Complementarity of solution and solid state mechanochemical reaction conditions demonstrated by 1,2-debromination of tricyclic imides

• Petar Štrbac and
• Davor Margetić

Beilstein J. Org. Chem. 2022, 18, 746–753, doi:10.3762/bjoc.18.75

• synthetic organic chemistry. Advantageously, more difficult substrates or limitations of the conditions can be overcome by the change of the reaction methods. One of the emerging synthetic methods is mechanochemistry [4][5][6][7], a greener alternative to carry out synthesis which complements heating

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

• Conrad Kuhwald Sibel Turkhan Andreas Kirschning Institute of Organic Chemistry, Leibniz University Hannover, Schneiderberg 1b, 30167 Hannover, Germany 10.3762/bjoc.18.70 Abstract Inductive heating has developed into a powerful and rapid indirect heating technique used in various fields of

Mechanochemical halogenation of unsymmetrically substituted azobenzenes

• Dajana Barišić,
• Mario Pajić,
• Ivan Halasz,
• Darko Babić and
• Manda Ćurić

Beilstein J. Org. Chem. 2022, 18, 680–687, doi:10.3762/bjoc.18.69

• studied functional groups, and new methods for their preparation, especially by environmentally friendly protocols, are of great synthetic importance in organic chemistry [54]. The succinimide products L4-III and L5-III (Table 1, entries 11 and 12) were obtained within one and five hours in 39 and 38

A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments

• Constantine V. Milyutin,
• Andrey N. Komogortsev,
• Boris V. Lichitsky and
• Valeriya G. Melekhina

Beilstein J. Org. Chem. 2022, 18, 588–596, doi:10.3762/bjoc.18.61

• Constantine V. Milyutin Andrey N. Komogortsev Boris V. Lichitsky Valeriya G. Melekhina N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow 119991, Russian Federation 10.3762/bjoc.18.61 Abstract The photochemical properties behavior of 3-hydroxy-4

• in synthetic organic chemistry [1][2][3][4][5][6][7]. The advantage of photochemical methods is the possibility of the preparation of diverse products that are problematic to obtain using other chemical approaches. It should be noted that light can be considered as a traceless agent, therefore, UV

Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives

• Martin Pošta,
• Václav Zima,
• Lenka Poštová Slavětínská,
• Marika Matoušová and
• Petr Beier

Beilstein J. Org. Chem. 2022, 18, 549–554, doi:10.3762/bjoc.18.57

• Martin Posta Vaclav Zima Lenka Postova Slavetinska Marika Matousova Petr Beier Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Flemingovo nám. 2, 16610 Prague 6, Czech Republic 10.3762/bjoc.18.57 Abstract The only known sulfur-containing karrikin, 3-methyl-2H-thiopyrano[3,4

Chemistry of polyhalogenated nitrobutadienes, 17: Efficient synthesis of persubstituted chloroquinolinyl-1H-pyrazoles and evaluation of their antimalarial, anti-SARS-CoV-2, antibacterial, and cytotoxic activities

• Viktor A. Zapol’skii,
• Isabell Berneburg,
• Ursula Bilitewski,
• Melissa Dillenberger,
• Katja Becker,
• Stefan Jungwirth,
• Aditya Shekhar,
• Bastian Krueger and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2022, 18, 524–532, doi:10.3762/bjoc.18.54

• Viktor A. Zapol'skii Isabell Berneburg Ursula Bilitewski Melissa Dillenberger Katja Becker Stefan Jungwirth Aditya Shekhar Bastian Krueger Dieter E. Kaufmann Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstr. 6, 38678 Clausthal-Zellerfeld, Germany Biochemistry and

BINOL as a chiral element in mechanically interlocked molecules

• Matthias Krajnc and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2022, 18, 508–523, doi:10.3762/bjoc.18.53

• Matthias Krajnc Jochen Niemeyer Faculty of Chemistry (Organic Chemistry) and Centre of Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstr. 7, 45141 Essen, Germany 10.3762/bjoc.18.53 Abstract In this minireview we present the use of the axially chiral 1,1

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

• Martin Vrbicky Karel Macek Jaroslav Pochobradsky Jan Svoboda Milos Sedlak Pavel Drabina Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic 10.3762/bjoc.18.46 Abstract The human drugs – the

Cs₂CO₃-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones

• Ol'ga G. Volostnykh,
• Olesya A. Shemyakina,
• Anton V. Stepanov and
• Igor' A. Ushakov

Beilstein J. Org. Chem. 2022, 18, 420–428, doi:10.3762/bjoc.18.44

• bromopropargylic alcohols and Cs2CO3. Keywords: acetylenic alcohol; bromoacetylene; 1,3-dioxolan-2-one; phenols; phenoxyketone; Introduction Due to the relative stability, ease of handling and the presence of reactive sites, bromoacetylenes are widely applied in synthetic organic chemistry. They are known to be

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• , Chinchilla et al. reviewed the Sonogashira reaction demonstrating its wide generality and applicability, and the protocol has become a booming methodology in synthetic organic chemistry [6]. Thereafter, the same authors again compiled the Sonogashira reaction covering literature up to 2011 attesting the

• Sonogashira coupling reaction and the catalyst. A mechanism was also suggested where this in situ formed colloidal layer acts as the anchoring agent (Scheme 37). Conclusion The Sonogashira reaction is an important coupling reaction in organic chemistry. Even though most of the reactions are well explored by

New advances in asymmetric organocatalysis

• Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 240–242, doi:10.3762/bjoc.18.28

• Radovan Sebesta Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia 10.3762/bjoc.18.28 Keywords: asymmetric organocatalysis; covalent activation; noncovalent activation; Asymmetric catalysis is

• disclosed important discoveries with proline and imidazolidinones as ample chiral catalysts for aldol [7][8], Diels–Alder [9], dipolar cycloaddition [10], and Mannich reactions [11]. The organic chemistry community this time took a tremendous interest in this concept, which led to many valuable developments

• combination of activation modes in bifunctional or multifunctional catalysis. Important is also a “green” aspect of organocatalysis as well as its fruitful overlap with many sustainability ideas [15]. In 2012, there has been a thematic issue of the Beilstein Journal of Organic Chemistry devoted to asymmetric

Trichloroacetic acid fueled practical amine purifications

• Aleena Thomas,
• Baptiste Gasch,
• Enzo Olivieri and
• Adrien Quintard

Beilstein J. Org. Chem. 2022, 18, 225–231, doi:10.3762/bjoc.18.26

• success. Keywords: amines; decarboxylation; eco-compatible; out of equilibrium; purification; Introduction Isolation of pure amines from reaction mixtures or natural extracts is crucial in modern organic chemistry. However, the most widely applied methods for these purifications have remained unchanged

• operations and waste generation, this methodology should rapidly find applications in organic chemistry laboratories but also possibly on industrial scale. Experimental Typical experimental procedure with dicyclohexylamine 1: Dicyclohexylamine (37 mg, 0.21 mmol, 1 equiv) and 2-methoxynaphthalene (33 mg, 0.21

The role of chemistry in the success of oligonucleotides as therapeutics

• Pawan Kumar and
• Tom Brown

Beilstein J. Org. Chem. 2022, 18, 197–199, doi:10.3762/bjoc.18.22

• sincere thanks to the authors and reviewers who have contributed despite the challenges posed by the COVID pandemic. Support from the editorial team of the Beilstein Journal of Organic Chemistry is also greatly appreciated. The issue comprises many excellent contributions in the form of original research

Synthesis and late stage modifications of Cyl derivatives

• Phil Servatius and
• Uli Kazmaier

Beilstein J. Org. Chem. 2022, 18, 174–181, doi:10.3762/bjoc.18.19

• Phil Servatius Uli Kazmaier Organic Chemistry, Saarland University, Campus C4.2, 66123 Saarbrücken, Germany 10.3762/bjoc.18.19 Abstract A peptide Claisen rearrangement is used as key step to generate a tetrapeptide with a C-terminal double unsaturated side chain. Activation and cyclization give

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

• Irina Kuznetcova,
• Felix Bacher,
• Daniel Vegh,
• Hsiang-Yu Chuang and
• Vladimir B. Arion

Beilstein J. Org. Chem. 2022, 18, 143–151, doi:10.3762/bjoc.18.15

• Irina Kuznetcova Felix Bacher Daniel Vegh Hsiang-Yu Chuang Vladimir B. Arion Institute of Inorganic Chemistry of the University of Vienna, Währinger Strasse 42, 1090 Vienna, Austria Institute of Organic Chemistry, Catalysis and Petrochemistry, Department of Organic Chemistry, Slovak Techmical

• University of Technology in Bratislava, Radlinského 9, SK-81237 Bratislava, Slovak Republic Institute of Organic Chemistry of the University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria 10.3762/bjoc.18.15 Abstract Paullone isomers are known as inhibitors of tubulin polymerase and cyclin dependent

Mechanistic studies of the solvolysis of alkanesulfonyl and arenesulfonyl halides

• Malcolm J. D’Souza and
• Dennis N. Kevill

Beilstein J. Org. Chem. 2022, 18, 120–132, doi:10.3762/bjoc.18.13

• acknowledged, in his participation as a co-author of a chapter in “Progress in Physical Organic Chemistry” [31], that this equilibrium needs to be incorporated into treatments based on the magnitudes of the heat capacities of activation (∆Cp#). The need to incorporate the return from an ion pair to a covalent

• temperature variation to investigate this aspect were not reported. In reading the section “Substitutions at Sulphur” in the second edition of Ingold’s classical “Structure and Mechanism in Organic Chemistry” text [53], it is surprising to see that the section starts with the statement “No kinetic studies

• structure to the transition state. One can in this regard quote Hammett from the second edition of his classical “Physical Organic Chemistry” text [79] “The hope, which at one time seemed bright, for a simple correlation of the solvent isotope effect with the mechanism of a reaction involving proton

Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks

• Jolita Bruzgulienė,
• Greta Račkauskienė,
• Aurimas Bieliauskas,
• Vaida Milišiūnaitė,
• Miglė Dagilienė,
• Gita Matulevičiūtė,
• Vytas Martynaitis,
• Sonata Krikštolaitytė,
• Frank A. Sløk and
• Algirdas Šačkus

Beilstein J. Org. Chem. 2022, 18, 102–109, doi:10.3762/bjoc.18.11

• Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, Kaunas LT-50254, Lithuania Vipergen ApS, Gammel Kongevej 23A, DK-1610 Copenhagen V, Denmark 10.3762/bjoc.18.11 Abstract A convenient and efficient synthesis of novel achiral and chiral heterocyclic amino acid-like building

Earth-abundant 3d transition metals on the rise in catalysis

• Nikolaos Kaplaneris and
• Lutz Ackermann

Beilstein J. Org. Chem. 2022, 18, 86–88, doi:10.3762/bjoc.18.8

• authors for their dedication and time in contributing to this effort. Finally, the senior author thank the staff at the Beilstein Journal of Organic Chemistry for their assistance. Nikolaos Kaplaneris and Lutz Ackermann Göttingen, December 2021 Funding Generous support from the ERC Advanced Grant no

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

• Yelong Lei Jiaxi Xu State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People’s Republic of China 10.3762/bjoc.18.6 Abstract Alkyl 2-diazo-3-oxoalkanoates generate

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

• employing two equivalents of isoxazolylamines in aqueous solution under reflux with HCl catalysis, resulting in bis(isoxazolyl)naphthoquinones 29 (Scheme 6). The development of synthetic methodologies for the preparation of many bioactive substances is still a challenge. The main issues in synthetic organic

• chemistry and medicinal chemistry of naphthoquinones are the diversification of the strategies to obtain derivatives [8][80]. β-NQS are excellent electrophiles and have been used for obtaining naphthoquinones substituted by alkyl- or arylamines. The reactivity of aminopyrazolopyridine 30 with β-NQSNa (18

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

• ruthenium complexes which are efficient as catalysts elevated the scope of this metal in synthetic organic chemistry. For clarity and ease of understanding of the topic, this review is categorized into four sections: cyanation of amines, cyanation of arenes and heteroarenes, photocatalyzed cyanation, and

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

• Jiang-Song Zhai and
• Da-Ming Du

Beilstein J. Org. Chem. 2022, 18, 25–36, doi:10.3762/bjoc.18.3

• field of synthetic organic chemistry and pharmaceutical chemistry all over the world. In the previous few decades, a large number of strategies emerged to construct heterocyclic compounds with this skeleton or similar ones [6][7][8][9][10], aiming to explore biological activity and medicinal value

The enzyme mechanism of patchoulol synthase

• Houchao Xu,
• Bernd Goldfuss,
• Gregor Schnakenburg and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 13–24, doi:10.3762/bjoc.18.2

• Houchao Xu Bernd Goldfuss Gregor Schnakenburg Jeroen S. Dickschat Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany Department of Chemistry, University of Cologne, Greinstraße 4, 50939 Cologne, Germany Institute of Inorganic

Polymer chemistry: fundamentals and applications

• Bernhard V. K. J. Schmidt

Beilstein J. Org. Chem. 2021, 17, 2922–2923, doi:10.3762/bjoc.17.200

• Bernhard V. K. J. Schmidt School of Chemistry, University of Glasgow, G12 8QQ Glasgow, UK 10.3762/bjoc.17.200 Keywords: polymer chemistry; Ever since the introduction of the term macromolecule and the early days of polymer science [1], organic chemistry and polymer chemistry have been closely

• related [2]. It only seems to be a logical step to give room for a thematic issue on polymer chemistry in the Beilstein Journal of Organic Chemistry. The connection between organic and polymer chemistry has been highlighted frequently [3][4], up to the point where one can talk about macroorganic chemistry

• , where oligomers bring molecular precision from organic chemistry together with materials properties from polymer chemistry [5]. Especially in the challenge of transformation to a more sustainable polymer science, organic chemistry can give significant support in the development of greener polymer

A two-phase bromination process using tetraalkylammonium hydroxide for the practical synthesis of α-bromolactones from lactones

• Yuki Yamamoto,
• Akihiro Tabuchi,
• Kazumi Hosono,
• Takanori Ochi,
• Kento Yamazaki,
• Shintaro Kodama,
• Akihiro Nomoto and
• Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 2906–2914, doi:10.3762/bjoc.17.198

• facilitate the industrial use of α-bromolactones as important intermediates. Keywords: α-bromolactone; metal-free; one-pot operation; tetraalkylammonium hydroxide; two-phase system; Introduction Lactones are important heterocycles in the organic chemistry, materials science, and medicinal chemistry fields

• yields without any handling difficulties. We expect that this new bromination system will lead to the use of various α-bromolactones as synthetic intermediates in organic chemistry. Experimental General comments. Unless otherwise stated, all starting materials and catalysts were purchased from commercial