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

• ) and C-6-methyl (1.56 ppm) and was assigned as the E-diastereomer. This assignment is further supported by the 13C NMR spectra. The major diastereomer shows C-7 at 39.7 ppm, a typical value for (E)-configured aliphatic chains with allylmethyl groups [29], while the (Z)-isomers show values around 30 ppm

• column chromatography [28]. Yellow oil: 1.95 g (45% over 2 steps); 1H NMR (CDCl3, 300 MHz) δ 9.64 (s, 1H), 3.68 (s, 3H), 2.40 (m, 3H), 2.07 (m, 1H), 1.70 (m, 1H), 1.13 (d, J = 7 Hz, 3H); 13C NMR (CDCl3, 75 MHz) δ 200.9, 173.4, 51.6, 45.5, 31.2, 25.3, 13.2; EIMS (70 eV) m/z (%): 116 (10), 113 (15), 112

• (18%); 1H NMR (CDCl3, 500 MHz) δ 4.83 (d, J = 12 Hz, 1H), 3.65 (s, 3H), 2.40–2.30 (m, 1H), 2.3–2.2 (m, 2H), 2.05–1.90 (m, 2H), 1.66 (d, J = 13 Hz, 1.2H), 1.56 (d, J = 13 Hz, 1.8H), 1.38–1.21 (m, 10H), 0.93 (d, J = 7 Hz, 1.2H), 0.93 (d, J = 1.8 Hz, 1.8H), 0.88 (t, J = 14 Hz, 3H); 13C NMR (CDCl3, 125

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

• classes. Experimental 1H and 13C NMR spectra were recorded on a Bruker Avance III 500 MHz spectrometer at 500.13 MHz (1H) and 125.73 MHz (13C) with 5 mm QNP sensors at a constant sample temperature of 298 K. The solvents were DMSO-d6, D2O, CDCl3 and the internal standard was SiMe4. Chemical shifts in the

• 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

Synthesis and cytotoxicity studies of novel N-arylbenzo[h]quinazolin-2-amines

• Battini Veeraiah,
• Kishore Ramineni,
• Dabbugoddu Brahmaiah,
• Nangunoori Sampath Kumar,
• Hélène Solhi,
• Rémy Le Guevel,
• Chada Raji Reddy,
• Frédéric Justaud and
• René Grée

Beilstein J. Org. Chem. 2024, 20, 2592–2598, doi:10.3762/bjoc.20.218

• bromides and other reagents were used as they were received from commercial suppliers, unless otherwise noted. THF and Et2O were dried over sodium-benzophenone and distilled prior to use. 1H NMR spectra were recorded at 300 and 400 MHz, and 13C NMR spectra at 75 and 100 MHz, in CDCl3 or DMSO-d6 using TMS

• , filtered and dried to get compound 3 as a brown colored solid (63% yield). 1H NMR (400 MHz, DMSO-d6, δ ppm) 9.06 (s, 1H), 8.91 (d, J = 8.0 Hz, 1H), 7.93 (d, J = 7.6 Hz, 1H), 7.76–7.64 (m, 3H), 7.56 (d, J = 8.8 Hz, 1H), 6.99 (br s, 2H); 13C NMR (75 MHz, DMSO-d6, δ ppm) 162.18, 161.31, 152.03, 136.05, 130.07

• , 129.07, 128.36, 126.72, 124.51, 124.38, 122.67, 116.44; 1H-13C NMR ((300, 75) MHz, DMSO-d6, δ ppm) (9.09 161.23), (8.95 124.31), (7.95 128.17), (7.76 129.93), (7.69 126.77), (7.61 124.66), (7.58 122.55); FTIR (KBr 1%, cm−1) ν̃: 3440, 3316, 3192, 1625, 1611, 1598, 1571, 1496, 1471, 1460, 1410, 801, 763

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

• formation of various unidentified byproducts. The obtained tetronic acids 4 are solid crystalline compounds, whose structure was proved by 1H, 13C NMR spectroscopy and high-resolution mass spectrometry. The 1H NMR spectra of the synthesized products contain characteristic signals of protons of the methyl

• solvent signals (DMSO-d6: 2.50 ppm (1H NMR) and 39.52 ppm (13C NMR)). High-resolution mass spectra (HRMS) were obtained on a Bruker micrOTOF II instrument using electrospray ionization (ESI). The melting points were determined on a Kofler hot stage apparatus. A magnetic stirrer IKA C-MAG HS 7 was used for

• -ylidene)furan-2,4(3H,5H)-dione (4a). Pale yellow powder; yield 62% (0.25 g); mp 121–123 °C; 1H NMR (300 MHz, DMSO-d6) δ 7.31–7.13 (m, 5H), 4.34 (t, J = 7.5 Hz, 2H), 2.74 (t, J = 7.6 Hz, 2H), 2.56–2.48 (m, 2H in DMSO), 2.46 (s, 3H), 2.14 (t, J = 11.8 Hz, 2H), 1.64–1.54 (m, 3H), 1.41–1.09 (m, 5H); 13C NMR

Transition-metal-free synthesis of arylboronates via thermal generation of aryl radicals from triarylbismuthines in air

• Yuki Yamamoto,
• Yuki Konakazawa,
• Kohsuke Fujiwara and
• Akiya Ogawa

Beilstein J. Org. Chem. 2024, 20, 2577–2584, doi:10.3762/bjoc.20.216

• without further purification. All solvents were used without distillation. Triarylbismuthines 1 were synthesized according to the previously reported procedures [62]. 1H, 13C{1H}, and 11B NMR spectra were recorded in CDCl3 using a Bruker AVANCE III HD 500 spectrometer at 500, 126, and 160 MHz

• , respectively. 1H chemical shifts are reported in ppm relative to Me4Si using the solvent residual as the internal standard (δ = 7.26 ppm for chloroform). 13C chemical shifts are reported in ppm relative to Me4Si, referenced to the resonances of CDCl3 (δ = 77.2 ppm). 11B chemical shifts are reported in ppm

• File 138: Investigation of the boron residue in the crude mixture by 11B NMR measurement, characterization data of the compounds, and copies of 1H NMR and 13C{1H} NMR spectra. Acknowledgements We acknowledged Dr. Tran Dat Phuc and Mr. Soichiro Mita (Osaka Prefecture University) for their initial

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

• assemblies, 2+-BF4− was further treated with NaPF6, LiB(C6F5)4, and NaPCCp for the ion-pair metathesis to afford ion pairs 2+-X− (X− = PF6−, B(C6F5)4−, and PCCp−) in 44–68% yields. The obtained ion pairs were characterized using 1H, 13C, and 19F nuclear magnetic resonance (NMR) and matrix-assisted laser

• , 0.209 mmol, 19%) as a red solid. Rf 0.33 (MeOH/EtOAc/CH2Cl2 1:2:8); 1H NMR (600 MHz, CDCl3, 20 °C) δ (ppm) 7.68 (t, J = 8.4 Hz, 3H, TATA-H), 7.51 (t, J = 7.8 Hz, 3H, Ar-H), 7.44 (d, J = 7.8 Hz, 6H, Ar-H), 6.37 (d, J = 8.4 Hz, 6H, TATA-H), 2.10 (s, 18H, CH3); 13C NMR (151 MHz, CDCl3, 20 °C) δ (ppm

• , TATA-H), 2.11 (s, 18H, CH3); 13C NMR (151 MHz, CDCl3, 20 °C) δ (ppm) 142.40, 140.77, 138.59, 136.46, 135.03, 130.73, 130.69, 110.66, 106.15, 17.61; 19F NMR (564 MHz, CDCl3, 20 °C) δ (ppm) −77.26 (d, J = 712 Hz, 6F); UV–vis (CH3CN), λmax, nm (ε, 105 M−1 cm−1): 272 (1.30), 337 (0.07), 349 (0.09), 523

Visible-light-mediated flow protocol for Achmatowicz rearrangement

• Joachyutharayalu Oja,
• Sanjeev Kumar and
• Srihari Pabbaraja

Beilstein J. Org. Chem. 2024, 20, 2493–2499, doi:10.3762/bjoc.20.213

• corresponding products (3o, 3p) in good yields. All the products obtained were characterized by 1H NMR, 13C NMR and mass spectrometry techniques. A plausible catalytic cycle has been postulated based on a literature study [13], and is shown in Figure 2. With the exposure of photocatalyst to sunlight/LED light

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

• . However, the comparison of their specific region of the 13C NMR charts and sharp peaks readily led us to qualitative understanding of the high purity of 11a-D possibly as a single diastereomer (Figure 3). Conclusion As described above, we have succeeded in the facile preparation of 2,3-epoxyesters 2 with

• column chromatography using AcOEt/Hex 1:20 as an eluent, 0.2117 g (0.86 mmol) of the title compound (86% yield) were isolated. Rf 0.52 (Hex/AcOEt 5:1); 1H NMR (300.40 MHz, CDCl3) δ 3.71–3.76 (m, 2H), 5.21 (d, J = 12.3 Hz, 1H), 5.28 (d, J = 12.3 Hz, 1H), 7.34–7.44 (m, 5H); 13C NMR (75.45 MHz, CDCl3) δ

• –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

Efficient one-step synthesis of diarylacetic acids by electrochemical direct carboxylation of diarylmethanol compounds in DMSO

• Hisanori Senboku and
• Mizuki Hayama

Beilstein J. Org. Chem. 2024, 20, 2392–2400, doi:10.3762/bjoc.20.203

• a novel, efficient, facile, and green organic method. Experimental General information 1H (400 MHz) and 13C (100 MHz) NMR spectra were recorded in CDCl3 or DMSO-d6 with a JEOL JNM-ECS400 FT NMR spectrometer. The chemical shifts δ are given in ppm with tetramethylsilane (δ 0 ppm) or DMSO (δ 2.50 ppm

• ) for 1H and CDCl3 (δ 77.0 ppm) or DMSO-d6 (δ 39.5 ppm) for 13C as internal references. J values are in Hz. Peak multiplicities are given as follows: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; br, broad. Reagents and solvents, including anhydrous DMSO, are commercially available and

• ) [36], and phenyl(thiophen-2-yl)acetic acid (2l) [30] are known compounds, and their spectral data were good agreement with previously reported values. Spectral data of the products 2 Diphenylacetic acid (2a): 1H NMR (400 MHz, CDCl3, δ) 5.05 (s, 1H), 7.25–7.34 (m, 10H); 13C NMR (100 MHz, CDCl3, δ) 56.9

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

gem-Difluorination of carbon–carbon triple bonds using Brønsted acid/Bu₄NBF₄ or electrogenerated acid

• Mizuki Yamaguchi,
• Hiroki Shimao,
• Kengo Hamasaki,
• Keiji Nishiwaki,
• Shigenori Kashimura and
• Kouichi Matsumoto

Beilstein J. Org. Chem. 2024, 20, 2261–2269, doi:10.3762/bjoc.20.194

• of spectra of 1H NMR and 13C NMR. Acknowledgements We are grateful for Kindai University Joint Research Center for use of facilities. Funding This work was supported in part by JSPS KAKENHI Grants JP20K05588 (Grant-in-Aid for Scientific Research (C)). We appreciate 2021 Kindai University Research

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

• O–O bond cleavage to give compounds 1 and 5 (Scheme 2). Owing to the high reactivity of the DAntM radical, cyclic voltammogram (CV) was measured by using the stable DAntM cation, prepared from compound 3 oxidized by antimony(V) chloride, which can be characterized by 1H, 13C NMR, and UV–vis

• . Decomposition pathway of the DAntM radical under air conditions. Supporting Information Supporting Information File 81: Synthetic procedure and compound characterization data (1H, 13C NMR, MS, melting point, X-ray crystallography) of new compounds. DFT calculation results and optimized structural Cartesian

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

• . Chemical shifts of NMR were reported in ppm relative to the residual solvent peak at 7.26 ppm for 1H NMR spectroscopy and 77.6 ppm for 13C NMR spectroscopy. Coupling constants (J) were given in Hz. The resonance multiplicity was described as s (singlet), t (triplet), and m (multiplet). FTIR spectra were

• , 300 MHz, 297 K) δ 8.40 (s, 2H), 7.80 (s, 2H), 7.40–7.18 (m, 10H), 5.53 (s, 4H), 4.34–4.29 (m, 8H), 1.74–1.71 (m, 8H), 1.37–1.32 (m, 24H), 0.92–0.88 (m, 12H); 13C NMR (CDCl3, 75 MHz, 297 K) δ 166.26, 147.55, 135.76, 133.90, 133.67, 133.36, 131.92, 130.83, 128.74, 128.70, 128.34, 120.99, 119.57, 103.11

Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides

• Haifeng Yu,
• Wanting Zhang,
• Xuejing Cui,
• Zida Liu,
• Xifu Zhang and
• Xiaobo Zhao

Beilstein J. Org. Chem. 2024, 20, 2225–2233, doi:10.3762/bjoc.20.190

• thioesters and β-keto amides by simply changing reaction conditions. These features, including a good substrate scope, excellent yield and selectivity and ease of scale-up, rendered the green hydrolysis reaction very environment-friendly, practical, and attractive. Experimental 1H and 13C{1H} NMR spectra

• were recorded on a Bruker DRX-600 spectrometer and all chemical shift values are referenced to TMS (δ = 0.00 ppm for 1H) and CDCl3 (δ = 77.16 ppm for 13C). HRMS analysis was achieved with a Bruck microTof using the ESI method. All melting points are uncorrected. Analytical TLC plates (Sigma-Aldrich

• ]. Supporting Information Supporting Information File 68: Analytic data and copies of 1H and 13C NMR spectra of compounds 2 and 3. Funding We are grateful to Funds for the Natural Science Foundation of Jilin Province, China (20240101156JC, 20210101128JC) and the Program for Innovative Research Team of Baicheng

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

• purified through silica-gel column chromatography. After successfully synthesizing these easy-to-make yet interesting molecules, they were fully characterized by means of the standard spectroscopic techniques (1H NMR, 13C NMR and HRMS). We are of the opinion that these truxene-based systems will be useful

• derivatives were successfully characterized and their structures were established by means of the 1H and 13C NMR spectroscopy, besides further confirmation by mass spectrometry (see Supporting Information File 1). The UV–vis absorption, emission and time-resolved fluorescence spectra Emission and absorption

• like 1H NMR, 13C NMR, and mass spectral data. The preliminary UV–vis absorption as well as fluorescence emission spectral data for thus prepared truxene-based compounds were recorded in chloroform and compared as well. Additionally, time-resolved fluorescence lifetime decays were also measured for thus

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

• /9.26→9.75/10.50→10.26/10.85 ppm) and become more equivalent (Δδ = 1.39→0.75→0.59 ppm accordingly). The key signal in the 13C NMR spectra is located in the regions 174.04–174.69 ppm (C=S), 151.44–151.86 ppm (C=O), and 170.15–170.91 ppm (C=Se) accordingly. Utilization of reaction products The Biginelli

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

• . Analysis of 1H NMR, 13C NMR (Table 1), and HSQC spectra revealed a formyl group (δC 186.3/δH 9.89), an olefinic methine (δC 131.1/δH 7.64), an acyl carbonyl carbon (δC 163.3), three non-protonated olefinic carbons (δC 133.4, 126.4, and 123.1), a deshielded non-protonated sp3 carbon (δC 70.1), six sp3

• -configurations were proposed for compounds 2 and 3. However, this prediction was not confirmed by chemical derivatization due to their limited availability. 1H and 13C NMR spectra of compounds 4 and 5 were superimposable to those of 1 except for methylene resonances, supporting that both 4 and 5 possess the same

• 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

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

• ], respectively, while reference [68] provides UV-spectral data of both isomers. 1H, 19F, and 13C NMR data [69][70] are given in Table 2. Chemistry of HFO-1132 Isomerization Iodine-catalyzed cis–trans isomerization of 1,2-difluoroethylene and corresponding equilibrium measurements were described in the 1960s [47

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

A new platform for the synthesis of diketopyrrolopyrrole derivatives via nucleophilic aromatic substitution reactions

• Vitor A. S. Almodovar and
• Augusto C. Tomé

Beilstein J. Org. Chem. 2024, 20, 1933–1939, doi:10.3762/bjoc.20.169

• than the oxygen due to the preferential existence of 4-hydroxypyridine in the pyridin-4-one tautomeric form [37][38][39]. The structures of dyes 3a–f, 4a, 4d and 4f were unambiguously established through their 1H, 13C and 19F NMR and mass spectra. The 1H NMR spectra of the symmetrical compounds

• apparatus. NMR spectra were recorded on a Bruker DRX 300 Avance operating at 300.13 MHz (for 1H NMR), at 75.47 MHz (for 13C NMR) and 282 MHz (for 19F NMR). Deuterated chloroform (CDCl3) was used as the solvent and tetramethylsilane (TMS) as the internal reference. The chemical shifts (δ) are expressed in

• ), 5.03 (s, 4H); 13C NMR (75 MHz, CDCl3) δ (ppm) 161.7, 147.2, 138.01, 129.8, 129.6, 125.6, 110.0, 29.7; 19F NMR (282 MHz, CDCl3) δ (ppm) −138.11 to −138.29 (m, 4F), −149.90 (t, J = 21.4 Hz, 2F), −157.63 to −157.91 (m, 4F); ESIMS m/z: 717.0 (M + H+, 100%). General procedure for the nucleophilic aromatic

Novel oxidative routes to N-arylpyridoindazolium salts

• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2024, 20, 1906–1913, doi:10.3762/bjoc.20.166

• -arylpyridoindazolium salts S1–S3 was confirmed with HRMS and 1H, 13C and 19F NMR data; the complete assignment of the signals was performed using 2D NMR methods. The N–N bond formation was additionally confirmed via comparison of the 1H spectra for the salts and their diarylamine precursors. The absence of the signals

Electrochemical radical cation aza-Wacker cyclizations

• Sota Adachi and
• Yohei Okada

Beilstein J. Org. Chem. 2024, 20, 1900–1905, doi:10.3762/bjoc.20.165

• cyclization.a Supporting Information Supporting Information File 6: General remarks and characterization data, including copies of 1H and 13C NMR spectra. Funding This work was supported in part by JSPS KAKENHI Grant No. 22K05450 (to Y. O.), and TEPCO Memorial Foundation (to Y. O.).

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

• Ivana Weisheitelová,
• Radek Cibulka,
• Marek Sikorski and
• Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

• -aryldeazaalloxazines in any case. Finally, the unsubstituted derivative 2x was formed with a yield of only 15% using DMF/AlCl3. The isolated products 2a–x were characterized by 1H, 13C NMR and mass-spectral methods. The 1H NMR spectra of 5-aryldeazaalloxazines 2a–x, along with protons of aryl substituents of aldehyde

• moiety and pyrimido[4,5-b]quinoline core, contained singlets with 3H intensity of the N(1)–CH3 and N(3)–CH3 groups of the barbituric acid fragment at 3.20–3.56 ppm. The 13C NMR spectra of 5-aryldeazaalloxazines 2a–x were represented by groups of singlets at 27.9–57.2 and 100.0–160.5 ppm. The

• unexpected structure of product 6 was confirmed by 1H, 13C NMR and mass spectrometry. The main feature of the 1H NMR spectrum of compound 6 is the absence of the signals of the aromatic aldehyde moiety and the appearance of the singlet of the 5-CH methyne group at 9.56 ppm and the singlets of the protons of

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

• Samuel M. G. Dearman,
• Xiang Li,
• Yang Li,
• Kuldip Singh and
• Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

• ppm and 7.96 ppm, respectively, for iodine(V) product 6. Similarly, the 13C NMR spectrum showed a major downfield shift for the aromatic carbon attached to iodine from a chemical shift of 105.3 ppm in iodine(III) substrate 10 to 132.4 ppm for difluoroiodane(V) product 6. Since Selectfluor was shown to

• deposition numbers CCDC: 2351949 and 2351950. Supporting Information File 18: Experimental procedures, characterisation data, DFT calculations and 1H, 13C and 19F NMR spectra and crystallographic data. Funding SMGD and AMS thank the School of Chemistry, University of Leicester, for their generous support