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

Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions

• Dat Phuc Tran,
• Yuki Sato,
• Yuki Yamamoto,
• Shin-ichi Kawaguchi,
• Shintaro Kodama,
• Akihiro Nomoto and
• Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 866–872, doi:10.3762/bjoc.17.72

• BioSpin Ascend 400 spectrometer (162 MHz). 19F NMR spectra were recorded on a Bruker BioSpin Ascend 400 spectrometer (377 MHz). IR spectra were recorded on JASCO FT/IR-680Plus instrument. High-resolution mass spectra (HRMS) were recorded on a Bruker micrOTOF II ESI(+)/TOF instrument. General procedure for

Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

• David Weinzierl and
• Mario Waser

Beilstein J. Org. Chem. 2021, 17, 800–804, doi:10.3762/bjoc.17.68

• ), 35.4 (1C, -CH2), 34.9 (1C, -CH2), 34.0 (1C, -CH2), 32.2 (1C, -CH2); HRMS (ESI) m/z: calcd for [C16H16O + H]+, 225.1274; found, 225.1280, HPLC: YMC Chiral ART Cellulose-SB, n-hexane/iPrOH 3:1, 1 mL/min, 10 °C; tR = 6.4 min [Sp; minor], 7.2 min [Rp; major]. (Sp)-3a: Analytical data match those reported

• (1C, -CH2), 35.0 (1C, -CH2), 34.4 (2C, -CH, -CH2), 31.8 (1C, -CH2), 19.4 (1C, -CH3), 19.1 (1C, -CH3); HRMS (ESI) m/z: calcd for [C20H22O2 + NH4]+, 312.1958; found, 312.1958, HPLC: YMC Chiral ART Cellulose-SB, n-hexane/iPrOH 3:1, 1 mL/min, 10 °C; tR = 7.3 min [Rp; minor], 8.4 min [Sp; major]. Overview

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

• Marek Kõllo,
• Marje Kasari,
• Villu Kasari,
• Tõnis Pehk,
• Ivar Järving,
• Margus Lopp,
• Arvi Jõers and
• Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

• 6540 UHD Accurate-Mass QTOF LC/MS spectrometer by using AJ-ESI as an ionization method. Construction of biocatalyst Plasmid cloning and amplification were performed in E. coli DH5 strain. E. coli strain BL21 (DE3) was used for biocatalysis experiments. Lysogeny broth (LB) medium was used for all cell

The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst

• Deniz Tözendemir and
• Cihangir Tanyeli

Beilstein J. Org. Chem. 2021, 17, 494–503, doi:10.3762/bjoc.17.43

• by chiral HPLC chromatography using Agilent instrument. All new products were further analyzed by LC/MS–HRMS–TOF or MALDI–ESI–TOFMS. Synthesis of organocatalyst 5 A solution of quinineamine 2 (226.40 mg, 0.70 mmol) and triethylamine (107 μL, 0.77 mmol) in CH2Cl2 was added to a screw-capped reaction

Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines

• Wilfred J. M. Lewis,
• David M. Shaw and
• Jeremy Robertson

Beilstein J. Org. Chem. 2021, 17, 334–342, doi:10.3762/bjoc.17.31

• pyrrole 18, and the appearance of new resonances at 3.21 (ddd, J = 11.5, 9.0, 2.5 Hz, 1H) and 3.64 (dt, J = 11.5, 8.5 Hz, 1H) ppm that correspond visually with those reported for the diastereotopic CH2N protons in legonmycin A. HRMS (ESI+) analysis of material isolated from this NMR experiment showed m/z

• , 36.2, 47.0 (three peaks), 63.3, 63.8, 64.5, 64.7, 80.5, 80.9, 81.0, 81.1, 117.8, 118.0, 118.1, 154.7, 155.4, 200.6 (two peaks), 201.0, 201.6; HRMS–ESI+ (m/z): [M + Na]+ calcd for C13H20N2O3Na, 275.1366; found, 275.1366. (S)-3-Amino-2-methyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one hydrochloride (17

• = 10.0, 8.5, 2.5 Hz, 1H), 4.44 (dd, J = 10.5, 5.5 Hz, 1H); 13C NMR (100 MHz, CD3OD) δ 5.8, 28.4, 30.2, 46.5, 70.0, 101.3 (from a separate spectrum of a stronger but impure sample), 174.4, 176.7; HRMS–ESI+ (m/z): [M]+ calcd for C8H13N2O, 153.1022; found, 153.1022. The free-base was also prepared in a

Hydrazides in the reaction with hydroxypyrrolines: less nucleophilicity – more diversity

• Dmitrii A. Shabalin,
• Evgeniya E. Ivanova,
• Igor A. Ushakov,
• Elena Yu. Schmidt and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2021, 17, 319–324, doi:10.3762/bjoc.17.29

• Center for collective use SB RAS. ESI-HRMS-TOF spectra were recorded at Shared Research Facilities for Physical and Chemical Ultramicroanalysis, Limnological Institute, SB RAS. Funding The reported study was funded by RFBR according to the research project No. 18-33-00089.

1,2,3-Triazoles as leaving groups in S_NAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

• Kārlis-Ēriks Kriķis,
• Irina Novosjolova,
• Anatoly Mishnev and
• Māris Turks

Beilstein J. Org. Chem. 2021, 17, 193–202, doi:10.3762/bjoc.17.19

• , 75.5 MHz) δ 154.3 (D, 3JC–P = 11.7 Hz), 154.2 (D, 3JC–P = 7.7 Hz), 152.5 (D, 1JC–P = 203.6 Hz), 147.5, 134.3 (D, 2JC–P = 21.4 Hz), 64.2 (D, 2JC–P = 6.1 Hz), 44.2, 31.5, 29.8, 28.6, 26.5, 22.5, 16.4 (D, 3JC–P = 6.2 Hz), 14.4; 31P NMR (CDCl3, 121 MHz) δ 5.3; HRMS-ESI (m/z): [M + H]+ calcd for

• -ESI (m/z): [M + H]+ calcd for C20H25N10O4, 469.2055; found, 469.2022. General procedure for the SNAr–Arbuzov reaction: synthesis of 9-alkyl-2-triazolyl-9H-purine C6-phosphonates 4 Methyl 1-(6-(diethoxyphosphoryl)-9-heptyl-9H-purin-2-yl)-1H-1,2,3-triazole-4-carboxylate (4a): Dimethyl 1,1'-(9-heptyl-9H

• , CDCl3) δ 160.9, 154.0 (D, 3JC–P = 11.1 Hz), 152.4 (D, 1JC–P = 220.6 Hz), 148.6, 148.3 (D, 3JC–P = 23.4 Hz), 140.3, 135.3 (D, 2JC–P = 20.8 Hz), 127.4, 64.5 (D, 2JC–P = 6.2 Hz), 52.6, 44.6, 31.6, 29.9, 28.7, 26.7, 22.7, 16.6 (D, 3JC–P = 5.9 Hz), 14.1; 31P NMR (202 MHz, CDCl3) δ 5.3; HRMS-ESI (m/z): [M + H

Control over size, shape, and photonics of self-assembled organic nanocrystals

• Chen Shahar,
• Yaron Tidhar,
• Yunmin Jung,
• Haim Weissman,
• Sidney R. Cohen,
• Ronit Bitton,
• Iddo Pinkas,
• Gilad Haran and
• Boris Rybtchinski

Beilstein J. Org. Chem. 2021, 17, 42–51, doi:10.3762/bjoc.17.5

• applicability of organic nanocrystals. Experimental General information The 1H and 13C NMR spectra were recorded at 20 °C on a 300 MHz NMR spectrometer (Bruker). Electrospray ionization (ESI) mass spectrometry was performed using a Micromass Platform instrument. UV–vis absorption and fluorescence measurements

Naphthalonitriles featuring efficient emission in solution and in the solid state

• Sidharth Thulaseedharan Nair Sailaja,
• Iván Maisuls,
• Jutta Kösters,
• Alexander Hepp,
• Andreas Faust,
• Jens Voskuhl and
• Cristian A. Strassert

Beilstein J. Org. Chem. 2020, 16, 2960–2970, doi:10.3762/bjoc.16.246

• characterization of H – NMe2 and its aggregates. 1H NMR, 13C NMR and EM-ESI-MS spectra of all the six compounds. Supporting Information File 404: Experimental procedures, NMR and EM-ESI-MS spectra. Acknowledgements We thankfully acknowledge Lic. Matias E. Gutierrez Suburu for his assistance with the DLS

Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives

• Jonas Becher,
• Daria V. Berdnikova,
• Heiko Ihmels and
• Christopher Stremmel

Beilstein J. Org. Chem. 2020, 16, 2795–2806, doi:10.3762/bjoc.16.230

• the corresponding solvent [δ(DMSO-d5) = 2.50 (1H) and 39.5 (13C); δ(CHCl3) = 7.26 (1H) and 77.2 (13C)]. Elemental analyses data were determined with a HEKAtech EURO EA combustion analyzer by Mr. Rochus Breuer (Organic Chemistry I, University of Siegen). Mass spectra (ESI) were recorded on a Finnigan

Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

• Viola Kolaříková,
• Markéta Rybáčková,
• Martin Svoboda and
• Jaroslav Kvíčala

Beilstein J. Org. Chem. 2020, 16, 2757–2768, doi:10.3762/bjoc.16.226

• internal standards. Chemical shifts are given in parts per million and coupling constants in hertz. Mass spectra (ESI, APCI) and HRMS spectra were measured with a hybrid LTQ Obitrap XL instrument (Thermo Fisher Scientific). All reactions were performed in a dry inert atmosphere (Ar) in oven-dried flasks

• ), 129.0 (s, 1C, CH3-C=C), 129.1 (s, 2C, CHAr), 131.9 (s, 1C, CAr), 176.8 (s, 1C, CH-CH-C=O), 178.5 (s, 1C, CH2-CH-C=O); MS (ESI+, m/z) (%): 372.2 [M + Na]+ (100), 350.2 [M + H]+ (20); HRMS (ESI+, m/z): [M + H]+ calcd for C22H24O3N, 350.1751; found, 350.1752; HRMS (ESI+, m/z): [M + Na]+ calcd for

• ), 128.5 (s, 1C, CHAr), 129.1 (s, 2C, CHAr), 131.8 (s, 1C, CAr), 177.0 (s, 1C, CH-CH-C=O), 178.5 (s, 1C, CH2-CH-C=O); MS (ESI+, m/z): 372.2 [M + Na]+ (100), 350.2 [M + H]+ (35); HRMS (ESI+, m/z): [M + H]+ calcd for C22H24O3N, 350.1751; found, 350.1752; HRMS (ESI+, m/z): [M + Na]+ calcd for C22H23O3NNa