Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions

• Manuel Anselmo,
• Lisa Moni,
• Hossny Ismail,
• Davide Comoretto,
• Renata Riva and
• Andrea Basso

Beilstein J. Org. Chem. 2017, 13, 1456–1462, doi:10.3762/bjoc.13.143

• decomposed during 13C NMR analysis). The interest of both academia and industry in flow chemistry has recently increased. In particular, photochemical reactions performed under continuous flow have been proven particularly effective [6], as the reduced size of the reaction channels allows for a more

Mechanochemical synthesis of graphene oxide-supported transition metal catalysts for the oxidation of isoeugenol to vanillin

• Ana Franco,
• Sudipta De,
• Alina M. Balu,
• Araceli Garcia and
• Rafael Luque

Beilstein J. Org. Chem. 2017, 13, 1439–1445, doi:10.3762/bjoc.13.141

• [1][2][3][4]. Vanillin is one of the most important chemicals in the aroma industry, because it is abundantly used in food, pharmaceutical, cosmetic, and fine chemical industries. Therefore much attention has been paid to research on the improvement of its production [5]. At the present time only 1

Mechanochemistry-assisted synthesis of hierarchical porous carbons applied as supercapacitors

• Desirée Leistenschneider,
• Nicolas Jäckel,
• Felix Hippauf,
• Volker Presser and
• Lars Borchardt

Beilstein J. Org. Chem. 2017, 13, 1332–1341, doi:10.3762/bjoc.13.130

• latter is a common process used in industry [55]. However, by doing so, it is impossible to remove the porogenous TiO2 completely from the carbon matrix (sample CarbHF-SF-3). The resulting material still contained 11.1 wt % of Ti and did not show a high porosity (Figure 5B and Table 1) with a pore volume

Biomimetic molecular design tools that learn, evolve, and adapt

• David A Winkler

Beilstein J. Org. Chem. 2017, 13, 1288–1302, doi:10.3762/bjoc.13.125

• pharmaceutical industry developed high-throughput chemical synthesis and screening technologies in the late 20th century. Materials scientists have recently begun adapting these technologies to the synthesis and characterization of materials. Figure 7 shows a new high-throughput-materials synthesis and

Aqueous semisynthesis of C-glycoside glycamines from agarose

• Juliana C. Cunico Dallagnol,
• Alexandre Orsato,
• Diogo R. B. Ducatti,
• Miguel D. Noseda,
• Maria Eugênia R. Duarte and
• Alan G. Gonçalves

Beilstein J. Org. Chem. 2017, 13, 1222–1229, doi:10.3762/bjoc.13.121

• (1→3)-β-D-galactopyranose-(1→4)-3,6-anhydro-α-L-galactopyranose [1]. Both 1 and its less refined versions (agar or agar-agar) are well known due to their wide applications in food industry, microbiology and laboratorial sciences [2][3]. Even though agar and pure 1 are readily and commercially

Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols

• Chandra Kant Maurya,
• Avik Mazumder and
• Pradeep Kumar Gupta

Beilstein J. Org. Chem. 2017, 13, 1184–1188, doi:10.3762/bjoc.13.117

• compounds. They have a specific odour and often used as gas odorants in many industrial applications [1][2]. They occur as flavouring compounds in several fruits and spices and are found in a variety of enzymes at their active sites [3]. Thiols are produced by the wood-pulping industry, manure & sewer

A concise and practical stereoselective synthesis of ipragliflozin L-proline

• Shuai Ma,
• Zhenren Liu,
• Jing Pan,
• Shunli Zhang and
• Weicheng Zhou

Beilstein J. Org. Chem. 2017, 13, 1064–1070, doi:10.3762/bjoc.13.105

• Shuai Ma Zhenren Liu Jing Pan Shunli Zhang Weicheng Zhou State Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of China

Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic

• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2017, 13, 960–987, doi:10.3762/bjoc.13.97

• reduce the reaction time scales significantly, complex work-up and offline analysis are some of the bottlenecks of easy implementation of multistep flow synthesis. It also brings the need for automation. Automation in chemical synthesis is not new for the chemical industry. However, for the multistep

• of human being, improve process safety, efficiently utilize the plant resources and minimize the emissions [51]. Process automation is in great demand in various industrial sectors like chemical industry, power generation industry and petroleum industry. In the recent years, the pharmaceutical

• important feature of P&ID is that it provides a graphical representation of the control structure of the process [68][69][70]. In industry, P&ID is always made before actually implementing process automation and control for any process. More importantly, P&ID is also used for doing and evaluating HAZOP

Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block

• Yuta Isoda,
• Norihiko Sasaki,
• Kei Kitamura,
• Shuji Takahashi,
• Sujit Manmode,
• Naoko Takeda-Okuda,
• Jun-ichi Tamura,
• Toshiki Nokami and
• Toshiyuki Itoh

Beilstein J. Org. Chem. 2017, 13, 919–924, doi:10.3762/bjoc.13.93

• silica gel F254 plates (thickness 0.25 mm). Flash chromatography was carried out on a column of silica gel (Kanto Chem. Co., Silica Gel N, spherical, neutral). Gel permeation chromatography (GPC) was carried out on a Japan Analytical Industry LC-918 equipped with JAIGEL-2H using CHCl3 as eluent. All

Chemoselective synthesis of diaryl disulfides via a visible light-mediated coupling of arenediazonium tetrafluoroborates and CS₂

• Jing Leng,
• Shi-Meng Wang and
• Hua-Li Qin

Beilstein J. Org. Chem. 2017, 13, 903–909, doi:10.3762/bjoc.13.91

• transformations with applications in industry is considered of high practical value. In this context, carbon disulfide, a cheap and abundant chemical, has been widely used as reactant and solvent in both industry and materials science. For example, Batanero and co-workers reported an electrochemical

The effect of cyclodextrin complexation on the solubility and photostability of nerolidol as pure compound and as main constituent of cabreuva essential oil

• Joyce Azzi,
• Pierre-Edouard Danjou,
• David Landy,
• Steven Ruellan,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2017, 13, 835–844, doi:10.3762/bjoc.13.84

• concentration of CD increased. These findings suggested that CDs are promising encapsulating carriers for Ner by enhancing its solubility and stability and thereby its application in food industry. Keywords: cabreuva essential oil; cyclodextrins; nerolidol; photostability; solubility; Introduction Nerolidol

• to produce functional foods with enhanced functionality and stability [6]. Various encapsulation materials are used for food applications such as liposomes, phytosomes, cyclodextrins, dendrimers and many others [7][8][9]. The use of cyclodextrins (CDs) in food industry is currently flourishing due to

Continuous-flow processes for the catalytic partial hydrogenation reaction of alkynes

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

Beilstein J. Org. Chem. 2017, 13, 734–754, doi:10.3762/bjoc.13.73

• liquid phase is a reaction of high relevance to the manufacture of a multitude of fine chemicals [1] including pharmaceutical building blocks, agrochemicals, food additives, flavours and fragrances [2][3]. It is also crucial in the bulk polymer industry to achieve the complete elimination of alkynes and

• observed in the fine-chemicals sector [22][23], as a consequence of the additives and manipulations required to achieve satisfactory selectivity. Indeed, the implementation of continuous-flow practices in the pharmaceutical industry is considered one of the most strategic fields of innovation toward

• of utmost importance for the reduction of metal residues in the food and pharmaceuticals manufacture industry [96]. The choice of appropriate support materials is therefore critical to this purpose. Alternative strategies to reduce metal contamination include the use of metal scavengers, usually in

Conjecture and hypothesis: The importance of reality checks

• David Deamer

Beilstein J. Org. Chem. 2017, 13, 620–624, doi:10.3762/bjoc.13.60

• thousands of scientists investigating health related research or chemistry and physics having applications in industry. Another reason is that the origin of life is best understood in interdisciplinary terms involving knowledge of astronomy, planetary science, biophysics, chemistry and biochemistry

Transition-metal-catalyzed synthesis of phenols and aryl thiols

• Yajun Liu,
• Shasha Liu and
• Yan Xiao

Beilstein J. Org. Chem. 2017, 13, 589–611, doi:10.3762/bjoc.13.58

• synthesis and also final products, playing important roles in pharmaceutical molecules, pesticides and polymers in both academia and industry [1][2][3][4]. Some classic drugs which employ phenols or aryl thiols as central structural motifs are shown in Figure 1. In the past decade, the transition-metal

• mercaptolization of aryl halides Transition-metal-catalyzed methods provides various thiolation protocols, which allow an access to aryl thiols. However, all these methods described above require two steps, causing more labor both in the laboratory and industry. In this context, one step conversions were desirable

Studies directed toward the exploitation of vicinal diols in the synthesis of (+)-nebivolol intermediates

• Runjun Devi and
• Sajal Kumar Das

Beilstein J. Org. Chem. 2017, 13, 571–578, doi:10.3762/bjoc.13.56

• chromans have become attractive synthetic targets in academia and pharmaceutical industry [1]. Nebivolol (1, Figure 1) is a chroman-based antihypertensive drug that was first reported in the racemic form [2][3]. Chiral HPLC was subsequently employed to access various stereoisomers of 1 in enantiomerically

NMR reaction monitoring in flow synthesis

• M. Victoria Gomez and
• Antonio de la Hoz

Beilstein J. Org. Chem. 2017, 13, 285–300, doi:10.3762/bjoc.13.31

• encountering the optimum position of the sample in the coil. Solenoid coils are usually wound by hand, resulting in a low reproducible and very time-consuming process. Planar coils Spiral planar coils were introduced in NMR spectroscopy derived from the semi-conductor industry by means of microfabrication

Diels–Alder reactions of myrcene using intensified continuous-flow reactors

• Christian H. Hornung,
• Miguel Á. Álvarez-Diéguez,
• Thomas M. Kohl and
• John Tsanaktsidis

Beilstein J. Org. Chem. 2017, 13, 120–126, doi:10.3762/bjoc.13.15

• –Alder adduct of myrcene and acrylonitrile for the use as an odorant in the perfume industry [12]. A series of Diels–Alder reactions of myrcene (1) and another sesquiterpene, farnesene, with various dienophiles have been reported by Tabor et al. [13] for the use as solvents and surfactants. The emergence

Extrusion – back to the future: Using an established technique to reform automated chemical synthesis

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9

• compounds including metal-organic frameworks (MOFs). To date, a vast amount of research has already been conducted into reactive extrusion (REX), particularly in the polymer industry, which in many cases has involved organic transformations, however, it has not received significant recognition for this

• . This review highlights these transformations and discusses how this previous research can be applied to the future of organic compound manufacture. Keywords: continuous; extrusion; industry; organic; synthesis; Review Extrusion methodology Extrusion is an umbrella term covering a family of processes

• and the screw root (ca. 2–3 mm for smaller extruders, and several centimetres or inches for extruders employed in industry), but again as with SSE, this channel depth decreases along the screw length, resulting in an increase of the compressive forces and shear. The equivalent to channel depth within

Synthesis of multi-lactose-appended β-cyclodextrin and its cholesterol-lowering effects in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2017, 13, 10–18, doi:10.3762/bjoc.13.2

• children, results in severe hepatosplenomegaly and neurodegeneration [3][6]. Hence, the sequestration of cholesterol is an important factor in the development of the NPC disease. Cyclodextrins (CDs) are cyclic glucose oligosaccharides used by the pharmaceutical industry to enhance solubility, stability

Stabilization of nanosized titanium dioxide by cyclodextrin polymers and its photocatalytic effect on the degradation of wastewater pollutants

• Tamás Zoltán Agócs,
• István Puskás,
• Erzsébet Varga,
• Mónika Molnár and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2016, 12, 2873–2882, doi:10.3762/bjoc.12.286

• oligosaccharides consisting of 6–8 glucose units (α-, β- and γ-CD) primarily used in the pharmaceutical, cosmetic and household chemical industry [8]. They form non-covalent inclusion complexes with a great number of the organic contaminants in soil (petroleum hydrocarbons, polycyclic aromatic hydrocarbons, etc

Chromium(II)-catalyzed enantioselective arylation of ketones

• Gang Wang,
• Shutao Sun,
• Ying Mao,
• Zhiyu Xie and
• Lei Liu

Beilstein J. Org. Chem. 2016, 12, 2771–2775, doi:10.3762/bjoc.12.275

• ; asymmetric catalysis; chromium; ketone; tertiary alcohol; Introduction Catalytic enantioselective carbon–carbon bond formation reactions have achieved enormous development during the last few decades as a consequence of the growing demand for enantiopure compounds in modern industry, especially the

• pharmaceutical industry. The chromium (Cr)-catalyzed enantioselective addition of carbo halides to carbonyl compounds is one of the most reliable methods in organic chemistry for chemoselective and structurally diverse synthesis [1][2][3][4][5][6][7][8][9]. To date, the Cr-catalyzed enantioselective carbonyl

• the National Science Foundation of China (21472112), Fok Ying Tung Education Foundation (151035), the Program for New Century Excellent Talents in University (NCET-13-0346), Shenzhen Strategic Emerging Industry Development Special Funds (JCYJ20150430160921949), the Shandong Science Fund for

Green chemistry

• Luigi Vaccaro

Beilstein J. Org. Chem. 2016, 12, 2763–2765, doi:10.3762/bjoc.12.273

• , green chemistry may be considered as the scientific and economical context in which academia, industry and government are attempting to converge their efforts for the development of a sustainable civilization. The first goal of green chemistry is to provide a solid solution to the need for an ex novo

• led to a different and hopefully more effective paradigm in the collaboration between industry and academia. It is obvious that the chemical yield represents just one of the many features that a process must possess to be considered efficient. It is of extreme importance nowadays to consider not only

Computational methods in drug discovery

• Sumudu P. Leelananda and
• Steffen Lindert

Beilstein J. Org. Chem. 2016, 12, 2694–2718, doi:10.3762/bjoc.12.267

• possibility of showing success. Therefore, computer-aided drug discovery (CADD) tools are getting a lot of attention in the pharmaceutical industry and academia. CADD technologies are powerful tools that can reduce the number of ligands that need to be screened in experimental assays. The most popular

• methods and technologies are being developed frequently. It has immense potential and promise in the drug discovery workflow. In this review we give an overview of structure-based and ligand-based methods used in CADD, focusing on recent successes of CADD in the pharmaceutical industry. We outline

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• chemistry [21][22][31], agriculture [15], food technology [16], catalysis [23][24][25][32], cosmetics [26], textile processing [28][33], and environmental protection technologies [27][34]. Nevertheless, the first global consumer of CDs is clearly the pharmaceutical industry [35][36]. Indeed, CDs are very

Selective synthesis of thioethers in the presence of a transition-metal-free solid Lewis acid

• Federica Santoro,
• Matteo Mariani,
• Federica Zaccheria,
• Rinaldo Psaro and
• Nicoletta Ravasio

Beilstein J. Org. Chem. 2016, 12, 2627–2635, doi:10.3762/bjoc.12.259

• substrates under mild reaction conditions. Keywords: no solvent; S-alkylation; solid acids; thioethers; transition-metal-free; Introduction The need for more sustainable processes in the fine chemical industry is growing continuously. An optimal use of resources, both energy and starting materials, and a