Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid

• Dong Cai,
• ZhiHua Zhang,
• Yufan Meng,
• KaiLi Zhu,
• LiYi Chen,
• ChangXiang Yu,
• ChangWei Yu,
• ZiYi Fu,
• DianShen Yang and
• YiXia Gong

Beilstein J. Org. Chem. 2020, 16, 798–808, doi:10.3762/bjoc.16.73

• , N,N-dimethylformamide (DMF), a solvent with a higher boiling point than acetonitrile, was also tested, yet the reaction led to the formation of unknown compounds (TLC monitoring, Table 2, entry 7). After screening several solvents, the optimal yield was obtained in acetonitrile, though a small

Design and synthesis of diazine-based panobinostat analogues for HDAC8 inhibition

• Sivaraman Balasubramaniam,
• Sajith Vijayan,
• Liam V. Goldman,
• Xavier A. May,
• Kyra Dodson,
• Sweta Adhikari,
• Fatima Rivas,
• Davita L. Watkins and
• Shana V. Stoddard

Beilstein J. Org. Chem. 2020, 16, 628–637, doi:10.3762/bjoc.16.59

• dimethylformamide (DMF) were degassed in 20 L drums and passed through two sequential purification columns (activated alumina; molecular sieves for DMF) under a positive argon atmosphere. Thin-layer chromatography (TLC) was performed on SiO2-60 F254 aluminum plates with visualization by ultraviolet (UV) detection

Six-fold C–H borylation of hexa-peri-hexabenzocoronene

• Mai Nagase,
• Kenta Kato,
• Akiko Yagi,
• Yasutomo Segawa and
• Kenichiro Itami

Beilstein J. Org. Chem. 2020, 16, 391–397, doi:10.3762/bjoc.16.37

• and then refilled with nitrogen. To this vessel were added 3 (100 mg, 78.3 μmol, 1.0 equiv), Pd(dppf)Cl2 (28.6 mg, 39.1 μmol, 0.5 equiv), bis(pinacolato)diboron (B2pin2; 199 mg, 783 μmol, 10 equiv), toluene (0.36 mL) and N,N-dimethylformamide (DMF; 0.36 mL). The mixture was stirred at 80 °C for 18 h

Effect of ring size on photoisomerization properties of stiff stilbene macrocycles

• Sandra Olsson,
• Óscar Benito Pérez,
• Magnus Blom and
• Adolf Gogoll

Beilstein J. Org. Chem. 2019, 15, 2408–2418, doi:10.3762/bjoc.15.233

• dichloromethane (DCM), ethyl acetate, pentane, tetrahydrofuran (THF) and toluene that were distilled before use. N,N-Dimethylformamide (DMF) was used as supplied (biotech. grade, ≥99.9%). Unless stated differently, all reactions were carried out under atmospheric pressure and with argon atmosphere. Microwave (MW

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

• Gagandeep Kour Reen,
• Ashok Kumar and
• Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

• enaminones 61 by conjugative addition of heteroarylamines 3 with α,β-ynones 60 (Scheme 20). Optimization of the reaction inferred that CuI with dimethylformamide (DMF) at 100 °C under air would be the best conditions for a maximum yield. The reaction viability was also tested without the isolation of product

Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP)

• Małgorzata Urbańczyk,
• Michał Jewgiński,
• Joanna Krzciuk-Gula,
• Jerzy Góra,
• Rafał Latajka and
• Norbert Sewald

Beilstein J. Org. Chem. 2019, 15, 1581–1591, doi:10.3762/bjoc.15.162

• ]. General methods All air- and moisture-sensitive reactions were carried out in a dry argon atmosphere in flame-dried glass flasks. Dichloromethane (DCM) was freshly distilled from CaH2 and toluene from Na. N,N-Dimethylformamide (DMF) was distilled from ninhydrine. All amino acids, coupling reagents and the

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

• András György Németh,
• György Miklós Keserű and
• Péter Ábrányi-Balogh

Beilstein J. Org. Chem. 2019, 15, 1523–1533, doi:10.3762/bjoc.15.155

• did not improve the yield of the reaction (Table 2, entry 6), nor did the use of Cs2CO3 (Table 2, entry 7). However, using N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMA) as the solvent provided 5a in 43% and 45% yield, respectively (Table 2, entries 8 and 9), while on the other hand, N

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• -dimethylformamide (DMF) for the synthesis of 4 and 5. Compounds 4 and 5 were isolated in good yields (55 and 75%, respectively) [27]. The syntheses of compounds 7 and 8 were carried out in DMF as well. As substantial amounts of 6 were isolated after the reaction, indicating an incomplete conversion to 8 (53%), the

Homo- and hetero-difunctionalized β-cyclodextrins: Short direct synthesis in gram scale and analysis of regiochemistry

• Gábor Benkovics,
• Mihály Bálint,
• Éva Fenyvesi,
• Erzsébet Varga,
• Szabolcs Béni,
• Konstantina Yannakopoulou and
• Milo Malanga

Beilstein J. Org. Chem. 2019, 15, 710–720, doi:10.3762/bjoc.15.66

• the homo-disubstituted derivatives, e.g., 6A,6X-diazido-β-CDs can be prepared using sodium azide in N,N-dimethylformamide (DMF) and moderate heating (Scheme 1). Although capping reagents are selective in disubstitution and this methodology revolutionized CD difunctionalization, their application has

A simple and effective preparation of quercetin pentamethyl ether from quercetin

• Jin Tatsuzaki,
• Tomohiko Ohwada,
• Yuko Otani,
• Reiko Inagi and
• Tsutomu Ishikawa

Beilstein J. Org. Chem. 2018, 14, 3112–3121, doi:10.3762/bjoc.14.291

• potassium carbonate (K2CO3) are generally selected as the solvent and base, acetone can be replaced with dimethylformamide (DMF) if the starting phenol is poorly soluble in acetone. To our knowledge four reactions [37][38][39][40] were found in the literature as successful per-O-methylations of quercetin (2

Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized α-cyclodextrin derivatives

• Iveta Tichá,
• Gábor Benkovics,
• Milo Malanga and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2018, 14, 2829–2837, doi:10.3762/bjoc.14.261

• ). On one hand, a direct bromination of α-CD was performed under Vilsmeier/Haack conditions (reaction 3, Scheme 2) with N-bromosuccinimide (NBS) and Ph3P in N,N-dimethylformamide (DMF). Previous studies have shown that this reaction is highly regioselective for the primary rim of CD [28]. After a fast

Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines

• Itaru Nakamura,
• Mao Owada,
• Takeru Jo and
• Masahiro Terada

Beilstein J. Org. Chem. 2018, 14, 1972–1979, doi:10.3762/bjoc.14.172

• solvents, such as CHCl3, CH2Cl2, and PhCl, ethereal solvent, such as Et2O and tert-butyl methyl ether (MTBE), and toluene were less efficient (Table 2, entries 2–7), while the use of polar solvents, such as tetrahydrofuran (THF), acetonitrile, and N,N-dimethylformamide (DMF), resulted in quantitative

Defining the hydrophobic interactions that drive competence stimulating peptide (CSP)-ComD binding in Streptococcus pneumoniae

• Bimal Koirala,
• Robert A. Hillman,
• Erin K. Tiwold,
• Michael A. Bertucci and
• Yftah Tal-Gan

Beilstein J. Org. Chem. 2018, 14, 1769–1777, doi:10.3762/bjoc.14.151

• ) procedures [34]. Phenylglycine and norvaline derivatives were prepared on a CEM Discover microwave synthesizer, with diisopropyl carbodiimide (DIC) as the coupling reagent along with Oxyma Pure. The ratio of DIC:Oxyma Pure:AA was 3.6:3:3 dissolved in N,N-dimethylformamide (DMF) for a final DIC concentration

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

• Jiyun Sun,
• Xiaohua Zhen,
• Huaibin Ge,
• Guangtao Zhang,
• Xuechan An and
• Yunfei Du

Beilstein J. Org. Chem. 2018, 14, 1452–1458, doi:10.3762/bjoc.14.123

• in the presence of CuI in N,N-dimethylformamide (DMF) [62] at room temperature for two hours afforded the β-trifluoromethylated enamine 6a in a 23% yield. Subjecting enamine 6a to PhIO in 1,2-dichloroethane (DCE) for 12 hours at room temperature led to the formation of the desired β

Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst

• Kimihiro Komeyama,
• Shunsuke Sakiyama,
• Kento Iwashita,
• Itaru Osaka and
• Ken Takaki

Beilstein J. Org. Chem. 2018, 14, 1413–1420, doi:10.3762/bjoc.14.118

• solvent used; for example, dimethylformamide (DMF), tetrahydrofuran (THF), 1,4-dioxane, and toluene did not result in any formation of 4a. With the optimized conditions in hand, the use of aldehydes in the Co/Cr-catalyzed three-component coupling reaction was explored, as shown in Scheme 6. Electron-rich

Design and biological characterization of novel cell-penetrating peptides preferentially targeting cell nuclei and subnuclear regions

• Anja Gronewold,
• Mareike Horn and
• Ines Neundorf

Beilstein J. Org. Chem. 2018, 14, 1378–1388, doi:10.3762/bjoc.14.116

• (Marktredwitz, Germany). Other chemicals and consumables including 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), N,N-diisopropylethylamine (DIPEA), acetonitrile (ACN), and trifluoroacetic acid (TFA), dimethylformamide (DMF), N-methylpyrrolidine (NMP

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery

• Sabine Schuster,
• Beáta Biri-Kovács,
• Bálint Szeder,
• Viktor Farkas,
• László Buday,
• Zsuzsanna Szabó,
• Gábor Halmos and
• Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64

• )) were obtained from Sigma-Aldrich Kft (Budapest, Hungary). Daunorubicin hydrochloride was a gift from IVAX (Budapest, Hungary). N,N-Dimethylformamide (DMF), dichloromethane (DCM) and diethyl ether (Et2O) were purchased from Molar Chemicals Kft (Budapest, Hungary). All reagents and solvents were of

Position-dependent impact of hexafluoroleucine and trifluoroisoleucine on protease digestion

• Susanne Huhmann,
• Anne-Katrin Stegemann,
• Kristin Folmert,
• Damian Klemczak,
• Johann Moschner,
• Michelle Kube and
• Beate Koksch

Beilstein J. Org. Chem. 2017, 13, 2869–2882, doi:10.3762/bjoc.13.279

• non-fluorinated amino acids were performed in dimethylformamide (DMF) with the Fmoc-L-amino acid, 1-hydroxybenzotriazole (HOBt) and N,N’-diisocarbodiimide (DIC) in an eight-fold excess with respect to the resin amount. In order to ensure completion of the reaction the couplings were performed twice

Development of a fluorogenic small substrate for dipeptidyl peptidase-4

• Futa Ogawa,
• Masanori Takeda,
• Kanae Miyanaga,
• Keita Tani,
• Ryuji Yamazawa,
• Kiyoshi Ito,
• Atsushi Tarui,
• Kazuyuki Sato and
• Masaaki Omote

Beilstein J. Org. Chem. 2017, 13, 2690–2697, doi:10.3762/bjoc.13.267

• information All experiments were carried out under an argon atmosphere in flame-dried glassware using standard inert techniques for introducing reagents and solvents, unless otherwise noted. N,N-Dimethylformamide (DMF) was distilled over calcium hydride and stored in a bottle with activated molecular sieves

Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes

• Takeshi Fujita,
• Ryo Kinoshita,
• Tsuyoshi Takanohashi,
• Naoto Suzuki and
• Junji Ichikawa

Beilstein J. Org. Chem. 2017, 13, 2682–2689, doi:10.3762/bjoc.13.266

• chromatography (PTLC) were conducted on silica gel (Silica Gel 60 N, Kanto Chemical Co., Inc. for column chromatography and Wakogel B-5F, Wako Pure Chemical Industries, Ltd. for PTLC). Tetrahydrofuran (THF), dichloromethane, and N,N-dimethylformamide (DMF) were purified by a solvent-purification system

Synthesis of naturally-derived macromolecules through simplified electrochemically mediated ATRP

• Paweł Chmielarz,
• Tomasz Pacześniak,
• Katarzyna Rydel-Ciszek,
• Izabela Zaborniak,
• Paulina Biedka and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2017, 13, 2466–2472, doi:10.3762/bjoc.13.243

• solutions contained N,N-dimethylformamide (DMF) and tert-butyl acrylate (tBA). One can observe, that quercetin is not reduced in the applied potential window (Figure S2, Supporting Information File 1), meanwhile it shows two small anodic peaks at 0.2 V and 0.5 V. According to the commonly accepted mechanism

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

• Vânia André,
• Sílvia Quaresma,
• João Luís Ferreira da Silva and
• M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

• to incorporate APIs as a guest. Indeed, they synthesized two BioMOFs by grinding together zinc, fumaric acid and 4,4’-bipyridyl (bipy) or trans-1,2-di(4-pyridyl)ethylene (bpe) as ligands in the presence of a space-filling liquid agent (N,N-dimethylformamide, DMF). This synthesis also proceeded when

• Bi38 cluster with coordinated N,N-dimethylformamide (DMF) molecules instead of acetone, showing the structural robustness of this core in solution. The crystal structure solution from powder X-ray diffraction data of the disalicylate revealed the first crystal structure of a bismuth salicylate without

New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties

• Daria G. Selivanova,
• Alexei A. Gorbunov,
• Olga A. Mayorova,
• Alexander N. Vasyanin,
• Igor V. Lunegov,
• Elena V. Shklyaeva and
• Georgii G. Abashev

Beilstein J. Org. Chem. 2017, 13, 1583–1595, doi:10.3762/bjoc.13.158

• dichloromethane (DCM), acetone (DMK), benzene, tetrahydrofuran (THF), dimethylformamide (DMF), dimethyl sulfoxide (DMSO), but are poorly soluble in hot ethanol and not soluble in hexane. On the enlargement of the conjugated system the colour of the compounds solutions in the sunlight expectedly changes from

Synthesis of novel 13α-estrone derivatives by Sonogashira coupling as potential 17β-HSD1 inhibitors

• Ildikó Bacsa,
• Rebeka Jójárt,
• János Wölfling,
• Gyula Schneider,
• Bianka Edina Herman,
• Mihály Szécsi and
• Erzsébet Mernyák

Beilstein J. Org. Chem. 2017, 13, 1303–1309, doi:10.3762/bjoc.13.126

• to differ depending on the position of the iodo substituent on the sterane skeleton (Scheme 1). Couplings at C-2 could efficiently be achieved using 0.1 equiv of Pd(PPh3)4 and CuI in tetrahydrofuran (THF) or dimethylformamide (DMF) as solvent in the presence of Et3N as a base at 50 °C for 20 min in a