Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

• Attila Palágyi,
• Jindřich Jindřich,
• Juraj Dian and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2022, 18, 1346–1354, doi:10.3762/bjoc.18.140

• ; imine; kinetics; pro-fragrance; Schiff base; Introduction The fragrance and flavor industry is one of the most intensively developing sectors of the chemical industry. Encapsulation techniques are widely used in both food and cosmetic industries to control the delivery of the encapsulated guest

• industry, the covalent bond that links the fragrance to its substrate must be cleaved under environmental conditions found in everyday life, and the substrate should be non-volatile and non-toxic [17]. Typical triggers that may be used for mild chemical reactions are temperature, enzymatic or pH-dependent

• …) to attach the fragrance covalently with various functional groups. Additionally, CDs already occur in many daily products [16] and fulfill the requirements of biocompatibility and cost for designing pro-fragrances that could find applications in the flavor and fragrance industry [18]. In this article

Enantioselective total synthesis of putative dihydrorosefuran, a monoterpene with an unique 2,5-dihydrofuran structure

• Irene Torres-García,
• Josefa L. López-Martínez,
• Rocío López-Domene,
• Manuel Muñoz-Dorado,
• Ignacio Rodríguez-García and
• Miriam Álvarez-Corral

Beilstein J. Org. Chem. 2022, 18, 1264–1269, doi:10.3762/bjoc.18.132

• the perfumery industry [1]. In addition, A. pallens has been used in Indian traditional medicine (Ayurveda) for the treatment of measles, cough, cold, depression, diabetes, and high blood pressure [2]. More recently other biological activities have been reported, such as the blood glucose lowering

Heterogeneous metallaphotoredox catalysis in a continuous-flow packed-bed reactor

• Wei-Hsin Hsu,
• Susanne Reischauer,
• Peter H. Seeberger,
• Bartholomäus Pieber and
• Dario Cambié

Beilstein J. Org. Chem. 2022, 18, 1123–1130, doi:10.3762/bjoc.18.115

• 2008 – 390540038 – UniSysCat. B.P. acknowledges financial support by a Liebig Fellowship of the German Chemical Industry Fund (Fonds der Chemischen Industrie, FCI). W.-H. H. thanks the Taiwanese ministry of education for a scholarship.

First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell

• Daniele Rocco,
• Ana A. Folgueiras-Amador,
• Richard C. D. Brown and
• Marta Feroci

Beilstein J. Org. Chem. 2022, 18, 979–990, doi:10.3762/bjoc.18.98

• 1,3-diketones [21], etc. Electrosynthesis is considered as a more sustainable approach to perform chemical reactions, and an interesting alternative to conventional synthetic methods both in laboratory and industry processes. In fact, the electron may be considered to be a clean reagent, which

Electroreductive coupling of 2-acylbenzoates with α,β-unsaturated carbonyl compounds: density functional theory study on product selectivity

• Naoki Kise and
• Toshihiko Sakurai

Beilstein J. Org. Chem. 2022, 18, 956–962, doi:10.3762/bjoc.18.95

• . Starting materials. Methyl 2-formylbenzoate (1a) and methyl 2-benzoylbenzoate (1h) were purchased from Tokyo Chemical Industry Corporation. Methyl 2-acetylbenzoate (1g) [17] was prepared from commercially available 2-acetylbenzoic acids (Tokyo Chemical Industry Corporation) by usual esterification using

Synthesis of α-(perfluoroalkylsulfonyl)propiophenones: a new set of reagents for the light-mediated perfluoroalkylation of aromatics

• Durbis J. Castillo-Pazos,
• Juan D. Lasso and
• Chao-Jun Li

Beilstein J. Org. Chem. 2022, 18, 788–795, doi:10.3762/bjoc.18.79

• perfluoroalkylating reagent that participated in such condensation (around 30%), giving us the final yields of perfluoroalkylating reagents 1a–c displayed in Scheme 3. Afterward, to show the practicality of application of these reagents in industry, we proceeded to scale up their synthesis in gram-scale

• interest in academia and industry, namely, for the synthesis of molecules with novel properties in the fields of material and bioorganic chemistry. Envisioned Minisci perfluoroalkylation facilitated by “dummy group” reagents 1a–c. Control experiments for the nucleophilic substitution of

A trustworthy mechanochemical route to isocyanides

• Francesco Basoccu,
• Federico Cuccu,
• Federico Casti,
• Rita Mocci,
• Claudia Fattuoni and
• Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 732–737, doi:10.3762/bjoc.18.73

• industry such as TsCl (mechanochemical approach: EcoScale → 81; E-Factor → 9.5; in-solution approach: EcoScale → 55; E-Factor → 131.1; see Supporting Information File 1 for more details) [47][48]. Not only did we plummet the reaction expenditures, but we also undoubtedly proved that our method could be

Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

• Conrad Kuhwald,
• Sibel Türkhan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70

• chemistry, but also in medicine. Traditionally, inductive heating is used in industry, e.g., for heating large metallic objects including bending, bonding, and welding pipes. In addition, inductive heating has emerged as a partner for flow chemistry, both of which are enabling technologies for organic

• % yields, respectively, in a fraction of the time required for the corresponding batch processes. In a simplified purification protocol, potential metal impurities were then removed using a magnet. This approach could facilitate the use of metal oxides in industry for a broader range of oxidative

• reaction. Reactions with soluble metal complexes or metal nanoparticles, utilized in transition-metal catalysis, are often avoided, especially if the metal contamination in the product exceeds certain limits. This is particularly true for the pharmaceutical industry. A continuous flow protocol for

Shift of the reaction equilibrium at high pressure in the continuous synthesis of neuraminic acid

• Jannis A. Reich,
• Miriam Aßmann,
• Kristin Hölting,
• Paul Bubenheim,
• Jürgen Kuballa and
• Andreas Liese

Beilstein J. Org. Chem. 2022, 18, 567–579, doi:10.3762/bjoc.18.59

• Abstract The importance of a compound that helps fight against influenza is, in times of a pandemic, self-evident. In order to produce these compounds in vast quantities, many researchers consider continuous flow reactors in chemical industry as next stepping stone for large scale production. For these

• believe that this will be the next stepping stone for industry [25][26], the aim of this research was to first establish a continuous reactor at high pressure, and then to investigate the influence of pressure on the reaction sequence to produce Neu5Ac. While high-pressure processes that operate semi

• -continuously already exist in the food industry, continuous reactors containing a high-performance liquid chromatography (HPLC) pump and a fixed-bed reactor at high pressure are still a relatively new concept. The use of a back pressure regulator up to 10 MPa (100 bar) was already demonstrated by Ötvös et al

The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban

• Martin Vrbický,
• Karel Macek,
• Jaroslav Pochobradský,
• Jan Svoboda,
• Miloš Sedlák and
• Pavel Drabina

Beilstein J. Org. Chem. 2022, 18, 438–445, doi:10.3762/bjoc.18.46

• catalysts based on copper(II) complexes with chiral nitrogen ligands were chosen. Generally, chiral copper complexes possess many advantages valuable for the pharmaceutical industry. They exhibit low toxicity (compared to other metal-based complexes) and many of them exist in forms suitable for recycling

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

• significant development in continuous flow platforms, particularly in industry [16][17][18][19][20]. 1,3,4-Oxadiazoles are biologically relevant 5-membered heterocyclic compounds with various favourable pharmacokinetic properties and have been investigated as potential candidates for antiviral, antifungal and

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• delivery [11], biomedical uses [12], removal of toxic metals from wastewater [13], in manufacturing processes [14], in the food industry [15], in agriculture [16], and as catalyst in transesterification reactions [17]. Chitosan is regarded as one of the most effective bio-based polymers to chelate

Chemoselective N-acylation of indoles using thioesters as acyl source

• Tianri Du,
• Xiangmu Wei,
• Honghong Xu,
• Xin Zhang,
• Ruiru Fang,
• Zheng Yuan,
• Zhi Liang and
• Yahui Li

Beilstein J. Org. Chem. 2022, 18, 89–94, doi:10.3762/bjoc.18.9

• , heterocycles, such as carbazole, can also be used as nucleophiles in this reaction. Keywords: indole; N-acylation; nucleophilic substitution; thioesters; Introduction Molecules containing N-acylindoles have attracted wide attention in the synthetic polymers and pharmaceutical industry because of their unique

Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines

• Yelong Lei and
• Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 70–76, doi:10.3762/bjoc.18.6

• ether (PE) used for column chromatography was the 60–90 °C fraction, and the removal of residual solvent was accomplished under rotovap. Reactions were monitored by thin-layer chromatography on silica gel GF254 coated 0.2 mm plates from Institute of Yantai Chemical Industry. Microwave-assisted reactions

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• with antibacterial, fungicidal, antimalarial, antiviral, trypanocidal, leishmanicidal, and antitumor activity serve as inspiration for the pharmaceutical industry [21][22][23][24]. However, they are considered as Pan Assay Interference compounds (PAINS) because they display biological activity in many

• , eNovation Chemicals, Tokyo Chemical Industry, Acros Organics, Abcr GmbH, Sigma-Aldrich, and others. Due to this wide commercial availability, these compounds have been widely used in several industrial applications as analytical reagents for the determination of amines and in the synthesis of other hybrid

Recent advances and perspectives in ruthenium-catalyzed cyanation reactions

• Thaipparambil Aneeja,
• Cheriya Mukkolakkal Abdulla Afsina,
• Padinjare Veetil Saranya and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 37–52, doi:10.3762/bjoc.18.4

• 2021. Keywords: cyanation; nitriles; photocatalyst; ruthenium; tertiary amines; Introduction Nitriles are a major class of organic compounds having wide significance in materials science, agrochemical and pharmaceutical industry [1]. They are the privileged compounds finding broad applications in

Stepwise PEG synthesis featuring deprotection and coupling in one pot

• Logan Mikesell,
• Dhananjani N. A. M. Eriyagama,
• Yipeng Yin,
• Bao-Yuan Lu and
• Shiyue Fang

Beilstein J. Org. Chem. 2021, 17, 2976–2982, doi:10.3762/bjoc.17.207

• ][26]. Perhaps, the most widely used methods in academia and in industry involve the use of monomers such as compound 1, which contain the acid-labile DMTr protecting group. PEG elongation is achieved by deprotection under acidic conditions, purifying the intermediate, and setting up a separate

• PEG synthesis approach. However, it is reminded that in an industry setting where the reaction is performed at multiple gram or kilogram scales and the relative molar quantities of KHMDS and PEG starting materials can be controlled with high accuracy, cooling to low temperature is not needed. The

A tribute to Carsten Schmuck

• Jochen Niemeyer,
• Ivo Piantanida and
• Thomas Schrader

Beilstein J. Org. Chem. 2021, 17, 2795–2798, doi:10.3762/bjoc.17.190

• “Beyer/Walter”, together with his long-time colleagues Tanja Schirmeister and Peter Wich. This outstanding piece of work was rightfully honored with the Literature Prize of the Chemical Industry Fund in 2017. Carsten’s enthusiasm for science also spread to his team. Over his career, he mentored more than

• have successfully transitioned to fulfilling jobs in academia, industry or other fields was very important to Carsten, and he made it a tradition to invite all former and current groups members to a summer barbecue at his home every year. Last but not least, Carsten hosted a number of assistant

Me₃Al-mediated domino nucleophilic addition/intramolecular cyclisation of 2-(2-oxo-2-phenylethyl)benzonitriles with amines; a convenient approach for the synthesis of substituted 1-aminoisoquinolines

• Krishna M. S. Adusumalli,
• Lakshmi N. S. Konidena,
• Hima B. Gandham,
• Krishnaiah Kumari,
• Krishna R. Valluru,
• Satya K. R. Nidasanametla,
• Venkateswara R. Battula and
• Hari K. Namballa

Beilstein J. Org. Chem. 2021, 17, 2765–2772, doi:10.3762/bjoc.17.186

• heterocyclic frameworks. On the other hand, organonitrile, the polar unsaturated carbon−nitrogen multiple bond, recognized as one of the most versatile chemotypes in both the laboratory and industry because of their vital role displayed in various transformations [1][2][3][4]. They capture a major area in the

Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds

• Alemayehu Gashaw Woldegiorgis and
• Xufeng Lin

Beilstein J. Org. Chem. 2021, 17, 2729–2764, doi:10.3762/bjoc.17.185

• molecules with axial chirality, which will be widely used in science and industry in the near future. Representative examples of axially chiral biaryls, heterobiaryls, spiranes and allenes as ligands and catalysts. Selected examples of axially chiral drugs and bioactive molecules. Axially chiral functional

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

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

• ][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

Transition-metal-free intramolecular Friedel–Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives

• Tülay Yıldız,
• İrem Baştaş and
• Hatice Başpınar Küçük

Beilstein J. Org. Chem. 2021, 17, 2203–2208, doi:10.3762/bjoc.17.142

• anticarcinogenic [1][2], antiviral [3], antibacterial [4][5], and anti-inflammatory [6]. Because of their pharmaceutical activity, they are used in photodynamic therapy [7][8][9]. In addition, they have an important place in the dye industry due to their photochemical and photophysical properties. They are also

Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution

• Ryan M. Alam and
• John J. Keating

Beilstein J. Org. Chem. 2021, 17, 1939–1951, doi:10.3762/bjoc.17.127

• regioselective N-alkylation of the indazole scaffold would be of great value to the pharmaceutical industry. Focusing on 3-substituted indazoles, highly selective N-1 alkylations can be achieved using NaH in THF (conditions A) and Cs2CO3 in DMF (conditions B) as applied to primary and secondary alkyl

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

• Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

• transformation, has been widely investigated in medicinal chemistry and in the pharmaceutical industry as it generally imparts the targeted fluorinated molecules with dramatically improved physical, biological, and/or chemical properties [17][18][19][20][21]. Among the catalytic C–F forming processes, aliphatic