Flow synthesis of oxadiazoles coupled with sequential in-line extraction and chromatography

• Kian Donnelly and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 232–239, doi:10.3762/bjoc.18.27

• an integrated quenching and extraction step. Lastly, the use of an automated in-line chromatography system was exploited to realise a powerful flow platform for the generation of the heterocyclic targets. Keywords: chromatography; flow synthesis; in-line purification; oxadiazole; reaction

• reaction is potentially explained by the reaction reaching steady state during this longer run, thus providing a more accurate indication of the yield. This productivity could potentially be further increased, simply by increasing the volume of the glass column reactor. With an in-line extraction system in

• product) on a 1 mmol scale. Conclusion In summary, we have developed a continuous flow platform for the synthesis of 1,3,4-oxadiazoles in high yields and short residence times of 10 minutes. The incorporation of an in-line extraction reduced the risk of contact with toxic and corrosive iodine in addition

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• authenticated by Prof. Yongbo Xue of the Research Department of Pharmacognosy, Sun Yat-sen University. A voucher specimen (SYSUSZ-2019-X1) has been deposited in the Department of Natural Medicinal Chemistry, Sun Yat-sen University. Extraction and isolation The dried root of W. nutans (3.5 kg) was extracted

Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

• Yasuhiro Igarashi,
• Yiwei Ge,
• Tao Zhou,
• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku and
• Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

• uniquely, both of the olefinic proton resonances (H12 and H13) were broadened at 25 °C (Figure 3a). However, upon heating to 50 °C, H12 split into doublet-triplet, which allowed the extraction of 3JH12,H13 = 11.4 Hz to deduce a cis configuration. H13, in contrast, broadened more severely at the raised

• inoculated flasks were placed on a rotary shaker (200 rpm) at 30 °C for 7 days. Extraction and isolation At the end of the fermentation period, 100 mL of 1-butanol were added to each flask and the flasks were shaken for 1 h. The mixture was centrifuged at 6000 rpm for 10 min and the organic layer was

Chemical and chemoenzymatic routes to bridged homoarabinofuranosylpyrimidines: Bicyclic AZT analogues

• Sandeep Kumar,
• Jyotirmoy Maity,
• Banty Kumar,
• Sumit Kumar and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2022, 18, 95–101, doi:10.3762/bjoc.18.10

• its extraction in the organic phase during work up procedure. So, the classical chemical route to synthesize nucleosides 9a,b started with the conversion of diacetone ᴅ-glucofuranose 10 to 3′-azido-3′-deoxy-β-ᴅ-allofuranoside 11, which on acidification with 80% acetic acid gave furanoside diol 17. The

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

• silica gel thin-layer plate (Kieselgel 60F254; Merck Co.) developed by a mixture of CHCl3/MeOH (5:1). Extraction of the collected silica gel powder with MeOH gave (R)-PGME amide 6a (0.5 mg). (R)-PGME amide 6a: 1H NMR (500 MHz, DMSO-d6) δ 10.61 (s, 1H, NH-1), 7.01 (s, 1H, H-2), 7.46 (d, J = 8.1 Hz, 1H, H

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure

• Agnieszka Grajewska,
• Maria Chrzanowska and
• Wiktoria Adamska

Beilstein J. Org. Chem. 2021, 17, 2511–2519, doi:10.3762/bjoc.17.168

• cyclization reaction was easily performed by treatment of 6a with 20% HCl for 24 h to give dihydromethanodibenzoazocine-5-carboxylic acid (7a, Scheme 5) in 72% yield by extraction of the neutralized reaction mixture. Compound 7a was obtained in two simple steps from 3a with an overall yield of 67%. Then the

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

• Yi Liu,
• Puying Luo,
• Yang Fu,
• Tianxin Hao,
• Xuan Liu,
• Qiuping Ding and
• Yiyuan Peng

Beilstein J. Org. Chem. 2021, 17, 2462–2476, doi:10.3762/bjoc.17.163

• or ligand in organic chemistry [6][7][8][9][10]. Therefore, the development of efficient methods for the synthesis of pyridine derivatives has attracted considerable attention [11][12][13][14]. The industrial synthetic methods of pyridines mainly involve: i) extraction from coal tar; ii) condensation

• ][28][29]. In industry, pyrrole mainly comes from the extraction of coal tar, the condensation reaction of furan and ammonia under high temperature, or the cascade cyclization reaction of acetylene, formaldehyde, and ammonia. In the laboratory, there are many efficient methods for the synthesis of

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

• by inoculating a 250 mL baffled Erlenmeyer flask containing a modified SGG medium with a stock culture of Pseudomonas UIAU-6B (2 mL) and growth for 3 days. The entire fermentation process employed similar conditions as the small-scale culture. Extraction and isolation After the incubation, 15 g of HP

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

• the School of Pharmacy, Sungkyunkwan University, Suwon, Republic of Korea. Extraction and isolation. Twigs of A. fordii (7.0 kg) were extracted three times with 80% aqueous MeOH (each 10 L × 1 day) under reflux and filtered. The filtrate was evaporated under vacuum to obtain a crude MeOH extract (325

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• . Additionally, polysaccharides can be converted into useful chemicals upon biodegradation [2][3], contributing to the sustainable development of future materials. Despite polysaccharides’ utility, there are limitations associated with their exploitation. Extraction from natural sources is laborious, low

• polysaccharides longer than hexasaccharides. Shorter oligomers are discussed when they represent a key step towards the synthesis of the corresponding polysaccharide. Polymers based on a sugar backbone connected via glycosidic linkages are analyzed, excluding glycopolymers and other mimetics. Extraction

• methodologies or post-extraction modifications are not discussed. Review Glucose-based polysaccharides Cellulose Cellulose is a polymer consisting of glucose units connected by β(1–4) glycosidic bonds. It is mainly found in two allomorphs – Cellulose I (natural) and Cellulose II (synthetic) – that differ in the

Volatile emission and biosynthesis in endophytic fungi colonizing black poplar leaves

• Christin Walther,
• Pamela Baumann,
• Katrin Luck,
• Beate Rothe,
• Peter H. W. Biedermann,
• Jonathan Gershenzon,
• Tobias G. Köllner and
• Sybille B. Unsicker

Beilstein J. Org. Chem. 2021, 17, 1698–1711, doi:10.3762/bjoc.17.118

• diameter) growing on PDA. The mycelium was flash frozen in liquid nitrogen and ground using plastic pestles in 1.5 mL Eppendorf tubes. After homogenization of the mycelium, 500 µL extraction buffer (100 mM Tris HCl, pH 8; 10 mM EDTA, pH 8; 2% w/v SDS) and 100 µL proteinase K (Sigma) were added and the

• representative total ion chromatogram for each fungus is shown in Supporting Information File 1, Figure S1. Mass spectra of unknown compounds are shown in Supporting Information File 1, Figure S2. Fungal RNA extraction, reverse transcription, and sequencing Total RNA was isolated from fresh mycelium

• by a 4 × 20 s treatment with a sonicator (Bandelin UW2070, Berlin, Germany) in chilled extraction buffer (10 mM Tris-HCl, pH 7.5, 1 mM dithiothreitol, 10% (v/v) glycerol). Cell fragments were removed by centrifugation at 14,000g and the supernatant was further processed via an Illustra NAP-5 gravity

Recent advances in the application of isoindigo derivatives in materials chemistry

• Andrei V. Bogdanov and
• Vladimir F. Mironov

Beilstein J. Org. Chem. 2021, 17, 1533–1564, doi:10.3762/bjoc.17.111

• -coating technique, the authors succeeded in obtaining a thin film by immersing a substrate in a polymer solution, followed by slow extraction, accompanied by slow evaporation of the solvent. The device thus obtained showed one of the highest values of hole conductivity of μe = 8.3 cm2⋅V−1⋅s−1 [78]. It was

Total synthesis of ent-pavettamine

• Memory Zimuwandeyi,
• Manuel A. Fernandes,
• Amanda L. Rousseau and
• Moira L. Bode

Beilstein J. Org. Chem. 2021, 17, 1440–1446, doi:10.3762/bjoc.17.99

• , using our previously published methodology in an overall yield of 8% over 8 steps (Scheme 1) [1]. An alternative strategy for the synthesis of 4 was developed so as to avoid a cumbersome continuous extraction step of a triol associated with the established method, in addition to improving the overall

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

• corresponding cultures were deposited at the mycological herbarium of Mae Fah Luang University, Chiang Rai, Thailand, accession number MFLUCC 14-0681. The DNA extraction was performed using an EZ-10 Spin Column Genomic DNA Miniprep kit (Bio Basic Canada Inc., Markham, Ontario, Canada) following the

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

• Santiago Ramos-Carreño,
• Ivone Giffard-Mena,
• Jose N. Zamudio-Ocadiz,
• Alfredo Nuñez-Rivera,
• Ricardo Valencia-Yañez,
• Jaime Ruiz-Garcia,
• Maria Teresa Viana and
• Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

• purification. The plant virus CCMV was produced in California cowpea plants (Vigna ungiculata). The plants were mechanically inoculated with a solution containing the virus. After two weeks, the infected leaves were collected and ground in a virus extraction buffer (0.5 M sodium acetate, 0.08 M magnesium

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Nitroalkene reduction in deep eutectic solvents promoted by BH₃NH₃

• Chiara Faverio,
• Monica Fiorenza Boselli,
• Patricia Camarero Gonzalez,
• Alessandra Puglisi and
• Maurizio Benaglia

Beilstein J. Org. Chem. 2021, 17, 1041–1047, doi:10.3762/bjoc.17.83

• physicochemical properties can be easily tuned and designed to meet specific requirements; they also offer the possibility to develop convenient methodologies to isolate the product by extraction or precipitation, and thus making the reuse of the DES mixture feasible. The large number of biodegradable raw

• extraction of the product and its separation from the eutectic mixture. However, when the recycling protocol was studied, in order to reuse the DES, at the end of the reaction, water was not added, and the product was extracted by simply adding ethyl acetate and separating the upper, organic phase. The DES

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

• Roslyn M. Ray,
• Anders Højgaard Hansen,
• Maria Taskova,
• Bernhard Jandl,
• Jonas Hansen,
• Citra Soemardy,
• Kevin V. Morris and
• Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

• ’-flouronated base; italics and underlined = 2’-O-methyl base Complementary DNA A-1: (Cy5/AGG CTA TCT AGA ATG TAC) G-3: (Cy5/TCT ATC AAT CTA TCA) Peptide synthesis, purification, and characterization Peptide assembly was carried out by solid-phase peptide synthesis in standard solid-phase extraction filtration

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson’s reagent

• Ke Wu,
• Yichen Ling,
• An Ding,
• Liqun Jin,
• Nan Sun,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2021, 17, 805–812, doi:10.3762/bjoc.17.69

• scaling up the preparation of two pincer-type thioamides, we have successfully developed a convenient process with ethylene glycol to replace ethanol during the workup, including a traditional phase separation, extraction, and recrystallization. The newly developed chromatography-free procedure did not

• the LR upon thio-substitution [11][12][13]. It has been observed that the polarity of compound A is generally similar to the desired products, thus making the purification of the desired products by extraction operations less efficient. Therefore, the purification is rather difficult and usually a

• thionation reactions, considerable efforts have been devoted to the improvement of the workup procedures of these reactions. For example, Soós and co-workers introduced perfluoroalkylated derivatives of LR, which simplified the product isolation via a fluorous reversed-phase solid extraction technique [9][10

Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B

• Takashi Nishiyama,
• Erina Hamada,
• Daishi Ishii,
• Yuuto Kihara,
• Nanase Choshi,
• Natsumi Nakanishi,
• Mari Murakami,
• Kimiko Taninaka,
• Noriyuki Hatae and
• Tominari Choshi

Beilstein J. Org. Chem. 2021, 17, 730–736, doi:10.3762/bjoc.17.62

• material. However, after the workup, extraction, and removal of solvent (in vacuo), the appearance of the TLC plate changed due to the formation of various byproducts. Then, the reaction mixture was purified, but the desired carbodiimide 17a was not obtained, but aminopyrroloquinoline 18 formed through

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents

• Anuj Kumar Chhalodia and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 569–580, doi:10.3762/bjoc.17.51

• stripping apparatus (CLSA) [33], followed by the extraction of the filters with CH2Cl2 and analysis by gas chromatography–mass spectrometry (GC–MS) of the resulting extracts. Most of the compounds were readily identified by the comparison of their mass spectra and retention indices to published data. Every

• extraction to a CLSA [33] for 24 h. The released volatiles were collected on charcoal filters (Chromtech, Idstein, Germany), followed by the extraction of the filters with dichloromethane (50 μL), and analysis of the extracts by GC–MS. For comparison, blank experiments with MB medium alone and with MB agar

Identification of volatiles from six marine Celeribacter strains

• Anuj Kumar Chhalodia,
• Jan Rinkel,
• Dorota Konvalinkova,
• Jörn Petersen and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 420–430, doi:10.3762/bjoc.17.38

• 27375T, C. halophilus DSM 26270T and C. indicus DSM 27257T, were collected through a closed-loop stripping apparatus (CLSA) on charcoal [37]. After extraction with dichloromethane the obtained extracts were analyzed by GC–MS (Figure 1). The compounds were identified by the comparison of the recorded EI

Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride

• Beatrice Lansbergen,
• Catherine S. Meister and
• Michael C. McLeod

Beilstein J. Org. Chem. 2021, 17, 404–409, doi:10.3762/bjoc.17.36

• 5m compared to the longer chain substrates (e.g., 5c and 5l) could be explained mechanistically by the formation of a terminal carbocation upon the extraction of a fluorine atom by the aluminium species (Scheme 3). This carbocation could be stabilised to varying degrees by the ketone moiety