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

• -unsaturated ketone group (1644 cm−1), as additionally supported by the UV absorption at λmax 245 nm (log ε 3.8). Careful analysis of the NMR spectra of (+)-1 (Table 1 and Figures S8–S13 in Supporting Information File 1) showed a close similarity with those of co-occurring 2 [12][13][14], indicating compound

• with 4. The IR absorption band at 3386 cm−1 suggested the presence of hydroxy groups. A careful analysis of its 1D and 2D NMR spectra revealed that the NMR spectroscopic features of compound 5 (Table 1 and Figures S24–S31 in Supporting Information File 1) extremely resembled those of 4. The main

• ; 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

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

• Maxime Pypec,
• Laurent Jouffret,
• Claude Taillefumier and
• Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

• characterized by Fourier-transform infrared spectroscopy. The spectra show two distinct N–H stretching bands in the 3500–3200 cm−1 region whose relative intensity varies with chain elongation. A first band, the more intense of the two, is observed at about 3300 cm−1. A higher energy band of much lower intensity

• at about 3450–3500 cm−1 is also observed, especially from the trimer stage. We can assume that the lower energy bands (3300 cm−1) are due to hydrogen-bonded N–H while the higher energy bands could be attributed to non-hydrogen bonded NH. This observation may indicate that not all NHs can form

• hydrogen bonds within an assembly, and that this is dependent on the size of the oligomers. Also, the region of the spectra corresponding to the C=O stretching (1800–1600 cm−1) show a band at 1743 cm−1 corresponding to C=O stretching of the ester and a band at 1648 cm−1 which increases with the oligomer

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

• Hengjia Liu and
• Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

• Lewis basic fluorescent compounds 3–14. (a) PL spectra of compound 6 in toluene after addition of 0.0 (black line), 0.1 (red line), 0.3 (green line), 0.7 (blue line), 1.3 mol equiv (orange line) B(C6F5)3. (b) EL spectra of the device with compound 6 at a constant current density of 111 mA cm−2 for 0.00

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

• , 1427, 1367, 920, 831 cm−1; DARTMS (m/z): [M + H]+ 854.8 (75); HRMS-DART (m/z): [M + H]+ calcd for C32H31S2Se4Si2, 854.8071; found, 854.8067. 1,3-Bis(2-(5-(trimethylsilyl)diselenopheno[2,3-b:3',2'-d]selenophen-2-yl)vinyl)benzene (5c) was synthesized according to the procedure described for compound 5a

• , 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

Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

• Conrad Kuhwald,
• Sibel Türkhan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70

• could be achieved with high flow rates (125 mL/min; reactor dimensions according to SI: 2 cm diameter and 1 cm height of catalyst filling) in an external electromagnetic field of 28 mT. Heating can be problematic when exothermic reactions are performed. To prevent catalyst deactivation, the group of

Mechanochemical halogenation of unsymmetrically substituted azobenzenes

• Dajana Barišić,
• Mario Pajić,
• Ivan Halasz,
• Darko Babić and
• Manda Ćurić

Beilstein J. Org. Chem. 2022, 18, 680–687, doi:10.3762/bjoc.18.69

• bromination of L2 confirmed its conversion to the product L2Br-I (Figure 2). The formation of L2Br-I was accompanied by the intensity decrease of L2 ν(N=N) and ν(C–N) bands in the range 1400–1450 and 1080–1200 cm−1, respectively. Compounds L2 and L2Br-I were identified in the reaction mixture by the Raman

• azo nitrogen and a carbon atom of the unsubstituted phenyl ring. The tosylate ion is at the trans position to the carbon atom. In situ Raman monitoring of the bromination of L6–8 in the presence of 30 mol % PdII catalyst revealed a new band around 1380 cm−1 (Figure 5a and Figures S23–S27 in Supporting

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

• , 3412, 2933, 2871, 2324, 1925, 1817, 1703, 1604, 1474, 1442, 1339, 1172, 1091, 1010, 904, 824, 716 cm−1; HRMS–ESI (m/z): [M + Na]+ calcd for C38H34ClNaNO4, 626.2069; found, 626.2066. 3. General procedure for the preparation of the spiro[cyclohexane-1,3'-indolines] 8a–m: In an atmosphere of nitrogen

• , 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

Shift of the reaction equilibrium at high pressure in the continuous synthesis of neuraminic acid

• Jannis A. Reich,
• Miriam Aßmann,
• Kristin Hölting,
• Paul Bubenheim,
• Jürgen Kuballa and
• Andreas Liese

Beilstein J. Org. Chem. 2022, 18, 567–579, doi:10.3762/bjoc.18.59

• 80 mg of particles, 5 µL of 10 mM potassium phosphate buffer was used as tracer and injected with a speed of 1 mL/min. Reactor set-up (left to right): UHPLC pump, heated fixed-bed reactor, capillaries (ID: 25 µm or 50 µm, length: 30 cm), back pressure regulator (up to 30 MPa). List of carriers used

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

• Irina Fiodorova,
• Tomas Serevičius,
• Rokas Skaisgiris,
• Saulius Juršėnas and
• Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 497–507, doi:10.3762/bjoc.18.52

• spectra were rather similar for all compounds, described with, typical for tCbz units, vibronic progression-having peaks bellow ≈340 nm [41]. Molar absorption coefficients were in the range of 19700–34200 M−1 cm−1, being in line with DFT predicted S0→S1 oscillator strengths and LUMO energies. The

Sesquiterpenes from the soil-derived fungus Trichoderma citrinoviride PSU-SPSF346

• Wiriya Yaosanit,
• Vatcharin Rukachaisirikul,
• Souwalak Phongpaichit,
• Sita Preedanon and
• Jariya Sakayaroj

Beilstein J. Org. Chem. 2022, 18, 479–485, doi:10.3762/bjoc.18.50

• previously reported. Trichocitrinovirene A (1) was isolated as a colorless gum and had the molecular formula C15H22O5 on the basis of the HRESIMS peak at m/z 305.1359 [M + Na]+. The IR spectrum exhibited absorption bands at 3336, 1684, and 1649 cm−1 for hydroxy, conjugated carboxyl carbonyl, and double bond

• mg) was then washed with acetone to afford compound 5 (3.7 mg). Trichocitrinovirene A (1): Colorless gum; +46.1 (c 0.67, MeOH); UV (MeOH) λmax, nm (log ε): 210 (3.32); ECD (MeOH, c 0.0008) λmax, nm (Δε): 227 (+4.3); IR (neat) νmax: 3336, 1684, 1649 cm−1; 1H and 13C NMR (CD3OD) see Table 1; HRMS–ESI

• (m/z): [M + Na]+ calcd for C15H22O5Na, 305.1356; found, 305.1359. Trichocitrinovirene B (2): Colorless gum; +44.6 (c 0.67, MeOH); UV (MeOH) λmax, nm (log ε): 210 (3.67); IR (neat) νmax: 3386, 1683, 1645 cm−1; 1H and 13C NMR (CD3OD) see Table 1; HRMS–ESI (m/z): [M + Na]+ calcd for C15H22O6Na

Cs₂CO₃-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones

• Ol'ga G. Volostnykh,
• Olesya A. Shemyakina,
• Anton V. Stepanov and
• Igor' A. Ushakov

Beilstein J. Org. Chem. 2022, 18, 420–428, doi:10.3762/bjoc.18.44

• model substrates for our investigation (Table 1). Completion of the reaction was monitored by IR and 1H NMR spectroscopy by the disappearance of the bands at 2196–2212 cm–1 (–C≡C–Br) and signals of the bromopropargylic alcohol 1a, respectively. Under the conditions previously used [18][19][20][21] for

• mixture was stirred at 50–55 °C for 3 h, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (5.0 × 4.0 cm, gradient elution, C6H14/Et2O, 2:1 followed by Et2O, Me2CO) to give products 3a (10 mg, 4%), 4a (214 mg, 55%), 5a (30 mg, 22%) and 7 (11 mg, 5%). Scope of

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• electrolysis (Scheme 10). For this approach, two smooth platinum foil electrodes placed 1 cm apart in the upper aqueous phase were electrolyzed galvanostatically (30 mA/cm2). Additionally, a NaBr solution acidified with H2SO4 was used as electrolyte. The voltage during electrolysis was 2.1 V and when the

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

• 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

• and 125 MHz) see Table 1; HRESIMS (m/z) [M + H]+ calcd for C28H49O4, 449.3625; found, 449.3626. Compound 4: yelllow crystals; [α]D25 −27.83 (c 0.13, MeOH); IR (KBr) νmax: 3391, 2957, 2872, 1683, 1650, 1558, 1540, 1357 cm−1; 1H and 13C NMR data (CDCl3, 500 and 125 MHz) see Table 1; HRESIMS (m/z) [M + H

Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor

• Yuki Naito,
• Naoki Shida and
• Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 350–359, doi:10.3762/bjoc.18.39

• mol−1; current density, 12.7 mA cm−2; solvent, THF; substrate, 0.06 M benzylideneaniline (1) and 0.12 M 1,4-dibromobutane (2a); base added, 0.06M DBU; supporting electrolyte, 0.14 M n-Bu4N∙ClO4; flow rate, 11 mL h−1 (residence time, 3.9 s); collection volume and time for each fraction, 2 mL, 10 min 55

• microreactor was constructed with a platinum plate (3 × 3 cm) and cathode plate (3 × 3 cm) (Supporting Information File 1, Figure S1). A spacer (double faced adhesive type with thicknesses of 20, 40, or 80 μm) was used to leave a rectangular channel exposed (1 × 3 cm), and the two electrodes were simply

• sandwiched together. After connecting Teflon tubings to the inlets and outlet, the reactor was sealed with epoxy resin (Supporting Information File 1, Figure S2). Thus, the dimensions of the flow channel in the reactor are 1 cm width and 3 cm length, and the channel height corresponds to the thickness of the

Flow synthesis of oxadiazoles coupled with sequential in-line extraction and chromatography

• Kian Donnelly and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 232–239, doi:10.3762/bjoc.18.27

• setup. The initial setup consisted of a heated glass column (i.d. 7 mm, length 7 cm), packed with K2CO3, through which a solution of acyl hydrazone and iodine were passed. It was anticipated that the larger excess of K2CO3 present in the packed bed reactor (when compared to batch mode), in addition to

• larger quantity of K2CO3. As a result of the increased volume of the reactor column (i.d. 15 mm, length 12 cm) a proportional increase in flow rate was necessary to maintain the residence time consistent with our small-scale experiments. Following reaction, the excess iodine must be quenched via a wash

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

• absorption bands at 325 and 293 nm indicated the presence of a coumarin-type chromophore. The IR spectrum of 1 demonstrated absorption bands characteristic for an hydroxy group (3266 cm−1), α,β-unsaturated carbonyl group (1739 and 1701 cm−1), and an aromatic ring (1624 and 1457 cm−1). The 1H NMR spectrum of

• products generated by plant species from the genus Wikstroemia. Experimental General experimental procedures Optical rotations were measured with a Horiba SEPA-300 polarimeter. UV spectra were recorded using a Waters UV-2401A spectrophotometer equipped with a DAD and a 1 cm path length cell. Methanolic

• the solvent signals. Mass spectra were recorded on a VG Auto Spec-3000 instrument or an API QSTAR Pulsar 1 spectrometer. Semi-preparative HPLC was performed on an Agilent 1120 apparatus equipped with a UV detector and a Zorbax SB-C-18 (Agilent, 9.4 mm × 25 cm) column. Column chromatography was

Diametric calix[6]arene-based phosphine gold(I) cavitands

• Gabriele Giovanardi,
• Andrea Secchi,
• Arturo Arduini and
• Gianpiero Cera

Beilstein J. Org. Chem. 2022, 18, 190–196, doi:10.3762/bjoc.18.21

• atmosphere. Subsequently, a tip of spatula (micro spatula, Heyman type 16 cm) of AgSbF6 (≈2.0 mol %, ≈2 mg) was added along with 20 mg of 4 Å molecular sieves. The flask was covered with an aluminum foil and the mixture stirred for 5 minutes. Subsequently, 1a (0.2 mmol, 63.0 mg) was added and the reaction

Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions

• José G. Hernández,
• Karen J. Ardila-Fierro,
• Dajana Barišić and
• Hervé Geneste

Beilstein J. Org. Chem. 2022, 18, 182–189, doi:10.3762/bjoc.18.20

• performed in situ reaction monitoring of the milling process by Raman spectroscopy [32][33]. In an experiment milling 1c with NFSI (1 equiv) we observed the consumption of NFSI after ca. 30 min of milling as evidenced by a reduction in the intensity of the band at 1197 cm−1 of NFSI (Figure S3 in Supporting

• Information File 1). However, the very strong bands around 998 cm−1 (in-plane bending; phenyl ring), 1177 cm−1 (stretching; SO2), and 1583 cm−1 (stretching; phenyl ring) of NFSI and byproducts [(PhSO2)2NH [34], and (PhSO2)2NCH3], prevented the observation of the less Raman active fluorinated products 2c and

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• bare chitosan was carried out, and the spectrum exhibited characteristic peaks for the O–H and N–H stretching vibrations in the range of 3300–3400 cm−1 (Figure 1b). For the chitosan-supported nickel catalyst, the band around 3400 cm−1 became much sharper and stronger compared to bare chitosan (Figure

•  1a). The spectroscopic FTIR study revealed the interaction between the metal and the NH2 and OH groups of chitosan. In both spectra, the peaks around 1100, 1400, 1600, and 2900 cm−1 corresponded to the C–O, C–N, and N–H (bending) as well as to the C–H bonds of the chitosan moiety, respectively. The

Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

• Yasuhiro Igarashi,
• Yiwei Ge,
• Tao Zhou,
• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku and
• Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

• ): pale brown powder; UV (MeOH) λmax nm (log ε): 201 (4.82) nm; IR (ATR) νmax: 3305, 2916, 2849, 1613, 1538, 1466 cm−1; 1H and 13C NMR, Table 1; HR–ESITOFMS (m/z): [M − H]− calcd for C33H60N5O8, 654.4447; found, 654.4449; [M + Na]+ calcd for C33H61N5O8Na, 678.4412; found, 678.4412. Tenacibactin L (2

• ): pale brown powder; UV (MeOH) λmax nm (log ε): 202 (4.21) nm; IR (ATR) νmax: 3306, 2916, 2849, 1613, 1538, 1466 cm−1; 1H and 13C NMR, Table 2; HR–ESITOFMS (m/z): [M − H]− calcd for C33H60N5O8, 654.4447; found, 654.4445; [M + Na]+ calcd for C33H61N5O8Na, 678.4412; found, 678.4410. Tenacibactin M (3

• ): pale brown powder; UV (MeOH) λmax nm (log ε): 202 (4.35) nm; IR (ATR) νmax: 3306, 2916, 2849, 1613, 1538, 1466 cm−1; 1H and 13C NMR, Table 2; HR–ESITOFMS (m/z): [M − H]− calcd for C33H62N5O8, 6546.4604; found, 656.4604; [M + Na]+ calcd for C33H63N5O8Na, 680.4569; found, 680.4567. Bioassays

Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks

• Jolita Bruzgulienė,
• Greta Račkauskienė,
• Aurimas Bieliauskas,
• Vaida Milišiūnaitė,
• Miglė Dagilienė,
• Gita Matulevičiūtė,
• Vytas Martynaitis,
• Sonata Krikštolaitytė,
• Frank A. Sløk and
• Algirdas Šačkus

Beilstein J. Org. Chem. 2022, 18, 102–109, doi:10.3762/bjoc.18.11

• structural assignment of regiospecific compound 4a was readily deduced via detailed spectral data analysis. The IR spectrum of 4a contained characteristic absorption bands such as 1723 (C=O, ester), and 1687 (C=O, Boc) cm−1. The 1H NMR spectrum of compound 4a revealed a characteristic resonance for the Boc

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

Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

• Shun Saito,
• Kanji Indo,
• Naoya Oku,
• Hisayuki Komaki,
• Masashi Kawasaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203

• determined to be C10H16O2 on the basis of its NMR and HR–ESI–TOFMS data (m/z 191.1044 [M + Na]+, Δ + 0.1 mmu). Three degrees of unsaturation, calculated from the molecular formula, a UV absorption maximum at 264 nm, and IR absorption bands at 1679 and 2800–3200 cm−1, suggested dienone and hydroxy

• at 3310 and 1656 cm–1 suggested the presence of OH/NH and carbonyl groups. 1H, 13C, and HSQC spectra (Table 3) revealed the composition of this molecule to be two shielded carbonyls, five other sp2 nonprotonated carbons, five sp2 methines, one sp3 methine, two sp3 methylenes, three singlet methyls

• extract 0.5%, and glucose 0.2% (pH 7.3) solidified by agar 2%, was inoculated into test tubes (inner diameter, 15 mm; length 16.5 cm) each containing 5 mL of YG seed medium consisting of glucose 1% and yeast extract 1% (pH 7.0). The tubes were shaken at 260 strokes/min at 28 °C for 3 days (TC-500R

Effect of a twin-emitter design strategy on a previously reported thermally activated delayed fluorescence organic light-emitting diode

• Ettore Crovini,
• Zhen Zhang,
• Yu Kusakabe,
• Yongxia Ren,
• Yoshimasa Wada,
• Bilal A. Naqvi,
• Prakhar Sahay,
• Tomas Matulaitis,
• Stefan Diesing,
• Ifor D. W. Samuel,
• Wolfgang Brütting,
• Katsuaki Suzuki,
• Hironori Kaji,
• Stefan Bräse and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2021, 17, 2894–2905, doi:10.3762/bjoc.17.197

• %, with Commission Internationale de l’Éclairage coordinate of (0.22, 0.47), at 1 mA cm−2. Keywords: blue emitters; dimer; indolocarbazole; orientation; outcoupling effect; solution-processed OLEDs; TADF emitters; triazine; Introduction Organic thermally activated delayed fluorescence (TADF) materials

• mA cm−2. The 20 wt % ICzTRZ-based OLEDs exhibited a slightly higher EQEmax of 11.6% and blue-shifted emission with λEL of 485 nm. This result is consistent with that of the photophysical measurements for 20 wt % TADF emitter:CzSi films (ΦPL = 57% and λPL = 488 nm for DICzTRZ, ΦPL = 63% and λPL = 475