Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris

• Angelique Ladwig,
• Markus Kroll and
• Stefan Schulz

Beilstein J. Org. Chem. 2023, 19, 167–175, doi:10.3762/bjoc.19.16

• chromatography; enantioselective synthesis; GC/MS; semiochemicals; Introduction Hyperolius cinnamomeoventris (Figure 1) is one of the largest species of reed frogs (Hyperoliidae), which are commonly found in Africa, south of the Sahara. Males of the Hyperoliidae possess a characteristic yellow gular patch on

• their vocal sac that also serves as a gland which emits volatile organic compounds during calling [1]. These courtship calls are trimodal, consisting of calls, yellow flashing signals, and volatile chemicals released from the gland [2]. The semiochemical signal, the glandular secretion, seems to be used

• mass spectrometric and gas chromatographic data to be acquired, clarifying the identity and stereochemistry of several cadinols. Calling male Hyperolius cinnamomeoventris with exposed vocal sac carrying the yellow gular gland. Figure 1 was reprinted from [2], I. Starnberger et al., “Take time to smell

Synthesis and characterisation of new antimalarial fluorinated triazolopyrazine compounds

• Kah Yean Lum,
• Jonathan M. White,
• Daniel J. G. Johnson,
• Vicky M. Avery and
• Rohan A. Davis

Beilstein J. Org. Chem. 2023, 19, 107–114, doi:10.3762/bjoc.19.11

• = 2.7 Hz, C-13); LRESIMS m/z: 451 [M + H]+, 473 [M + Na]+, 923 [2M + Na]+; HRESIMS (m/z): [M + H]+ calcd for C21H16F5N4O2, 451.1188; found, 451.1195. 8-(1,1-Difluoroethyl)-3-(4-(difluoromethoxy)phenyl)-5-phenethoxy-[1,2,4]triazolo[4,3-a]pyrazine (11). Yellow amorphous solid (23 mg, 51%); UV (MeOH) λmax

• ]pyrazine (14). Yellow amorphous solid (18 mg, 44%); UV (MeOH) λmax (log ε): 243 (4.23), 286 (3.81), 317 (3.80) nm; 1H NMR (800 MHz, CDCl3) δH 2.26 (t, J = 18.9 Hz, 3H, H-25), 2.95 (t, J = 6.5 Hz, 2H, H-17), 4.49 (t, J = 6.5 Hz, 2H, H-16), 6.88 (m, 2H, H-19, H-23), 7.23 (m, 1H, H-21), 7.24 (m, 2H, H-20, H

• ), 146.4 (C-3); LRESIMS m/z: 410 [M + H]+, 432 [M + Na]+; HRESIMS (m/z): [M + H]+ calcd for C21H15F3N5O, 410.1223; found, 410.1221. 4-(8-(1,1-Difluoroethyl)-5-phenethoxy-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)benzonitrile (17). Yellow amorphous solid (23 mg, 56%); UV (MeOH) λmax (log ε): 226 (4.41), 250 (4.33

Preparation of β-cyclodextrin/polysaccharide foams using saponin

• Max Petitjean and
• José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

• same trends are observed for all the polysaccharide types (Figure 7). Those matrices with cyclodextrin (yellow bars in Figure 7) absorbed better all the phenolic compounds tested. In addition, the incorporation of saponin does not produce a higher sorption capacity except for the XG matrices. In these

• -cyclodextrin/polysaccharides (blue curves for chitosan, red for locust bean gum, green for xanthan gum) with saponin (yellow curves correspond to cyclodextrin matrices, without polysaccharide). Sorption of phenols (V, vanillin; Ph, phenol; m-c, m-cresol; 4eP, 4-ethylphenol; Eu, eugenol) in β-cyclodextrin

Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B

• Adwoa P. Nartey,
• Aboagye K. Dofuor,
• Kofi B. A. Owusu,
• Anil S. Camas,
• Hai Deng,
• Marcel Jaspars and
• Kwaku Kyeremeh

Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185

• isolated by repeated semi-preparative reversed-phase HPLC with diode array detection (0–400 nm) at retention time of 27.5 min (see Supporting Information File 1, Figures S3–S7). It was obtained as a white amorphous powder which was bright yellow when in solution. The molecular formula of 1 was determined

Navigating and expanding the roadmap of natural product genome mining tools

• Friederike Biermann,
• Sebastian L. Wenski and
• Eric J. N. Helfrich

Beilstein J. Org. Chem. 2022, 18, 1656–1671, doi:10.3762/bjoc.18.178

• yellow, genes in green and motifs in violet. Concepts of algorithms in order of complexity and examples of genome mining tools that employ the respective concept. Examples of peptide NPs, the corresponding BGCs of which were determined through retrobiosynthetic analysis and then experimentally verified

• : polytheonamide A (13) [76], closthioamide (14) [77], and biarylitide YYH (15) [33]. gcBGC prioritization process. The bar represents all identified gene clusters in one organism and is subdivided into primary (green) on the left and secondary metabolism (yellow) on the right. Gene clusters associated with

Simple synthesis of multi-halogenated alkenes from 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane)

• Yukiko Karuo,
• Atsushi Tarui,
• Kazuyuki Sato,
• Kentaro Kawai and
• Masaaki Omote

Beilstein J. Org. Chem. 2022, 18, 1567–1574, doi:10.3762/bjoc.18.167

• concentrated under reduced pressure. The residue was purified by column chromatography (hexane only) to afford 7 in 80% yield (107.2 mg) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 0.127 and 0.239 (s, 9H), 7.06–7.14 (m, 2H), 7.16–7.22 (m, 1H), 7.32–7.41 (m, 2H); 13C NMR (100 MHz, CDCl3) δ −0.364, −0.259, 85.3

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• time. 5-Debromopurealidin H (1) was isolated as a stable yellow film. The LRESIMS of 1 showed 1:1 ion cluster peaks at m/z 382/384 [M + H]+ and 380/382 [M − H]−, indicating the presence of one bromine atom [16]. Furthermore, a molecular formula of C14H17BrN5O3 was assigned following analysis of the 1D

• a further 10 min, all at a flow rate of 9 mL/min. Sixty 1 min fractions were collected from time 0 to 60 min to afford 5-debromopurealidin H (1, 11.1 mg, tR 32–34 min, 0.111% dry wt), and the known alkaloid ianthesine E (2, 161.2 mg, tR 40–41 min, 1.612% dry wt). 5-Debromopurealidin H (1): Yellow

• for C14H1779BrN5O3, 382.0509). Ianthesine E (2): Yellow film; + 76.3 (c 0.4 in MeOH), lit. + 50.6 (c 0.3 in MeOH) [15]; (+)-LRESIMS m/z 714/716/718/720/722 (1:4:6:4:1) [M + H]+, (−)-LRESIMS m/z 792/794/796/798/800 (1:4:6:4:1) [M − H]−. Preparation of nematode larvae for bioassays Haemonchus

A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4 + 1] annulation reaction of fused 1H-pyrrole-2,3-diones with diazooxindoles

• Pavel A. Topanov,
• Anna A. Maslivets,
• Maksim V. Dmitriev,
• Irina V. Mashevskaya,
• Yurii V. Shklyaev and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2022, 18, 1532–1538, doi:10.3762/bjoc.18.162

• the solution being turned from purple to red. The starting FPD 1a is bright violet; thus, the disappearance of the violet color was used as an indicator of the reaction’s completion. Product 3aa was isolated as yellow crystals in 73% yield and characterized by NMR, IR, and mass spectra, and single

New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling

• Elenilson F. da Silva,
• Krist Helen Antunes Fernandes,
• Denise Diedrich,
• Jessica Gotardi,
• Marcia Silvana Freire Franco,
• Carlos Henrique Tomich de Paula da Silva,
• Ana Paula Duarte de Souza and
• Simone Cristina Baggio Gnoatto

Beilstein J. Org. Chem. 2022, 18, 1524–1531, doi:10.3762/bjoc.18.161

• Figure 3, compound 8 (in yellow sticks) interacted through hydrogen bonds with Arg108 and Tyr421, represented by magenta dots, similar to the interactions observed in the crystallographic complex with IMP and the inhibitor MAD1, in cyan sticks. Moreover, the acetate group (at C-3 position) and nitroaryl

• with compound 8. (B) Viral load quantification by real-time PCR after treatment with compound 8. Superposition of the top-ranked docking solution of compound 8 (carbon atoms in yellow, in stick representation) with the crystallographic poses of IMP and inhibitor MAD1 (color by atoms in stick

Comparison of crystal structure and DFT calculations of triferrocenyl trithiophosphite’s conformance

• Ruslan P. Shekurov,
• Mikhail N. Khrizanforov,
• Ilya A. Bezkishko,
• Tatiana P. Gerasimova,
• Almaz A. Zagidullin,
• Daut R. Islamov and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1499–1504, doi:10.3762/bjoc.18.157

• vacuo. The product was extracted with benzene (3 × 30 mL) and after evaporation of the solvent triferrocenyl trithiophosphite (1.34 g, 76%) was obtained as a yellow powder. Single crystals suitable for X-ray diffraction were obtained by dissolving the compound in a mixture of benzene/hexane 1:1 and

• atoms – orange, S atoms – yellow. Quantum chemically optimized conformations of the (PhS)3P molecule and their relative energies (kcal/mol). Calculated relative energies and dihedral angles Fc(C)–S–P=X (°) (X = LEP, O, S) of four possible conformers of (FcS)3P, (FcS)3PO, and (FcS)3PS. Supporting

Naphthalimide-phenothiazine dyads: effect of conformational flexibility and matching of the energy of the charge-transfer state and the localized triplet excited state on the thermally activated delayed fluorescence

• Kaiyue Ye,
• Liyuan Cao,
• Davita M. E. van Raamsdonk,
• Zhijia Wang,
• Jianzhang Zhao,
• Daniel Escudero and
• Denis Jacquemin

Beilstein J. Org. Chem. 2022, 18, 1435–1453, doi:10.3762/bjoc.18.149

• chromatography (silica gel, DCM/MeOH 50:1, v:v). NI-PTZ-O was obtained as yellow solid. Yield: 180 mg (87.2%). Mp 176.2–177.2 °C; 1H NMR (CDCl3, 400 MHz) δ 0.88–0.98 (m, 6H), 1.27–1.43 (m, 8H), 1.95–2.01 (m, 1H), 4.11–4.22 (m, 2H), 6.67 (d, J = 8.26 Hz, 2H), 7.29 (d, J = 7.38 Hz, 2H), 7.38–7.42 (m, 2H), 7.88

• anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography (silica gel, DCM/PE 6:1, v:v). The product NI-Ph-PTZ was obtained as yellow solid. Yield: 40 mg (62.4%). Mp 126.7–128.3 °C; 1H NMR (CDCl3, 400 MHz) δ 0.94–0.97 (m, 6H), 1.33–1.42

• over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography (silica gel, DCM/PE 1:5, v:v). The product NI-PhMe2-PTZ was obtained as yellow solid. Yield: 50 mg (28.3%). Mp 121.2–122.4 °C; 1H NMR (CDCl3, 400 MHz) δ 0.89–0.97 (m, 6H

Mechanochemical synthesis of unsymmetrical salens for the preparation of Co–salen complexes and their evaluation as catalysts for the synthesis of α-aryloxy alcohols via asymmetric phenolic kinetic resolution of terminal epoxides

• Shengli Zuo,
• Shuxiang Zheng,
• Jianjun Liu and
• Ang Zuo

Beilstein J. Org. Chem. 2022, 18, 1416–1423, doi:10.3762/bjoc.18.147

• outlined in Scheme 3. Reaction conditions were described previously [17][46]. For reactions using Zn and Cu, Zn(OAc)2·2H2O or Cu(OAc)2·H2O in methanol was dropwise added to 1a, b, or d in ethanol under nitrogen gas. The reaction mixture was refluxed for 4 hours and a light yellow or dark green solid was

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

• yellow amorphous powder. The negative HRESIMS [M − H]− at m/z 371.1133 (calcd for 371.1136) suggested its molecular formula to be C20H20O7, corresponding to 11 degrees of unsaturation. The IR spectrum showed absorption bands characteristic of hydroxy group (3450 cm−1), carbonyl (1765 cm−1), and aromatic

• 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

Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition

• Anaïs Rousseau,
• Guillaume Vincent and
• Cyrille Kouklovsky

Beilstein J. Org. Chem. 2022, 18, 1385–1395, doi:10.3762/bjoc.18.143

• (MgSO4), filtered and concentred under reduced pressure to give a brown oil. Purification by column chromatography (25% AcOEt/cyclohexane) gave the enol phosphate 17 as a yellow oil (200 mg, 26%). Rf: 0.47 (30% AcOEt/cyclohexane); 1H NMR (360 MHz, CDCl3) δ 6.15 (dd, J = 17.3, 10.8 Hz, 1H), 5.47 (d, J

• dichloromethane (3 × 74 mL). The combined organic layers were dried (MgSO4), filtered and concentred under reduced pressure. Purification of the crude product by column chromatography (30% AcOEt/cyclohexane) gave the cycloadduct 10b as a yellow oil (404 mg, 73%). Rf: 0.42 (30% AcOEt/cyclohexane); 1H NMR (360 MHz

• reduced pressurre, the residue taken up with dichloromethane (10 mL) and filtered, washing with dichloromethane (3 × 5 mL). The filtrate was concentred under reduced pressure to give a yellow oil (300 mg) consisting in a mixture of the ketone 11b and the over-reduced alcohol. This mixture was carried into

Computational model predicts protein binding sites of a luminescent ligand equipped with guanidiniocarbonyl-pyrrole groups

• Neda Rafieiolhosseini,
• Matthias Killa,
• Thorben Neumann,
• Niklas Tötsch,
• Jean-Noël Grad,
• Alexander Höing,
• Thies Dirksmeyer,
• Jochen Niemeyer,
• Christian Ottmann,
• Shirley K. Knauer,
• Michael Giese,
• Jens Voskuhl and
• Daniel Hoffmann

Beilstein J. Org. Chem. 2022, 18, 1322–1331, doi:10.3762/bjoc.18.137

• two binding grooves for protein ligands, e.g., the C-Raf peptides (yellow). The structure is based on PDB entry 4IHL [20]. Workflow of the computational approach used in this study. The protein structure and the structure of the ligand fragments are the required inputs. Charges and radii are assigned

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

• Merve Karaman,
• Abhishek Kumar Gupta,
• Subeesh Madayanad Suresh,
• Tomas Matulaitis,
• Lorenzo Mardegan,
• Daniel Tordera,
• Henk J. Bolink,
• Sen Wu,
• Stuart Warriner,
• Ifor D. Samuel and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

• plots and energies for the two lowest-lying singlet and triplet excited states for DiKTa-OMe and DiKTa-DPA-OMe calculated at SCS-CC2/cc-pVDZ in the gas phase (isovalue = 0.001). The blue color represents an area of decreased electron density, and yellow represents an increased electron density between

Enantioselective total synthesis of putative dihydrorosefuran, a monoterpene with an unique 2,5-dihydrofuran structure

• Irene Torres-García,
• Josefa L. López-Martínez,
• Rocío López-Domene,
• Manuel Muñoz-Dorado,
• Ignacio Rodríguez-García and
• Miriam Álvarez-Corral

Beilstein J. Org. Chem. 2022, 18, 1264–1269, doi:10.3762/bjoc.18.132

• -methylhepta-5,6-dienoate (3, 225 mg, 81%) isolated as light yellow oil. IR (ATR) ν (cm−1): 3434, 2972, 2928, 1958, 1723, 1436, 1374, 1172, 1028, 925, 853; 1H NMR (300 MHz, CDCl3) δ 4.77 (dq, J = 2.3, 3.2 Hz, 2H), 4.12 (q, J = 7.1 Hz, 2H), 4.05 (m, 1H), 2.42 (t, J = 7.2 Hz, 2H), 2.18 (s, 1H), 2.04–1.77 (m, 2H

A Streptomyces P450 enzyme dimerizes isoflavones from plants

• Run-Zhou Liu,
• Shanchong Chen and
• Lihan Zhang

Beilstein J. Org. Chem. 2022, 18, 1107–1115, doi:10.3762/bjoc.18.113

• using organic solvent (CHCl3/MeOH 1:1, v/v, 20 L in total). After removing the solvent in vacuo, the crude extract was redissolved in methanol and separated by Sephdex LH-20 (GE healthcare) column chromatography using methanol as eluent. The yellow band at the elution tail on the LH-20 column (Figure S2

Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof

• Laura Holzhauer,
• Chloé Liagre,
• Olaf Fuhr,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2022, 18, 1088–1099, doi:10.3762/bjoc.18.111

• complexation of the 3-nitrogen of the triazole ring and the nitrogen of the amine side chain. The complex has a yellow color in contrast to the red complexes 27a–d. Using TIQ ligand 25b for a complexation attempt with Re(CO)5Br, an orange complex (30) was successfully isolated in 79% yield. Single crystals

Synthesis, optical and electrochemical properties of (D–π)₂-type and (D–π)₂Ph-type fluorescent dyes

• Kosuke Takemura,
• Kazuki Ohira,
• Taiki Higashino,
• Keiichi Imato and
• Yousuke Ooyama

Beilstein J. Org. Chem. 2022, 18, 1047–1054, doi:10.3762/bjoc.18.106

• and OTT-2 are nearly-colorless and greenish-yellow, and show blue and green fluorescent colors, respectively. The photoabsorption spectra demonstrate that the photoabsorption maximum wavelength (λmax, abs = 424 nm) of OTT-2 occurs at a by 29 nm longer wavelength than that (λmax, abs = 395 nm) of OTK-2

• fluorescence spectroscopy for the solids (Figure 1c,d). As shown in insets of Figure 1c,d, in the solid state, the colors are yellowish orange for OTK-2 and orange for OTT-2, and the fluorescent colors are greenish yellow for OTK-2 and yellow for OTT-2. The photoabsorption bands of OTK-2 and OTT-2 in the solid

• , and then, the solution was extracted with dichloromethane. The dichloromethane extract was dried over anhydrous MgSO4, filtrated, and concentrated. The residue was chromatographed on silica gel (ethyl acetate/hexane 1:4 ) to give OTK-2 (19 mg, yield 27%) and OTT-2 (9 mg, yield 14%) as a light yellow

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

• DatA, which catalyzes the Claisen–Dieckmann condensation of phenylpyruvic acid (7) to generate the key intermediate polyporic acid (8). Finally, we proposed a biosynthetic pathway for daturamycins. Results and Discussion Daturamycin A (1), a yellow powder, possessed a molecular formula of C19H16O5 with

• ): 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

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

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

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

• -hydroxy-4-(4-methoxyphenyl)cyclopent-2-ene-1-carboxamido)-5-(4-methoxyphenyl)cyclopenta-2,4-diene-1,2-dicarboxylate (4a): yellow solid, 62%; mp 182–184 °C; 1H NMR (400 MHz, CDCl3) δ 8.92 (s, 1H, NH), 7.46 (d, J = 8.4 Hz, 2H, ArH), 7.34 (d, J = 8.4 Hz, 2H, ArH), 6.90 (s, 1H, CH), 6.88–6.84 (m, 4H, ArH

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

• Valentin H. K. Fell,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Eman J. Hussien and
• Peter J. Skabara

Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

• -bromobenzoate) (27), which is a yellow solid (Scheme 2). This step was found to be problematic. Purification was difficult, moreover, the batch-to-batch yield strongly fluctuated and was generally low. Intermediate 27 degraded during column chromatography, but this could be prevented by adding a small amount of

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

• HCl, TFA, and BBr3 as dopants which were respectively added to the donor–acceptor–donor (D–A–D) molecule 2,5-bis((N,N-diphenylamino)phenyl)thiazolothiazole (compound 2 in Figure 2) containing thiazolothiazole units. As shown in Figure 3b, four different colors ranged from green, yellow, red and NIR

• colors of green (524 nm), yellow (576 nm), red (640 nm), and NIR (739 nm) (Figure 3b) [27]. The stronger Lewis acidity resulted in a stronger emission and bathochromic shift when comparing the effects of BCF and B(C6H5)3 on the optoelectronic properties of the organic UV fluorescent material 35DCzPPy (14

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

• ), and then dried over MgSO4. The residue was purified by column chromatography (eluent: hexane/CH2Cl2 3:1 (v/v) and recrystallized from CHCl3/CH3OH to yield 5a (20.9 mg, 46%) as a yellow solid; mp > 300 °C; 1H NMR (400 MHz, CDCl3) δ (ppm) 7.58 (s, 1H), 7.45 (s, 2H), 7.41–7.36 (m, 3H), 7.34 (s, 2H), 7.31

• ); HRMS-MALDI (m/z): [M]+ calcd for C32H30S6Si2, 662.0216; found, 662.0205. 1,3-Bis(2-(5-(trimethylsilyl)diselenopheno[2,3-b:3',2'-d]thiophen-2-yl)vinyl)benzene (5b) was synthesized according to the procedure described for compound 5a. 5b: yellow solid in yield of 64% (46.2 mg); mp > 300 °C; 1H NMR (300

• . Mixture of cis and trans isomers 5c: yellow solid in yield of 50% (24.4 mg); mp > 300 °C; 1H NMR (400 MHz, CDCl3) δ (ppm): 7.76 (s, trans-), 7.73 (s, cis- and trans-), 7.72 (s, cis- and trans-), 7.57 (s, cis- and trans-), 7.56 (s, trans-), 7.49–7.33 (m, trans-, cis- and trans-), 7.30 (d, J = 16.0 Hz, cis