Cryptophycin unit B analogues

• Thomas Schachtsiek,
• Jona Voss,
• Maren Hamsen,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2025, 21, 526–532, doi:10.3762/bjoc.21.40

• % probability. Synthesis of modified unit B derivatives. a) HNO3, H2SO4, 0 °C, 5 h, 48% (isolated as monohydrate); b) SOCl2, MeOH, 0 °C, 90 min, then reflux, 17 h, 95%; c) Boc2O, NEt3, MeCN, H2O, rt, 22 h, 88%; d) H2, Pd/C, MeOH, rt, 25 h, 98%; e) either: formalin, NaBH3CN, HOAc, MeOH, rt, 20 min, 37%, or

Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

• Long K. San,
• Sebastian Balser,
• Brian J. Reeves,
• Tyler T. Clikeman,
• Yu-Sheng Chen,
• Steven H. Strauss and
• Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

• emission (anaerobic, dashed line) spectra in cyclohexane. Top: X-ray structure of 9,10-ANTH(BnF)2, thermal ellipsoids 50% probability. Bottom: a view down the crystallographic c-axis (left) and an off-side view (right) of the solid-state packing in the X-ray structure of 9,10-ANTH(BnF)2. Two different

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

• catalysis, rather than the more rigidly preorganized functionality required for transition-state binding. If it is easier for a cage to flex [146] or disassemble than to withstand the strain of a transition barrier, the entropic probability of effective transition-state binding is reduced (one can imagine

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

• protection: The pivaloyl (OPiv) ester is another such participating ester protection with decreased migratory properties. Moreover, the intrinsic neopentyl property of the ester significantly reduces the probability of nucleophilic attack at the oxocarbenium centre instead of the anomeric carbon, thereby

Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene

• Islam S. Marae,
• Jingyun Tan,
• Rengo Yoshioka,
• Zakaria Ziadi,
• Eugene Khaskin,
• Serhii Vasylevskyi,
• Ryota Kabe,
• Xiushang Xu and
• Akimitsu Narita

Beilstein J. Org. Chem. 2025, 21, 270–276, doi:10.3762/bjoc.21.19

• BPP-OiPr 3: a) top view, b) side view (thermal ellipsoids shown at 50% probability), and c) molecular packing of 3 in a unit cell. All the hydrogen atoms are omitted for clarity. a) UV–vis absorption spectra of BPP 2, BPP-OiPr 3, and BPP-dione 4 measured in toluene. Inset: magnified spectra of 2 and 3

Hydrogen-bonded macrocycle-mediated dimerization for orthogonal supramolecular polymerization

• Wentao Yu,
• Zhiyao Yang,
• Chengkan Yu,
• Xiaowei Li and
• Lihua Yuan

Beilstein J. Org. Chem. 2025, 21, 179–188, doi:10.3762/bjoc.21.10

• the macrocycle marginally influenced the new set of signals, suggesting formation of an n:n complex of H1 and G2. Job plot experiments afforded a stoichiometry of n:n (Figure S10, Supporting Information File 3), purporting the probability of 2:2 complexation in solution. A strong indication of the

Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone)

• Yongming Xiong,
• Xue Lin Ma,
• Shilong Su and
• Qian Miao

Beilstein J. Org. Chem. 2025, 21, 1–7, doi:10.3762/bjoc.21.1

• crystallography. Structures of compounds 1–3 and the polycyclic skeleton of 1 as mapped on a carbon schwarzite unit cell. (a) Structures of 1 in the colorless crystal; (b) structures of (P,M,P)-1 in the yellow crystal. (Carbon atoms are shown as ellipsoids at 50% probability level, in and H atoms are removed for

• clarification). Structure of (M,P,M)-3 in the crystal of 3·CH2Cl2 (carbon and oxygen atoms are shown as grey and red ellipsoid at the level of 50% probability, and hexyl groups and hydrogen atoms are removed for clarity). UV–vis absorption spectrum (black line) and emission spectrum (blue line, excited at 400

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

• )benziodoxolones (BBXs) 2 with ORTEP-3 diagram of compound 2d, using 50% probability level ellipsoids. One co-crystallized water molecule was omitted for clarity. CCDC 2368436 contains the supporting crystallographic data for this paper. Scope of the different β-sulfinyl esters 4 [32][33]. Isolated yields. rt

Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

• Yang Chen,
• Jiao He,
• Hang Lin,
• Hai-Feng Wang,
• Ping Hu,
• Bi-Qin Wang,
• Ke-Qing Zhao and
• Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

• along the main axes: ORTEP diagram showing 50% thermal ellipsoid probability: carbon (gray), fluorine (green), and hydrogen (white). POM textures, observed between crossed polarizers of Janus and dimer, F6, F12, G66, and G48, respectively, as representative examples. More images can be seen in

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

• moieties in the asymmetric axis viewed along the b-axis. (B) The asymmetric unit of 3 at 90 K viewed along the c-axis. Thermal displacement ellipsoids depicted at 50% probability. Effect of [1.1.1]propellane (1) equivalents relative to SF5Cl on selectivitya. Effect of [1.1.1]propellane (1) equivalents

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

• dihydroxyviolanthrone. Chemical structures of 2b and 3b. Optimised ground state geometries of compounds 2 and 3 calculated using B3LYP/6-311G(d,p) in the gas phase. Views of the crystal structure of 3b (left, shows displacement ellipsoids drawn at 50% probability level, right showing the twisted conformation

C–C Coupling in sterically demanding porphyrin environments

• Liam Cribbin,
• Brendan Twamley,
• Nicolae Buga,
• John E. O’ Brien,
• Raphael Bühler,
• Roland A. Fischer and
• Mathias O. Senge

Beilstein J. Org. Chem. 2024, 20, 2784–2798, doi:10.3762/bjoc.20.234

• (top right) with atomic displacements at 50% probability and hydrogen atoms omitted for clarity. Bottom left: Neoplastic representation of the molecular symmetry of compound 26. Bottom right: Neoplastic representation of the molecular symmetry of compound 27. Left: packing diagram of 27 viewed normal

• for clarity. Left: view of part 0 2 in the molecular structure of the α2β2-atropisomer, 11 in the crystal, hydrogen atoms omitted for clarity. Displacement parameters shown at 50% probability and heteroatoms labelled only. Right: view of part 0 1 of the molecular structure of the α2β2-atropisomer, 11

• in the crystal. Displacement parameters shown at 50% probability and heteroatoms labelled only. Schematic representation of porphyrin 37 showing a doubly intercalated structure. Reaction scheme for the synthesis of OET-xBrPPs and subsequent Ni(II) metalation. Scope of arm-extended dodecasubstituted

Machine learning-guided strategies for reaction conditions design and optimization

• Lung-Yi Chen and
• Yi-Pei Li

Beilstein J. Org. Chem. 2024, 20, 2476–2492, doi:10.3762/bjoc.20.212

• density estimators to efficiently explore parameter space. This method updates prior probability distributions with new experimental results and optimizes the reaction conditions by focusing on regions of the parameter space predicted to improve objectives. The power of BO lies in its ability to balance

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

• set at 50% probability level. Resorcin[n]arene synthesis. Scope of resorcin[n]arene synthesis using HFIP. aAll reactions were performed with resorcinol (1.0 mmol), aldehyde (1.0 mmol), and HCl (30 mol %) in HFIP (5 mL) at room temperature, and the yields of the reactions are given as isolated yields

Synthesis and conformational analysis of pyran inter-halide analogues of ᴅ-talose

• Olivier Lessard,
• Mathilde Grosset-Magagne,
• Paul A. Johnson and
• Denis Giguère

Beilstein J. Org. Chem. 2024, 20, 2442–2454, doi:10.3762/bjoc.20.208

• , 17, and α-ᴅ-talose 18. ORTEP diagram showing 50% thermal ellipsoid probability (except for 18): carbon (gray), oxygen (red), fluorine (green), chlorine (orange), bromine (dark red), iodine (purple), and hydrogen (white). Packing arrangement of compound compound 15; a) View down the b axis; b

• ) proposed intermolecular interactions involving halogens. ORTEP diagram showing 50% thermal ellipsoid probability: carbon (gray), oxygen (red), fluorine (green), iodine (purple), and hydrogen (white). Synthesis of halogenated talopyranose analogues 13–15, and 17 that include a 2,3-cis, 3,4-cis relationship

Evaluating the halogen bonding strength of a iodoloisoxazolium(III) salt

• Dominik L. Reinhard,
• Anna Schmidt,
• Marc Sons,
• Julian Wolf,
• Elric Engelage and
• Stefan M. Huber

Beilstein J. Org. Chem. 2024, 20, 2401–2407, doi:10.3762/bjoc.20.204

• ). Halogen bonding dimer found in the crystal structure of 7Br. Ellipsoids are shown at 50% probability (carbon: grey, nitrogen: blue, oxygen: red, bromine: orange, iodine: purple) and hydrogen atoms are shown in standard ball-and-stick model (white). Halogen and hydrogen bonding is indicated dashed. 1H NMR

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

• ellipsoids of 50% probability). The hydrogen atoms except those of hydroxy groups are omitted. The X-ray structures of catechols 6 (a) and 8 (b) (the thermal ellipsoids of 50% probability). The hydrogen atoms except those of hydroxy groups are omitted. Fragment of the pack of catechol 5 in crystal (the H

O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

• Kateryna V. Dil and
• Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

• of condensed thiazoles and tetrazoles. In silico assessment of ADMET parameters shows that most compounds meet the lead-likeness requirements. The biological profiles of new compounds demonstrate high probability levels of activity against the following pathogens/diseases: Candida albicans, Alphis

• biotargets (pathogens, species, diseases) for new synthesized compounds. If we focus on high levels of biological activity probability (80% and above), the following pathogens and diseases may be potential areas of interest: Alphis gossypii, Tripomastigote Chagas, Candida albicans, Tcruzi amastigota

Radical reactivity of antiaromatic Ni(II) norcorroles with azo radical initiators

• Siham Asyiqin Shafie,
• Ryo Nozawa,
• Hideaki Takano and
• Hiroshi Shinokubo

Beilstein J. Org. Chem. 2024, 20, 1967–1972, doi:10.3762/bjoc.20.172

• governed the regioselectivity. Reactivities of norcorroles with various reagents. Top and side views of the X-ray structures of a) 2a and b) 1 [2]. Mesityl groups and hydrogen atoms were omitted for clarity. Thermal ellipsoids are drawn at 50% probability. UV–vis–NIR absorption spectra of 1 and 2a in

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

• . Molecular structure of ethyl (Z)-4-(3-(N-(4-bromophenyl)-2-chloroacetamido)-4-(tert-butylamino)-1-chloro-4-oxobut-1-en-1-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylate (8c) according to the X-ray diffraction study. Non-hydrogen atoms are presented as thermal ellipsoids with 50% probability. Molecular structure

• of ethyl (E)-4-(4-(tert-butylamino)-3,4-dioxobut-1-en-1-yl)-3,5-dimethyl-1H-pyrrole-2-carboxylate (10d) according to X-ray diffraction data. Non-hydrogen atoms are presented as thermal ellipsoids with 50% probability. Molecular structure of ethyl 4-(3-(N-(4-bromophenyl)-2-chloroacetamido)-4-(tert

• -butylamino)-4-oxobutanoyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate (12e) according to the X-ray diffraction data. Non-hydrogen atoms are presented as thermal ellipsoids with 50% probability. The use of α,β-unsaturated aldehydes in the Ugi reaction. Comparison of isocyanide conversion conditions. Hydrolysis of

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

• (right). The thermal ellipsoid plot (Olex2) is at the 40% probability level. X-ray diffraction structure of dipyrrolopiperazinone 12c. The thermal ellipsoid plot (Olex2) is at the 40 % probability level. Synthesis of benzodiazepinones 5 from anthranilic acid derivatives. Diastereoselective one-pot

Oxidation of benzylic alcohols to carbonyls using N-heterocyclic stabilized λ³-iodanes

• Thomas J. Kuczmera,
• Pim Puylaert and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 1677–1683, doi:10.3762/bjoc.20.149

• coordination of the triflate to two positions of the iodane. Thermal ellipsoids are displayed with 50% probability. Selected bond lengths and angles: I1–N1: 2.44(4) Å; I1–O1: 1.94(9) Å; I1–O2: 3.04(1) Å; C1–I1–N1: 73.5(8)°; O1–I1–N1: 166.6(5)°; N1–I1–C1–O1: 177.8(3)°. 1H NMR spectra of the time-dependent

Generation of multimillion chemical space based on the parallel Groebke–Blackburn–Bienaymé reaction

• Evgen V. Govor,
• Vasyl Naumchyk,
• Ihor Nestorak,
• Dmytro S. Radchenko,
• Dmytro Dudenko,
• Yurii S. Moroz,
• Olexiy D. Kachkovsky and
• Oleksandr O. Grygorenko

Beilstein J. Org. Chem. 2024, 20, 1604–1613, doi:10.3762/bjoc.20.143

• the relatively high computational costs of this method, we randomly selected 50,000 compounds to represent each database. The dimension reduction algorithm uses molecular features as the starting inputs to generate a few coordinates (in this case, t-SNE1 and t-SNE2) reflecting the probability of the

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

• ORTEP diagrams of triazole products 21sd and 21vg with the thermal ellipsoids shown at 50% probability. NaAsc = sodium ascorbate. One-pot synthesis of triazole–pyrazole hybrid 21gd. aOne-pot setup yielded 21gd with unknown impurities; bwith an additional evaporation step after the triazene cleavage, a

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

• + Na]+ calcd for C54H48N6NaO18, 1091.2917; found, 1091.2885; FTIR (KBr) ν̃max: 3444, 3354, 1677, 1625, 1423, 1304, 1237, 820 cm−1. X-ray data Table 2 and Table 3 show single-crystal X-ray structure refinement data. Molecular structure of 3. Thermal ellipsoids drawn at 50% probability. Selected bond

• lengths (Å): O(1)–C(7) 1.2207 (16), N(1)–C(7) 1.3356 (17), N(1)–C(1) 1.4193 (16), N(1)–H(1) 0.8600. Molecular structure of 9. Thermal ellipsoids drawn at 50% probability. Selected bond lengths (Å): O(1)–C(7) 1.2192 (18), N(1)–C(7) 1.3396, N(1)–C(1) 1.4050 (19), N(1)–H(1) 0.8600, O(2)–C(2) 1.3674 (18), O(2

• )–C(8) 1.420 (2). Molecular structure of 13. Thermal ellipsoids drawn at 50% probability. Selected bond lengths (Å): O(3)–C(7) 1.2070 (16), O(1)–C(7) 1.3322 (16), N(1)–H(1) 0.8600, N(1)–C(6) 1.4044 (16), N(1)–C(9) 1.3440 (16), O(2)–C(9) 1.2160 (16). Molecular structure of 10. Thermal ellipsoids drawn