Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives

• Shuxian Qiu,
• Duan Dong,
• Jiahui Li,
• Huiting Wen,
• Jinpeng Li,
• Yu Yang,
• Shengxian Zhai and
• Xingyuan Gao

Beilstein J. Org. Chem. 2024, 20, 3299–3305, doi:10.3762/bjoc.20.274

• available 2-bromo-4-fluoro-1-nitrobenzene, featuring a noble-metal-free system, mild reaction conditions, and a good yield, especially for the final Cs2CO3-facilitated nucleophilic substitution (77–91% yield). The characterization data obtained from IR and NMR spectroscopy (1H, 13C, 19F, and 31P) as well as

• 2–7 was performed by NMR spectroscopy, which confirmed the synthetic outcomes (Figures S1–S11, Supporting Information File 1). The structures of compounds 7 were further confirmed by HRMS and IR analyses (Figures S12–S18, Supporting Information File 1). In addition, the chemical structure of 7-H was

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• reaction cascade starting from diarylalkynes 8, which involves indole formation/peri-C–H annulation and N-dealkylation reactions to afford acenaphthylene-fused indole products 9 (Scheme 1b) [41]. Recently, Takeuchi and co-workers reported an effective Ir-catalyzed [2 + 2 + 2] cycloaddition between 1,8

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

• , 126.3, 123.8, 122.7, 118.3, 115.4, 43.3, 31.9, 29.5, 29.3, 27.3, 27.1, 22.7, 14.2; IR (ATR): 2959, 2929, 2856, 1661, 751 cm−1; HRMS–DART+ (m/z): [M + H]+ calcd for C24H27N2O, 359.2123; found, 359.2134. Structures of multiply fused heterocyclic compounds composed of pyridine rings. Synthesis of C–H

Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina

• Shin-ichiro Kurimoto,
• Kouta Inoue,
• Taito Ohno and
• Takaaki Kubota

Beilstein J. Org. Chem. 2024, 20, 3215–3220, doi:10.3762/bjoc.20.267

• existence of a substituted benzenoid chromophore was suggested by the UV absorption maximum at 258 nm. The presence of hydroxy and/or amino groups and a carbonyl group was indicated by IR absorptions at 3337 cm−1 and 1671 cm−1, respectively. The analysis of the HSQC spectrum, along with the 1H and 13C NMR

• cyano group in compound 1 [13][14][15]. In the IR spectrum of 1, an absorption attributed to the stretching vibration of the C≡N bond was observed at 2234 cm−1, although its intensity was very weak (Figure S8 in Supporting Information File 1). It is known that when an atom with an electron-withdrawing

• inductive effect is attached to the carbon bearing the cyano group, the intensity of the absorption derived from the cyano group in the IR spectrum decreases significantly. This phenomenon has been reported, particularly in compounds where halogen or oxygen atoms are bonded to the carbon bearing the cyano

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

• recombination of radicals F and D leads to the product 67. Photochemical peroxidation of isochromans and other benzylic C(sp3)–H substrates 68 with TBHP was developed using Ir(ppy)3 as the photocatalyst and Bronsted acid as an additive (Scheme 25) [68]. Visible light irradiation of [IrIII(ppy)3] to give the

• –peroxidation of alkenes 155 with TBHP and aldehydes 156 through visible-light photocatalysis was developed using fac-Ir(ppy)3 as the photoredox catalyst (Scheme 49) [113]. Under visible light irradiation, the excited state Ir(III)* is generated, and the single electron transfer of Ir(III)* with TBHP results in

• tert-butoxy radical A. Generated Ir(IV) can produce tert-butylperoxy radical D from TBHP. Hydrogen atom abstraction from aldehyde 156 with tert-butoxy radical A leads to acyl radical B, which adds to alkene 155 to form the C-centered radical C. Two pathways are then possible for the formation of the

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

• , 117.1 (CAr), 91.1 (CN), 56.8, 29.4, 20.9 (CAliphatic), respectively. In its mass spectrum, the calculated value matched the found value m/z 419 calculated for [M]+ C28H25N3O. In the IR spectrum, the absorption peak index in 2213 is related to the CN group. For final confirmation, the derivative 4h was

• analysis, mass spectrum, and IR are consistent with the structure (for details see Supporting Information File 1). Finally, a single crystal X-ray analysis of compound 6a was performed, confirming the structure (Figure 4). The proposed mechanism for an isocyanide-based multicomponent domino reaction for

• on a Bruker Avance spectrometer at 300.13 MHz and 75.47 MHz, respectively. IR spectra were created on a Thermo Nicolet Nexus 470 FT-IR spectrometer in cm−1. Mass spectra with an HP (Agile Technologies) 5975C Mass Selective Detector were used to confirm the mass of the synthesized products. The PL

Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates

• Kento Iwai,
• Akari Hikasa,
• Kotaro Yoshioka,
• Shinki Tani,
• Kazuto Umezu and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2024, 20, 2827–2833, doi:10.3762/bjoc.20.238

• . Ltd. and purified by distillation. 1H and 13C{1H} NMR spectra were recorded on a JEOL JMN-ECZ400S spectrometer (400 MHz and 100 MHz, respectively) using TMS as internal standard. The assignments of the 13C{1H} NMR signals were reaffirmed by DEPT experiments. IR spectra were recorded with a JASCO FT/IR

• ), 84.9 (C), 82.6 (C), 63.8 (CH2), 61.0 (C), 21.6 (CH3), 14.0 (CH3); IR (KBr, ATR) vmax: 1754, 1672, 1477, 1281, 1214, 1071, 751 cm−1; HRMS–APCI-TOF (m/z): [M + H]+ calcd for C23H24NO5, 394.1649; found, 394.1672. When other alkynes and N,O-acetals were used, the experiments were conducted in the same way

• ), 128.5 (CH), 128.3 (C), 128.1 (CH), 126.8 (CH), 126.2 (CH), 123.4 (C), 60.9 (CH2), 31.6 (CH2), 20.2 (CH3), 13.3 (CH3); IR (KBr, ATR) vmax: 1735, 1710, 1178, 1087, 1054, 720 cm−1; HRMS–APCI-TOF (m/z): [M + H]+ calcd for C20H20NO3, 322.1438; found, 322.1458. When other propargylamines were used, the

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

• borylation of porphyrin 13 to yield 46. Mean geometrical parameters of OET-meta/para-ArylPP and out-of-plane and in-plane distortion magnitudes. Supporting Information Supporting Information File 9: Experimental methods, synthetic procedures, 1H, 11B and 13C NMR, VT-NMR, UV–vis, IR, HRMS (m/z)-APCI and HRMS

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light

• Francesco Gambuti,
• Jacopo Pizzorno,
• Chiara Lambruschini,
• Renata Riva and
• Lisa Moni

Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230

• %) due to difficulties in the purification. IR spectra were recorded as solid, oil, or foamy samples, with the ATR (attenuated total reflectance) method. TLC analyses were carried out on pre-coated Merck silica gel 60 F254 plates or Aluminum oxide on TLC-plates and viewed at UV (254 nm) and developed

• without further purification. Graphene oxide (GO) was purchased from Graphenea. All products were characterized by 1H,13C, 19F (when fluorine is present) NMR, IR and HRMS. General procedure for the one-pot synthesis of spiro[indole-isoquinoline] 3a: A solution of N-phenyltetrahydroisoquinoline (1 equiv

• °C at 451 nm (blue LEDs) under magnetic stirring for 24 h. The reaction mixture was treated with Et3N (3 equiv, 1.44 mmol, 200 µL), concentrated and the residue was purified by column chromatography on silica gel with PE/Et2O (from 85:15 to 75:25) to give 3a (121 mg, 61%), as yellow oil; IR (ATR) ν̃

Synthesis of benzo[f]quinazoline-1,3(2H,4H)-diones

• Ruben Manuel Figueira de Abreu,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228

• doublet, m = multiplet; they are further described by their coupling constants J. Infrared spectra (IR) were measured as attenuated total reflection (ATR) experiments using a Nicolet 380 FT-IR spectrometer. The signals were characterised by their wavenumbers and corresponding absorption as very strong (vs

• )-dione (4g). Compound 4g was obtained as a brown solid in 58% yield (58.3 mg, 184 µmol, Rf 0.19 (heptane/ethyl acetate 3:2)); mp 152–154 °C; IR (ATR) ν̃: 1695 (s), 1642 (vs), 1582 (s), 1493 (s), 1440 (s), 1421 (s), 1176 (m), 1079 (m), 756 (s) cm−1; 1H NMR (500 MHz, chloroform-d) δ 7.51–7.48 (m, 2H), 7.45

• acetate 3:2)); mp 187–189 °C; IR (ATR) ν̃: 1708 (s), 1654 (vs), 1574 (s), 1514 (s), 1506 (s), 1446 (s), 1423 (s), 1232 (s), 1158 (s) cm−1; 1H NMR (500 MHz, chloroform-d) δ 7.48–7.44 (m, 2H), 7.26–7.22 (m, 2H), 7.15–7.10 (m, 2H), 7.06–7.02 (m, 2H), 3.70 (s, 3H), 3.44 (s, 3H); 19F NMR (471 MHz, chloroform-d

5th International Symposium on Synthesis and Catalysis (ISySyCat2023)

• Anthony J. Burke and
• Elisabete P. Carreiro

Beilstein J. Org. Chem. 2024, 20, 2704–2707, doi:10.3762/bjoc.20.227

• imidazolium ring formation. The resulting carbene was metalated at the C2 position with Au(I), Cu(I), and Ir(I), obtaining an L-shaped NHC ligand scaffold. Līpiņš et al. introduced a new method for synthesizing 4-azido-6,7-dimethoxy-2-alkyl/arylsulfonylquinazolines, which are key intermediates in the

Transition-metal-free decarbonylation–oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones

• Bhaskar B. Dhotare,
• Seema V. Kanojia,
• Chahna K. Sakhiya,
• Amey Wadawale and
• Dibakar Goswami

Beilstein J. Org. Chem. 2024, 20, 2655–2667, doi:10.3762/bjoc.20.223

• rearrangement of 2-aryloxybenzaldehydes yielded 2-hydroxybenzophenone [12]. Pd-catalyzed o-hydroxylation of benzophenones gave moderate yield of the title compound, and Br-substituted substrates were found to be not compatible with this method [13]. Various metals (Rh, Cu, Ir etc.) were applied to catalyze the

The scent gland composition of the Mangshan pit viper, Protobothrops mangshanensis

• Jonas Holste,
• Paul Weldon,
• Donald Boyer and
• Stefan Schulz

Beilstein J. Org. Chem. 2024, 20, 2644–2654, doi:10.3762/bjoc.20.222

• -dimethylalk-5-enoates in a homologous series from C11–C16, were characterized by GC–MS and GC–IR analysis and various microderivatization reactions including hydrogenation and esterification leading to methyl and pyridylmethyl esters. In addition, dimethyloxazoline formation helped to localize the double bond

• ) were observed with similar mass spectra. The amount of secretion available and the complex mixture did not allow for the isolation of enough material for NMR analysis. Therefore, for the structure elucidation of these unknown compounds, we used different analytical methods, including GC–MS, GC–IR, and

• , Figure S1), confirming the acid functional group in the natural compounds. In support of these data, GC/IR analysis of Dm (Supporting Information File 1, Figure S2) showed strong carbonyl bands at 1741 cm−1 accompanied by two intermediate bands at 1198 cm−1 and 1177 cm−1, characteristic of ester valence

Efficient modification of peroxydisulfate oxidation reactions of nitrogen-containing heterocycles 6-methyluracil and pyridine

• Alfiya R. Gimadieva,
• Yuliya Z. Khazimullina,
• Aigiza A. Gilimkhanova and
• Akhat G. Mustafin

Beilstein J. Org. Chem. 2024, 20, 2599–2607, doi:10.3762/bjoc.20.219

• 13C and 1H NMR spectra are given in parts per million (ppm). Elemental analyses were performed on a CHNS Euro-EA 3000 automatic analyzer. Melting points were determined on combinated Boetius tables. IR spectra were obtained on an IR Prestige-21 Shimadzu spectrophotometer in KBr pellets. Freshly

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

• group. Based on extensive mechanistic studies, they proposed the formation of a formal Ni(IV) complex during the process. Remarkably, nickel proved to be uniquely effective for this protocol, as other transition-metal catalysts based on Cu, Co, Pd, Ir, Ru, and Rh did not catalyze the reaction (Scheme 36

• functionalization of complex molecules without the need for directing groups, thereby simplifying the synthesis process and enhancing the exploration of new drug candidates. 1.3.7 Ir-assisted anodic oxidation. An Ir-electrocatalyzed vinylic C(sp2)–H activation method for the preparation of α-pyrones via annulation

• mechanism. Initially, C–H activation occurs, resulting in the formation of a cyclometalated Ir(III) intermediate. Ligand exchange with the alkyne substrate, followed by migratory insertion, leads to the formation of a seven-membered 18-electron Ir(III) complex. This complex then undergoes reductive

Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles

• Yutaro Miyashita,
• Sae Someya,
• Tomoko Kawasaki-Takasuka,
• Tomohiro Agou and
• Takashi Yamazaki

Beilstein J. Org. Chem. 2024, 20, 2421–2433, doi:10.3762/bjoc.20.206

• 49.4 (q, J = 2.5 Hz), 52.7 (q, J = 42.2 Hz), 68.0, 121.4 (q, J = 276.0 Hz), 128.5, 128.7, 128.8, 134.3, 165.6; 19F NMR (282.65 MHz, CDCl3) δ −75.12 (d, J = 4.5 Hz); IR (neat) ν: 3944, 3689, 3054, 2987, 2685, 2306, 1756, 1456, 1422, 1382, 1341, 1265, 1169, 1089, 988, 929, 896, 664 cm−1; Anal. calcd for

• –6.81 (m, 4H), 7.26–7.36 (m, 5H); 13C NMR (75.45 MHz, acetone-d6) δ 55.5, 59.3, 67.9, 70.0 (q, J = 30.2 Hz), 114.8, 117.7, 124.1 (q, J = 283.5 Hz), 128.5, 128.6, 128.7, 134.4, 139.5, 154.3, 170.2; 19F NMR (282.65 MHz, CDCl3) δ −76.83 (d, J = 9.0 Hz); IR (KBr) ν: 3454, 3315, 2955, 2924, 2854, 2360, 1741

• = 34.1 Hz), 122.5 (q, J = 282.9 Hz), 128.61, 128.63, 128.8, 134.0, 165.1, 165.6, 167.4; 19F NMR (282.65 MHz, CDCl3) δ −75.84 (d, J = 6.8 Hz); IR (neat) ν: 2987, 1813, 1742, 1457, 1389, 1321,1218, 1182, 1128, 1023, 972, 755 cm−1; HRMS–FAB+ (m/z): [M + H]+ calcd for C16H16F3O6, 361.0893; found, 361.0911

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

• , compounds 6–9 are products of alkylation of the nitrogen atom of the heterocycle. Thiones 6–9 were obtained in 40–79% yield (Scheme 1,b). The structures of synthesized compounds were confirmed by the spectral methods IR-, 1H NMR, 13C{1H} NMR spectroscopy (Figures S1–S18 in Supporting Information File 1

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

• , indicating that the developed tandem protocol does not depend on the presence of the N-oxide moiety in the parent heterocycle. All synthesized triazinones 1 and 7 were fully characterized by IR, 1H and 13C NMR spectroscopy, and high-resolution mass spectrometry. The structure of compounds 1b and 7h was

• . Supporting Information Supporting Information File 96: Experimental procedures, characterization data of all products, copies of 1H, 13C NMR, 15N spectra of new compounds, DSC curves,X-ray crystallographic data and copies of IR spectra. Acknowledgements The crystal structure determination was performed at

Synthesis and reactivity of the di(9-anthryl)methyl radical

• Tomohiko Nishiuchi,
• Kazuma Takahashi,
• Yuta Makihara and
• Takashi Kubo

Beilstein J. Org. Chem. 2024, 20, 2254–2260, doi:10.3762/bjoc.20.193

• Figure 6a and 6b, respectively. The DAntM radical exhibited a forbidden near-IR (NIR) band centered at 900 nm and relatively intense bands at 580 and 540 nm, whose spectral pattern is similar to the spectrum pattern of the TAntM radical [17]. The result of TD-DFT calculations could reproduce the obtained

Metal-free double azide addition to strained alkynes of an octadehydrodibenzo[12]annulene derivative with electron-withdrawing substituents

• Naoki Takeda,
• Shuichi Akasaka,
• Susumu Kawauchi and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2024, 20, 2234–2241, doi:10.3762/bjoc.20.191

• recorded on a JASCO FT/IR-4100 spectrometer in the range from 4000 to 600 cm−1. MALDI–TOF mass spectra were measured on a Shimadzu/Kratos AXIMACFR mass spectrometer equipped with a nitrogen laser (λ = 337 nm) and pulsed ion extraction, which was operated at an accelerating potential of 20 kV. THF solutions

Allostreptopyrroles A–E, β-alkylpyrrole derivatives from an actinomycete Allostreptomyces sp. RD068384

• Marwa Elsbaey,
• Naoya Oku,
• Mohamed S. A. Abdel-Mottaleb and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2024, 20, 1981–1987, doi:10.3762/bjoc.20.174

• total 6.5 mg of 1, 3.1 mg of 2, 2.6 mg of 3, 7.2 mg of 4, and 5.6 mg of 5 from 12 L culture. Allostreptopyrrole A (1): greenish yellow amorphous solid; UV (MeOH) λmax nm (log ε) 234 (3.86), 273 sh (3.44); IR (ATR) νmax: 3275, 2964, 2928, 2855, 1658, 1554, 1418 cm−1; 1H and 13C NMR data, see Table 1

• ; HRESITOFMS (m/z): [M – H]– calcd for C15H22NO4, 280.1554; found, 280.1550. Allostreptopyrrole B (2): greenish yellow amorphous solid; +15 (c 0.10, MeOH); UV (MeOH) λmax, nm (log ε): 235 (3.87), 273 sh (3.49); IR (ATR) νmax: 3263, 2964, 2925, 2854, 1658, 1556, 1417 cm−1; 1H and 13C NMR data, see Table 2

• ; HRESITOFMS (m/z): [M – H]– calcd for C15H22NO4, 280.1554; found, 280.1554. Allostreptopyrrole C (3): greenish yellow amorphous solid; −6.1 (c 0.10, MeOH); UV (MeOH) λmax, nm (log ε): 235 (3.82), 276 sh (3.46); IR (ATR) νmax: 3265, 2925, 2856, 1657, 1555, 1417 cm−1; 1H and 13C NMR data, see Table 2

1,2-Difluoroethylene (HFO-1132): synthesis and chemistry

• Liubov V. Sokolenko,
• Taras M. Sokolenko and
• Yurii L. Yagupolskii

Beilstein J. Org. Chem. 2024, 20, 1955–1966, doi:10.3762/bjoc.20.171

• catalyst (Pd, Pd, Pt, Rh, Ru, Ir, Ni/Cu, Ag, Au, Zn, Cr, Co, Scheme 5) [62][63]. Further, 1,2-Dichloroethylene was reacted with hydrogen fluoride in the presence of metal fluorides or transition metals (Cr, Al, Co, Mn, Ni, Fe) to form 1,2-difluoroethylene (Scheme 6) [56][58]. In patents [59][60], an exotic

• is not clear which of these can be used for the commercial production of HFO-1132. Physical properties of HFO-1132 The physical properties of the E- and Z-isomers of HFO-1132 are summarized in Table 1 [47][64][65][66]. IR-spectral data of (E)- and (Z)-HFO-1132 can be found in references [67] and [50

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

• (dd, J = 8.9, 1.9 Hz, 1H), 4.17 (s, 3H), 3.92 (s, 3H); 13C{1H} NMR (75 MHz, DMSO-d6) δ 161.8, 139.4, 132.7, 129.4, 124.1, 123.0, 116.0, 113.0, 51.8, 36.6; IR (KBr disk): 1722, 1466, 1433, 1395, 1354, 1289, 1200, 1183, 1153 cm−1; HRESIMS (m/z): [M + H]+ calcd for C10H10BrN2O2+, 268.9921; found

• (s, 3H); 13C{1H} NMR (75 MHz, DMSO-d6) δ 159.4, 144.7, 129.3, 123.6, 123.2, 122.8, 120.0, 118.0, 64.2, 52.2, 41.4, 14.4, 13.9; IR (KBr disk): 1708, 1459, 1442, 1392, 1326, 1252, 1196 cm−1; HRESIMS (m/z): [M + H]+ calcd for C10H10BrN2O2+, 268.9921; found, 268.9918. Indazole-containing bioactive

• : Characterization of all compounds (1H NMR, 13C NMR, LC–MS, IR), and crystallographic methods and data for products P1 and P2. Supporting Information File 23: DFT methods, relative energy comparisons, TS imaginary frequencies, and XYZ coordinates. Supporting Information File 24: GoodVibes outputs. Acknowledgements

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

• 1,2,5,6- [9][10] and 2,3,6,7-naphthalene diimides (NDIs) have been produced and utilized in electronically active polymers (Figure 1). The linear extension of 1,4,5,8-naphthalene diimide to produce tetracene [11] and hexacene [12] diimides, some with interesting properties such as near-IR absorption, has

New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)

• Fátima C. Teixeira,
• António P. S. Teixeira and
• C. M. Rangel

Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145

• 400 (1H 400 MHz, 13C NMR 100 MHz, 31P 162 MHz) spectrometer, with the chemical shifts (δ) indicated in ppm, and coupling constants (J) in Hz. The FTIR characterization of the dopants was done on a PerkinElmer FT-IR Spectrum BX Fourier Transform spectrometer, using KBr discs, and the characterization