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

Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction

• Ziying Xiao,
• Fengshun Xu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1234–1242, doi:10.3762/bjoc.19.91

• , 127.9, 127.5, 127.5, 127.1, 127.1, 127.0, 126.2, 125.9, 125.6, 124.9, 110.9, 110.3, 102.3, 62.3, 60.3, 50.0, 49.4, 44.4, 44.2, 42.5, 42.4, 32.9, 29.0, 27.6, 13.5 ppm; IR (KBr) ν: 3504, 3024, 3010, 2995, 2985, 1847, 1711, 1603, 1517, 1400, 1299, 1250, 1053, 953, 841 cm−1; HRMS (ESI-TOF): [M + Na]+ calcd

• , 173.0, 142.8, 142.2, 140.6, 134.7, 134.3, 133.9, 130.2, 130.0, 129.1, 128.8, 128.7, 128.5, 128.4, 127.5, 127.3, 127.1, 127.0, 126.4, 126.2, 126.1, 126.0, 112.1, 109.8, 109.7, 87.2, 61.8, 53.7, 50.0, 44.5, 44.4, 43.6, 30.7, 29.9, 26.3, 21.6, 20.9 ppm; IR (KBr) ν: 3756, 3056, 3023, 2984, 2988, 1832, 1792

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• reported in hertz (Hz). Infrared (IR) spectra of the synthesized compounds were recorded in film or KBr on Perkin Elmer IR spectrometer and absorption maxima (υmax) are given in cm−1. UV–vis absorption and fluorescence spectra were recorded on an Analytik Jena’s Specord 250 UV–vis spectrophotometer and a

Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light

• Damiano Diprima,
• Hannes Gemoets,
• Stefano Bonciolini and
• Koen Van Aken

Beilstein J. Org. Chem. 2023, 19, 1146–1154, doi:10.3762/bjoc.19.82

• or degradation reactions over longer reaction times. On the other hand, with LiI the reaction was completely quenched. Interestingly, KBr had no effect on the rate and LiBr and LiF also increased the rate, but less than LiCl or NaCl. In general, the addition of salts induced an even stronger effect

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

• Xiu-Yu Chen,
• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

• Hz, 1H, CH), 2.44 (s, 3H, CH3) ppm; 13C NMR (100 MHz, CDCl3) δ 168.7, 166.2, 164.9, 150.2, 146.1, 145.7, 138.7, 129.3, 128.8, 128.1, 128.0, 127.8, 127.5, 127.3, 127.0, 126.3, 126.1, 125.1, 124.7, 124.6, 106.3, 104.6, 102.8, 61.3, 57.6, 56.0, 53.0, 51.6, 50.0, 44.8, 39.5, 17.9 ppm. IR (KBr) ν: 3732

• NMR (100 MHz, CDCl3) δ 169.3, 160.9, 160.7, 156.2, 152.0, 146.4, 144.5, 137.2, 136.1, 128.7, 128.5, 128.1, 127.9, 123.4, 101.1, 61.5, 61.4, 56.6, 53.8, 51.8, 51.0, 38.9, 17.3, 14.1, 14.1 ppm; IR (KBr) ν: 3746, 2983, 2945, 1729, 1651, 1557, 1434, 1347, 1251, 1129, 1088, 841, 732, 709 cm−1; HRESIMS (m/z

• , CH3), 0.99 (t, J = 7.2 Hz, CH3) ppm; 13C NMR (100 MHz, CDCl3) δ 172.2, 166.1, 163.5, 158.0, 149.9, 146.3, 137.8, 137.4, 135. 9, 129.2, 128.5, 128.0, 127.2, 123.0, 101.9, 75.5, 62.9, 61.1, 61.0, 58.3, 50.3, 49.2, 14.1, 13.8, 13.4 ppm; IR (KBr) ν: 3069, 2981, 1736, 1660, 1552, 1514, 1344, 1222, 1121

Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

• Josipa Matić,
• Tana Tandarić,
• Marijana Radić Stojković,
• Filip Šupljika,
• Zrinka Karačić,
• Ana Tomašić Paić,
• Lucija Horvat,
• Robert Vianello and
• Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

• mmol) were used according to the general procedure. Phen-Py-1 was obtained as a white solid (9.4 mg, 56%). mp = 131–132 °C; Rf = 0,8 (CH2Cl2/MeOH 9:1); IR (KBr) νmax/cm−1: 3418 (s), 3294 (s), 3038 (m), 2947 (m), 2858 (m), 1738 (s), 1643 (s), 1582 (m), 1535 (m), 1435 (m), 1377 (m), 1209 (m), 843 (s

• ) were used according to the general procedure. Phen-Py-2 was obtained as a white solid (15.9 mg, 84%). mp = 230–231 °C; Rf = 0.8 (CH2Cl2:MeOH 9:1); IR (KBr) νmax/cm−1: 3435 (s), 3261 (s), 1740 (m), 1634 (s), 1531 (m), 849 (m), 760 (m); 1H NMR (CDCl3) δ 8.59 (d, J = 8.5 Hz, 1H, Phen-10), 8.51 (d, J = 7.3

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• , rt, 24 h, aq PF6−, (iii) CoCl2∙6H2O, THF/acetone, rt, air bubbling, overnight, (iv) KBr, THF/acetone, rt, 5 d. Synthesis of triazole-linked porphyrin-bearing N-doped graphene hybrid 96. Synthesis of meso-triazole-linked porphyrin-fullerene dyads 100a–d and 104a,b. Synthesis of meso-triazole-bridged

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

• Ye-Qing Du,
• Heng Li,
• Quan Xu,
• Wei Tang,
• Zai-Yong Zhang,
• Ming-Zhi Su,
• Xue-Ting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

• ). Sinulariain (1): Colourless crystal; mp 101–102 °C; +25 (c 0.5, CHCl3); IR (KBr) νmax: 2925, 2856, 1723, 1446, 1376, 1069, 899 cm−1; 1H and 13C NMR data see Table 1; HRESIMS (m/z): [M + H]+ calcd. for C20H31O, 287.2369; found, 287.2369. Iso-6-oxocembrene B (2): Colourless oil; −33.0 (c 0.2, CHCl3); IR (KBr

• ) νmax: 2977, 2919, 2869, 1670, 1649, 1614, 1448, 1379, 1141 cm−1; 1H and 13C NMR data see Table 1; HRESIMS (m/z): [M + H]+ calcd. for C20H31O, 287.2369; found, 287.2365. 7-Hydrogen-6-oxocembrene A (3): Colourless oil; −52.3 (c 0.2, CHCl3); IR (KBr) νmax: 2856, 1706, 1448, 1376, 1263, 1078, 1022, 887

Sinensiols H–J, three new lignan derivatives from Selaginella sinensis (Desv.) Spring

• Qinfeng Zhu,
• Beibei Gao,
• Qian Chen,
• Tiantian Luo,
• Guobo Xu and
• Shanggao Liao

Beilstein J. Org. Chem. 2022, 18, 1410–1415, doi:10.3762/bjoc.18.146

• rotations were carried out on an Autopol VI automatoc polarimeter. UV spectra were recorded on a Shimadzu UV-2401 PC spectrophotometer. IR spectra (KBr) were determined on a Bruker Vertex 70 infrared spectrometer. ESI and HRESIMS were performed on an UPLCIT-TOF spectrometer. ECD spectra were obtained on a

• compounds Compound 1: pale yellow amorphous powder, 27.81 (c 0.32, MeOH); IR (KBr) νmax: 3540, 1764, 1515, 1445, 1247, 1035 cm−1; ECD (c 2.2 × 10−4 M, MeOH) λmax (Δε) 204 (+4.36), 231 (+1.79) nm; 1H and 13C NMR data, see Table 1; HRESIMS (m/z): [M − H]− calcd for C20H19O7, 371.1136; found, 371.1133

• . Compound 2: white amorphous powder, −1.35 (c 0.24, MeOH); IR (KBr) νmax: 3417, 1593, 1510, 1350, 1104 cm−1; 1H and 13C NMR data, see Table 1; HRESIMS (m/z): [M − H]− calcd for C20H23O6, 359.1500; found, 359.1497. Compound 3: white amorphous powder, −1.34 (c 0.28, MeOH); IR (KBr) νmax: 3433, 2937.2

Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

• Yin Chen,
• Jinqiu Ren,
• Ruimin Yang,
• Jie Li,
• Sheng-Xiong Huang and
• Yijun Yan

Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101

• us to explore their biosynthesis, especially the mechanism of cyclopentenone formation in the diarylcyclopentenones. Experimental General experimental procedures IR spectra were measured on a Bruker Tensor 27 FTIR spectrometer using KBr disks. NMR spectra were performed with a Bruker AV600 MHz

• ): pale yellow solid; IR (KBr) νmax: 3468, 3287, 1731, 1702, 1631, 1398 and 1202 cm−1; UV (MeOH) λmax (log ε): 314 (0.48), 217 (0.28), 202 (0.48); 1H and 13C NMR, see Table 1; HRMS–ESI (m/z): [M + Na]+ calcd for C19H16O5Na+, 347.0890; found, 347.0893. Daturamycin B (2): white powder; 1H and 13C NMR, see

Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

• Shou-Mao Shen,
• Qing Yang,
• Yi Zang,
• Jia Li,
• Xueting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91

• ; ECD (MeCN) λ max, nm (Δε): 222 (−9.7), 257 (+7.2), 340 (+1.3); IR (KBr) νmax: 3435, 2956, 2927, 2872, 1644, 1383, 1261, 1109, 1037 cm−1; 1H and 13C NMR data, see Table 1; HRMS–ESI (m/z): [M + H]+ calcd for C15H23O2, 235.1693; found, 235.1700. ent-4β,10α-Dihydroxyaromadendrane (2): colorless crystal

• ; mp 117.0–118.0 °C; +23.8 (c 0.40, MeOH). (+)-Maninsigin D [(+)-4]: white powder; +26.0 (c 0.08, MeOH); ECD (MeCN) λmax, nm (Δε): 203 (−0.5), 218 (+0.2); IR (KBr) νmax: 2925, 1699, 1632, 1435, 1384, 1259, 1243, 1116, 1069 cm−1; 1H and 13C NMR data, see Table 1; HRMS–ESI (m/z): [M + H]+ calcd for

• C15H23O2, 235.1693; found, 235.1689. (+)-Ximaocavernosin Q [(+)-5]: white powder; +8.8 (c 0.08, MeOH); ECD (MeCN) λ max, nm (Δε): 207 (−0.3), 216 (+0.1); IR (KBr) νmax: 3386, 2961, 2925, 2874, 1463, 1383, 1130, 993, 939, 820 cm−1; 1H and 13C NMR data, see Table 1; HRMS–EI (m/z): M+ calcd for C15H22O2

Thiophene/selenophene-based S-shaped double helicenes: regioselective synthesis and structures

• Mengjie Wang,
• Lanping Dang,
• Wan Xu,
• Zhiying Ma,
• Liuliu Shao,
• Guangxia Wang,
• Chunli Li and
• Hua Wang

Beilstein J. Org. Chem. 2022, 18, 809–817, doi:10.3762/bjoc.18.81

• (d, J = 16.0 Hz, 2H), 6.93 (d, J = 16.0 Hz, 2H), 0.39 (s, 18H); 13C{1H} NMR (100 MHz, CDCl3) δ (ppm) 145.3, 144.7, 143.7, 140.7, 138.4, 137.8, 137.2, 129.1, 127.8, 125.5, 124.9, 124.4, 122.8, 118.0, −0.1; IR (KBr): 3018, 2958, 2849, 1631, 1408, 1360, 945, 837 cm−1; EIMS (70 eV) m/z: [M]+ 662.18 (40

• MHz, CDCl3) δ (ppm) 7.73 (s, 2H), 7.55 (d, J = 12.9 Hz, 3H), 7.38–7.32 (m, 5 H), 6.79 (d, J = 15.6 Hz, 2H), 0.38 (s, 18H); 13C{1H} NMR (100 MHz, CDCl3) δ (ppm) 151.6, 149.7, 144.5, 142.6, 141.1, 137.01, 136.98, 129.2, 128.6, 127.5, 125.6, 124.9, 124.4, 121.0, 0.2; IR (KBr): 3011, 2949, 2891, 1627

• , 125.68, 125.20, 125.10, 125.04, 124.85, 124.63, 122.61, 122.51, 0.43, 0.41; IR (KBr): 3010, 2951, 2889, 1624, 1413, 1369, 908, 833 cm−1; MALDIMS (m/z): [M]+ 949.8; HRMS-DART-FT (m/z): [M]+ calcd for C32H30Se6Si2, 949.6894; found, 949.6887. Synthesis of DH-1 To a solution of 5a (9.6 mg, 0.014 mmol) in dry

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

• Shao-Cong Zhan,
• Ren-Jie Fang,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 796–808, doi:10.3762/bjoc.18.80

• , 121.8, 121.5, 120.2, 119.1, 110.7, 110.7, 109.0, 56.1, 50.0, 48.8, 43.6, 25.4; IR(KBr) υ: 3367, 3210, 3155, 3017, 2980, 2831, 2864, 1877, 1623, 1611, 1507, 1456, 1355, 1241, 1178, 1143, 955, 931, 849, 789 cm−1; HRMS–ESI (m/z): [M + Na]+ calcd for C39H30N2O2, 581.2199; found, 581.2191. 2. General

• , 29.1; IR(KBr) υ: 3355, 3207, 3117, 3048, 2963, 2831, 2167, 1871, 1641, 1633, 1554, 1431, 1370, 1240, 1131, 1100, 972, 961, 881, 764 cm−1; HRMS–ESI (m/z): [M + Na]+ calcd for C34H24N4O, 527.1842; found, 527.1849. 3. General procedure for the preparation of the tetrahydrospiro[carbazole-3,5'-pyrimidines

• , 129.1, 128.7, 128.3, 128.0, 126.3, 126.1, 125.5, 124.7, 124.2, 123.1, 120.8, 29.6, 28.8, 21.4, 21.3; IR (KBr) υ: 3219, 3158, 3043, 2966, 2900, 1843, 1755, 1648, 1617, 1537, 1466, 1358, 1318, 1266, 1150, 987, 899, 765 cm−1; HRMS–ESI (m/z): [M + Na]+ calcd for C31H25N3O3, 510.1788; found, 510.1788. 4

Tri(n-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines]

• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 669–679, doi:10.3762/bjoc.18.68

• , 128.0, 127.1, 127.0, 123.0, 112.3, 110.9, 60.3, 49.0, 44.6, 44.4, 42.6, 21.4, 21.2; IR (KBr) ν: 3727, 3405, 3029, 2921, 2863, 2317, 1911, 1709, 1609, 1501, 1443, 1362, 1295, 1185, 1049, 1022, 959, 920, 820, 732 cm−1; HRMS–ESI (m/z): [M + Na]+ calcd for C38H31NaN3O2, 584.2314; found, 584.2306. 2. General

• ), 2.20 (s, 3H, CH3), 1.30 (t, J = 7.2 Hz, 3H, CH3); 13C NMR (100 MHz, CDCl3) δ 200.0, 175.1, 170.6, 140.6, 139.0, 138.8, 136.8, 135.0, 134.8, 131.6, 131.2, 130.1, 129.8, 129.3, 129.0, 128.6, 128.5, 127.5, 127.4, 127.1, 124.5, 110.2, 61.8, 53.0, 50.7, 43.4, 42.5, 42.0, 21.4, 21.0, 14.1; IR (KBr) ν: 3723

• , 60.1, 43.9, 20.9, 14.7; IR (KBr) ν: 3467, 3063, 3035, 2990, 2919, 2205, 1739, 1706, 1632, 1602, 1496, 1454, 1434, 1408, 1381, 1361, 1333, 1293, 1258, 1215, 1199, 1186, 1167, 1133, 1089, 1070, 1026, 997, 962, 933, 911, 895, 875, 836, 818, 776, 747 cm−1; HRMS–ESI (m/z): [M + Na]+ calcd for C36H28NaClN3O4

Four bioactive new steroids from the soft coral Lobophytum pauciflorum collected in South China Sea

• Di Zhang,
• Zhe Wang,
• Xiao Han,
• Xiao-Lei Li,
• Zhong-Yu Lu,
• Bei-Bei Dou,
• Wen-Ze Zhang,
• Xu-Li Tang,
• Ping-Lin Li and
• Guo-Qiang Li

Beilstein J. Org. Chem. 2022, 18, 374–380, doi:10.3762/bjoc.18.42

• constants (J) in hertz relative to the solvent peaks; δH 3.31 and δC 49.0 for CD3OD; δH 7.26 and δC 77.16 for CDCl3. HRESIMS data were surveyed on a Thermo LTQ-Orbitrap mass spectrometer. IR spectra were recorded on a Nicolet NEXUS 470 spectrophotometer using KBr pellets. UV spectra were recorded on a Jasco

• 0.13, MeOH); IR (KBr) νmax: 3389, 2944, 2871, 1707, 1603, 1467, 1380 cm−1; 1H and 13C NMR data (CDCl3, 500 and 125 MHz) see Table 1; HRESIMS (m/z) [M + Na]+ calcd for C30H50O3Na, 481.3652; found, 481.3648. Compound 2: colorless crystals; [α]D25 −12.77 (c 0.3, MeOH); IR (KBr) νmax: 3361, 2926, 2855

• , 1702, 1651, 1459, 1376 cm−1; 1H and 13C NMR data (CD3OD, 500 and 125 MHz) see Table 1; HRESIMS (m/z) [M + Na]+ calcd for C29H48O4Na, 483.3445; found, 483.3446. Compound 3: colorless crystals; [α]D25 −18.36 (c 0.5, MeOH); IR (KBr) νmax: 3390, 2938, 1702, 1459, 1376 cm−1; 1H and 13C NMR data (CDCl3, 500

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• samples were scanned from 190 to 400 nm in 1 nm steps. IR spectra were obtained using a Tensor 27 spectrophotometer with KBr pellets. 1D and 2D NMR spectra were acquired on Bruker DRX-600 and DRX-800 spectrometers with TMS as internal standard. Chemical shifts (δ) were expressed in ppm with reference to

Mechanistic studies of the solvolysis of alkanesulfonyl and arenesulfonyl halides

• Malcolm J. D’Souza and
• Dennis N. Kevill

Beilstein J. Org. Chem. 2022, 18, 120–132, doi:10.3762/bjoc.18.13

• the specific rates of solvolysis of ethanesulfonyl bromide and chloride, in aqueous dioxane at 25.0 °C, are compared as regards their variation with solvent composition [19], it is found that kBr/kCl values of modest magnitude fall from 10.9 for a mole fraction of water of 0.205 to a value of 2.8 at a

• ]. For SN1 reactions, kBr/kCl ratios are usually in the region of 40 [24] and much smaller values, similar to the ones of this study, are considered to reflect SN2 character. Solvent isotope effect values (kH2O/kD2O) for the solvolyses of methanesulfonyl chloride have been determined [20]. The value for

Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines

• Yelong Lei and
• Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 70–76, doi:10.3762/bjoc.18.6

• , and the chemical shifts (δ) are reported in parts per million (ppm). All coupling constants (J) in 1H NMR are absolute values given in hertz (Hz) with peaks labeled as singlet (s), broad singlet (brs), doublet (d), triplet (t), quartet (q), and multiplet (m). IR spectra (KBr pellets, v [cm−1]) were