group also exists on the cis

Synthesis of substituted triazole–pyrazole hybrids using triazenylpyrazole precursors

• Simone Gräßle,
• Laura Holzhauer,
• Nicolai Wippert,
• Olaf Fuhr,
• Martin Nieger,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2024, 20, 1396–1404, doi:10.3762/bjoc.20.121

• suitable for single-crystal X-ray diffraction could be obtained and confirmed the product structure with the presumed regioisomer (Scheme 3). A library of over 50 triazole products 21aa–vg was successfully synthesized with yields ranging from 28% to quantitative, combining four different pyrazole-carbon

Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide

• Vishnu Selladurai and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2024, 20, 1221–1235, doi:10.3762/bjoc.20.105

• electrons over the adjacent carboxylate function, which prompted the selenation pathway, leading to the formation of two of the isomeric diorganyl selenides of methyl anthranilate. The diaryl selenides were structurally characterized using single-crystal X-ray diffraction. Density functional theory

• in Hz. The calibration was done with respect to the signal of residual undeuterated solvent or in relationship to TMS (CDCl3: 1H 7.26 ppm, 13C 77.34 ppm). Single-crystal X–ray diffraction was recorded on a Bruker D8 Quest system. HRESIMS spectra were recorded on a Waters Xevo G2-XS QTof device. UV