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

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

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

• a Jasco P-2000 polarimeter using methanol as solvent. High-resolution ESI mass spectrometer data were recorded on a Waters SYNAPT G2 mass spectrometer. ECD spectra were garnered with a JASCO J-1500 CD spectrometer (JASCO, Easton, MD, USA). The NMR spectra were recorded on a Bruker AVANCE III 700 NMR

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

• recorded using either the ultrafleXtreme MALDI-TOF mass spectrometer (Bruker) with α-cyano-4-hydroxycinnamic acid (HCCA) as a matrix, or by electrospray ionization (ESI) on a Waters G2-XS QTOF instrument connected to a Waters H-class UPLC equipped with a Waters BEH C18 column using an eluent consisting of

• (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

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

• 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

• 1.54 (s, 36H, (CH3)3C), 1.96 (s, 3H, CH3), 7.52–7.59 (m, 7H, ArH, CHCbz) 7.61–7.66 (m, 4H, CHCbz), 8.20 (s, 4H, CHCbz), 8.58–8.63 (m, 2H, ArH) ppm; 13C NMR (100 MHz, CDCl3) δ 15.2, 32.0, 34.86; 111.0, 116.5, 118.4, 124.0, 124.6, 128.4, 128.7, 131.1, 136.9, 137.9, 144.4, 160.2, 163.0 ppm; HRMS–ESI (m/z

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

• -2000 polarimeter. ESI-TOF mass spectra were obtained using a TOF/Q-TOF Mass spectrometer. Thin-layer chromatography (TLC) and preparative TLC were performed on silica gel 60 GF254 (Merck). Column chromatography (CC) was conducted on silica gel (Merck) type 100 (70–230 mesh ASTM) and type 60 (230–400

• 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

Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives

• Sayan Pramanik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 469–478, doi:10.3762/bjoc.18.49

• (multiplet). HRMS with an ESI resource were acquired using a Waters XEVO-G2S Q TOF mass spectrometer. HPLC were recorded using an Agilent 1200 Series auto sampler HPLC system. Melting points were recorded with an open capillary on an electrical melting point apparatus and the single crystal structure of the

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

• Irina Kuznetcova,
• Felix Bacher,
• Daniel Vegh,
• Hsiang-Yu Chuang and
• Vladimir B. Arion

Beilstein J. Org. Chem. 2022, 18, 143–151, doi:10.3762/bjoc.18.15

• hampered this transformation [24]. Therefore, the same synthetic way was repeated with ethoxymethyl ether as the protecting group to give 17. The ESI mass spectrum provided evidence that cyclization occurred with formation of 18. However, protection with chloromethyl ethyl ether was achieved only in 18

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

• Jiang-Song Zhai and
• Da-Ming Du

Beilstein J. Org. Chem. 2022, 18, 25–36, doi:10.3762/bjoc.18.3

• an Agilent 6520 Accurate-Mass Q-TOF MS system equipped with an electrospray ionization (ESI) source. Optical rotations were measured with a Krüss P8000 polarimeter at the indicated concentration with the units of g/100 mL. Enantiomeric excesses were determined by chiral HPLC analysis using an Agilent

The enzyme mechanism of patchoulol synthase

• Houchao Xu,
• Bernd Goldfuss,
• Gregor Schnakenburg and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 13–24, doi:10.3762/bjoc.18.2

• natural product 17 [HRMS–ESI (m/z): 221.1904 [M + H]+, calculated for C15H25O+ 221.1900 and [α]D25 = −7.7, (c 0.26, benzene)] whose structure was elucidated by NMR spectroscopy (Table 1 and Figures S29–S35 in Supporting Information File 1). The 13C NMR spectrum showed signals for 15 carbons, including

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

• this methyl proton (H-8/H-9) and a methine proton (H-7) and HMBC correlations from H-8/H-9 to the methine carbon (C-7) and the allylic methylene carbon (C-6). The deduced structure was consistent with a molecular formula C11H18O2 established by HR–ESI–TOFMS analysis (m/z 205.1202 [M + Na]+, Δ + 0.3 mmu

• molecular formula was determined to be C18H22N2O3 based on its NMR and HR–ESI–TOFMS data (m/z 313.1556 [M – H]–, Δ – 0.2 mmu), corresponding to nine degrees of unsaturation. The UV spectrum, exhibiting the absorption maxima at 229 and 282 nm, was typical of an indole functionality. The IR absorption bands

First total synthesis of hoshinoamide A

• Haipin Zhou,
• Zihan Rui,
• Yiming Yang,
• Shengtao Xu,
• Yutian Shao and
• Long Liu

Beilstein J. Org. Chem. 2021, 17, 2924–2931, doi:10.3762/bjoc.17.201

• , 66.74, 60.75, 59.32, 36.55, 30.88, 28.45, 23.94; HRMS–ESI (m/z): [M + H]+ calcd. for C22H26N2O3, 588.2671; found, 588.2673. Fmoc-Val-N-Me-ᴅ-Phe-Val-Pro-OBn (7). To a stirred solution of dipeptide 6 (118 mg, 0.20 mmol) was added 20% Et2NH in CH3CN (5 mL) at rt for 0.5 h. The Et2NH and CH3CN were

• , 128.20, 127.72, 127.08, 126.65, 125.17, 125.08, 119.99, 67.04, 66.84, 59.43, 55.87, 55.59, 47.17, 46.92, 35.00, 30.72, 30.47, 28.78, 25.25, 19.82, 16.33; HRMS–ESI (m/z): [M + H]+ calcd. for C42H45N3O6, 688.3381; found, 688.3384. Comparison of the effects of different coupling reagents on the reaction

• , 57.06, 56.41, 56.08, 38.96, 37.58, 37.01, 36.60, 35.79, 35.61, 33.11, 32.20, 31.89, 31.73, 31.53, 31.40, 30.88, 30.83, 30.66, 30.53, 30.39, 29.98, 29.64, 28.18, 26.97, 26.10, 23.80, 23.34, 19.88, 19.48, 18.17, 18.07, 17.64, 14.58; HRMS–ESI (m/z): [M + H]+ calcd. for C35H39N3O6, 598.2912; found, 598.2915

Photophysical, photostability, and ROS generation properties of new trifluoromethylated quinoline-phenol Schiff bases

• Inaiá O. Rocha,
• Yuri G. Kappenberg,
• Wilian C. Rosa,
• Clarissa P. Frizzo,
• Nilo Zanatta,
• Marcos A. P. Martins,
• Isadora Tisoco,
• Bernardo A. Iglesias and
• Helio G. Bonacorso

Beilstein J. Org. Chem. 2021, 17, 2799–2811, doi:10.3762/bjoc.17.191

• ), 123.36 (q, J = 274.0 Hz, CF3), 121.85 (C-4a), 119.64 (q, J = 5.3 Hz, C-3), 119.29 (C6H4OH), 119.01 (C6H4OH), 117.37 (C6H4OH), 114.75 (t, J = 2.2 Hz, C-5), 25.34 (CH3) ppm; 19F NMR (565 MHz, CDCl3) δ −61,71 (CF3) ppm; FTIR (ATR) ν: 3061 (ν OH), 1627 (ν CH=N), 1118 (ν C-O) cm−1; HRMS–ESI (m/z): [M + H

• (565 MHz, CDCl3) δ −61.62 (CF3); FTIR (ATR) ν: 3057 (ν OH), 1625 (ν CH=N), 1029 (ν C-O) cm−1; HRMS–ESI (m/z): [M + Na]+ calcd for C23H15F3N2NaO, 415.1029; found, 415.1007. (E)-2-(((2-(p-Tolyl)-4-(trifluoromethyl)quinolin-6-yl)imino)methyl)phenol (3ca): Yellow solid, yield 81%; mp 210–213 °C; 1H NMR

• ), 125.04 (C-7), 123.59 (q, J = 274.7 Hz, CF3), 122.37 (C-4a), 119.34 (C6H4OH), 119.10 (C6H4OH), 117.44 (C6H4OH), 116.40 (q, J = 7.3 Hz, C-3), 114.80 (C-5), 21.42 (4-CH3C6H4); 19F NMR (565 MHz, CDCl3) δ −61.65 (CF3); FTIR (ATR) ν: 3035 (ν OH), 1621 (ν CH=N), 1112 (ν C-O) cm−1; HRMS–ESI (m/z): [M + H]+ calcd

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones

• Alla I. Vaskevych,
• Nataliia O. Savinchuk,
• Ruslan I. Vaskevych,
• Eduard B. Rusanov,
• Oleksandr O. Grygorenko and
• Mykhailo V. Vovk

Beilstein J. Org. Chem. 2021, 17, 2787–2794, doi:10.3762/bjoc.17.189

• –5.82 (m, 1H, CH), 5.07 (d, J = 17.2 Hz, 1H, =CH2), 4.98 (d, J = 10.4 Hz, 1H, =CH2), 2.70 (t, J = 7.2 Hz, 2H, CH2), 2.49–2.47 (m, 2H, CH2); 13C NMR (125 MHz, DMSO-d6) δ 161.8, 156.7, 148.9, 137.2, 134.2, 126.8, 125.9, 125.7, 120.9, 115.5, 33.7, 30.6; HRMS–ESI (m/z): [M + H]+ calcd for C12H12N2O

• –3.82 (m, 1H, CH2), 3.67–3.61 (m, 1H, CH2), 3.22–3.15 (m, 1H, CH2), 2.83–2.81 (m, 1H, CH2), 2.44–2.33 (m, 1H, CH2), 2.22–2.16 (m, 1H, CH2); 13C NMR (125 MHz, DMSO-d6) δ 169.2, 167.4, 138.3, 133.4, 127.6, 125.3, 118.7, 116.1, 62.2, 61.3, 32.2, 22.7; HRMS–ESI (m/z): [M + H]+ calcd for C12H12N2O2

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet–Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

• Marco Keller,
• Karl Sauvageot-Witzku,
• Franz Geisslinger,
• Nicole Urban,
• Michael Schaefer,
• Karin Bartel and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183

• Finnigan LTQ FT Ultra Fourier Transform Ion Cyclotron Resonance device at 250 °C for ESI. IR spectra were recorded on a Perkin Elmer FT-IR Paragon 1000 instrument as neat materials. Absorption bands were reported in wave numbers (cm−1), obtained on a ATR PRO450-S accessory (Jasco). Melting points were

Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 2450–2461, doi:10.3762/bjoc.17.162

• ) relative to tetramethylsilane (SiMe4) as internal standard. High-resolution MS (HRMS–ESI) was performed on an Agilent 1969 A TOF. The photophysical studies were carried out in freshly prepared dichloromethane solutions with concentrations of 1 × 10−5 M. The UV–vis spectra were recorded on a Shimadzu 2401

• (CAr), 127.8 (CAr), 127.8 (CAr), 128.9 (CAr), 129.0 (CAr), 130.0 (CAr), 131.0 (CAr), 138.8 (Cl-CAr), 139.2 (CAr), 140.3 (CAr), 140.4 (CAr), 141.8 (CAr), 143.4 (N-CAr), 159.1 (N =CAr); HRMS–ESI (m/z): [M + H]+ calcd for C25H20ClN, 370.1355; found, 370.1357. 2,4-Bis(4-methoxyphenyl)-9-chloro-5,6,7,8

• ); HRMS–ESI (m/z): [M + H]+ calcd for C27H24ClNO2, 430.1496; found, 430.1498. 2,4-Bis(4-trifluoromethoxyphenyl)-9-chloro-5,6,7,8-tetrahydroacridine (4c): white solid; (Hep/EA 9:1), 57%; mp 127–129 °C; 1H NMR (300 MHz, CDCl3) δ 1.71–1.89 (m, 4H, 2CH2), 2.91–2.99 (m, 4H, 2CH2), 7.11–7.27 (m, 4H, aryl-H

Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

• Ren-Jie Fang,
• Chen Yan,
• Jing Sun,
• Ying Han and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2021, 17, 2425–2432, doi:10.3762/bjoc.17.159

• , 125.6, 121.7, 120.7, 120.3, 119.2, 111.3, 21.1; IR (KBr) ν: 2988, 1786, 1734, 1611, 1485, 1456, 1357, 1314, 1185, 1021, 988, 786, 734 cm−1; HRMS–ESI-TOF (m/z): [M + Na]+ calcd for C34H22NaN2O3, 529.1523; found, 529.1512. 2. General procedure for the preparation of carbazoles 6a–n: To a round-bottomed

• , 127.0, 126.9, 126.4, 122.4, 122.0, 121.8, 121.6, 119.6, 108.7, 32.1; IR (KBr) ν: 3057, 3023, 2907, 2360, 2339, 1720, 1605, 1482, 1320, 1267, 1172, 1009, 936, 805, 743, 612, 447 cm−1; HRMS–ESI (m/z): [M + Na]+ calcd for C39H27NO2, 564.1934; found, 564.1926. The crystallographic data of the compounds 3a

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

• Emmanuel T. Oluwabusola,
• Olusoji O. Adebisi,
• Fernando Reyes,
• Kojo S. Acquah,
• Mercedes De La Cruz,
• Larry L. Mweetwa,
• Joy E. Rajakulendran,
• Digby F. Warner,
• Deng Hai,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

• Figure 1 and Supporting Information File 1 for details) which were comparable with those reported in the literature [28][36][37]. Pseudomonin A (1) was isolated as a yellowish compound. The molecular formula of C11H15O4N2 with 6 degrees of unsaturation was established by high-resolution ESI-Orbitrap-MS

• system (Accela PDA detector, Accela PDA autosampler, and Accela pump) or an Agilent 6540 in ESI-TOF MS coupled to an HPLC Agilent 1290 Infinity equipped with a diode array detector (DAD). Chromatographic fractionation was carried out on a Reveleris preparative flash system equipped with a reversed-phase

Phenolic constituents from twigs of Aleurites fordii and their biological activities

• Kyoung Jin Park,
• Won Se Suh,
• Da Hye Yoon,
• Chung Sub Kim,
• Sun Yeou Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2021, 17, 2329–2339, doi:10.3762/bjoc.17.151

• ), 248 (5.1), 229 (−8.5) nm; 1H and 13C NMR data, see Table 1; positive HRMS–ESI (m/z): [M + Na]+ calcd for C26H34O10Na, 529.2050; found, 529.2050. Aleuritiside C (3). Colorless gum; [α]D25 −23.4 (c 0.05, MeOH); IR (KBr) νmax: 3361, 2946, 2830, 1462, 1029 cm−1; UV (MeOH) λmax, nm (log ε): 275 (2.53); ECD

• (MeOH) λmax, nm (Δε): 273 (−8.1), 236 (−8.3); 1H and 13C NMR data, see Table 1; positive HRMS–ESI (m/z): [M + Na]+ calcd for C26H36O11Na, 547.2155; found, 547.2155. Aleuriteoside A (15). Colorless gum; [α]D25 −13.7 (c 0.08, MeOH); IR (KBr) νmax: 3321, 2975, 1675, 1601, 1453, 1065 cm−1; UV (MeOH) λmax

• , nm (log ε): 280 (2.31); 1H and 13C NMR data, see Table 2; positive HRMS–ESI (m/z): [M + Na]+ calcd for C17H24O10Na, 411.1267; found, 411.1260. Aleucyanoglucoside (16). Colorless gum; [α]D25 −33.5 (c 0.30, MeOH); IR (KBr) νmax: 3535, 3330, 2832, 2218, 1453, 1033 cm−1; UV (MeOH) λmax, nm (log ε): 283

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• behaves as a terminal oxidant to form α-aminoalkyl radicals, whereas the formation of an Fe-peroxo species in the catalytic cycle was confirmed using a combination of EPR and ESI mass spectrometry experiments (Scheme 31D). One-pot processes for the synthesis of benzo[b]furans from aryl- or alkylketones

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli,
• Noureddine Chaaben,
• Kamel Alimi,
• Stefan Jopp and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

• -CAr), 161.1 (N =CAr); HRMS (ESI): [M]+ calcd for C29H20ClN, 417.1284; found, 417.1265. 2,4-Bis(o-tolylethynyl)-9-chloro-5,6,7,8-tetrahydroacridine (4b): pale green solid (385 mg, 0.85 mmol, 85%); mp 119–120 °C; 1H NMR (300 MHz, CDCl3) δ 1.78–1.93 (m, 4H, 2CH2), 2.52 (s, 3H, aryl-CH3), 2.66 (s, 3H

• (Csp), 90.2 (Csp), 92.3 (Csp), 95.8 (Csp), 119.7 (CAr), 121.80 (CAr), 122.9 (CAr), 123.1 (CAr), 125.5 (CAr), 126.8 (CAr), 128.6 (CAr), 128.8 (CAr), 129.4 (CAr), 129.6 (CAr), 130.3 (CAr), 130.4 (CAr), 132.1 (CAr), 135.8 (Cl-CAr), 141.1 (CAr), 145.0 (N-CAr), 160.8 (N =CAr); HRMS (ESI): [M]+ calcd for

• ), 121.53 (CAr), 122.58 (CAr), 122.96 (CAr), 123.15 (CAr), 125.51 (CAr), 127.08 (CAr), 128.19 (CAr), 128.36 (CAr), 129.15 (CAr), 129.62 (CAr), 130.25 (CAr), 132.60 (CAr), 136.37 (CAr), 138.16 (Cl-CAr), 141.79 (CAr), 145.15 (N-CAr), 160.99 (N =CAr); HRMS (ESI): [M]+ calcd for C31H24ClN, 445.1597; found

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

• Greta Utecht-Jarzyńska,
• Karolina Nagła,
• Grzegorz Mlostoń,
• Heinz Heimgartner,
• Marcin Palusiak and
• Marcin Jasiński

Beilstein J. Org. Chem. 2021, 17, 1509–1517, doi:10.3762/bjoc.17.108

• , HMQC, and HMBC). The UV–vis spectra were measured on a PerkinElmer Lambda 45 spectrophotometer in spectroscopic grade CH2Cl2. MS (ESI) were performed with a Varian 500-MS LC Ion Trap. The IR spectra were measured neat with an Agilent Cary 630 FTIR spectrometer. Elemental analyses were obtained with a

Analogs of the carotane antibiotic fulvoferruginin from submerged cultures of a Thai Marasmius sp.

• Birthe Sandargo,
• Leon Kaysan,
• Rémy B. Teponno,
• Christian Richter,
• Benjarong Thongbai,
• Frank Surup and
• Marc Stadler

Beilstein J. Org. Chem. 2021, 17, 1385–1391, doi:10.3762/bjoc.17.97

• distinct. Considering other rDNA regions currently leads to more questions than answers regarding the phylogeny and clearly shows the need for further taxonomic re-evaluation. Experimental General experimental procedures An Agilent 1200 series HPLC-UV system (Santa Clara, CA, USA) with an ESI-TOF-MS (MaXis

• are provided in Supporting Information File 1. Fulvoferruginin B (2): faint yellow solid; [α]D20 +14 (c 1, MeOH); UV (MeOH) λmax (log ε) 200 (3.7), 249 (3.5) nm; 1H NMR and 13C NMR data (1H 700 MHz, 13C 175 MHz) in CD3OD: see Table 1; HRMS–ESI (m/z): [M + H]+ calcd for C15H21O3+, 249.1477; found

• –ESI (m/z): [M + H]+ calcd for C15H18O4+, 263.1283; found, 263.1276. Fulvoferruginin D (4): light yellow solid; [α]D20 +19 (c 1, MeOH); UV (MeOH) λmax (log ε) 201 (4.4), 249 (4.2) nm; 1H (700 MHz) and 13C NMR (175 MHz) data in CD3OD are collected in Table 1 and copies of spectra are collected in

Structural effects of meso-halogenation on porphyrins

• Keith J. Flanagan,
• Maximilian Paradiz Dominguez,
• Zoi Melissari,
• Hans-Georg Eckhardt,
• René M. Williams,
• Dáire Gibbons,
• Caroline Prior,
• Gemma M. Locke,
• Alina Meindl,
• Aoife A. Ryan and
• Mathias O. Senge

Beilstein J. Org. Chem. 2021, 17, 1149–1170, doi:10.3762/bjoc.17.88

• quadrupole time-of-flight (Q-TOF) mass spectrometer equipped with Z-spray electrospray ionization (ESI) and matrix-assisted laser desorption ionization (MALDI) sources either in a positive or negative mode with DCTB (trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malononitrile) as the matrix. UV

Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties

• Peter Jonas Wickhorst,
• Mathilda Blachnik,
• Denisa Lagumdzija and
• Heiko Ihmels

Beilstein J. Org. Chem. 2021, 17, 991–1000, doi:10.3762/bjoc.17.81

• = 77.2 ppm). Elemental analyses: HEKAtech EUROEA combustion analyzer, determined by Rochus Breuer, Organische Chemie I, Universität Siegen. Mass spectra (ESI): Finnigan LCQ Deca (U = 6 kV; working gas: Ar; auxiliary gas: N2; temperature of the capillary: 200 °C). Circular dichroism (CD) and linear