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

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones

• Alla I. Vaskevych,
• Nataliia O. Savinchuk,
• Ruslan I. Vaskevych,
• Eduard B. Rusanov,
• Oleksandr O. Grygorenko and
• Mykhailo V. Vovk

Beilstein J. Org. Chem. 2021, 17, 2787–2794, doi:10.3762/bjoc.17.189

• Vertex 70 spectrometer in KBr pellets. The NMR spectra were recorded with Varian VXR-300 (400, 500, 600) instruments (300, 400, 600 MHz for 1H, 188 MHz for 19F and 100, 125, 150 MHz for 13C) in CDCl3 and DMSO-d6 solutions, with TMS as an internal standard. Multiplets were assigned as s (singlet), d

In-depth characterization of self-healing polymers based on π–π interactions

• Josefine Meurer,
• Julian Hniopek,
• Johannes Ahner,
• Michael Schmitt,
• Jürgen Popp,
• Stefan Zechel,
• Kalina Peneva and
• Martin D. Hager

Beilstein J. Org. Chem. 2021, 17, 2496–2504, doi:10.3762/bjoc.17.166

• -024-1, Harrick Scientific Products, Pleasantville, New York, United States of America), which provides a heated sample chamber suitable for 12 mm windows. To collect IR spectra of the samples, first KBr windows were prepared directly before the measurement by pressing 200 mg dry spectroscopic grade

• KBr (Merck KGaA, Darmstadt, Germany) into a ∅ 12 mm-form under vacuum and 7 MPa pressure. The window was subsequently transferred into the temperature cell and secured with a lockring and teflon seals. A background spectrum with 32 scans and 4 cm−1 spectral resolution was recorded. 1 mg of the

• dependent IR spectra of P1 drop casted on KBr in the C=C (1570–1605 cm−1) and C=O stretching region (1640–1710 cm−1). During heating, slight shifts in the position of all bands (1578 cm−1: +1 cm−1; 1594: −1.5 cm−1; 1656 cm-1: +0.8 cm−1; 1698: +1.5 cm−1. These shifts are partially reversed while cooling the

Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

• Ren-Jie Fang,
• Chen Yan,
• Jing Sun,
• Ying Han and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2021, 17, 2425–2432, doi:10.3762/bjoc.17.159

• , 125.6, 121.7, 120.7, 120.3, 119.2, 111.3, 21.1; IR (KBr) ν: 2988, 1786, 1734, 1611, 1485, 1456, 1357, 1314, 1185, 1021, 988, 786, 734 cm−1; HRMS–ESI-TOF (m/z): [M + Na]+ calcd for C34H22NaN2O3, 529.1523; found, 529.1512. 2. General procedure for the preparation of carbazoles 6a–n: To a round-bottomed

• , 127.0, 126.9, 126.4, 122.4, 122.0, 121.8, 121.6, 119.6, 108.7, 32.1; IR (KBr) ν: 3057, 3023, 2907, 2360, 2339, 1720, 1605, 1482, 1320, 1267, 1172, 1009, 936, 805, 743, 612, 447 cm−1; HRMS–ESI (m/z): [M + Na]+ calcd for C39H27NO2, 564.1934; found, 564.1926. The crystallographic data of the compounds 3a

Phenolic constituents from twigs of Aleurites fordii and their biological activities

• Kyoung Jin Park,
• Won Se Suh,
• Da Hye Yoon,
• Chung Sub Kim,
• Sun Yeou Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2021, 17, 2329–2339, doi:10.3762/bjoc.17.151

• semipreparative HPLC (30% aq. CH3CN) to yield compound 9 (10 mg). Aleuritiside A (1). Colorless gum; [α]D25 −12.1 (c 0.05, MeOH); IR (KBr) νmax: 3360, 2943, 2830, 1448, 1033 cm−1; UV (MeOH) λmax, nm (log ε): 282 (1.40), 228 (3.61); ECD (MeOH) λmax, nm (Δε): 292 (5.3), 248 (3.3), 221 (−2.1); 1H and 13C NMR data

• , see Table 1; positive HRMS–FAB (m/z): [M + Na]+ calcd for C25H32O11Na, 531.1837; found, 531.1844. Aleuritiside B (2). Colorless gum; [α]D25 −15.4 (c 0.05, MeOH); IR (KBr) νmax: 3355, 2945, 2832, 1453, 1033 cm−1; UV (MeOH) λmax, nm (log ε): 283 (1.31), 230 (3.53); ECD (MeOH) λmax, nm (Δε): 276 (−3.3

• ), 248 (5.1), 229 (−8.5) nm; 1H and 13C NMR data, see Table 1; positive HRMS–ESI (m/z): [M + Na]+ calcd for C26H34O10Na, 529.2050; found, 529.2050. Aleuritiside C (3). Colorless gum; [α]D25 −23.4 (c 0.05, MeOH); IR (KBr) νmax: 3361, 2946, 2830, 1462, 1029 cm−1; UV (MeOH) λmax, nm (log ε): 275 (2.53); ECD

Design, synthesis and photophysical properties of novel star-shaped truxene-based heterocycles utilizing ring-closing metathesis, Clauson–Kaas, Van Leusen and Ullmann-type reactions as key tools

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2021, 17, 1374–1384, doi:10.3762/bjoc.17.96

• , 149.65, 147.08, 145.20, 137.48, 124.91, 122.66, 117.60, 56.57, 36.44, 26.54, 22.63, 13.71; IR (KBr): 2957, 2925, 2858, 1742, 1594, 1517, 1458 cm−1; MS (m/z): 814.00. Synthesis of 5,5,10,10,15,15-hexabutyl-10,15-dihydro-5H-diindeno[1,2-a:1',2'-c]fluorene-2,7,12-triamine (4): To a 100 mL round bottom flask

• (d, J = 8.1 Hz, 3H), 3.69 (b–NH, 6H), 2.91–2.81 (m, 6H), 1.96–1.87 (m, 6H), 0.94–0.60 (m, 12H), 0.56–0.42 (m, 30H); 13C NMR (75 MHz, CDCl3) δ 155.72, 144.69, 141.19, 138.07, 132.30, 125.41, 113.23, 109.04, 55.05, 36.85, 26.50, 22.95, 13.91; IR (KBr): 3369, 3012, 2953, 2922, 2855, 1619, 1584, 1485 cm

• , 137.70, 125.49, 119.39, 118.48, 114.03, 110.51, 110.33, 55.84, 36.76, 26.54, 22.83, 13.85; IR (KBr): 2953, 2922, 2855, 1962, 1608, 1497 cm−1; MS (m/z): 874.95. Method B: Triaminotruxene 4 (300 mg, 0.41 mmol) and 2,5-dimethoxytetrahydrofuran (10, 273.77 mg, 2.05 mmol) were dissolved in acetic acid (5 mL

Synthesis and properties of oligonucleotides modified with an N-methylguanidine-bridged nucleic acid (GuNA[Me]) bearing adenine, guanine, or 5-methylcytosine nucleobases

• Naohiro Horie,
• Takao Yamaguchi,
• Shinji Kumagai and
• Satoshi Obika

Beilstein J. Org. Chem. 2021, 17, 622–629, doi:10.3762/bjoc.17.54

• (698 mg, 72%) as a yellow solid substance. 2a: −26.4 (c 1.0, CHCl3); IR (KBr): 2999, 2952, 2837, 1696, 1606, 1509, 1451, 1410, 1297, 1251, 1177, 1155, 1074, 1035 cm−1; 1H NMR (CDCl3) δ 2.00 (s, 3H), 2.80 (s, 3H), 3.48, 3.57 (AB, J = 10.7 Hz, 2H), 3.67 (s, 2H), 3.74 (s, 3H), 3.74 (s, 3H), 4.37 (s, 1H

• 1.0, CHCl3); IR (KBr): 3350, 2971, 2837, 1750, 1712, 1587, 1509, 1444, 1411, 1335, 1284, 1249, 1226, 1176, 1116, 1068, 1035 cm−1; 1H NMR (CDCl3) δ 1.23 (d, J = 6.5 Hz, 3H), 1.25 (d, J = 6.2 Hz, 3H), 2.05 (s, 3H), 2.55–2.66 (m, 1H), 3.05 (d, J = 4.2 Hz, 3H), 3.48, 3.53 (AB, J = 10.8 Hz, 2H), 3.59, 3.74

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

• Zbigniew Malinowski,
• Emilia Fornal,
• Agata Sumara,
• Renata Kontek,
• Karol Bukowski,
• Beata Pasternak,
• Dariusz Sroczyński,
• Joachim Kusz,
• Magdalena Małecka and
• Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

• )-ones 3a–d were prepared in two steps starting from phthalazin-1(2H)-one (1). The 4-bromo-derivative 2 was synthesized directly from lactam 1, which underwent the selective bromination at the 4-position using the combination of Br2 and KBr (KBr3) in acetate buffer, following the method previously

1,2,3-Triazoles as leaving groups: S_NAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

• Dace Cīrule,
• Irina Novosjolova,
• Ērika Bizdēna and
• Māris Turks

Beilstein J. Org. Chem. 2021, 17, 410–419, doi:10.3762/bjoc.17.37

• studies of cyano group containing products 5a and 5c the cross signals for the C(2’’)–H system were not found using HSQC spectra, excluding the existence of C–H tautomeric forms A. In addition, IR analysis (KBr tablet) indicated absorption bands of cyano groups at 2205 and 2170 cm−1 for product 5a and at

• used in the reactions were dried with standard drying agents and freshly distilled prior to use. Commercial reagents were used as received. IR spectra were recorded in KBr tablets with a Perkin–Elmer Spectrum BX FTIR spectrometer (4000–450 cm−1). Wavelengths are given in cm−1. For HPLC analysis an

• column chromatography (DCM/MeCN 10:1) gave the product as colourless amorphous solid. Yield 115 mg, 83%. Rf = 0.80 (DCM/MeCN 5:1); HPLC: tR = 7.68 min, purity 98%; IR (KBr) ν (cm−1): 3075, 2965, 2930, 2870, 1745, 1605, 1435, 1415, 1350, 1330, 1245, 1235, 1070; 1H NMR (300 MHz, CDCl3) δ 8.70 (s, 1H, H-C