A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety

• Ilya V. Taydakov,
• Yuliya M. Kreshchenova and
• Ekaterina P. Dolotova

Beilstein J. Org. Chem. 2018, 14, 3106–3111, doi:10.3762/bjoc.14.290

• molar ratio of ketone, ester and NaH was found to be 1:1:2. The excess NaH acts as an alcohol and water scavenger, thus making the synthetic protocol more robust. Commercial NaH is supplied in a relatively safe form of 60% dispersion in mineral oil. Although other researchers recommended to use this

• mentioned before, an excess of NaH was used to improve the yields of diketones. It must be decomposed by careful addition of an anhydrous alcohol (MeOH or EtOH) before treatment of the reaction mixture with an aqueous acid. With this precaution, the whole synthetic procedure is safe. The results of the

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

• Nadia Bouzayani,
• Jamil Kraїem,
• Sylvain Marque,
• Yakdhane Kacem,
• Abel Carlin-Sinclair,
• Jérôme Marrot and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271

• directed toward the development of environmentally safe conditions for the synthesis of heterocyclic compounds starting from natural (L)-α-amino acids [19][20][21][22][23] and the reactivity of α-amino acid phenylhydrazides [24][25], we now report a green and eco-friendly procedure for the synthesis of new

• conditions, we investigated the reaction in nontoxic solvents such as water and dimethyl carbonate (DMC). Indeed, DMC is well-known as safe reagent and solvent that has been used for many green applications [31][32][33]. On the other hand, water is a simply and environmentally benign solvent and interest has

• were obtained in this case. Interestingly, acidic (phenolic 5j) and basic moieties (as indolyl 5i) on the amino acid residue did not affect the selectivity. Conclusion In summary, we have developed environmentally safe conditions for the synthesis of new chiral 1-(arylamino)-1H-imidazo[2,1-a]isoindole

Protein–protein interactions in bacteria: a promising and challenging avenue towards the discovery of new antibiotics

• Laura Carro

Beilstein J. Org. Chem. 2018, 14, 2881–2896, doi:10.3762/bjoc.14.267

• antibiotic-insensitive strains, the steady decline in the number of new antibacterial drugs and the insufficient investment in antimicrobial research and development (R&D) by the major pharmaceutical companies have led to a global health crisis in which the prospect of a future without a safe and effective

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• aqueous solution is probably well recognized in the literature. Less corrosive and toxic effects and the lack of dangerous vapors make it safe to handle under normal conditions. MSA as a biodegradable chemical is decomposed within 28 days by living organisms and is part of the natural sulfur cycle. During

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

• Keishiro Tahara,
• Ling Pan,
• Toshikazu Ono and
• Yoshio Hisaeda

Beilstein J. Org. Chem. 2018, 14, 2553–2567, doi:10.3762/bjoc.14.232

• to AB in the presence of GSH and iodoacetic acid in phosphoric acid–citric acid buffer at 37 °C, a safe and eco-friendly detoxification of inorganic arsenics was developed via methyl transfer reactions mediated by biomimetic vitamin B12. 4. Dehalogenation reactions “Dehalorespiration” is also a model

A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N-chloramines

• Katherine E. Jolley,
• Michael R. Chapman and
• A. John Blacker

Beilstein J. Org. Chem. 2018, 14, 2220–2228, doi:10.3762/bjoc.14.196

• Information File 1, S2). A maximum safe operating temperature of 110 °C was implemented to avoid thermal decomposition and thermal runaway. The direct reaction of N-chloramine 11, or the benzyl-substituted variant 12, led to a single regioisomer of the amine product in a lower reaction time than the analogous

Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester

• Takao Shoji,
• Hiroki Fukutomi,
• Yohei Okada and
• Kazuhiro Chiba

Beilstein J. Org. Chem. 2018, 14, 1946–1955, doi:10.3762/bjoc.14.169

• linkages that can be formed between native functional groups would be safe alternatives, and are known as natural conjugates such as nucleopeptides and nucleolipids [49]. We have been developing alkyl chain soluble support (ACSS)-assisted liquid-phase methods, specifically for peptide and oligonucleotide

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

• Xiang Li,
• Pinhong Chen and
• Guosheng Liu

Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

• under mild conditions [78]. The authors proposed a radical pathway involving the in situ generation of Br2, which opens the avenue for a reliable, ecologically benign, and safe dibromination method. Conclusion In the last two decades, great progress was made in hypervalent iodine(III) catalytic systems

Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

• Livia Polgár,
• Eszter Lajkó,
• Pál Soós,
• Orsolya Láng,
• Marilena Manea,
• Béla Merkely,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

• HMC or on HUVEC cells, it might be a promising and safe candidate for targeted therapy. None of the conjugates (12–15) containing two drug molecules, independent on their type (Dau, Mtx) or attachment site, showed cytotoxicity on any of the tested cell types. The two Dau containing conjugates (12, 14

Direct electrochemical generation of organic carbonates by dehydrogenative coupling

• Tile Gieshoff,
• Vinh Trieu,
• Jan Heijl and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2018, 14, 1578–1582, doi:10.3762/bjoc.14.135

• polymer formation with less reactive epoxides (other than ethylene oxide) [7][8][9][10]. Electrochemistry has the capability to access products by extraordinary reaction pathways. Electric current is an inexpensive reagent and inherently safe reaction set-ups ensure a resource saving and applicable

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

• effects, there is a need to develop suitable delivery vectors for the safe transport of drugs to the nucleus. Such nuclear-targeting sequences have already proven to be successful delivery tools. According to their often basic nature, they are also able to traverse the cellular membrane [8]. Based on this

Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

• Toshifumi Dohi,
• Shohei Ueda,
• Kosuke Iwasaki,
• Yusuke Tsunoda,
• Koji Morimoto and
• Yasuyuki Kita

Beilstein J. Org. Chem. 2018, 14, 1087–1094, doi:10.3762/bjoc.14.94

• , reports aimed at realizing efficient and selective metal-free C(sp3)–H transformations are rather limited; however, investigations by several research groups are still ongoing [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30]. Hypervalent iodine reagents are now widely accepted as a safe

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

Volatiles from three genome sequenced fungi from the genus Aspergillus

• Jeroen S. Dickschat,
• Ersin Celik and
• Nelson L. Brock

Beilstein J. Org. Chem. 2018, 14, 900–910, doi:10.3762/bjoc.14.77

• genus comprising several hundreds of known species. Some of these species are human pathogens, e.g., Aspergillus fumigatus can cause infections especially in immunocompromised patients, while other species are safe, e.g., Aspergillus oryzae is traditionally used in Japanese sake brewing. The genus has a

Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

• Morten M. C. H. van Schie,
• Tiago Pedroso de Almeida,
• Gabriele Laudadio,
• Florian Tieves,
• Elena Fernández-Fueyo,
• Timothy Noël,
• Isabel W. C. E. Arends and
• Frank Hollmann

Beilstein J. Org. Chem. 2018, 14, 697–703, doi:10.3762/bjoc.14.58

• described in the literature to alleviate the inactivation issue described above [9][10][11][12]. The continuous-flow microreactor technology has emerged as a safe and scalable way to approach oxidation reactions [13][14]. Due to its small dimensions, hazardous reactions can be easily controlled, owing to

AuBr₃-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars

• Jayashree Rajput,
• Srinivas Hotha and
• Madhuri Vangala

Beilstein J. Org. Chem. 2018, 14, 682–687, doi:10.3762/bjoc.14.56

• their operationally simple, safe and neutral reaction conditions, had widely contributed to the development of new glycosylation methods. Gold(I) and gold(III) complexes are usually alkynophilic [2], carbophilic and oxophilic because of their affinity towards the alkynes’ and C–O π systems [3][4][5][6

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

• Fabio Tonin and
• Isabel W. C. E. Arends

Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33

• industry; additional steps of purification and control of sterility are necessary to obtain a safe product for the market. Otherwise, the circumvention of protein isolation and production makes it cheaper than their free-enzyme analogues. In this way, the use of lyophilized whole-cell containing

• the purification processes necessary to eliminate byproducts formed at each step of reaction involved. All this extends the time, increases costs and decreases production yields. Therefore, research nowadays is geared towards more economical synthesis methods that are waste-free and safe to operate

Continuous-flow retro-Diels–Alder reaction: an efficient method for the preparation of pyrimidinone derivatives

• Imane Nekkaa,
• Márta Palkó,
• István M. Mándity and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2018, 14, 318–324, doi:10.3762/bjoc.14.20

• optimization, acceleration [6], and easy scale-up with a wide and growing range of chemical transformations in combination with an inherently safe and green nature [7][8][9][10][11][12]. Advantageously, safety issues are complied with excellent mixing and heat transfer [7][8][9][10][11][12][13][14]. These

• allow the access to elevated temperatures and pressures accredited to superheating of organic solvents in a controlled and safe fashion [6][14][15][16][17]. The accurate tuning of residence time can further broaden the versatility of CF processes by governing the outcome of chemical reactions

• cyclohexadiene. The stereochemistry (di-endo versus di-exo condensation) of the starting pyrimidinones 1, 2, 7 and 8 has no significant effect on the reaction yields. By using this safe, stable and scalable flow process, pyrimidinones 9–14 were afforded in high purity without the need for further purification

Volatiles from the tropical ascomycete Daldinia clavata (Hypoxylaceae, Xylariales)

• Tao Wang,
• Kathrin I. Mohr,
• Marc Stadler and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2018, 14, 135–147, doi:10.3762/bjoc.14.9

• biocontrol agents [6]. On the contrary, fungi can also produce mycotoxins, which must be excluded for their safe usage in agricultural biocontrol. Some volatiles, especially terpenes, point to the production of certain toxins in fungi, e.g., aristolochene (3) is the precursor of PR toxin in Penicillium

Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

• was shown to greatly enhance the adaptive immune responses [100]. Monophosphoryl lipid A (MPLA), an efficient and safe vaccine adjuvant registered for the use in Europe [59] is derived from the LPS of Salmonella minnesota R595 by following chemical modifications: elimination of the core

Nucleophilic dearomatization of 4-aza-6-nitrobenzofuroxan by CH acids in the synthesis of pharmacology-oriented compounds

• Alexey M. Starosotnikov,
• Dmitry V. Shkaev,
• Maxim A. Bastrakov,
• Ivan V. Fedyanin,
• Svyatoslav A. Shevelev and
• Igor L. Dalinger

Beilstein J. Org. Chem. 2017, 13, 2854–2861, doi:10.3762/bjoc.13.277

• Discussion The only method for the synthesis of 1 described so far deals with the reaction of commercially available 2-chloro-3,5-dinitropyridine (4) with NaN3 followed by thermolysis of the intermediate azide [25][26]. We developed an alternative safe and efficient method for the synthesis of 1 starting

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

• Hélène Guyon,
• Hélène Chachignon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

• scavenger TEMPO or with benzoquinone were performed and a radical process was proposed. This mild and safe transformation had a good tolerance for various functional groups. In 2013, Shibata and co-workers reported a transition-metal-free oxidative trifluoromethylation of arenes with CF3SO2Na and

A semisynthesis of 3'-O-ethyl-5,6-dihydrospinosyn J based on the spinosyn A aglycone

• Kai Zhang,
• Shenglan Liu,
• Anjun Liu,
• Hongxin Chai,
• Jiarong Li and
• Lamusi A

Beilstein J. Org. Chem. 2017, 13, 2603–2609, doi:10.3762/bjoc.13.257

• contrast with spinosad [14]. Spinetoram has been widely applied in insect control and sterilization. Similar to spinosad, spinetoram can be rapidly degraded into natural components by several ways, such as photodegradation and biodegradation [15], suggesting that spinetoram is safe for the environment. In

A concise flow synthesis of indole-3-carboxylic ester and its derivatisation to an auxin mimic

• Marcus Baumann,
• Ian R. Baxendale and
• Fabien Deplante

Beilstein J. Org. Chem. 2017, 13, 2549–2560, doi:10.3762/bjoc.13.251

• the optimum additive (Table 2, entries 11–14). Stronger acids or higher loading of acid often resulted in the generation of high internal pressures and in certain cases the formation of precipitates was noted requiring premature termination of the run and a safe shutdown. Using acetic acid and

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

• be studied for their potential medicinal applications. Here, the main focus was their use as drug-delivery systems [71][72][89], with particular attention to the toxicity of the metal centers [84]. Toxicity is a concern not only for the safe use of these compounds for humans but also for

• (encapsulated) as a guest within the pores of the MOF. In the second situation, the choice of the linker is crucial, as it needs to be an organic molecule listed of the generally regarded as safe (GRAS) compounds, an endogenous compound or a bioactive molecule. In both classes, the judicious choice of the

• liquid led to the formation of a 1D coordination polymer monohydrate, a tetrahydrate complex and an octahydrate, respectively (Figure 2) [7][29]. BioMOFs based on generally regarded as safe (GRAS), bioactive or endogenous linkers for the encapsulation of APIs Another approach to build a BioMOF consists