Allostreptopyrroles A–E, β-alkylpyrrole derivatives from an actinomycete Allostreptomyces sp. RD068384

• Marwa Elsbaey,
• Naoya Oku,
• Mohamed S. A. Abdel-Mottaleb and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2024, 20, 1981–1987, doi:10.3762/bjoc.20.174

• . Analysis of 1H NMR, 13C NMR (Table 1), and HSQC spectra revealed a formyl group (δC 186.3/δH 9.89), an olefinic methine (δC 131.1/δH 7.64), an acyl carbonyl carbon (δC 163.3), three non-protonated olefinic carbons (δC 133.4, 126.4, and 123.1), a deshielded non-protonated sp3 carbon (δC 70.1), six sp3

• -configurations were proposed for compounds 2 and 3. However, this prediction was not confirmed by chemical derivatization due to their limited availability. 1H and 13C NMR spectra of compounds 4 and 5 were superimposable to those of 1 except for methylene resonances, supporting that both 4 and 5 possess the same

• total 6.5 mg of 1, 3.1 mg of 2, 2.6 mg of 3, 7.2 mg of 4, and 5.6 mg of 5 from 12 L culture. Allostreptopyrrole A (1): greenish yellow amorphous solid; UV (MeOH) λmax nm (log ε) 234 (3.86), 273 sh (3.44); IR (ATR) νmax: 3275, 2964, 2928, 2855, 1658, 1554, 1418 cm−1; 1H and 13C NMR data, see Table 1

1,2-Difluoroethylene (HFO-1132): synthesis and chemistry

• Liubov V. Sokolenko,
• Taras M. Sokolenko and
• Yurii L. Yagupolskii

Beilstein J. Org. Chem. 2024, 20, 1955–1966, doi:10.3762/bjoc.20.171

• ], respectively, while reference [68] provides UV-spectral data of both isomers. 1H, 19F, and 13C NMR data [69][70] are given in Table 2. Chemistry of HFO-1132 Isomerization Iodine-catalyzed cis–trans isomerization of 1,2-difluoroethylene and corresponding equilibrium measurements were described in the 1960s [47

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations

• Pengcheng Lu,
• Luis Juarez,
• Paul A. Wiget,
• Weihe Zhang,
• Krishnan Raman and
• Pravin L. Kotian

Beilstein J. Org. Chem. 2024, 20, 1940–1954, doi:10.3762/bjoc.20.170

• (dd, J = 8.9, 1.9 Hz, 1H), 4.17 (s, 3H), 3.92 (s, 3H); 13C{1H} NMR (75 MHz, DMSO-d6) δ 161.8, 139.4, 132.7, 129.4, 124.1, 123.0, 116.0, 113.0, 51.8, 36.6; IR (KBr disk): 1722, 1466, 1433, 1395, 1354, 1289, 1200, 1183, 1153 cm−1; HRESIMS (m/z): [M + H]+ calcd for C10H10BrN2O2+, 268.9921; found

• (s, 3H); 13C{1H} NMR (75 MHz, DMSO-d6) δ 159.4, 144.7, 129.3, 123.6, 123.2, 122.8, 120.0, 118.0, 64.2, 52.2, 41.4, 14.4, 13.9; IR (KBr disk): 1708, 1459, 1442, 1392, 1326, 1252, 1196 cm−1; HRESIMS (m/z): [M + H]+ calcd for C10H10BrN2O2+, 268.9921; found, 268.9918. Indazole-containing bioactive

• : Characterization of all compounds (1H NMR, 13C NMR, LC–MS, IR), and crystallographic methods and data for products P1 and P2. Supporting Information File 23: DFT methods, relative energy comparisons, TS imaginary frequencies, and XYZ coordinates. Supporting Information File 24: GoodVibes outputs. Acknowledgements

A new platform for the synthesis of diketopyrrolopyrrole derivatives via nucleophilic aromatic substitution reactions

• Vitor A. S. Almodovar and
• Augusto C. Tomé

Beilstein J. Org. Chem. 2024, 20, 1933–1939, doi:10.3762/bjoc.20.169

• than the oxygen due to the preferential existence of 4-hydroxypyridine in the pyridin-4-one tautomeric form [37][38][39]. The structures of dyes 3a–f, 4a, 4d and 4f were unambiguously established through their 1H, 13C and 19F NMR and mass spectra. The 1H NMR spectra of the symmetrical compounds

• apparatus. NMR spectra were recorded on a Bruker DRX 300 Avance operating at 300.13 MHz (for 1H NMR), at 75.47 MHz (for 13C NMR) and 282 MHz (for 19F NMR). Deuterated chloroform (CDCl3) was used as the solvent and tetramethylsilane (TMS) as the internal reference. The chemical shifts (δ) are expressed in

• ), 5.03 (s, 4H); 13C NMR (75 MHz, CDCl3) δ (ppm) 161.7, 147.2, 138.01, 129.8, 129.6, 125.6, 110.0, 29.7; 19F NMR (282 MHz, CDCl3) δ (ppm) −138.11 to −138.29 (m, 4F), −149.90 (t, J = 21.4 Hz, 2F), −157.63 to −157.91 (m, 4F); ESIMS m/z: 717.0 (M + H+, 100%). General procedure for the nucleophilic aromatic

Novel oxidative routes to N-arylpyridoindazolium salts

• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2024, 20, 1906–1913, doi:10.3762/bjoc.20.166

• -arylpyridoindazolium salts S1–S3 was confirmed with HRMS and 1H, 13C and 19F NMR data; the complete assignment of the signals was performed using 2D NMR methods. The N–N bond formation was additionally confirmed via comparison of the 1H spectra for the salts and their diarylamine precursors. The absence of the signals

Electrochemical radical cation aza-Wacker cyclizations

• Sota Adachi and
• Yohei Okada

Beilstein J. Org. Chem. 2024, 20, 1900–1905, doi:10.3762/bjoc.20.165

• cyclization.a Supporting Information Supporting Information File 6: General remarks and characterization data, including copies of 1H and 13C NMR spectra. Funding This work was supported in part by JSPS KAKENHI Grant No. 22K05450 (to Y. O.), and TEPCO Memorial Foundation (to Y. O.).

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

• Ivana Weisheitelová,
• Radek Cibulka,
• Marek Sikorski and
• Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

• -aryldeazaalloxazines in any case. Finally, the unsubstituted derivative 2x was formed with a yield of only 15% using DMF/AlCl3. The isolated products 2a–x were characterized by 1H, 13C NMR and mass-spectral methods. The 1H NMR spectra of 5-aryldeazaalloxazines 2a–x, along with protons of aryl substituents of aldehyde

• moiety and pyrimido[4,5-b]quinoline core, contained singlets with 3H intensity of the N(1)–CH3 and N(3)–CH3 groups of the barbituric acid fragment at 3.20–3.56 ppm. The 13C NMR spectra of 5-aryldeazaalloxazines 2a–x were represented by groups of singlets at 27.9–57.2 and 100.0–160.5 ppm. The

• unexpected structure of product 6 was confirmed by 1H, 13C NMR and mass spectrometry. The main feature of the 1H NMR spectrum of compound 6 is the absence of the signals of the aromatic aldehyde moiety and the appearance of the singlet of the 5-CH methyne group at 9.56 ppm and the singlets of the protons of

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

• Samuel M. G. Dearman,
• Xiang Li,
• Yang Li,
• Kuldip Singh and
• Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

• ppm and 7.96 ppm, respectively, for iodine(V) product 6. Similarly, the 13C NMR spectrum showed a major downfield shift for the aromatic carbon attached to iodine from a chemical shift of 105.3 ppm in iodine(III) substrate 10 to 132.4 ppm for difluoroiodane(V) product 6. Since Selectfluor was shown to

• deposition numbers CCDC: 2351949 and 2351950. Supporting Information File 18: Experimental procedures, characterisation data, DFT calculations and 1H, 13C and 19F NMR spectra and crystallographic data. Funding SMGD and AMS thank the School of Chemistry, University of Leicester, for their generous support

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

• Alexander V. Tsygankov,
• Vladyslav O. Vereshchak,
• Tetiana O. Savluk,
• Serhiy M. Desenko,
• Valeriia V. Ananieva,
• Oleksandr V. Buravov,
• Yana I. Sakhno,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

• stirring for three hours (Scheme 3, conditions A). However, the results of this attempted post-Ugi transformation were quite unexpected: Instead of acid 11, we isolated the amide of the unsaturated derivative of pyruvic acid 10a according to the 1H and 13C NMR spectra and mass spectrometry data. In order

• conventional thermal heating, amide 10a was isolated, albeit in a lower yield and accompanied with tar formation. In addition to the 1H, 13C NMR spectra and mass spectrometry data, the structure of compound 10d was established by X-ray diffraction analysis (Figure 3). It was also found that the substituents at

• case of bisamides 5d, 6a, 6c, 7b, 8a, and 8c (Table 2), additional transformation products were also isolated from the reaction mixture. According to 1H and 13C NMR, MS, and X-ray diffraction studies these were the corresponding ketobisamides 12, which are products of a nucleophilic substitution of the

Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty

• Weimao Zhong and
• Vinayak Agarwal

Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146

• group in 25 is rare. Feeding [1-13C]acetate to the culture resulted the enrichment of C1, C3, C5, C7, and C9 carbons, which verified the origin of the carbon skeleton as being fatty acid-derived. Feeding experiments with ʟ-[methyl-13C]methionine yielded only enrichment of C11 methyl, indicating that

New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)

• Fátima C. Teixeira,
• António P. S. Teixeira and
• C. M. Rangel

Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145

• for 35Cl and 37Cl isotopes, respectively, with an approximately 3/4 and 1/4 proportion. The symmetry of the obtained compound TP1 gives simple NMR spectra, with the 31P NMR spectrum showing a singlet signal (Figure 2) and the signal at 169.5 ppm, on the 13C NMR spectrum, confirming the presence of a

• different conditions tested. The spectroscopic data are in agreement with the proposed structure for compound TP3 (Scheme 5), namely the presence of the chlorine atom in the mass spectrum, due to the presence of isotope peaks, the signal at 168.2 ppm at 13C NMR spectrum attributed to the carbon atom bonded

• characterization of the dopants was carried out by Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). 1H, 13C and 31P NMR characterization was done using different one- and two-dimensional techniques, and were obtained on a Bruker Avance III HD

Primary amine-catalyzed enantioselective 1,4-Michael addition reaction of pyrazolin-5-ones to α,β-unsaturated ketones

• Pooja Goyal,
• Akhil K. Dubey,
• Raghunath Chowdhury and
• Amey Wadawale

Beilstein J. Org. Chem. 2024, 20, 1518–1526, doi:10.3762/bjoc.20.136

• ent-3aa-ent-3na, 1H, 13C NMR spectra of 3aa–na, 1H NMR of ent-3aa–ent-3na and their HPLC traces and single crystal data of ent-3ba. Acknowledgements The authors are thankful to Ms. Ketki Lele for her help in some preliminary experiments. Funding The authors thank the Department of Atomic Energy (DAE

Tetrabutylammonium iodide-catalyzed oxidative α-azidation of β-ketocarbonyl compounds using sodium azide

• Christopher Mairhofer,
• David Naderer and
• Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1510–1517, doi:10.3762/bjoc.20.135

• pronucleophile, followed by a phase-transfer-catalyzed nucleophilic substitution by the azide. Furthermore, we also obtained a first proof-of-concept for the conceptually analogous α-nitration by using NaNO2 under otherwise identical conditions. Experimental General details 1H, 13C and 19F NMR spectra were

• Research Center “RERI uasb”. All NMR spectra were referenced on the solvent residual peak (CDCl3: δ = 7.26 ppm for 1H NMR, δ = 77.16 ppm for 13C NMR,19F NMR unreferenced). IR spectra were recorded on a Bruker Alpha II FTIR spectrometer with diamond ATR-module using the OPUS software package. HRMS spectra

• = 17.2 Hz, 1H), 2.99 (d, J = 17.2 Hz, 1H), 1.45 (s, 9H); 13C NMR (75 MHz, CDCl3, 298 K, δ/ppm) 198.1, 167.4, 152.3, 136.4, 133.3, 128.4, 126.5, 125.6, 84.6, 70.6, 38.6, 28.0; IR (neat, FT-ATR, 298 K, ν̃/cm−1): 2984, 2928, 2853, 2110, 1747, 1736, 1718, 1604, 1589, 1548, 1466, 1431, 1397, 1372, 1353, 1326

Towards an asymmetric β-selective addition of azlactones to allenoates

• Behzad Nasiri,
• Ghaffar Pasdar,
• Paul Zebrowski,
• Katharina Röser,
• David Naderer and
• Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1504–1509, doi:10.3762/bjoc.20.134

• giving access to the acyclic α-amino acid-based amides 6 straightforwardly. Experimental General details 1H and 13C NMR spectra were recorded on a Bruker Avance III 300 MHz spectrometer with a broad band observe probe. All NMR spectra were referenced on the solvent residual peak (CDCl3: δ 7.26 ppm for 1H

• NMR and δ 77.16 ppm for 13C NMR). NMR data are reported as follows: chemical shift (δ ppm), multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = doublet of doublet), coupling constants (Hz), relative integration value. High-resolution mass spectra were obtained using a

• ), 3.52–3.16 (m, 4H), 1.15 (t, J = 7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3, 298.0 K) δ/ppm = 177.4, 171.0, 160.3, 139.1, 133.8, 132.6, 130.5, 128.6, 128.0, 127.8, 127.3, 125.6, 118.1, 75.9, 60.9, 44.9, 39.3, 13.9; IR (neat): 3080, 3070, 2917, 1815, 1732, 1656, 1480, 1175, 1093, 1059, 1030, 974, 893, 694 cm−1

Photoswitchable glycoligands targeting Pseudomonas aeruginosa LecA

• Yu Fan,
• Ahmed El Rhaz,
• Stéphane Maisonneuve,
• Emilie Gillon,
• Maha Fatthalla,
• Franck Le Bideau,
• Guillaume Laurent,
• Samir Messaoudi,
• Anne Imberty and
• Juan Xie

Beilstein J. Org. Chem. 2024, 20, 1486–1496, doi:10.3762/bjoc.20.132

• silica gel (60 Å pore size, 40–63 µm). 1H and 13C NMR spectra were recorded on a JEOL ECS-400 spectrometer or on Bruker Avance 300 and 400 spectrometers. Structural assignments were made with additional information from gCOSY, HMBC, and gHMQC experiments. High-resolution mass spectra (HRMS) were

Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

• Lu Li,
• Na Li,
• Xiao-Tian Mo,
• Ming-Wei Yuan,
• Lin Jiang and
• Ming-Long Yuan

Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130

• -cyclohexenone. This is further supported by the 13C NMR spectrum, which contains two peaks at δ = 38.4 and 47.7 indicating the two types of benzylic carbons. The NMR data of known compound 4ab were also in good correlation with previously reported data [19]. The synthetic practicability of the protocol was

Selectfluor and alcohol-mediated synthesis of bicyclic oxyfluorination compounds by Wagner–Meerwein rearrangement

• Ziya Dağalan,
• Muhammed Hanifi Çelikoğlu,
• Saffet Çelik,
• Ramazan Koçak and
• Bilal Nişancı

Beilstein J. Org. Chem. 2024, 20, 1462–1467, doi:10.3762/bjoc.20.129

• rearrangement. Optimizing the conditions for the oxyfluorination of bicyclic alkenesa. Supporting Information Supporting Information File 2: Experimental procedures, copies of 1H NMR, 13C NMR, and HRMS(Q-TOF) spectra. Acknowledgements The authors wish to express their sincerest gratitude to Dr. Barış Anıl for

Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction

• Xiu-Yu Chen,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2024, 20, 1436–1443, doi:10.3762/bjoc.20.126

• ), 2.28 (s, 3H, CH3), 1.89–1.86 (m, 2H, CH2), 1.80–1.68 (m, 4H, CH2), 1.55–1.33 (m, 3H, CH2), 1.20–1.13 (m, 1H, CH2) ppm; 13C NMR (100 MHz, CDCl3) δ 170.1, 168.3, 167.8, 166.5, 162.5, 161.9, 157.2, 157.0, 144.7, 137.6, 131.4, 130.9, 129.1, 128.0, 127.9, 127.1, 112.0, 113.6, 111.0, 110.2, 98.9, 84.0, 72.2

• 2346135) and 6g (CCDC 2346136) have been deposited at the Cambridge Crystallographic Database Center (http://www.ccdc.cam.ac.uk). Supporting Information File 24: Characterization data and 1H NMR, 13C NMR, and HRMS spectra of compounds. Funding This work was financially supported by the National Natural

Rhodium-catalyzed homo-coupling reaction of aryl Grignard reagents and its application for the synthesis of an integrin inhibitor

• Kazuyuki Sato,
• Satoki Teranishi,
• Atsushi Sakaue,
• Yukiko Karuo,
• Atsushi Tarui,
• Kentaro Kawai,
• Hiroyuki Takeda,
• Tatsuo Kinashi and
• Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 1341–1347, doi:10.3762/bjoc.20.118

• Information Supporting Information File 98: General procedures and analytical data, including copies of 1H NMR and 13C NMR spectra. Acknowledgements We would like to thank Dr. Antal Harsányi at Euroapi Hungary for his helpful comments to improve the quality of the article.

Synthesis of 1,2,3-triazoles containing an allomaltol moiety from substituted pyrano[2,3-d]isoxazolones via base-promoted Boulton–Katritzky rearrangement

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

Beilstein J. Org. Chem. 2024, 20, 1334–1340, doi:10.3762/bjoc.20.117

• hydrazones also can be utilized in the considered rearrangement. It should be mentioned that the presented reaction is the first example of a recyclization of the pyrano[2,3-d]isoxazolone core. The obtained 1,2,3-triazoles 4 are solid crystalline products, whose structures were proved by 1H, 13C NMR

• obtained the recyclized product 6a (Scheme 6), whose structure was confirmed by 1H, 13C NMR spectroscopy, high-resolution mass spectrometry and X-ray analysis. Based on the aforementioned reaction we have synthesized a set of pyrazolylisoxazoles 6 (Scheme 7). The proposed mechanism of investigated

• File 96: Experimental procedures, characterization data of all products, copies of 1H, 13C NMR, spectra of all new compounds, and X-ray crystallographic data. Acknowledgements The crystal structure determination was performed in the Department of Structural Studies of Zelinsky Institute of Organic

Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

• Ayhan Yıldırım

Beilstein J. Org. Chem. 2024, 20, 1308–1319, doi:10.3762/bjoc.20.114

• the bis structure are in equilibrium with maleamic acid precursors (Scheme 3) complicates the interpretation of their 1H and 13C NMR spectra. The existence of these precursors is clearly demonstrated by both their 1H and 13C NMR spectra (Supporting Information File 1). It should be noted that in the

• ), 4.63 (d, J = 15.1 Hz, 1H, Hh), 4.42 (d, J = 15.1 Hz, 1H, Hi), 3.83 (d, J = 12 Hz, 1H, Hd), 3.65 (d, J = 12 Hz, 1H, He), 2.96 (d, J = 9.1 Hz, 1H, Ha), 2.84 (d, J = 9.1 Hz, 1H, Hb); 13C NMR (150 MHz, CDCl3) δ 173.10, 172.51, 137.22, 135.20, 134.83, 128.92, 127.98, 127.87, 88.79, 82.36, 50.72, 48.53

Diameter-selective extraction of single-walled carbon nanotubes by interlocking with Cu-tethered square nanobrackets

• Guoqing Cheng and
• Naoki Komatsu

Beilstein J. Org. Chem. 2024, 20, 1298–1307, doi:10.3762/bjoc.20.113

• (Scheme 2) [11]. The products were fully characterized by 1H and 13C NMR, and MALDI-TOF mass spectroscopy (see Supporting Information File 1). The total yield of 4b (5.5%) based on 2,7-dibromopyrene is much lower than that of 4a (44%) [11], because a larger amount of the product 4b was lost in the

• measurements and analyzed with mMass [29] software. 1H and 13C NMR spectra were recorded on JNM-ECS 400 spectrometer using the sample solutions in chloroform-d (CDCl3). Raman spectra were recorded on LabRam HR800 (Horiba Ltd.) and take the average of more than ten different spots for the final curve. UV–Vis

• , rt, 1.5 h; iv) p-chloranil, dichloromethane, rt, 5 h. Supporting Information Supporting Information File 86: Details of theoretical calculations, experimental procedures, copies of 1H and 13C NMR spectra. Acknowledgements Computation time was provided by supercomputer system, Academic Center for

Synthesis of indano[60]fullerene thioketone and its application in organic solar cells

• Yong-Chang Zhai,
• Shimon Oiwa,
• Shinobu Aoyagi,
• Shohei Ohno,
• Tsubasa Mikie,
• Jun-Zhuo Wang,
• Hirofumi Amada,
• Koki Yamanaka,
• Kazuhira Miwa,
• Naoyuki Imai,
• Takeshi Igarashi,
• Itaru Osaka and
• Yutaka Matsuo

Beilstein J. Org. Chem. 2024, 20, 1270–1277, doi:10.3762/bjoc.20.109

• of Lawesson's reagent and the reaction temperature. The transformation from ketone to thioketone was confirmed by 13C NMR, which showed a downfield shift from 198 ppm for the carbonyl carbon to 235 ppm for the thiocarbonyl carbon. With the optimized conditions (Table 1, entry 9) in hand, different

Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide

• Vishnu Selladurai and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2024, 20, 1221–1235, doi:10.3762/bjoc.20.105

• + Na]+, [2M + Na]+, and [3M + Na]+. Spectroscopic data of this compound, including FTIR as well as 1H and 13C NMR, matched those reported earlier [54]. Relative extent of polymerization To compare the relative polymerization tendency, we conducted reactions of arylamines with SeO2 in acetonitrile in

• account. Characterization of the organoselenium compounds by HRMS, 1H, and 13C NMR was supported by 77Se NMR and single-crystal X-ray analysis in order to confirm the identity of the compounds. Experimental General procedures All syntheses were carried out using the standard Schlenk line in a nitrogen

• environment. Acetonitrile (99.9%) was bought from Avra Chemicals Private Ltd. and used without any further purification. Selenium dioxide and a range of reactants were purchased from Sigma-Aldrich. TLC was performed using silica-gel-coated aluminum sheets (TLC silica gel 60 F254). 1H, 13C, and 77Se NMR (500

Introduction of peripheral nitrogen atoms to cyclo-meta-phenylenes

• Koki Ikemoto and
• Hiroyuki Isobe

Beilstein J. Org. Chem. 2024, 20, 1207–1212, doi:10.3762/bjoc.20.103

• total, 3a was obtained in 7% yield (325 mg, 0.707 mmol). N3-[6]CMP (3a): 1H NMR (CDCl3, 600 MHz) δ 9.05 (d, J = 2.1 Hz, 6H), 8.58 (t, J = 2.1 Hz, 3H), 8.23 (t, J = 2.1 Hz, 3H), 7.89 (dd, J = 7.6, 2.1 Hz, 6H), 7.69 (t, J = 7.6 Hz, 3H); 13C NMR (CDCl3, 150 MHz) δ 146.6 (CH), 138.3, 135.7, 133.9 (CH

• ), 130.2 (CH), 127.5 (CH), 125.9 (CH); HRMS (APCI) (m/z): [M + H]+ calcd. for C33H22N3, 460.1808; found, 460.1808. N4-[8]CMP (3b): 1H NMR (CDCl3, 600 MHz) δ 8.81 (d, J = 1.4 Hz, 8H), 8.13 (t, J = 1.4 Hz, 4H), 7.76 (s, 4H), 7.66–7.73 (m, 12H); 13C NMR (CDCl3, 150 MHz) δ 147.9 (CH), 139.2, 137.0, 133.5 (CH