Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

• Recep Isci and
• Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

• properties indicated that the composition of thienothiophene, triphenylamine, and boron is a highly suitable combination for fluorescent organic electronics in display technology. Experimental General methods 1H and 13C NMR spectra were recorded on a Varian model NMR spectrometer (500 and 126 MHz) and

• = 8.7 Hz, 5H), 7.20 (d, J = 8.7 Hz, 2H), 7.13 (d, J = 7.6 Hz, 4H), 7.05 (t, J = 7.3 Hz, 2H), 6.95 (d, J = 8.7 Hz, 2H), 6.92 (d, J = 8.8 Hz, 2H), 3.86 (s, 3H); 13C NMR (126 MHz, CDCl3) δ 158.89, 147.36, 147.17, 142.04, 139.51, 135.73, 130.12, 129.87, 129.29, 128.34, 127.96, 125.86, 124.80, 123.24, 122.53

• ), 2.17 (s, 12H); 13C NMR (126 MHz, CDCl3) δ 158.92, 153.46, 151.26, 147.60, 147.20, 143.95, 141.05, 140.90, 138.50, 137.96, 132.59, 130.25, 129.86, 129.49, 129.33, 128.14, 127.85, 127.57, 125.01, 123.45, 122.08, 114.12, 55.23, 23.54, 21.22. Absorption and emission of DMB-TT-TPA (8) in THF. Figure 1 was

Substituent-controlled construction of A₄B₂-hexaphyrins and A₃B-porphyrins: a mechanistic evaluation

• Seda Cinar,
• Dilek Isik Tasgin and
• Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

• -tosylimines. Experimental General method: All reagents and solvents were purchased from Sigma-Aldrich, Fisher Scientific, or Acros Organics and were used without further purification. 1H NMR (400 MHz), 13C NMR (100 MHz), and 19F NMR (376 MHz) spectra were recorded on a Bruker 400, Ultra Shield high

• -performance digital FT-NMR spectrometer. Data for 1H NMR, 13C NMR, and 19F NMR are reported as follows: chemical shift (δ, ppm), multiplicity (s = singlet, d = doublet, t = triplet, m = multiplet, q= quartet, bs = broad singlet, dd = doublet of doublets, td = triplet of doublets, qd = quartet of doublets

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

• Gyula Dargó,
• Dóra Erdélyi,
• Balázs Molnár,
• Péter Kisszékelyi,
• Zsófia Garádi and
• József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

• and high-performance liquid chromatography–mass spectrometry (HPLC–MS). The solvent ratios of the eluents are given in volume units (mL mL−1). Nuclear magnetic resonance (NMR) spectra were recorded on a Bruker DRX-500 Avance spectrometer (at 500 and 126 MHz for the 1H and 13C spectra, respectively) or

• on a Bruker 300 Avance spectrometer (at 300 and 75.5 MHz for the 1H and 13C spectra, respectively) or on a Bruker Avance III HD (at 600 MHz for 1H and at 150 MHz for 13C spectra) at specified temperatures. High-resolution MS was measured on a Bruker MicroTOF II instrument using positive electrospray

• (m, 1H), 2.86 (m, 1H), 2.82 (m, 1H), 2.41 (bs, 1H), 1.69 (m, 1H), 1.68 (m, 2H), 1.54 (m, 1H), 0.85 (m, 1H); 13C NMR (methanol-d4, 150 MHz, 295 K) δ 185.7, 182.1, 170.4, 164.8, 158.3, 147.6, 145.3, 144.6, 142.5, 142.3, 133.9 (q, 2JC,F = 33.4 Hz), 131.7, 129.7, 124.5 (q, 1JC,F = 272.0 Hz), 123.9, 120.0

Active-metal template clipping synthesis of novel [2]rotaxanes

• Cătălin C. Anghel,
• Teodor A. Cucuiet,
• Niculina D. Hădade and
• Ion Grosu

Beilstein J. Org. Chem. 2023, 19, 1776–1784, doi:10.3762/bjoc.19.130

• HRMS, most probably because of the lower efficiency of the [1 + 1] reaction combined with the smaller size of the macrocycle. The [2]rotaxane R2 obtained by intramolecular clipping was successfully isolated as unique compound and its structure was validated by HRMS, 1H,13C and 1H-DOSY NMR experiments

• –7.04 (overlapped signals, 8H, HAr), 6.75 (d, 3J = 8.9 Hz, 2H, HAr), 3.94 (t, 3J = 6.3 Hz, 2H, OCH2), 3.43 (t, 3J = 6.8 Hz, 2H, CH2Br), 1.93 (qv, 3J = 6.9 Hz, 2H, CH2), 1.83–1.77 (m, 2H, CH2), 1.65–1.58 (m, 2H, CH2), 1.30 (s, 27H, C(CH3)3) ppm; 13C NMR (CDCl3, 150 MHz) δ 156.9, 148.5, 144.3, 139.7

• ), 4.55 (s, 4H, CH2), 2.57 (t, 3J = 2.4 Hz, 2H, CH) ppm; 13C APT NMR (CD2Cl2, 150 MHz) δ 158.6, 157.8, 137.7, 132.1, 129.9, 120.5, 115.4, 79.2, 75.8, 73.6, 72.9, 56.5. Compound 6: Compound 5 (0.36 g, 0.6 mmol, 1 equiv) and compound 3 (0.82 g, 1.33 mmol, 2.2 equiv) were dissolved in DCM/MeOH (20 mL/5 mL

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 1H,13C-HSQC and 1H,13C-HMBС spectra, as well as by comparing the experimental carbon chemical shifts in DMSO-d6 with those calculated for 6 by the GIAO method at the PBE1PBE/6-311+G(2d,p) level of theory using the DFT B3LYP/6-311++G(d,p) optimized geometries (DMSO solution) and applying a multi

• C11H18N12 for bis-pyrazole 6. According to NMR spectroscopic data, the amount of bis-pyrazole 6 in the crude product formed under above conditions was about 18 mol %. The structure of macrocycle 5 was confirmed by comparing its 1H and 13C NMR spectra with those reported in ref. [40]. It should be noted that

• the 1H and 13C{1H} NMR spectra of compound 5 in DMSO-d6 show only a half-number set of proton or carbon signals (five and six signals, respectively), thus indicating its C2-symmetric dimeric structure. The analysis of 2D NMR spectroscopic data provided additional evidence for the macrocycle 5

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

• and hdz-NO2 (Figure 5A and 5B, respectively). 13C NMR and 2D homonuclear (COSY) and heteronuclear (13C,1H-HSQC and HMBC) experiments were employed for the full characterization of these hydrazones, and the spectra can be seen in Supporting Information File 1, Figures S5–S12. Both compounds exhibit

• Fisatom Model 431 apparatus. Hydrogen and carbon nuclear magnetic resonance spectra (NMR), homonuclear 1H,1H (COSY and NOESY) and heteronuclear 1H,13C (HSQC, HMBC) experiments were recorded on a 400 MHz Avance III (Bruker, Billerica, MA) spectrometer. Samples were dissolved in 0.5 mL DMSO-d6 and spectra

• were referenced based on the residual solvent signal (quintet at 2.50 ppm for 1H and septet at 39.52 for 13C). Mass spectra were obtained on a Trace 1300 gas chromatograph connected to ISQ QD single quadrupole mass spectrometer (Thermo Fisher Scientific Inc., Waltham, MA, USA). Samples were prepared in

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• )diboron catalyzed by Pd(dpf)Cl2/KOAc. Finally, TPECNz was obtained as red solid in a reasonable yield by a Suzuki-type cross-coupling reaction between 3 and 4,9-dibromonaphtho[2,3-c][1,2,5]thiadiazole. The chemical structure and purity of compound 3 were verified by 1H NMR, 13C NMR, and high-resolution

• purchased from commercial resources and used without further purification. 1H NMR and 13C NMR spectra were recorded with a Bruker AVANCE III HD 600 (600 MHz for 1H and 151 MHz for 13C) using CDCl3 as a solvent containing TMS as an internal standard. High-resolution mass spectrometry (HRMS) analysis was

• chromatography over silica gel eluting with CH2Cl2/hexane 1:4 to give white solids (2.11 g, 87%). 1H NMR (600 MHz, CDCl3) δ 8.12 (d, J = 7.7 Hz, 2H), 7.40 (t, J = 7.8 Hz, 2H), 7.34 (d, J = 8.2 Hz, 2H), 7.28 (t, J = 8.0 Hz, 4H), 7.24 (d, J = 8.1 Hz, 2H), 7.21–7.07 (m, 15H); 13C NMR (151 MHz, CDCl3) δ 143.55

Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity

• Swagat K. Mohapatra,
• Khaled Al Kurdi,
• Samik Jhulki,
• Georgii Bogdanov,
• John Bacsa,
• Maxwell Conte,
• Tatiana V. Timofeeva,
• Seth R. Marder and
• Stephen Barlow

Beilstein J. Org. Chem. 2023, 19, 1651–1663, doi:10.3762/bjoc.19.121

• [34]. In the case of molecules with aryl Y-substituents – 1b2 and 1g2 – the room-temperature 1H and 13C NMR spectra (see Supporting Information File 1, Figures S2, S26 and S27, and reference [26]) display more resonances than expected based on the highest symmetry possible for the molecule indicating

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

• Kathryn M. Wolfe,
• Shahidul Alam,
• Eva German,
• Fahad N. Alduayji,
• Maryam Alqurashi,
• Frédéric Laquai and
• Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

• adding a methanol/water mixture; thus, no lengthy purification steps were required for any of the syntheses. Yields of 52.4%, 80.2%, 58.1%, and 68.3% were obtained for PDIN-FB, PDIN-B, CN-PDIN-FB, and CN-PDIN-B, respectively. All compounds were structurally characterized using 1H NMR spectroscopy, 13C

Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

• Aaron H. Shoemaker,
• Elizabeth A. Foker,
• Elena P. Uttaro,
• Sarah K. Beitel and
• Daniel R. Griffith

Beilstein J. Org. Chem. 2023, 19, 1615–1619, doi:10.3762/bjoc.19.118

• of X-ray structure data for compound 8. Supporting Information File 11: Copies of 1H and 13C NMR spectra of all purified novel compounds. Supporting Information File 12: Chrystallographic information file (cif) of X-ray structure for compound 8. Acknowledgements We acknowledge Prof. Dasan Thamattoor

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

• the ethyl acetate fraction (Figure 1). The structures of known compounds 5–7 were identified based on 1H and 13C NMR data [2][3][10]. Breynin J (1) was isolated as an amorphous, colorless powder. The HRESIMS spectrum exhibited a sodium adduct ion peak at m/z 1107.3177, consistent with a molecular

• . In addition, signals corresponding to a p-hydroxybenzoate group [δH 8.02 (d, J = 8.9 Hz, 2H, H-21, 25), 6.94 (d, J = 8.9 Hz, 2H, H-22, 24)] were observed. The 13C NMR spectrum (Table 1) suggested the presence of a breynogenin-α-S-oxide moiety, similar to that in breynins B, D, G, and I [2], with the

• aglycone of 2 also consisted of a breynogenin-S-oxide moiety. However, a comparison of the 1H and 13C NMR data for the aglycones of 1 and 2 revealed markedly different tetrahydrothiophene signals [for 2, δC 61.7 (C-2), 87.4 (C-3), 39.9 (C-4), 62.3 (C-17)] (Table 1). According to previous literature [2

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis

• Bel Youssouf G. Mountessou,
• Élodie Gisèle M. Anoumedem,
• Blondelle M. Kemkuignou,
• Yasmina Marin-Felix,
• Frank Surup,
• Marc Stadler and
• Simeon F. Kouam

Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112

• (d, 2.0 Hz, 1H each), and at δH 7.57 and 6.62 (d, 1.0 Hz, 1H each), in addition to a singlet signal at δH 2.71 (s, CH3, 3H). The alternariol skeleton was further confirmed by the 13C NMR and HSQC spectra (Figures S10 and S11 in Supporting Information File 1), in conjunction with the HMBC spectrum

• overlapping at δH 2.28 due to two acetyl groups, which showed strong HMBC cross peaks with the carbonyl carbon signals at δH 169.0. The structure of 2 was fully assigned by using the 13C NMR spectrum which displayed sixteen carbon signals sorted into three methyl signals of which two overlapping ones at δC

• /USA) 500 MHz Avance III spectrometer with a BBFO (plus) Smart Probe (1H NMR: 500 MHz and 13C NMR: 125 MHz). Chemical shifts (δ) were reported in ppm using tetramethylsilane (TMS) (Sigma-Aldrich) as an internal standard, while coupling constants (J) were measured in hertz (Hz). Optical rotations were

Morpholine-mediated defluorinative cycloaddition of gem-difluoroalkenes and organic azides

• Tzu-Yu Huang,
• Mario Djugovski,
• Sweta Adhikari,
• Destinee L. Manning and
• Sudeshna Roy

Beilstein J. Org. Chem. 2023, 19, 1545–1554, doi:10.3762/bjoc.19.111

• . Proposed mechanism. Scale-up experiment. Optimization of reaction conditions.a Supporting Information Supporting Information File 2: General information, experimental procedures for all the substrates and intermediates, characterization data, and NMR spectra (1H, 19F, and 13C NMR). Funding Research

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

• Stéphanie Hesse

Beilstein J. Org. Chem. 2023, 19, 1537–1544, doi:10.3762/bjoc.19.110

• -Hydroxymethylfurfurylidene)-2-thioxothiazolidin-4-one (3j). ochre yellow solid obtained after 1 h at 60 °C in 36% yield (two-step yield). Mp 149 °C; 1H NMR (400 MHz, DMSO-d6) δ (ppm) 4.49 (s, 2H), 5.52 (br s, 1H, OH), 6.58 (d, J = 3.6 Hz, 1H), 7.11 (d, J = 3.6 Hz, 1H), 7.44 (s, 1H, =CH), 13.62 (br s, 1H, NH); 13C NMR (100

Complexes of resorcin[4]arene with secondary amines: synthesis, solvent influence on “in-out” structure, and theoretical calculations of non-covalent interactions

• Waldemar Iwanek

Beilstein J. Org. Chem. 2023, 19, 1525–1536, doi:10.3762/bjoc.19.109

• ) ppm; 13C NMR (100 MHz, DMSO-d6, T = 298 K) δ 152.0, 124.6, 123.3, 102.6, 43.7, 37.1, 30.7, 25.8, 22.8 ppm. 1:1 Complex of R[4]A with diethylamine: 68% yield; white solid; 1H NMR (400 MHz, DMSO-d6, T = 298 K) δ 7.16 (s, 4H, PhCH), 6.10 (s, 4H, PhCH), 5.6–3.6 (br s, 8H, OH), 4.34 (t, J = 7.70 Hz, 4H, CH

• , 4H, PhH), 4.43 (m, 4H, CH), 3.42 (q, J = 6.97 Hz, 2H, NCH2CH3), 3.41 (q, J = 6.97 Hz, 2H, NCH2CH3), 2.08 (m, 8H, CH2), 1.47 (m, 4H, CH), 1.24 (m, 3H, NCH2CH3), 0.97 (t, J = 6.60 Hz, 24H, CH3), 0.22 (br t, 3H, NCH2CH3) ppm; 13C NMR (100 MHz, DMSO-d6, T = 298 K) δ 151.8, 124.9, 123.2, 102.5, 42.9, 42.7

• , 2H, N(CH2)2(CH2)2), 1.49 (m, 4H, CH), 0.99 (t, J = 6.24 Hz, 24H, CH3), −0.7 (m, 4H, N(CH2)2(CH2)2) ppm; 13C NMR (100 MHz, DMSO-d6, T = 298 K) δ 152.0, 124.3 123.3, 102.7, 45.7, 42.5, 31.6, 25.7, 24.6, 22.7 ppm. 1:1 Complex of R[4]A with piperidine: 78% yield; white solid; 1H NMR (400 MHz, DMSO-d6, T

Cyclization of 1-aryl-4,4,4-trichlorobut-2-en-1-ones into 3-trichloromethylindan-1-ones in triflic acid

• Vladislav A. Sokolov,
• Andrei A. Golushko,
• Irina A. Boyarskaya and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2023, 19, 1460–1470, doi:10.3762/bjoc.19.105

• of enones 2a,e,n with an excess (5 equiv) of AlBr3 or AlCl3 in CH2Cl2 solution at room temperature for 3 days afforded complex mixtures of compounds. Then, the protonation of compounds 1 and 2 in TfOH was investigated by means of NMR spectroscopy. According to the 1H, 13C, and 19F NMR data, hydroxy

• to the 13C NMR spectra, the largest downfield shift was observed for the carbonyl carbon С1, with ∆δ = 17.7–21.1 ppm, showing a substantial degree of protonation of the carbonyl group in TfOH. The tendencies are the same for the protonation of enones 2a,c,d,m leading to cations Ba,c,d,m (Table 2

• ). Thus, in the 1H NMR spectra, downfield shifts of vinyl protons H2 and H3 upon protonation were 0.50–0.61 and 0.41–0.54 ppm, respectively. In the 13C NMR spectra, ∆δ values for carbons С1 and С3 were 12.7–21.3 and 6.0–13.4 ppm, respectively. The NMR data revealed that the positive charge in the O

Functions of enzyme domains in 2-methylisoborneol biosynthesis and enzymatic synthesis of non-natural analogs

• Binbin Gu,
• Lin-Fu Liang and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1452–1459, doi:10.3762/bjoc.19.104

• by the positioning of the ethyl groups in the products 2 and 3. Notably, the findings correspond to those made with the native substrate 2-Me-GPP in feeding experiments with (1-13C)-1-deoxyxylulose [30]. Conclusion In the present study we have investigated two aspects of 2-methylisoborneol

• ppm) for 1H NMR and the 13C signal of C6D6 (δ = 128.06 ppm) for 13C NMR [39]. Coupling constants are given in Hz. IR spectra were recorded on a Bruker α infrared spectrometer with a diamond ATR probehead. Peak intensities are given as s (strong), m (medium), w (weak) and br (broad). Optical rotations

• ; 13C NMR (126 MHz, D2O) δ 135.80 (Cq), 133.72 (Cq), 125.03 (d, 3JC,P = 8.5, CH), 124.26 (CH), 67.10 (d, 2JC,P = 5.6, CH2), 34.11 (CH2), 25.67 (CH2), 24.83 (CH3), 17.41 (CH3), 16.86 (CH3), 15.67 (CH3) ppm; 31P NMR (202 MHz, D2O) δ −7.90 (d, 2JP,P = 21.3), −10.40 (d, 2JP,P = 21.4) ppm; HRMS–TOF (m/z

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

• Nadia Ledermann,
• Alae-Eddine Moubsit and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

• compounds 5 in yields between 11–69% after chromatographic workup. The structures of the products were unambiguously confirmed by 1H and 13C NMR spectroscopy, as well as by mass spectrometry. Assuming that four new bonds are being formed in this one-pot process, the range of yield from 11 to 69% (after

• -trisubstitued indoles 8 in good yield (Scheme 4). The 1,2,3-trisubstitued indoles 8 were unambiguously confirmed by 1H and 13C NMR spectroscopy, as well as by mass spectrometry and elemental analysis. Miura et al. could show that 1-alkyl-2,3-diarylindoles constitute a class of blue-emissive indole derivatives

• ), 7.23–7.26 (m, 1H), 7.46–7.54 (m, 5H); 13C NMR (150 MHz, CDCl3) δ 1.9 (Cquat), 32.4 (CH3), 106.7 (CH), 110.8 (CH), 111.5 (CH), 128.6 (Cquat), 129.3, 130.9, 131.5 (Cquat), 134.5 (Cquat), 143.5 (Cquat), 160.0 (Cquat); IR (cm−1) ν̃: 604 (w), 619 (w), 662 (w), 689 (s), 733 (m), 756 (s), 789 (m), 860 (w

Correction: Non-peptide compounds from Kronopolites svenhedini (Verhoeff) and their antitumor and iNOS inhibitory activities

• Yuan-Nan Yuan,
• Jin-Qiang Li,
• Hong-Bin Fang,
• Shao-Jun Xing,
• Yong-Ming Yan and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 1370–1371, doi:10.3762/bjoc.19.97

• HMBC correlations of H-2/C-1, C-3, C-4, C-8a, H-4/C-3, C-4a, C-5, C-8a, C-9, H-5/C-4, C-4a, C-6, C-7, C-8a, H-9/C-2, C-3, C-4, H-10/C-7, C-8, C-8a, H-11/C-6, and H-12/C-7. Table 1 provides the revised 1D 1H and 13C NMR data of compound 1. The structural revision of 1 also required recalculation of the

• compound 1 and key HMBC correlations. Recalculated and experimental ECD spectra of compound 1. Revised 1H (600 MHz) and 13C NMR (150 MHz) data of compound 1 (δ in ppm, J in Hz, methanol-d4).

Organic thermally activated delayed fluorescence material with strained benzoguanidine donor

• Alexander C. Brannan,
• Elvie F. P. Beaumont,
• Nguyen Le Phuoc,
• George F. S. Whitehead,
• Mikko Linnolahti and
• Alexander S. Romanov

Beilstein J. Org. Chem. 2023, 19, 1289–1298, doi:10.3762/bjoc.19.95

• , and 1H/13C NMR spectroscopy. Proton NMR shows a complicated set of overlapping multiplets indicating that the reaction results in the formation of various isomers (rotamers) which are different by relative orientation of the benzoguanidine donor moieties with respect to each other (Figure 2, see

• mineral oil with diethyl ether and dried prior to use. 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (benzoguanidine) was obtained according to the literature protocol [10] while 2,4,5,6-tetrafluoroisophthalonitrile was purchased from Fluorochem Ltd. and used as received. 1H and 13C{1H} NMR spectra were

• recorded using a Bruker AVIII HD 500 MHz NMR spectrometer. 1H NMR spectra (500.19 MHz) and 13C{1H} (125.79 MHz) were referenced to dichloromethane-d2 at δ 5.32 (13C, δ 53.84). All electrochemical experiments were performed using an Autolab PGSTAT 302N computer-controlled potentiostat. Cyclic voltammetry

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

• Olfa Mhasni,
• Jalloul Bouajila and
• Farhat Rezgui

Beilstein J. Org. Chem. 2023, 19, 1251–1258, doi:10.3762/bjoc.19.93

• ) onto acyclic MBH alcohols 1a–f. Supporting Information Supporting Information File 69: Full experimental details and characterization data of all new compounds. Supporting Information File 70: 1H and 13C NMR and HRMS spectra of compounds. Acknowledgements We thank the Tunisian Chemical Society for

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

• structures of the obtained dispiro compounds 3a–m were fully characterized by IR, HRMS, 1H and 13C NMR spectroscopy. Because of the three chiral carbon atoms in the product, several diastereomers might be formed in the reaction. However, TLC monitoring and 1H NMR spectra of the crude products clearly

• , 1H, CH2), 2.46 (d, J = 16.0 Hz, 1H, CH2), 2.39 (d, J = 16.0 Hz, 1H, CH2), 2.37–2.34 (m, 2H, CH2), 1.30 (s, 3H, CH3), 1.15 (s, 3H, CH3), 0.76 (t, J = 7.2 Hz, 3H, CH3) ppm; 13C NMR (101 MHz, CDCl3) δ 193.0, 173.8, 171.9, 171.2, 155.6, 142.0, 141.8, 134.8, 134.1, 131.0, 129.3, 129.1, 128.8, 128.7, 128.6

• = 4.8 Hz, 1H, CH2), 4.43 (d, J = 5.2 Hz, 1H, CH2), 2.41 (d, J = 26.8 Hz, 1H, CH2), 2.40 (s, 3H, CH3), 2.21 (d, J = 18.4 Hz, 1H, CH2), 2.10 (s, 1H, CH3), 2.05 (s, 1H, CH2), 1.87 (d, J = 16.0 Hz, 1H, CH2), 1.00 (s, 3H, CH3), 0.99 (s, 3H, CH3) ppm; 13C NMR (101 MHz, CDCl3) δ 197.5, 181.6, 177.4, 177.2

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

• copper(II) porphyrins 3–8. Finally, the structures of all newly synthesized benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 3–16 and benzo[f]quinoxalinoporphyrin 17 were assigned on the basis of IR, 1H and 13C NMR, and HRMS data analysis. Photophysical characteristics The UV–vis spectra of the newly

• MHz) and 13C NMR (100 MHz) spectra were recorded in CDCl3 on a Jeol ECX-400P (400 MHz) NMR spectrometer. Chemical shifts are reported in δ scale in parts per million (ppm) relative to CDCl3 (δ = 7.26 ppm for 1H NMR and δ = 77.00 ppm for 13C NMR). The coupling constants are expressed as (J) and are

• ]chromeno[2,3-h]quinoxalinoporphyrin 3. Optimization of the reaction conditions for the synthesis of copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrin 3.a Supporting Information Supporting Information File 186: Characterization data, 1H and 13C NMR spectra of newly prepared porphyrin products

Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

• Valeriy O. Filimonov,
• Alexandra I. Topchiy,
• Vladimir G. Ilkin,
• Tetyana V. Beryozkina and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87

• -diaminopyrazoles 4a–c (Scheme 2). The structures of compounds 4a–c were confirmed by 1H and 13C NMR spectroscopy data, as well as high-resolution mass spectrometry (HRMS). Compound 4a was previously obtained by another method [18]. The spectral characteristics of diaminopyrazole 4a reported in [18] correspond to

• group during the reaction. The structures of compounds 5a–e were confirmed by 1H and 13C NMR spectroscopy and HRMS, as well as X-ray diffraction analysis of a single crystal of compound 5b. The involvement of arylhydrazines 3b,c in the reaction with enamines 2a–d similarly leads to the formation of 1

• upon addition of hydrochloric acid. This is probably due to the protonation of the dimethylamino moiety or/and that dimethylamine hydrochloride is a better leaving group than the free base. The structures of compounds 6a–f were confirmed by 1H and 13C NMR spectroscopy and HRMS, as well as X-ray

New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones

• Vladislav Yu. Shuvalov,
• Ekaterina Yu. Vlasova,
• Tatyana Yu. Zheleznova and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2023, 19, 1155–1160, doi:10.3762/bjoc.19.83

• Information Supporting Information File 124: Experimental procedures, characterization data, and 1H and 13C NMR spectra for all new compounds. Funding This work was supported by the Russian Science Foundation (grant No. 22-13-00356).