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

• that all tricyclic compounds have this kind of relative configuration on the basis of NMR spectra and single crystal structure. In order to develop the scope of the reaction, another kind of 5,6-unsubstituted 1,4-dihydropyridines 5 were also employed in the reaction, which were previously prepared from

A comparison of structure, bonding and non-covalent interactions of aryl halide and diarylhalonium halogen-bond donors

• Nicole Javaly,
• Theresa M. McCormick and
• David R. Stuart

Beilstein J. Org. Chem. 2024, 20, 1428–1435, doi:10.3762/bjoc.20.125

• (THF) incorporating Huber, Truhlar, and Cramer’s correction for bromine and iodine [32] using Gaussian 09 [33]. Our prior work on the orbital analysis of diarylhalonium salts [21], showed good agreement between crystal structure data and energy-minimized structures at the B3LYP/cc-pvtz level with def2

Synthesis of 1,2,3-triazoles containing an allomaltol moiety from substituted pyrano[2,3-d]isoxazolones via base-promoted Boulton–Katritzky rearrangement

• Constantine V. Milyutin,
• Andrey N. Komogortsev and
• Boris V. Lichitsky

Beilstein J. Org. Chem. 2024, 20, 1334–1340, doi:10.3762/bjoc.20.117

• recyclization. The structures of one example of the 1,2,3-triazole derivatives and one synthesized pyrazolylisoxazole were established by X-ray analysis. The X-ray crystal structure of compound 4g (CCDC 2343878). Synthesis of various triazole derivatives using Boulton–Katritzky rearrangement. Synthesis of

• File 96: Experimental procedures, characterization data of all products, copies of 1H, 13C NMR, spectra of all new compounds, and X-ray crystallographic data. Acknowledgements The crystal structure determination was performed in the Department of Structural Studies of Zelinsky Institute of Organic

Synthesis of indano[60]fullerene thioketone and its application in organic solar cells

• Yong-Chang Zhai,
• Shimon Oiwa,
• Shinobu Aoyagi,
• Shohei Ohno,
• Tsubasa Mikie,
• Jun-Zhuo Wang,
• Hirofumi Amada,
• Koki Yamanaka,
• Kazuhira Miwa,
• Naoyuki Imai,
• Takeshi Igarashi,
• Itaru Osaka and
• Yutaka Matsuo

Beilstein J. Org. Chem. 2024, 20, 1270–1277, doi:10.3762/bjoc.20.109

• time. A single crystal of t-Bu-FIDS was grown by liquid–liquid diffusion method (CS2/EtOH). The crystal structure was successfully analyzed using synchrotron radiation at SPring-8. The crystal exhibited the orthorhombic space group (No. 61) with the D2h point group, and the structure confirmed the 1,2

• -Bu-FIDS (black) and of toluene used to rinse the evaporated film of t-Bu-FIDS (red). Single-crystal structure of t-Bu-FIDS. (a) The π–π distance between two molecules. (b) Crystal packing. Cyclic voltammograms of fullerene derivatives in o-DCB solution containing Bu4N+(CF3SO2)2N− (0.1 M) as

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

• . It crystallized in a triclinic crystal system in the space group P−1. It was structurally similar to the other oxamides 3 and 9. It showed an intramolecular hydrogen bonding between the NH and the carbonyl group of the methoxy ester. A layer-by-layer packing was observed in the crystal structure

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

• Masahiro Kako,
• Masato Kai,
• Masanori Yasui,
• Michio Yamada,
• Yutaka Maeda and
• Takeshi Akasaka

Beilstein J. Org. Chem. 2024, 20, 1179–1188, doi:10.3762/bjoc.20.100

• 305-8577, Japan 10.3762/bjoc.20.100 Abstract The addition reaction of C60 with silylene 1, a silicon analog of carbene, yielded the corresponding bis-adduct 3. The structure of 3 was determined by single-crystal X-ray structure analysis, representing the first example of a crystal structure of a

• ][40][41][42], except for rare examples such as 3-(hydroxydimesitylsilyl)-1,1-dimesityl-2,2-bis(trimethylsilyl)-1-silirane [43]. In contrast, we earlier reported the crystal structure of the adduct of Lu3N@Ih–C80 with silylene Dep2Si (Dep = 2,6-diethylphenyl), which was revealed to be a sila-fulleroid

Enhancing structural diversity of terpenoids by multisubstrate terpene synthases

• Min Li and
• Hui Tao

Beilstein J. Org. Chem. 2024, 20, 959–972, doi:10.3762/bjoc.20.86

• distinct primary structures with class I TSs, its crystal structure reveals a similar overall structure of BalTS to the α-domain of class I TSs and therefore was proposed as class IB, a new subclass of TSs [37]. The discovery of TSs from bacteria not only expands the diversity of terpene skeletons but also

Synthesis and properties of 6-alkynyl-5-aryluracils

• Ruben Manuel Figueira de Abreu,
• Till Brockmann,
• Alexander Villinger,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

• were obtained by slow evaporation of the solvent from a mixture of the compound in dichloromethane and heptane at room temperature (Figure 3). Crystal structure analysis revealed that 5a crystallizes in a base-centered monoclinic system with the P21/c space group. The structure is mostly planar, except

• ). Samples were ionized by electron impact ionization (EI) on an Agilent 6890/5973 or Agilent 7890/5977 GC–MS equipped with a HP-5 capillary column using helium carrier gas or by electron spray ionization (ESI) on an Agilent 1200/6210 time-of-flight (TOF) LC–MS. X-ray single-crystal structure analysis was

Confirmation of the stereochemistry of spiroviolene

• Yao Kong,
• Yuanning Liu,
• Kaibiao Wang,
• Tao Wang,
• Chen Wang,
• Ben Ai,
• Hongli Jia,
• Guohui Pan,
• Min Yin and
• Zhengren Xu

Beilstein J. Org. Chem. 2024, 20, 852–858, doi:10.3762/bjoc.20.77

• suitable for X-ray diffraction [35]. The crystal structure of 13 clearly showed that the 19- and 20-methyl groups are cis-oriented in the D-ring which is consistent with that of spirograterpene A. This structural data reaffirms the revised structure of spiroviolene, and further support the unified

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

• Martyn Jevric,
• Julian Klepp,
• Johannes Puschnig,
• Oscar Lamb,
• Christopher J. Sumby and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

• chlorosulfite 25 or the alkoxytriphenylphosphonium chloride 26, respectively. With heating, SO2 or triphenylphosphine oxide is extruded with a concerted migration of the neighbouring O8 leading to an oxocarbenium ion 27, which is then trapped with chloride giving the observed products. The crystal structure for

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

• Andrew D. Gillie,
• Matthew G. Wakeling,
• Bethan L. Greene,
• Louise Male and
• Paul W. Davies

Beilstein J. Org. Chem. 2024, 20, 621–627, doi:10.3762/bjoc.20.54

• interatomic distances are between 3.53 and 3.66 Å leaving insufficient space for bond rotation about the C–N axis with the sulfonamide substituents being approximately perpendicular to the fused aromatic unit. A percentage buried volume of 44.6% was calculated from the crystal structure of 13 using Cavallo’s

Recent developments in the engineered biosynthesis of fungal meroterpenoids

• Zhiyang Quan and
• Takayoshi Awakawa

Beilstein J. Org. Chem. 2024, 20, 578–588, doi:10.3762/bjoc.20.50

• meroterpenoid biosynthetic pathways, enzymatic engineering, and feeding with unnatural substrates. Enzyme crystal structure analysis and AI structure prediction also facilitated these investigations. Besides terpene cyclases and αKG-dependent dioxygenases, P450 monooxygenases and UbiA-type prenyltransferases

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• -crystal structure [12]. Additionally, greenhouse trials have shown that thiazolopyridine 5 and a large number of closely related analogues display excellent control of grass weed species in preemergence applications [13][14]. Independently, researchers at Syngenta have shown that the pyridine unit in the

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• and mass spectrometric data. X-ray crystallographic analysis confirmed and established the structures and absolute configurations of compounds 1–3, thus providing the first characterized crystal structure of an ovalicin-type sesquiterpenoid. In the antimicrobial assays, compounds 1–3 showed broad

• stereogenic centers in compound 1 as 1R, 2R, 3R, 6R, 7R, 8S. This is likely the first characterized crystal structure of an ovalicin-type sesquiterpenoid. The molecular formula of pseudallene B (2) was assigned as C15H26O5S (three unsaturations), with one CH2 unit less than 1, based on positive HRESIMS data

• CS-793. To date, only three sulfur-containing ovalicin sesquiterpenoids have been reported [10][12]. Moreover, the first characterized crystal structure of an ovalicin-type sesquiterpenoid was obtained, which further confirmed the structures and absolute configurations of compounds 1–3. Biological

Enhanced host–guest interaction between [10]cycloparaphenylene ([10]CPP) and [5]CPP by cationic charges

• Eiichi Kayahara,
• Yoshiyuki Mizuhata and
• Shigeru Yamago

Beilstein J. Org. Chem. 2024, 20, 436–444, doi:10.3762/bjoc.20.38

• sp2 carbon of [10]CPP within 0.30 nm. HOMO−1, HOMO, LUMO, and LUMO+1 orbitals of [10]CPP⊃[5]CPP2+ (1), [5]CPP2+, and [10]CPP. X-ray crystal structure of [10]CPP⊃[5]CPP2+[B(C6F5)4]2. a) Side and b) top views of ORTEP drawings. The thermal ellipsoids are scaled at the 50% probability level. All hydrogen

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• , were synthesized as direct soluble precursors of PBIs 6a,b, along with the corresponding oxides, namely sulfoxides 4a,b and sulfone 5 (Scheme 4). An X-ray crystal structure of the extended thiepine 3b confirmed its bent structure, with a protrusion of the sulfur atom out of the π-surface (Figure 1). As

• hydride resulted in the formation of the oxepine ring by a double substitution reaction, to yield the desired dinaphthooxepine 33. The non-planar character of dinaphthooxepine bisimides was confirmed by X-ray crystal structure, and stability towards thermal or photoactivation was also established. Cyclic

• ) and side view (b) of the X-ray crystal structure of thiepine 3b showing its bent conformation. Thermal ellipsoids are shown at the 50% probability level, and all hydrogen atoms as well as propyl groups on imide substituents have been omitted for clarity. Reprinted with permission from [57]. Copyright

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

• Ekaterina V. Kolupaeva,
• Narek A. Dzhangiryan,
• Alexander F. Pozharskii,
• Oleg P. Demidov and
• Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

• 5. As the XRD study of the crystals showed (Figure 3), the molecular and crystal structure of the isolated compound is strongly dominated, on the one hand, by intra- and intermolecular hydrogen bonds with the participation of N, Cl, and O heteroatoms (forming an endless slightly corrugated ribbon

• divergence angle between them of only 1.33°) and are simultaneously connected by two bifurcated hydrogen bonds with the hydroxy groups of dichlororesorcinol. What would be the crystal structure of quinoquinoline 5 free of foreign particles? This is not an easy question to answer, since the superbasic nature

• 3.353 Å). Interestingly, as the acidity of the neighboring component in the crystal structure and the degree of proton transfer from it to the nitrogen atoms of quinoquinoline 5 decrease, the internitrogen distance regularly increases (N…N, Å): 2.709 (HCl), 2.808 (4,6-dichlororesorcinol), 2.813–2.835

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

• Christina Schøttler,
• Kasper Lund-Rasmussen,
• Line Broløs,
• Philip Vinterberg,
• Ema Bazikova,
• Viktor B. R. Pedersen and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

• Crystals suitable for single-crystal X-ray diffraction studies were obtained for compounds 25, 26, and 29. Their structures are shown in Figure 10, top, and their respective crystal packings below. All three compounds pack in a herringbone manner in the crystal structure, with the major difference that

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

• regarded as stable phosphonium enolate zwitterions. The first zwitterions of this type were published in 1955 [31], but the first crystal structure of a phosphonium enolate zwitterion was reported only in 2007 by Zhu et al., who synthesized the compound via a three-component coupling between an

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

• Nedra Touj,
• François Mazars,
• Guillermo Zaragoza and
• Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

• zwitterions.a Supporting Information Supporting Information File 26: Experimental procedures, X-ray crystal structure determinations, copies of 1H NMR, 13C NMR, and FTIR spectra. Acknowledgements The authors would like to thank Apeiron Synthesis for a gift of aldiminium tetrafluoroborate salts 3a and 3c, Mr

Studying specificity in protein–glycosaminoglycan recognition with umbrella sampling

• Mateusz Marcisz,
• Sebastian Anila,
• Margrethe Gaardløs,
• Martin Zacharias and
• Sergey A. Samsonov

Beilstein J. Org. Chem. 2023, 19, 1933–1946, doi:10.3762/bjoc.19.144

• and 4N8W complexes, respectively. The dodecamer ligand docked to the protein in such a way that the hexameric part with the 4-sulfation (as observed in the crystal structure) occupied the 4N8W site and the hexameric part with the 6-sulfation bound to the site observed in the 3C9E structure. The

• comparison of the final structure and that obtained after the docking yielded RMSatd of 10.2 Å, which shows that the pulling back results in the structure more similar to that of the crystal structure than to the initial docked pose. A similar comparison of the final structure obtained at the end of the

• sliding in process was done for the other complexes with their corresponding crystal structures and the one obtained after docking. The ligands’ RMSatd values (Tables S1 and S2 in Supporting Information File 1) show that in the majority of the complexes the final structure is more similar to the crystal

Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates

• Xing Liu,
• Wenjing Shi,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1923–1932, doi:10.3762/bjoc.19.143

• yields. The chemical structures of the spiro compounds 7a–n were established by various spectroscopy methods. In addition, the single crystal structure of compound 7a was also determined by X-ray diffraction (Figure 1). As can be seen from Figure 1, both the C–C and C–N double bonds are part of the

• cm−1; HRMS–ESI TOF (m/z): [M + Na]+ calcd for C34H28ClN4O3SNa, 595.1774; found, 595.1765. The crystallographic data of compound 7a (CCDC 2280223) have been deposited at the Cambridge Crystallographic Database Centre. Single crystal structure of the spiro compound 7a. Representative [4 + 3

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

• Xiaofeng Zhang,
• Xiaoming Ma and
• Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

• the R2 group. The stereochemistry of products 10 and 11 was confirmed by X-ray crystal structure and the 1H NMR analysis of both the major and minor diastereomers [69]. The first cycloaddition gives adducts 12 and 12’ as a diastereomeric mixture. At the second cycloaddition, both major and minor

• symmetry. The stereochemistry of the products was confirmed by X-ray crystal structure and NMR analysis. The reaction mechanism shown in Scheme 11 suggests that a semi-stabilized AMY 16 generated from the reaction of glycine and arylaldehydes undergoes a [3 + 2] cycloaddition with 14a via the favorable

Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity

• Swagat K. Mohapatra,
• Khaled Al Kurdi,
• Samik Jhulki,
• Georgii Bogdanov,
• John Bacsa,
• Maxwell Conte,
• Tatiana V. Timofeeva,
• Seth R. Marder and
• Stephen Barlow

Beilstein J. Org. Chem. 2023, 19, 1651–1663, doi:10.3762/bjoc.19.121

• , reacts more rapidly than any of the other dimers with VII via “electron-transfer-first”. Crystal structures show rather long central C–C bonds for 1b2 (1.5899(11) and 1.6194(8) Å) and 1h2 (1.6299(13) Å). Keywords: benzoimidazole; crystal structure; kinetics; n-dopant; reduction; Introduction Electrical

• broadening and then coalescence of some of these peaks on increasing the temperature, consistent with the room-temperature spectrum being affected by restricted rotation; interestingly the crystal structure of 1b2 contains molecules with two very different conformations (see below). The 12 dimers are

• , morpholinonyl dimers (22–52, respectively, Figure 2) have been reported in different chemical contexts [35][36][37][38]. The crystal structure of (N-DMBI)2, 1b2 (Figure 3), contains two crystallographically inequivalent molecules that are geometrically rather different from each other. One of the molecules has

Lewis acid-promoted direct synthesis of isoxazole derivatives

• Dengxu Qiu,
• Chenhui Jiang,
• Pan Gao and
• Yu Yuan

Beilstein J. Org. Chem. 2023, 19, 1562–1567, doi:10.3762/bjoc.19.113

• beneficial to the reaction outcome than electron-rich groups in the phenyl ring (3a–f). The crystal structure of product 3i is shown in Figure 2. Also, substituents in different positions of the phenyl ring in acetylene 1 smoothly reacted with NaNO2 under the reaction conditions affording the products in

• molecules containing isoxazole moieties. Crystal structure of 3i. Traditional methods for the synthesis of isoxazoles and the current approach. Reaction scope of alkynes. Conditions: 1 (0.1 mmol, 1 equiv), 2a (0.2 mmol, 2 equiv), AlCl3 (0.3 mmol, 3 equiv), NaNO2 (1 mmol, 10.0 equiv), DMAc (1.0 mL), N2