Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles

• Ziyi Li,
• Li Wang,
• Yunqi Huang,
• Haibo Mei,
• Hiroyuki Konno,
• Hiroki Moriwaki,
• Vadim A. Soloshonok and
• Jianlin Han

Beilstein J. Org. Chem. 2020, 16, 2671–2678, doi:10.3762/bjoc.16.217

• pharmaceuticals [1][2][3][4][5][6][7][8][9], agrochemicals [10][11][12][13][14], and advanced materials [15][16][17][18][19]. On the other hand, chiral propargylamine represents a very important type of organic intermediates, which has been successfully used in the synthesis of natural products and biologically

Palladium nanoparticles supported on chitin-based nanomaterials as heterogeneous catalysts for the Heck coupling reaction

• Tony Jin,
• Malickah Hicks,
• Davis Kurdyla,
• Sabahudin Hrapovic,
• Edmond Lam and
• Audrey Moores

Beilstein J. Org. Chem. 2020, 16, 2477–2483, doi:10.3762/bjoc.16.201

• highly relevant in areas of research such as pharmaceuticals and materials technology [21]. Furthermore, works in heterogeneous catalysis have shown that the catalyst support plays a major role in the activity of transition-metal NPs such as Pd [7]. A model reaction was performed under the conditions

Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction

• Daniela Rodrigues Silva,
• Joyce K. Daré and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2020, 16, 2469–2476, doi:10.3762/bjoc.16.200

• helps in explaining the expressive amount of fluorine-containing agrochemical candidates (around 30%) as well as pharmaceuticals (around 20%) [5][6]. In this sense, the chemistry of fluorine-containing compounds has been extensively investigated in order to better understand the effects of fluorination

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

• Shahboz Yakubov and
• Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

• elsewhere, and the readers are referred to the relevant reviews [1][2][3][4][5]. Over the last two decades, introducing fluorine atoms into molecules has become a crucial aspect in contemporary synthesis of pharmaceuticals. Extraordinarily, about half of the so-called “blockbuster drugs” contain fluorine

Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate

• Mysore Bhyrappa Harisha,
• Pandi Dhanalakshmi,
• Rajendran Suresh,
• Raju Ranjith Kumar and
• Shanmugam Muthusubramanian

Beilstein J. Org. Chem. 2020, 16, 2108–2118, doi:10.3762/bjoc.16.178

• -azidochalcones as the precursor [9], we herein report the preparation of highly substituted oxazoles and thiazoles. Oxazoles are ubiquitously found in various natural products [10][11][12][13][14], pharmaceuticals [15][16][17][18], functional materials [19][20] as well as in several organic building blocks [21

• ][41][42]. 2,4,5-Trisubstituted oxazoles are embedded in some natural products and pharmaceuticals with a broad range of biological activities prompting the development of efficient synthetic strategies for this useful heterocycle [43][44] (Figure 1). In the recent past, the readily accessible 2H

Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K₂S₂O₈

• Qiang Liu,
• Weibang Lu,
• Guanqun Xie and
• Xiaoxia Wang

Beilstein J. Org. Chem. 2020, 16, 1974–1982, doi:10.3762/bjoc.16.164

• afforded the title compounds in moderate yields. Keywords: chroman-4-ones; diphenylphosphine oxide; metal-free; potassium persulfate; radical cyclization; Introduction The chroman-4-one framework is a privileged structural motif found in numerous natural products and pharmaceuticals with extraordinary

• structural motifs found in numerous natural products and pharmaceuticals with extraordinary biological and pharmaceutical activities [34][35]. However, no desired product (3ka) was obtained when there was a nitro group in the substrate (1k). Then, N-allyl-N-(2-formylphenyl)-4-methylbenzenesulfonamide (1l

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

• Paola Vitale,
• Luciana Cicco,
• Ilaria Cellamare,
• Filippo M. Perna,
• Antonio Salomone and
• Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

• is an ongoing synthetic endeavor as these scaffolds are ubiquitous motifs in many biologically active compounds and pharmaceuticals. In this context, in the last decades, the so-called deep eutectic solvents (DESs) have received an increasing attention due to their biodegradability, high thermal

Natural dolomitic limestone-catalyzed synthesis of benzimidazoles, dihydropyrimidinones, and highly substituted pyridines under ultrasound irradiation

• Kumar Godugu,
• Venkata Divya Sri Yadala,
• Mohammad Khaja Mohinuddin Pinjari,
• Trivikram Reddy Gundala,
• Lakshmi Reddy Sanapareddy and
• Chinna Gangi Reddy Nallagondu

Beilstein J. Org. Chem. 2020, 16, 1881–1900, doi:10.3762/bjoc.16.156

• : benzimidazoles; dihydropyrimidinones; highly substituted pyridines; natural dolomitic limestone; ultrasound irradiation; Introduction Nitrogen heterocycles are recognized as “privileged medicinal scaffolds” because these compounds are found in a wide variety of bioactive natural products and pharmaceuticals [1

One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

• Isaline Bonnin,
• Raphaël Mereau,
• Thierry Tassaing and
• Karine De Oliveira Vigier

Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143

• 10.3762/bjoc.16.143 Abstract The catalytic conversion of (ligno)cellulose is currently subject of intense research. Isosorbide is one of the interesting products that can be produced from (ligno)cellulose as it can be used for the synthesis of a wide range of pharmaceuticals, chemicals, and polymers

• to sorbitol and 3) dehydration of sorbitol to isosorbide (Scheme 1). Isosorbide, a molecule obtained from biomass can find many applications such as additives, pharmaceuticals [2][3] and monomers for polymer industries [4][5][6]. For instance, one polymer obtained from isosorbide, poly(ethylene-co

Pauson–Khand reaction of fluorinated compounds

• Jorge Escorihuela,
• Daniel M. Sedgwick,
• Alberto Llobat,
• Mercedes Medio-Simón,
• Pablo Barrio and
• Santos Fustero

Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138

• in natural products, pharmaceuticals and other added-value compounds accounts for the great applicability that this reaction has found [26][27][28][29][30][31][32]. Despite the increasing demand of fluorinated compounds and the impressive development of the PKR, the combination of these two fields

Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study

• Csilla Hargitai,
• Györgyi Koványi-Lax,
• Tamás Nagy,
• Péter Ábrányi-Balogh,
• András Dancsó,
• Gábor Tóth,
• Judit Halász,
• Angéla Pandur,
• Gyula Simig and
• Balázs Volk

Beilstein J. Org. Chem. 2020, 16, 1636–1648, doi:10.3762/bjoc.16.136

• Csilla Hargitai Gyorgyi Kovanyi-Lax Tamas Nagy Peter Abranyi-Balogh Andras Dancso Gabor Toth Judit Halasz Angela Pandur Gyula Simig Balazs Volk Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, Hungary Medicinal Chemistry Research Group, Research

Facile synthesis of 7-alkyl-1,2,3,4-tetrahydro-1,8-naphthyridines as arginine mimetics using a Horner–Wadsworth–Emmons-based approach

• Rhys A. Lippa,
• John A. Murphy and
• Tim N. Barrett

Beilstein J. Org. Chem. 2020, 16, 1617–1626, doi:10.3762/bjoc.16.134

• ; Introduction Tetrahydronaphthyridines are prominent in peptidomimetic pharmaceuticals as arginine mimetics and they are widely used in Arg–Gly–Asp (RGD) peptide mimetics such as αv integrin inhibitors [1]. Tetrahydronaphthyridines represent less basic but more permeable alternatives to arginine (pKa ≈ 7 versus

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

• Aleksandar Pashev,
• Nikola Burdzhiev and
• Elena Stanoeva

Beilstein J. Org. Chem. 2020, 16, 1456–1464, doi:10.3762/bjoc.16.121

• . Keywords: benzo[a]quinolizidinones; Castagnoli–Cushman reaction; 3,4-dihydroisoquinolines; monocyclic anhydrides; pyrrolo[2,1-a]isoquinolinones; Introduction The benzo[a]quinolizidine ring system is an important heterocyclic framework found in natural products and prospective pharmaceuticals [1]. This

An overview on disulfide-catalyzed and -cocatalyzed photoreactions

• Yeersen Patehebieke

Beilstein J. Org. Chem. 2020, 16, 1418–1435, doi:10.3762/bjoc.16.118

• . In 1996, Burton and co-workers reported the stereoselective synthesis of cis-1,2-difluorotriethylsilyethylene and its conversion to a variety of cis-1,2-difluoroethylene synthons, which are important building blocks in the preparation of fluorine-containing pharmaceuticals, polymers, and bioactive

Distinctive reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditions

• Shrikant D. Tambe,
• Kwan Hong Min,
• Naeem Iqbal and
• Eun Jin Cho

Beilstein J. Org. Chem. 2020, 16, 1335–1342, doi:10.3762/bjoc.16.114

• applications as core structures in a variety of natural products, pharmaceuticals, and agrochemicals [34][35][36][37][38] and are valuable ligands [39][40] in stereoselective organic synthesis. Despite the availability of a plethora of synthetic methods for 1,2-diamines [41][42][43][44][45], the reported

Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones

• Valeria Nori,
• Antonio Arcadi,
• Armando Carlone,
• Fabio Marinelli and
• Marco Chiarini

Beilstein J. Org. Chem. 2020, 16, 1084–1091, doi:10.3762/bjoc.16.95

• aminopalladation/reductive elimination. Keywords: alkynylanilines; arylboronic acids; indoles; isoquinolinones; palladium; Introduction The isoquinolinone nucleus is a key constituent of many natural products [1][2][3] and pharmaceuticals [4][5][6]. Substituted isoquinolinones have been found in biologically

Fluorinated phenylalanines: synthesis and pharmaceutical applications

• Laila F. Awad and
• Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

• pharmaceutical applications with a focus on published synthetic methods that introduce fluorine into the phenyl, the β-carbon or the α-carbon of ᴅ-or ʟ-phenylalanines. Keywords: α-fluorophenylalanine; β- and β,β-difluorophenylalanine; fluorinated phenylalanines; PET; pharmaceuticals application; Introduction

Copper-catalysed alkylation of heterocyclic acceptors with organometallic reagents

• Yafei Guo and
• Syuzanna R. Harutyunyan

Beilstein J. Org. Chem. 2020, 16, 1006–1021, doi:10.3762/bjoc.16.90

• azaenolate with reactive Michael acceptors in a follow-up study [45]. While pyridines are among the most important classes of heterocyclic moieties that occur in many bioactive molecules, such as natural products, pharmaceuticals, and agrochemicals, the initial report by the Harutyunyan group did not include

Suzuki–Miyaura cross coupling is not an informative reaction to demonstrate the performance of new solvents

• James Sherwood

Beilstein J. Org. Chem. 2020, 16, 1001–1005, doi:10.3762/bjoc.16.89

• substrates that correspond to commercially important products (e.g., enantiopure pharmaceuticals, polymeric materials) and if a substrate screening should follow, the protocol established by Collins and Glorius is effective [29]. For the development of new catalysts, it is preferable to work with a benign

Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts

• David Schönbauer,
• Carlo Sambiagio,
• Timothy Noël and
• Michael Schnürch

Beilstein J. Org. Chem. 2020, 16, 809–817, doi:10.3762/bjoc.16.74

• ] and pharmaceuticals [10][11]. Consequently, the direct functionalization of this scaffold has attracted significant interest in recent years. Even though many transformations have been realized via a cross-dehydrogenative coupling approach [12][13] (e.g., arylations [14][15], cyanomethylation [16

Reaction of indoles with aromatic fluoromethyl ketones: an efficient synthesis of trifluoromethyl(indolyl)phenylmethanols using K₂CO₃/n-Bu₄PBr in water

• Thanigaimalai Pillaiyar,
• Masoud Sedaghati and
• Gregor Schnakenburg

Beilstein J. Org. Chem. 2020, 16, 778–790, doi:10.3762/bjoc.16.71

• have been used as key precursors for the construction of complex indole derivatives that would be useful in pharmaceuticals as drugs and agrochemicals [2][3][4][5][6][7][8][9][10][11][12][13][14]. The simple (1H-indol-3-yl)methanol, a breakdown product of glucobrassicin, which can be found in

• into organic molecules can dramatically influence their physiochemical and biological properties in comparison with non-fluorinated analogs [18] (see compounds I and II in Figure 1). Many pharmaceuticals and agrochemicals developed in recent decades have either a fluorine atom or a trifluoromethyl

Recent advances in Cu-catalyzed C(sp³)–Si and C(sp³)–B bond formation

• Balaram S. Takale,
• Ruchita R. Thakore,
• Elham Etemadi-Davan and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction

• Yong Li,
• Zheng Huang,
• Jia Xu,
• Yong Ding,
• Dian-Yong Tang,
• Jie Lei,
• Hong-yu Li,
• Zhong-Zhu Chen and
• Zhi-Gang Xu

Beilstein J. Org. Chem. 2020, 16, 663–669, doi:10.3762/bjoc.16.63

• are privileged scaffolds that can be found in a wide variety of bioactive pharmaceuticals and natural products [1]. For this reason, research towards the development of novel and efficient strategies for the construction of these compounds represents one of the most active areas in synthetic organic

Asymmetric synthesis of CF₂-functionalized aziridines by combined strong Brønsted acid catalysis

• Xing-Fa Tan,
• Fa-Guang Zhang and
• Jun-An Ma

Beilstein J. Org. Chem. 2020, 16, 638–644, doi:10.3762/bjoc.16.60

• or fluoroalkyl groups into three-membered N-heterocycles has emerged as an attractive direction due to the unique fluorine effect in pharmaceuticals and biology [7][8][9][10][11]. In this context, it is not surprising that the syntheses of trifluoromethylaziridines have been pursued from versatile

Exploring the scope of DBU-promoted amidations of 7-methoxycarbonylpterin

• Anna R. Bockman and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2020, 16, 509–514, doi:10.3762/bjoc.16.46

• molybdopterin [1]. Owing to this biological relevance, pterins are an attractive building block in the development of various pharmaceuticals, with methotrexate being the most well-known [2]. In addition to pteridine derivatives being used as inhibitors of dihydrofolate reductase and dihydropteroate synthase