Recent advances in the electrochemical synthesis of organophosphorus compounds

• Babak Kaboudin,
• Milad Behroozi,
• Sepideh Sadighi and
• Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

• phosphite in an undivided cell. The C–P product was selectively produced using n-Bu4NClO4 as electrolyte and carbon and platinum electrodes as the anode and cathode at a constant current for 4 h. Using n-Bu4NI instead of KI resulted in a similar outcome, but KBr was less effective (Table 4). The desired C2

• electrochemical process for the simultaneous C–H phosphorothiolation and S- to C-[1,4]-phosphoryl migration at room temperature. The reaction was carried out in an undivided cell using a carbon plate as the anode and platinum as the cathode at a constant current of 10 mA in the presence of KBr as a key mediator

Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

• Kirill A. Gomonov,
• Vasilii V. Pelipko,
• Igor A. Litvinov,
• Ilya A. Pilipenko,
• Anna M. Stepanova,
• Nikolai A. Lapatin,
• Ruslan I. Baichurin and
• Sergei V. Makarenko

Beilstein J. Org. Chem. 2025, 21, 340–347, doi:10.3762/bjoc.21.24

• . In turn, in the IR spectra (KBr) of compounds 7a–f, absorption bands of the ester fragment in the region of 1714–1750 cm−1 and absorption bands of the carbonyl group of the amide fragment in the region of 1674–1688 cm−1 are observed, which suggests the existence of these compounds in the solid phase

• expands the possibilities of further transformation and obtaining new compounds on their basis. Experimental General information IR spectra were recorded on a Shimadzu IRPrestige-21 FT-IR spectrometer for samples in KBr pellets over 400–4000 cm−1 range. The electronic absorption spectra were recorded on a

Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C–F bond activation

• Takeshi Fujita,
• Haruna Yabuki,
• Ryutaro Morioka,
• Kohei Fuchibe and
• Junji Ichikawa

Beilstein J. Org. Chem. 2025, 21, 146–154, doi:10.3762/bjoc.21.8

• Hz, 1H), 7.49–7.46 (m, 2H), 7.35 (dd, J = 7.7, 7.6 Hz, 1H), 7.16 (d, J = 7.6 Hz, 1H), 2.44 (s, 3H); 13C NMR (126 MHz, CDCl3) δ 155.6, 152.3, 138.5, 130.5, 130.4, 129.1, 128.8, 128.7, 127.6, 126.2, 125.3, 125.1, 124.6, 124.5, 123.4, 121.9, 112.3, 100.3, 21.5; IR (KBr): 3051, 1606, 1487, 1387, 1280

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

• 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

Hypervalent iodine-mediated intramolecular alkene halocyclisation

• Charu Bansal,
• Oliver Ruggles,
• Albert C. Rowett and
• Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 3113–3133, doi:10.3762/bjoc.20.258

• functional groups and avoids the use of highly toxic and corrosive bromine. Approaches using this approach are outlined below. Nitrogen nucleophiles In 2007, aminobromocyclisation of homoallylic sulfonamides 53 was reported by Fan, Wang and co-workers (Scheme 29) [50]. Using PhI(OAc)2 as an oxidant with KBr

• with KBr and NaOAc, a range of chiral 2,3,6-trisubstituted bromomethylmorpholines 73 were synthesised in excellent yields and diastereoselectivities that ranged from nothing to excellent depending on the substrate. The enantioselectivity of the reaction was not measured. The authors suggested a

Synthesis of fluorinated acid-functionalized, electron-rich nickel porphyrins

• Mike Brockmann,
• Jonas Lobbel,
• Lara Unterriker and
• Rainer Herges

Beilstein J. Org. Chem. 2024, 20, 2954–2958, doi:10.3762/bjoc.20.248

• 4 (65%), 5 (50%), and 6 (40%) by chromatography was straightforward. However, the subsequent oxidation of the alcohol with the usual oxidizing agents (Jones reagent, KMnO4, etc.) was not successful. A radical oxidation with TEMPO, potassium bromide (KBr), sodium hypochlorite (NaOCl), and sodium

• ether synthesis with 2-hydroxy-3,4,5-trimethoxybenzaldehyde (21). Conditions: a) K2CO3, benzyl bromide, abs. MeCN, N2, reflux, 18 h; b) TEMPO, KBr, NaOCl, NaHCO3, MeCN, rt, 76 h; c) MeOH, H2SO4, reflux, 18 h; d) Pd/C, H2, EtOH, rt, 24 h; e) Tf2O, pyridine, DCM, rt, 18 h. Synthesis of perfluoroalkyl

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

Mechanochemical difluoromethylations of ketones

• Jinbo Ke,
• Pit van Bonn and
• Carsten Bolm

Beilstein J. Org. Chem. 2024, 20, 2799–2805, doi:10.3762/bjoc.20.235

• with too much of it, side reactions occurred [31][32][33]. Next, various grinding auxiliaries were investigated at a reaction time of 60 min (Table 1, entries 6–9). A similar yield of 3a (69%) was obtained with KCl or KBr instead of CsCl (Table 1, entries 6 and 7 versus entry 3). Using NaCl, gave 3a in

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

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

• , 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

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

• -prefunctionalized materials in order to proceed with the rearrangement. However, the Achmatowicz reaction or similar methodologies involve a catalytic to stoichiometric amount of oxidants such as m-CPBA [7], PCC [8], Br2 [9], NBS [10], DMDO [11], KBr/Oxone [12], Na2S2O8 [13], photosensitizers/O21 [14], or Me2S [15

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

• –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

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

• Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

• aldehyde hydrazones and alkenes for the preparation of pyrazolines was proposed by Tong, Song, et al., achieving similar efficiency using oxone/KBr as an environmentally friendly oxidative system [59]. Most recently, Zhou and Ma et al. described the electrochemical access to 3‑aminopyrazoles 79 from

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

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

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

• , 58.2, 56.7, 55.2, 53.3, 52.2, 51.3, 50.4, 50.2, 32.4, 31.5, 31.2, 26.2, 25.7, 25.6, 18.2 ppm; IR (KBr) ν: 3435, 2931, 2862, 2360, 1737, 1698, 1587, 1547, 1435, 1385, 1335, 1251, 1204, 1125, 1092, 1001, 977, 895, 853, 792 cm−1; HRESIMS (m/z): [M + Na]+ calcd. for C41H46NaN2O11, 765.2994; found, 765.2993

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

• –vis spectra of all polymers were recorded on a PerkinElmer Lambda 365 UV–vis spectrophotometer. FTIR spectra were recorded on an Agilent Cary 630 KBr module. Reaction of aniline with SeO2 To a reaction vessel, 10 mL of acetonitrile were introduced along with aniline (10 mmol, ≈0.91 mL) and selenium

• )selanyl)aniline (2): Black solid (28.2 mg); 77Se NMR (95 MHz, DMSO-d6, δ) 371.2, 296.1; HRESIMS (m/z): [M + H]+ calcd for C12H13N2Se (ortho/para), 265.0238; found, 265.0229, [M + H − PhNH2]+ calcd for C6H6NSe (ortho/para), 172.0238; found, 171.9667; FTIR (KBr) ν̃max: 3436, 3354, 3220, 3026, 1595, 1490

• , 301.1408, [2M + K]+ calcd for C28H24KN4O4, 519.1429; found, 518.8590; FTIR (KBr) ν̃max: 3354, 3063, 3019, 2840, 1684, 1602, 1528, 1252, 1021, 760 cm−1. Reaction of o-anisidine with SeO2 A round-bottom flask was charged with 10 mL of acetonitrile, o-anisidine (10 mmol, ≈1.13 mL), and selenium dioxide (15

Light on the sustainable preparation of aryl-cored dibromides

• Fabrizio Roncaglia,
• Alberto Ughetti,
• Nicola Porcelli,
• Biagio Anderlini,
• Andrea Severini and
• Luca Rigamonti

Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95

• redox couple NaBr–NaBrO3 in acidic media [40][41]. Other variations include the system KBr–Oxone® [42]. However, based on a literature review, we concluded that unparalleled efficiency and sustainability can be achieved through the well-established redox equilibria between hydrogen peroxide and halide

Chemical and biosynthetic potential of Penicillium shentong XL-F41

• Ran Zou,
• Xin Li,
• Xiaochen Chen,
• Yue-Wei Guo and
• Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

• ; FeSO4 1 µM; KI 2 g/L, KCl 2 g/L, KBr 2 g/L, NaNO2 2 g/L; H2O2 20 µM; (methyl jasmonate) MeJA 10 µM). XISR III medium (yeast extract 4 g/L; soy flour 10 g/L; glucose 30 g/L; MgCl2 1 µM; FeSO4 1 µM; KI 2 g/L, KCl 2 g/L, KBr 2 g/L, NaNO2 2 g/L; H2O2 20 µM; MeJA 10 µM; 5-azacytidine 6 µM; suberoylanilide

• isolation of compound 3 (2.19 mg). Physical and spectroscopic data of compounds 1–3 Shentonin A (1): light green solid; [α]D20 +40.0 (c 0.17, CH3OH); UV (CH3OH) λmax, nm (log ε): 400 (3.45), 240 (4.24) nm; IR (KBr) νmax: 3347, 2960, 2926, 1688, 1654, 1612, 1260, 1078, 1021, 797 cm−1; for 1H NMR (CDCl3, 600

• MHz) and 13C NMR (CDCl3, 125 MHz) spectral data, see Table 1; HRESIMS (m/z): [M − H]− calcd for 341.1870; found, 341.1862. Shentonin B (2): light green solid; [α]D20 +5.3 (c 0.07, CH3OH); UV (CH3OH) λmaxm nm (log ε): 280 (3.59), 220 (4.30) nm; IR (KBr) νmax: 3315, 2969, 1667, 1461, 1159, 1138, 1061

Copper-promoted C5-selective bromination of 8-aminoquinoline amides with alkyl bromides

• Changdong Shao,
• Chen Ma,
• Li Li,
• Jingyi Liu,
• Yanan Shen,
• Chen Chen,
• Qionglin Yang,
• Tianyi Xu,
• Zhengsong Hu,
• Yuhe Kan and
• Tingting Zhang

Beilstein J. Org. Chem. 2024, 20, 155–161, doi:10.3762/bjoc.20.14

• and organic bromine-containing compounds such as Br2, CuBr, CuBr2, LiBr, NaBr, KBr, HBr, NH4Br, and tetrabutylammonium bromide (TBAB) as halogen sources have been realized (Scheme 1, reaction 1) [11][12][13][14][15][16][17][18][19][20]. Another category of extensively used bromination reagents are

Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

• Pavel S. Silaichev,
• Tetyana V. Beryozkina,
• Vsevolod V. Melekhin,
• Valeriy O. Filimonov,
• Andrey N. Maslivets,
• Vladimir G. Ilkin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3

• , 135.7, 143.8, 152.3, 152.9, 157.3, 162.4; IR (ATR, KBr, cm−1): ν 3402, 3316, 3201, 1700, 1688, 1649, 1629, 1594, 1568, 1520, 1497, 1476, 1454, 1444, 1426, 1386, 1358, 1335, 1311, 1276, 1264, 1248, 1194, 1090, 1057, 1028; HRMS–ESI-TOF (m/z): [M + H]+ calcd for C16H19N8O2+, 355.1625; found: 355.1628. (Z

• , 174.5; IR (ATR, KBr, cm−1): ν 3400, 3359, 3255, 1625, 1602, 1563, 1554, 1508, 1495, 1483, 1455, 1436, 1425, 1402, 1385, 1356, 1332, 1319, 1303, 1283, 1257, 1215, 1151, 1095, 1067, 1053, 1035, 1011; HRMS–ESI-TOF (m/z): [M + H]+ calcd for C13H14N7S+, 300.1026; found, 300.1031. X-ray structure

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

• , 125.5, 117.4, 109.9, 95.0, 52.3, 44.4, 37.0, 20.9 ppm; IR (KBr) ν: 2960, 2936, 2870, 2211, 1717, 1626, 1498, 1445, 1367, 1268, 1193, 1112, 1090, 1009, 903, 868, 815 cm−1; HRMS–ESI TOF (m/z): [M + Na]+ calcd for C34H26N4O2Na, 545.1956; found, 545.1948. General procedure for the preparation of

• , 127.5, 127.0, 124.4, 111.6, 110.4, 52.2, 51.1, 44.4, 36.8 ppm; IR (KBr) ν: 2924, 2853, 1721, 1608, 1484, 1456, 1430, 1340, 1170, 812 cm−1; HRMS–ESI TOF (m/z): [M + H]+ calcd for C34H27ClN3O4, 576.1685; found, 576.1683. General procedure for the preparation of dihydrospiro[indoline-3,5'-[1,2]diazepines

• , 135.1, 133.5, 132.7, 129.9, 129.9, 129.5, 129.2, 129.0, 128.8, 127.8, 127.3, 127.2, 124.5, 123.5, 117.3, 109.9, 91.9, 52.1, 44.3, 37.3, 21.8, 21.3 ppm; IR (KBr) ν: 3057, 3055, 2928, 2217, 1716, 1613, 1488, 1467, 1449, 1369, 1297, 1259, 1189, 1175, 1090, 1021, 999, 869, 804, 764, 754, 696, 667, 657, 639

Unprecedented synthesis of a 14-membered hexaazamacrocycle

• Anastasia A. Fesenko and
• Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

• the syntheses. Anhydrous N2H4 was obtained from N2H4·H2O according to the standard procedure. All other reagents were purchased from commercial sources and used without additional purification. FTIR spectra were recorded using a Bruker Alpha-T spectrophotometer in KBr. Band characteristics in the IR

• heating rate) [lit [40] mp 269–270 °C (MeOH)]; IR (KBr, cm−1) ν: 3423 (br s), 3365 (s), 3307 (br s), 3182 (br s), 1626 (sh), 1596 (vs), 1555 (s), 1547 (sh), 1242 (s), 1164 (s), 965 (s); 1H NMR (600.13 MHz, DMSO-d6) δ 11.82 (d, 3J = 11.2 Hz, 2Н, two NH), 8.01 (q, 4J = 0.5 Hz, 2Н, H-3 and H-11), 7.47 (d, 3J

• white solid which was used in the next step. IR (KBr, cm–1) ν: 3294 (m), 3251 (s), 3157 (m), 3130 (s), 1662 (vs), 1583 (s), 1552 (m), 1228 (s), 1155 (m), 961 (s), 853 (s), 764 (s); 1H NMR (600.13 MHz, DMSO-d6) δ 8.25 (unresolved q, 1Н, H-3), 7.87 (s, 1Н, H-6), 7.61 (very br s, 1H, C=NH), 5.40 (br s, 2Н

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• of the solid samples in spectroscopic grade potassium bromide (KBr). Thermogravimetric analyses were performed using a Pyris 1 TGA thermoanalyzer (Perkin-Elmer), at 10 °C min−1 heating rate, under nitrogen flow (20 mL min−1), from 25 to 350 °C. Melting points were determined in triplicate using a

• structures of hdz-CH3 and hdz-NO2 can be seen in Figure S4 in Supporting Information File 1. Mid-infrared spectra of the compounds. Experimental conditions: KBr pellets, room temperature. Calculated conditions: gas phase, level of theory B3LYP/6-311G(d,p). (A) Overlapping of the theoretical (black) and

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• compound 4 (1.2 mg). Breynin J (1): amorphous, colorless powder. [α]D22 −8.0 (c 0.05, MeOH); UV λmax (MeOH) nm (log ε): 257 (4.09); IR (KBr) cm−1: 3414, 2969, 2936, 2888, 1782, 1695, 1609, 1516, 1456, 1395, 1348, 1314, 1279, 1167, 1117, 1078, 1036, 854, 831, 773, 741, 700, 667, 619, 550, 511, 471; 1H and

• 13C NMR data, see Table 1 and Table 2. HRESIMS (m/z): [M + Na]+ calcd for C45H64O28SNa, 1107.3197; found, 1107.3177 . Epibreynin J (2): amorphous, colorless powder. [α]D22 −45.2 (c 0.05, MeOH); UV λmax (MeOH) nm (log ε): 257 (4.08); IR (KBr) cm−1: 3404, 2969, 2936, 2888, 1734, 1694, 1609, 1516, 1346

• (MeOH) nm (log ε): 257 (4.10); IR (KBr) cm–1: 3430, 2969, 2936, 2889, 1780, 1674, 1609, 1593, 1514, 1437, 1391, 1360, 1344, 1312, 1281, 1167, 1117, 1084, 1060, 1044, 999, 980, 853, 773; 1H and 13C NMR data, see Table 1. HRESIMS (m/z): [M + Na]+ calcd for C23H27NO11SNa, 548.1197; found, 548.1197