On Reuben G. Jones synthesis of 2-hydroxypyrazines

• Pierre Legrand and
• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 935–943, doi:10.3762/bjoc.18.93

• isomer 4{1,2} made it impossible to obtain a complete 13C NMR spectrum. On the other hand, following a sample recrystallization from acetic acid, an X-ray derived structure was obtained as seen with the ORTEP depiction in Figure 1. In this structure, the C–O bond length of 1.2425 Å is typical of a double

• compound 4{1,2} was achieved using the beamline PROXIMA-2 at Synchrotron SOLEIL and the data were deposited at the Cambridge Crystallographic Data Centre (CCDC), deposition number 2155463. Chemistry. 1H NMR and 13C NMR spectra were recorded on a Bruker Avance 400 spectrometer at 400 MHz and 100 MHz

• ), 7.40 (m, 2H), 7.28 (m, 1H), 2.37 (s, 3H); 13C NMR (DMSO-d6) δ 156.3, 155.8, 136.5, 131.3, 129.0, 127.6, 124.9, 122.2, 20.9. 3-Methyl-6-phenylpyrazin-2-ol (4{1,1}): HRMS (m/z): [M + H]+ calcd for C11H11N2O, 187.0866; found, 187.0864; 1H NMR (CD3COOD) δ 7.85 (s, 1H), 7.80–7.77 (m, 2H), 7.58–7.54 (m, 3H

Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products

• Nisha Devi and
• Virender Singh

Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92

• 10. Results of fluorescence studies of C-3-substituted pyrido[3,4-b]indole derivatives 7–8 and 10. Supporting Information Supporting information contains detailed experimental procedure for the synthesis of compounds 6–9 and 10 followed by detailed characterization data and copies of 1H NMR and 13C

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

• cadinane-type sesquiterpenoid of plant origin (leaves and stems of Manglietia insignis) [21], based on their identical 1H and 13C NMR data (Table 1 and Figures S16–S20 in Supporting Information File 1). Since the relative configuration of 4 (7S*, 10R*) was assigned, its absolute configuration was worth to

• ; 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

Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli

• Fang-Ru Li,
• Xiaoxu Lin,
• Qian Yang,
• Ning-Hua Tan and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89

• produced new peaks in the HPLC profiles after a 3-day fermentation. Larger scale (3 L) fermentations of DL10004 and DL10006 led to the isolation of 45 mg and 90 mg of terpentetriene and ent-kaurene, respectively, whose 1H and 13C NMR spectra supported their chemical structures (Figures S4–S7 in Supporting

Synthesis and HDAC inhibitory activity of pyrimidine-based hydroxamic acids

• Virginija Jakubkiene,
• Gabrielius Ernis Valiulis,
• Markus Schweipert,
• Asta Zubriene,
• Daumantas Matulis,
• Franz-Josef Meyer-Almes and
• Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 837–844, doi:10.3762/bjoc.18.84

• shifted by 0.8 ppm and 24.8 ppm in the 1H and 13C NMR spectra, respectively, in comparison with the signals of the methylthio group of compound 3 (see Supporting Information File 1, Figures S1, S2 and S5, S6). Heating compound 5 with primary and secondary amines in dimethyl sulfoxide at 50–70 °C for 0.5 h

• chromatography was performed using silica gel 60 (0.040–0.063 mm) (Merck). NMR spectra were recorded on a Bruker Ascend 400 spectrometer (400 MHz and 100 MHz for 1H and 13C, respectively). 1H NMR and 13C NMR were referenced to residual solvent peaks. High-resolution mass spectrometry (HRMS) analyses were carried

• out on a Dual-ESI Q-TOF 6520 (Agilent Technologies) mass spectrometer. The starting compounds 1 [39], 2 [39] and 19 [40] were prepared following the reported methods. Synthetic details, characterization and analytical data as well as 1H and 13C NMR spectra of all synthesized compounds are presented in

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

• , respectively [43]. As displayed in Figure 13c and 13d, the UV–vis–NIR absorption spectra manifested that the larger steric hindrance interrupted the binding of BCF more effectively than that of BBr3. Conclusion For fluorescent materials containing nitrogen atoms with Lewis basic nature, it is easily found that

The stereochemical course of 2-methylisoborneol biosynthesis

• Binbin Gu,
• Anwei Hou and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 818–824, doi:10.3762/bjoc.18.82

• suggested to proceed through degradation of a sesquiterpene [2], but first feeding experiments with 14C-labeled acetate and methionine pointed to a methylated monoterpene [22]. Further investigations by feeding of 13C-labeled methionine and deuterated mevalonolactone isotopomers to Nannocystis exedens

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

• employed. All starting materials and reagents were commercially available. 1H NMR and 13C{1H} NMR spectra were recorded on 300 or 400 MHz NMR instruments using CDCl3 as solvent. The chemical shift references were as follows: (1H) CDCl3, 7.26 ppm (CHCl3); (13C{1H}) CDCl3, 77.00 ppm (CDCl3). IR spectra were

• (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

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

• Hz, 1H, CH), 4.46 (d, J = 16.0 Hz, 1H, CH), 3.49 (t, J = 12.4 Hz, 1H, CH), 3.26 (dd, J1 = 16.8 Hz, J2 = 5.2 Hz, 1H, CH); 13C NMR (100 MHz, CDCl3) δ 199.3, 178.0, 143.6, 136.6, 136.5, 136.2, 135.2, 133.3, 132.3, 130.9, 130.0, 128.7, 128.6, 128.4, 128.2, 127.9, 127.7, 127.0, 126.9, 126.7, 126.5, 125.6

• (d, J = 15.6 Hz, 1H, CH), 4.89 (s, 1H, CH), 4.10 (dd, J1 = 16.4 Hz, J2 = 2.4 Hz, 1H, CH), 2.96 (d, J = 16.4 Hz, 1H, CH); 13C NMR (100 MHz, CDCl3) δ 173.2, 136.6, 134.7, 133.6, 130.9, 129.4, 128.8, 128.0, 127.6, 125.0, 123.6, 122.7, 120.2, 120.1, 112.7, 111.0, 110.4, 106.9, 51.8, 47.6, 46.2, 44.7

• ), 7.25–7.17 (m, 2H, ArH), 7.04 (s, 1H, ArH), 6.96–6.91 (m, 4H, ArH), 6.35 (d, J = 7.6 Hz, 1H, CH), 3.10 (s, 3H, CH3), 3.07 (s, 3H, CH3), 2.37 (s, 3H, CH3), 2.34 (s, 3H, CH3); 13C NMR (100 MHz, CDCl3) δ 165.3, 162.7, 157.9, 149.7, 149.0, 147.3, 142.6, 139.1, 138.7, 137.1, 136.0, 133.7, 130.6, 130.3, 130.0

Continuous flow synthesis of azobenzenes via Baeyer–Mills reaction

• Jan H. Griwatz,
• Anne Kunz and
• Hermann A. Wegner

Beilstein J. Org. Chem. 2022, 18, 781–787, doi:10.3762/bjoc.18.78

• 13C NMR spectra, and structures of unsuccessful substrates. Acknowledgements The authors thank Chiara Eleonora Campi for help with the graphical abstract. Funding This project was partially funded by the European Regional Development Fund (ERDF), the Germans Research Council DFG (WE5601/12-1) and TCI.

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple

• Alexander S. Filatov,
• Olesya V. Khoroshilova,
• Anna G. Larina,
• Vitali M. Boitsov and
• Alexander V. Stepakov

Beilstein J. Org. Chem. 2022, 18, 769–780, doi:10.3762/bjoc.18.77

• . The constitution of compounds 3b–g was established by analyzing 1H and 13C NMR spectra. In line with the structure of meso compound 3e, the relative configuration, that is shown in Scheme 3, was assigned to cycloadducts 3a, 3c, 3d, 3f, and 3g. Thus, the cycloadditions of 3-substituted-1,2

• electrophilicity index (ω, eV) for PRP (1) and cyclopropenes 2.a,b,c. Supporting Information Supporting Information File 156: Experimental details for the synthesis and characterization of all compounds, copies of 1H NMR and 13C NMR spectra, X-ray data and details of calculations. Acknowledgements This research

An isoxazole strategy for the synthesis of 4-oxo-1,4-dihydropyridine-3-carboxylates

• Timur O. Zanakhov,
• Ekaterina E. Galenko,
• Mikhail S. Novikov and
• Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2022, 18, 738–745, doi:10.3762/bjoc.18.74

• . According to the calculation results compounds 2 exist in the pyridone form in acetonitrile or chloroform solution (Table 1). All new compounds were characterized by 1H, 13C NMR and HRMS methods. Moreover, the structure of 2k was also confirmed by single-crystal X-ray diffraction analysis (Figure S1

A trustworthy mechanochemical route to isocyanides

• Francesco Basoccu,
• Federico Cuccu,
• Federico Casti,
• Rita Mocci,
• Claudia Fattuoni and
• Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 732–737, doi:10.3762/bjoc.18.73

• Ricerca d'Ateneo) core facility of the University of Cagliari and Dr. Sandrina Lampis for assistance with the generation of the 1H and 13C NMR spectroscopic data. Funding This research was funded by MIUR Italy, PRIN 2017 project (grant number: 2017B7MMJ5_001) “MultIFunctional poLymer cOmposites based on

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

• of electron-donating methyl groups in the isatins gave higher yields than electron-withdrawing groups such as chloro and fluoro substituents. The structures of the spiro compounds 8a–m were fully characterized by their IR, HRMS, 1H and 13C NMR spectra. In addition, the single crystal structure of

• , CH2), 4.86 (d, J = 15.0 Hz, 1H, CH2), 3.46 (t, J = 13.8 Hz, 1H, CH), 3.08 (d, J = 15.6 Hz, 1H, CH2), 2.40 (s, 3H, CH3), 2.38 (s, 3H, CH3), 2.34 (s, 3H, CH3); 13C NMR (100 MHz, CDCl3) δ 196.9, 171.7, 140.7, 140.4, 139.8, 139.6, 134.4, 134.0, 131.9, 131.6, 130.8, 130.1, 129.8, 129.3, 129.1, 129.0, 128.9

• ), 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

Direct C–H amination reactions of arenes with N-hydroxyphthalimides catalyzed by cuprous bromide

• Dongming Zhang,
• Bin Lv,
• Pan Gao,
• Xiaodong Jia and
• Yu Yuan

Beilstein J. Org. Chem. 2022, 18, 647–652, doi:10.3762/bjoc.18.65

• envisaged that this work will provide a simple amination strategy for synthesizing aromatic amines. Experimental All new compounds were fully characterized. 1H NMR and 13C NMR spectra were obtained with Agilent Technologies AVANCE-400 MHz or 600 MHz spectrometers in CDCl3 as the solvent with TMS as an

• . A plausible reaction mechanism. Optimization of the reaction conditions.a Supporting Information Supporting Information File 48: Synthetic schemes for products, characterization data, and copies of 1H, 13C, and 19F NMR spectra. Funding We gratefully acknowledge funding from Jiangsu Provincial

Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

• Anas J. Rasras,
• Mohamed El-Naggar,
• Nesreen A. Safwat and
• Raed A. Al-Qawasmeh

Beilstein J. Org. Chem. 2022, 18, 631–638, doi:10.3762/bjoc.18.63

• showed an amide doublet resonance at 7.09 ppm. On the other hand, the 13C NMR spectra showed all characteristic signals for all of the synthesized compounds, with multiple aliphatic peaks for the cholyl and aliphatic amine moieties. The fingerprint signals for the cholyl moiety (C–OH) were evident in all

A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments

• Constantine V. Milyutin,
• Andrey N. Komogortsev,
• Boris V. Lichitsky and
• Valeriya G. Melekhina

Beilstein J. Org. Chem. 2022, 18, 588–596, doi:10.3762/bjoc.18.61

• communication we have described for the first time the phototransformation of the 3-hydroxypyran-4-one fragment with the isolation of the resulting substituted α-hydroxy-1,2-diketone in pure form. The structure of the obtained compound 14a was confirmed using 1H, 13C NMR spectroscopy as well as 2D NMR

• nonequivalence of corresponding carbon atoms of the aromatic ring is also observed in the 13C NMR spectrum. The plausible route for the formation of α-hydroxy-1,2-diketone 14a is presented in Scheme 4. Based on literature data we suppose that the photoreaction proceeds through an excited state intramolecular

• : Experimental procedures, characterization data of all products, copies of 1H, 13C, 2D NMR, HRMS spectra of all new compounds, and X-ray crystallographic data.

Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties

• Masayori Hagimori,
• Tatsusada Yoshida,
• Yasuhisa Nishimura,
• Yukiko Ogawa and
• Keitaro Tanaka

Beilstein J. Org. Chem. 2022, 18, 580–587, doi:10.3762/bjoc.18.60

• compound, 10-imino-2-methylpyrido[1,2-a]pyrrolo[3,4-d]pyrimidine-1,3(2H,10H)-dione (3a), in 97% yield. The chemical structure of product 3a was confirmed by 1H and 13C NMR spectroscopy (Figures S1 and S2 in Supporting Information File 1) and was obtained via the following reaction mechanism: nucleophilic

• 13C NMR spectroscopy (Figures S5 and S6 in Supporting Information File 1). Similarly, the reaction of 1 with 2-aminopyridine derivatives 2d–g bearing electron-withdrawing groups, except for the nitro-group containing substrate 2h, at position 5 of the pyridine ring, afforded N-methyl-4-((pyridin-2-yl

Terpenoids from Glechoma hederacea var. longituba and their biological activities

• Dong Hyun Kim,
• Song Lim Ham,
• Zahra Khan,
• Sun Yeou Kim,
• Sang Un Choi,
• Chung Sub Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58

• = 10.9, 1.1 Hz)], and a glucopyranosyl unit [δH 4.20 (1H, d, J = 7.8 Hz), 3.78 (1H, dd, J = 11.9, 2.2 Hz), 3.59 (1H, dd, J = 11.9, 5.8 Hz), 3.31 (1H, overlap), 3.26 (1H, dd, J = 9.6, 9.0 Hz), 3.23 (1H, dd, J = 9.2, 7.8 Hz), and 3.05 (1H, ddd, J = 9.6, 5.8, 2.2 Hz)]. The 13C NMR spectrum of 1 showed 21

• carbon signals, including four oxygenated carbons (δC 70.0, 61.4, 60.5, and 57.9), a lactone moiety (δC 172.6, 159.0, 131.2, and 109.2), and a glucopyranosyl moiety (δC 97.2, 78.7, 78.1, 74.5, 71.4, and 62.5) (Table 1). Comparison of these 1H and 13C NMR spectra of 1 with those of 1β,10α;4α,5β-diepoxy-8β

• 13C NMR spectrum of 2 showed 22 carbon signals including five oxygenated carbons (δC 76.6, 70.7, 65.7, 62.3, and 57.9), a lactone moiety (δC 171.9, 151.4, 136.9, and 110.9), a methoxy carbon (δC 51.3), and a glucopyranosyl unit (δC 103.1, 78.6, 78.4, 75.4, 71.9, and 63.3) (Table 1). These NMR spectra

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

• Man-Ping Li,
• Nan Yang and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

• synthesized compounds were fully characterized by 1H and 13C NMR spectroscopy and mass spectrometry (see Supporting Information File 1) and the data were found to be consistent with the proposed structures. Host–guest complexation of TBTQ-CB6 with dimethyl viologen (MV). The host–guest complexation between

• were collected from a Mikrouna Solv Purer G3 solvent purification system. The 1H NMR and 13C NMR spectra were recorded on a 400 MHz Bruker NMR spectrometer and chemical shifts are reported in ppm (δ). The fluorescence spectra were measured on a HORIBA Fluorolog-3 spectrofluorometer. Mass spectra were

• (t, J = 7.1 Hz, 18H); 13C NMR (100 MHz, DMSO-d6, 25 °C) δ 167.20, 147.89, 143.15, 137.57, 126.07, 110.42, 62.61, 62.55, 62.15, 61.50, 50.38, 27.48, 13.93; (+)-ESI-HRMS (m/z): [M + H]+ calcd for C65H73N18O18, 1393.5345; found, 1393.5354 (Δ = +0.7 ppm). Synthesis of compound 3. To a methanol solution

Chemistry of polyhalogenated nitrobutadienes, 17: Efficient synthesis of persubstituted chloroquinolinyl-1H-pyrazoles and evaluation of their antimalarial, anti-SARS-CoV-2, antibacterial, and cytotoxic activities

• Viktor A. Zapol’skii,
• Isabell Berneburg,
• Ursula Bilitewski,
• Melissa Dillenberger,
• Katja Becker,
• Stefan Jungwirth,
• Aditya Shekhar,
• Bastian Krueger and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2022, 18, 524–532, doi:10.3762/bjoc.18.54

• ring system in the dienes 4a,l–o (Scheme 4). The obtained 5-aminopyrazoles 5a,l–o show the following 13C NMR shifts of the pyrazole ring and the dichloromethyl group: 149.5–149.9 ppm (C-NHR), 114.7–116.1 ppm (C-NO2), 147.0–147.2 ppm (C=N), and 62.2–62.3 ppm (CHCl2). On the other hand, the dienes 4b–k

• the butadiene chain is more likely due to the possibility of a rotation around the C1–C2 bond in 4b–k. The 3-aminopyrazoles 5b–k show considerable differences of the 13C shifts of C-NO2-, C-CHCl2- and CHCl2-groups in comparison with the corresponding 13C shifts of 5-aminopyrazoles 5a,l–o. The 13C NMR

• shifts of the pyrazole ring and the dichloromethyl group of 3-aminopyrazoles 5b–k are 151.1–154.0 ppm (C-NRR1), 120.6–122.2 ppm (C-NO2), 136.7–136.9 ppm (C-CHCl2), and 57.5–57.7 ppm (CHCl2). The obtained 13C NMR data of pyrazoles 5 match the calculated NMR shifts (Table S1 in Supporting Information File

BINOL as a chiral element in mechanically interlocked molecules

• Matthias Krajnc and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2022, 18, 508–523, doi:10.3762/bjoc.18.53

• thread also leads to a desymmetrization of the BINOL-based macrocycle (loss of C2 symmetry), as seen by 13C NMR spectroscopy. Stoddart and co-workers also used their π–π-recognition approach for the synthesis of BINOL-containing cationic catenanes [47][48]. They employed BINOL-based macrocycles

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

• the formation of the 2-cyano- and 2-(4-tert-butylphenylthio) derivatives 4 and 5 in 65% and 77% yield, respectively. Finally, compound 5 in the reaction with oxone furnished 2-(4-tert-butylphenylsulfonyl) derivative 6 in reasonable 68% yield. 1H and 13C NMR spectroscopy and HRMS were employed to

• and 100 MHz for 1H and 13C, respectively). 1H NMR and 13C NMR spectra were referenced to residual solvent peaks. High-resolution mass spectrometry (HRMS) analyses were carried out on a Dual-ESI Q-TOF 6520 (Agilent Technologies) mass spectrometer. Photophysical properties were analyzed in 10−5 M

• = 8 Hz, 4H, CHCbz), 7.62 (d, J = 8 Hz, 4H, CHCbz), 8.18 (s, 4H, CHCbz), 9.23 (s, 1H, CHpy) ppm; 13C NMR (100 MHz, CDCl3) δ 15.2, 31.9, 34.9, 110.7, 116.6, 121.8, 124.2, 124.7, 137.8, 144.6, 157.1, 160.2 ppm; HRMS–ESI (m/z): [M + H]+ calcd for C45H53N4, 649.4265; found, 649.4265. 2-Aryl-4,6-bis[3,6-di

Bioinspired tetraamino-bisthiourea chiral macrocycles in catalyzing decarboxylative Mannich reactions

• Hao Guo,
• Yu-Fei Ao,
• De-Xian Wang and
• Qi-Qiang Wang

Beilstein J. Org. Chem. 2022, 18, 486–496, doi:10.3762/bjoc.18.51

• data, copies of 1H and 13C NMR spectra. Funding This work was financially supported by National Key R&D Program of China (2021YFA1501600) and National Natural Science Foundation of China (22022112, 21871276).

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

• electronic circular dichroism (ECD) data with those of compound 3, whereas that of compound 2 was proposed based on biosynthetic considerations. The structures of the known compounds were further confirmed by comparison of their 1H and 13C NMR spectroscopic data, specific rotations, and ECD data with those

• , s, 2H), three sets of nonequivalent methylene protons (δH 3.40 and 3.30, each d, J = 16.8 Hz, 1H; δH 2.13 and 2.04, each m, 1H; δH 1.81 and 1.39, each m, 1H), and an isopropyl group (δH 1.71, m, 1H, and δH 0.95 and 0.82, each d, J = 6.9 Hz, 3H). The 13C NMR spectrum (Table 1) consisted of signals

• and 1.37, m, 1H; δH 1.84 and 1.64, each m, 1H), and an isopropyl group (δH 1.83, m, 1H, and δH 1.06 and 0.88, each d, J = 6.5 Hz, 3H). The 13C NMR spectrum (Table 1) consisted of signals for two carboxyl carbonyl carbons (δC 179.6 and 174.5), two quaternary carbons (one olefinic carbon, δC 150.2, and