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

• molecular density of 1.688 g cm−3. In more details, the crystal structure reveals two short intramolecular F···H hydrogen contacts in the triphenylene core part with lengths of 2.047 Å and 2.114 Å, respectively (see Figure S33 in Supporting Information File 1). The triphenylene part of the molecule is

• values in the range of 104 and 105 L·mol−1·cm−1, respectively, as G66 possesses two triphenylene units whereas F6 only one. Both compounds, however, display substantially different photoluminescent behavior. Both F6 and G66 show a single, broad emission band with a peak maximum around 410–430 nm for F6

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

• 28138) and 258 (ε 10233); IR (film/KBr) νmax: 3337, 2935, 2878, 2849, 2234 (weak), 1671, 1624, 1595, 1542, 1457, 1257, 1199, 1145, 1119, 1046, 954, 898, 738 cm−1; ECD (MeOH) λmax, nm: 211 (Δε −15.84), 239 (Δε 7.99), 281 (Δε 0.07); 1H and 13C NMR data (Table 1); HRESIMS (m/z): [M + Na]+ calcd for

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

• Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

• -containing macrocycles and metalloporphyrins. Despite the impressive progress in photoredox catalysis, due to their most intensive electronic absorption band at 420 nm (Soret band, extinction coefficient of 105 M−1 cm−1), most porphyrin photocatalysts reported so far have been mainly utilized under blue

• coefficients around 104 M−1 cm−1), but they had not been used as photocatalysts in red light-induced processes until very recently. In 2022, Gryko and co-workers screened metal-free porphyrin macrocycles for various organic photochemical reactions that proceed via both oxidative and reductive quenching under

Extension of the π-system of monoaryl-substituted norbornadienes with acetylene bridges: influence on the photochemical conversion and storage of light energy

• Robin Schulte,
• Dustin Schade,
• Thomas Paululat,
• Till J. B. Zähringer,
• Christoph Kerzig and
• Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 3061–3068, doi:10.3762/bjoc.20.254

• spectra during irradiation as upon direct irradiation, although the reaction times were significantly higher, most likely because of the much weaker molar absorption coefficient of [Ru(phen)3](PF6)2 at 520 nm (≈900 M−1 cm−1), and the fact that the photosensitization process is bimolecular (Figure 3

Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

• Anastasia I. Ershova,
• Sergey V. Fedoseev,
• Konstantin V. Lipin,
• Mikhail Yu. Ievlev,
• Oleg E. Nasakin and
• Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

• ) in tetrachloromethane (CTC) to 588 nm (orange) in formic acid. Therefore, it was found that compound 1c was characterized by a large Stokes shift upon increasing the solvent polarity, which reached 150 nm (5824 cm−1) in formic acid. This was associated with the bathochromic shift of the emission band

• highest fluorescence efficiency of 53.4% was observed for the para-methyl derivative 1b. Solutions of stilbazoles 1 in DMSO were also characterized by large Stokes shift values, reaching 207 nm (5846 cm−1) and showing nonradiative loss of excitation energy. It should be noted that stilbazoles 1, in

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

• properties of violanthrone is traced back to 1950, when Akamatu and Inokuchi measured its electrical conductivity (σ), which was found to be 3.4 × 10−4 Ω−1 cm−1 [27][28]. The chemical structure of violanthrone allows for its modification and hence the synthesis of materials with interesting spectral

• , and a λmax at 701 nm with ε of 4.69 × 104 L mol−1 cm−1 which might lead to the contribution of 3b to the photocurrent. All previous studies suggested that violanthrone and its derivatives display electronic functionality and could be potentially used in organic electronics. Nevertheless, to the best

• nm for all compounds. Compound 3a shows a slight hypsochromic shift (λmax = 741 nm) in comparison with 3b (λmax = 745 nm) and 3c (λmax = 746 nm). All compounds displayed very similar extinction coefficients between 45000 and 48000 L mol−1 cm−1. The optical gaps (Eopt) were estimated from the onset

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

• 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

• ), 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

Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions

• Hayato Takagi,
• Çetin Çelik,
• Ryosuke Fukuda,
• Qi Guo,
• Tomohiro Higashino,
• Hiroshi Imahori,
• Yoko Yamakoshi and
• Tatsuya Murakami

Beilstein J. Org. Chem. 2024, 20, 2732–2738, doi:10.3762/bjoc.20.231

• (LUMITRONIX LED-Technik GmbH, Hechingen, Germany) containing 120 LED lamps assembled in an aluminium cylindrical container with a diameter of 8.5 cm. ESR measurements conditions: microwave frequency 9.78 GHz, microwave power 10 mW, receiver gain 5.02 × 104, modulation amplitude 1.00 G, modulation frequency

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

• with Hanessian stain (dipping into a solution of (NH4)4MoO4·4H2O (21 g) and Ce(SO4)2·4H2O (1 g) in H2SO4 (31 mL) and H2O (469 mL) and warming). Rf were measured after an elution of 7–9 cm. Column chromatographies were done with the "flash" methodology using 220–400 mesh silica or 150 mesh aluminum

• (cm−1): 3393, 3367, 3051, 2995, 2967, 2923, 2860, 2828, 1916, 1851, 1706, 1623, 1598, 1562, 1525, 1491, 1472, 1464, 1451, 1437, 1422, 1387, 1359, 1327, 1296, 1274, 1250, 1222, 1207, 1186, 1176, 1151, 1119, 1096, 1080, 1057, 1040, 1026, 1009, 972, 964, 951, 943, 929, 909, 898, 854, 818, 810, 805, 782

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

• )-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

• 54% yield (189 mg, 488 µmol, Rf 0.21 (heptane/ethyl acetate 3:2)); mp 162–164 °C; IR (ATR) ν̃: 1695 (s), 1640 (vs), 1582 (s), 1510 (s), 1446 (s), 1428 (s), 1219 (m), 813 (s) cm−1; 1H NMR (300 MHz, chloroform-d) δ 7.94–7.87 (m, 1H), 7.65–7.59 (m, 1H), 7.58 (s, 1H), 7.39–7.31 (m, 2H), 7.06–7.01 (m, 2H

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

• , 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

• , 1456, 1438, 1357, 1276, 1195, 1170, 1061, 986, 901, 851, 725 cm−1; E-isomer: vmax 2956, 2925, 2856, 1741, 1456, 1438, 1372, 1294, 1262, 1195, 1167, 1060, 989, 859, 729 cm−1. Total ion chromatogram of an extract of the scent gland of a Mangshan pit viper. Compounds A–F are the acids discussed in this

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

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

• used to hold mp samples for capillary mp determination. FTIR spectra were recorded on a Bruker Alpha apparatus with spectra further analysed with spectragryph 1.2.4 version. The absorption bands were reported in cm−1. High-resolution mass spectra were recorded in the Centre Régional de Mesures

• , 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

• MHz, DMSO-d6, δ ppm) δ 161.2, 158.1, 151.2, 141.0, 136.1, 130.5, 129.2, 129.1, 128.6, 127.4, 124.5, 124.4, 124.3, 122.1, 119.3, 117.6; FTIR (KBr 1%, cm−1) ν̃: 3423, 3274, 1643, 1601, 1591, 1542, 1504, 1450, 1393, 1025, 993, 804, 750; HRESIMS (m/z): [M + H]+ calcd for C18H14N3, 272.1182; found

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

• ) 142.15, 140.66, 138.90, 136.12, 134.80, 130.88, 130.80, 110.29, 106.31, 17.63; 19F NMR (564 MHz, CDCl3, 20 °C) δ (ppm) −157.91 (s, 10BF4−), −157.96 (s, 11BF4−); UV–vis (CH3CN) λmax, nm (ε, 105 M−1 cm−1): 272 (1.28), 337 (0.06), 349 (0.09), 524 (0.21); MALDI–TOF MS (m/z) (% intensity): (positive) 594.3

• , 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

• –19F = 246 Hz), 134.76, 131.00, 130.84, 124.30, 110.24, 106.33, 17.37; 19F NMR (564 MHz, CDCl3, 20 °C) δ (ppm) −135.76 (s, 8F, Ar-F), −166.67 (t, J = 21.4 Hz, 4F, Ar-F), −170.25 (t, J = 18.0 Hz, 8F, Ar-F); UV–vis (CH3CN, λmax, nm (ε, 105 M−1 cm−1): 272 (1.26), 337 (0.07), 349 (0.10), 524 (0.20); MALDI

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

• illustrated in Figure S1, Supporting Information File 1, a flat photo-flow reactor was predesigned comprising a wide-surface polystyrene sheet (length 50 cm × width 50 cm × height 5 cm) bearing a reactor (PFA tubing) that was manually put and hooked on the polystyrene surface (Figure S1b, Supporting

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

• , 1519, 1458, 1238, 1204, 1156, 1138, 1097, 1030, 822, 749 cm−1; HRMS–FAB (m/z): [M]+ calcd for C18H18F3NO4, 369.1182; found, 369.1209. General procedure for the ring opening of epoxides by enolates (GP-3). 4-Benzyl 5-ethyl anti,syn-tetrahydro-2-oxo-3-(trifluoromethyl)-furan-4,5-dicarboxylate (anti,syn

• = 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

Homogeneous continuous flow nitration of O-methylisouronium sulfate and its optimization by kinetic modeling

• Jiapeng Guo,
• Weike Su and
• An Su

Beilstein J. Org. Chem. 2024, 20, 2408–2420, doi:10.3762/bjoc.20.205

• Co. Ltd.) and an electronic thermometer (Beijing Xiongchuan Technology Co. Ltd.). The second mixing unit consisted of a section of PTFE piping filled with SiO2 beads (SiO2 beads, 3 mm diameter; piping, 1/4-inch diameter,10 cm length, Wuxi Hongxin Special Material Technology Co.) and an electronic

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

• ) are commercially available. General procedure for electrochemical carboxylation of 1 A test-tube-like (≈25 mm ⌀) undivided cell equipped with a Pt plate cathode (2 × 2 cm2), a Mg rod anode (6 mm ⌀, 2 cm), and a Teflon® tube (1 mm ⌀) for supplying carbon dioxide were used for the electrolysis. A

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

• the double benzyl azide adduct of DBA-OHex was 21900 cm−1 and larger than that of 6a (20700 cm−1), the Φ was 4.3%. This result suggested that replacing the hexyloxy substituents with electron-withdrawing ones enhanced the fluorescence intensity by approximately 1.6 times. Crosslinker application Using

• 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

• , 82.18, 66.30, 53.55, 31.39, 28.42, 25.54, 22.48, 13.98; FTIR ν (cm−1): 2067 (C≡C), 1730 (C=O); MALDI–TOF MS (dithranol, m/z): [M]+ calcd for C62H70N6O8, 1026.53; found, 1026.98. Previously reported regioselective double azide addition to DBA with hexyloxy substituents and molecular design in this study

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

• (365 nm, irradiance = 6.00 mW⋅cm−2), blue (455 nm, 5.16 mW⋅cm−2) or green (525 nm, 0.06 mW⋅cm−2) light. For the SAXS studies at high concentration, samples were irradiated in a custom-build LED light box with UV (365 nm) light at an irradiance of 1.24 mW⋅cm−2 for 3.5 h. This resulted in 98 ± 2 and 71

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

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

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

• chromatography (TLC) was carried out on precoated sheets with silica gel (Merck 60, 0.2 mm thick). Preparative TLC was carried out on 20 cm × 20 cm glass plates precoated with a layer of silica gel 60 (0.5 mm thick) and activated in an oven at 100 °C for 12 h. Melting points were determined with a Büchi B-540