Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides

• Lingjun Xu,
• Shuwen Han,
• Linjie Yan,
• Haifeng Wang,
• Haihui Peng and
• Fener Chen

Beilstein J. Org. Chem. 2018, 14, 309–317, doi:10.3762/bjoc.14.19

• pharmaceuticals, such as γ-aminobutyric acid (GABA) and γ-amino-β-hydroxybutyric acid (GABOB) analogues (baclofen HCl and pregabalin) [51][52][53][54], HMG-CoA reductase inhibitors (“statins”) [55][56][57], etc. The generality and scope of this methodology was further demonstrated in the alcoholysis of 8a with

Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides

• Masanori Inaba,
• Tatsuya Sakai,
• Shun Shinada,
• Tsuyuka Sugiishi,
• Yuta Nishina,
• Norio Shibata and
• Hideki Amii

Beilstein J. Org. Chem. 2018, 14, 182–186, doi:10.3762/bjoc.14.12

• synthesis of useful bioactive compounds. There is a growing interest in the usefulness of phthalides and their derivatives. Organofluorine compounds often show attractive physical, chemical, and biological properties and are widely used in many fields, such as pharmaceuticals, agrochemicals, and materials

Progress in copper-catalyzed trifluoromethylation

• Guan-bao Li,
• Chao Zhang,
• Chun Song and
• Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

• such as metabolic stability, lipophilicity and permeability [1][2][3][4]. Therefore, organic molecules bearing trifluoromethyl groups are widely used in pharmaceuticals and agrochemicals, such as the antidepressant fluoxetine, the anti-ulcer drug lansoprazole and so on (Figure 1). The specific roles of

• -containing compounds at the allylic, propargylic, benzylic position, which were useful building blocks in pharmaceuticals. Building on a pioneering work, substantial progress has recently been made in the trifluoromethylation of aryl and alkyl halides, including the development of new trifluoromethylation

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

• Ananikov and co-workers (Scheme 9) [39]. Their aim was to develop a photocatalytic method that is applicable for the industrial synthesis of pharmaceuticals or bioactive compounds. Using metal-based photocatalysts may leave traces of metal impurities in the crude product causing elaborative purification

Position-dependent impact of hexafluoroleucine and trifluoroisoleucine on protease digestion

• Susanne Huhmann,
• Anne-Katrin Stegemann,
• Kristin Folmert,
• Damian Klemczak,
• Johann Moschner,
• Michelle Kube and
• Beate Koksch

Beilstein J. Org. Chem. 2017, 13, 2869–2882, doi:10.3762/bjoc.13.279

• this study when positioned N-terminal to the cleavage site. These results provide valuable information for the application of fluorinated amino acids in the design of proteolytically stable peptide-based pharmaceuticals. Keywords: fluorinated amino acids; hexafluoroleucine; peptide drugs; protease

• stability; trifluoroisoleucine; Introduction Peptide-based drugs are promising pharmaceuticals since they offer several advantages including high selectivity, specificity, and efficacy for recognizing and binding to their targets [1][2][3][4][5][6]. However, their application as drugs is often limited due

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

• heteroaromatics combining several pharmacophoric moieties in the same molecule, interesting from the standpoint of design of novel pharmaceuticals. The work continues our ongoing project on the synthesis of complex hybrid molecules – furoxan-containing potential NO donors [19][20][21][22][23][24]. Results and

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

• ; Introduction In organofluorine chemistry, the CF3 group occupies a place of choice as privileged structural motif in the development of multifaceted catalysts and ligands for organic synthesis as well as in the design of pharmaceuticals, agrochemicals and specialty materials [1][2][3][4]. The trifluoromethyl

Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes

• Takeshi Fujita,
• Ryo Kinoshita,
• Tsuyoshi Takanohashi,
• Naoto Suzuki and
• Junji Ichikawa

Beilstein J. Org. Chem. 2017, 13, 2682–2689, doi:10.3762/bjoc.13.266

• carbocycles that are promising candidates for pharmaceuticals, agrochemicals, and functional materials. In contrast, the cationic cyclization of 1,1-difluoro-1-alkenes using electrophilic reagents (under acidic conditions) has been quite limited because of their low electron densities caused by fluorine

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

• pharmaceuticals [1][2][3][4]. Indoles also play a significant role as phytohormones that promote and regulate the growth and development of plants. Indeed, four of the five endogenously synthesised auxins produced by plants contain the indole motif (Figure 1, structures 3–7). As a consequence of their regulatory

One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent

• Azim Ziyaei Halimehjani,
• Martin Dračínský and
• Petr Beier

Beilstein J. Org. Chem. 2017, 13, 2502–2508, doi:10.3762/bjoc.13.247

• fields of pharmaceuticals, agrochemicals, and materials sciences. The key properties such as metabolic and chemical stability, polarity, bioavailability, viscosity and lipophilicity can be altered in molecules containing the CF3 group in comparison with the nonfluorinated analogues. Numerous methods have

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

• coordination networks of pharmaceuticals involving lanthanides, showing different types of architectures based on mono-, di-, tri- and hexametallic centers and 1D polymeric chains. These new compounds proved to be unstable under shelf conditions. With regard to their thermal stability these compounds lose

• using environmentally more friendly solvents, such as methanol, ethanol or 2-propanol, making these BioMOFs acceptable for biological and pharmaceuticals applications (Figure 5) [136][138]. However, studies supporting this goal have not been reported so far. In 2015, Prochowicz et al. reported a new

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

• Joana M. Pais,
• Maria João Barroca,
• Maria Paula M. Marques,
• Filipe A. Almeida Paz and
• Susana S. Braga

Beilstein J. Org. Chem. 2017, 13, 2138–2145, doi:10.3762/bjoc.13.212

• , respectively [24], and are able to solubilize hydrophilic molecules such as nutraceuticals or pharmaceuticals, providing that these have the adequate size and geometry to fit into the CDs cavities [25][26][27][28]. Nowadays, native cyclodextrins are approved by the FDA and the WHO/FAO Joint Committee with the

New bio-nanocomposites based on iron oxides and polysaccharides applied to oxidation and alkylation reactions

• Daily Rodríguez-Padrón,
• Alina M. Balu,
• Antonio A. Romero and
• Rafael Luque

Beilstein J. Org. Chem. 2017, 13, 1982–1993, doi:10.3762/bjoc.13.194

• substituted benzyl alcohols. Although benzyl alcohol is industrially produced by reduction of benzaldehyde, this aldehyde is considered as the second most important flavoring molecule after vanillin, due to its variety of applications in cosmetics, perfumes, food, dyes, agrochemicals and pharmaceuticals [41

• ]. Regarding the acid-catalyzed processes, aromatic alkylation reactions are among the most versatile and widely investigated reactions which can grant access to a wide range of compounds as important intermediates, fragrances, agrochemicals and pharmaceuticals [47][48][49]. In this sense, the benzylation of

Synthesis of benzothiophene and indole derivatives through metal-free propargyl–allene rearrangement and allyl migration

• Jinzhong Yao,
• Yajie Xie,
• Lianpeng Zhang,
• Yujin Li and
• Hongwei Zhou

Beilstein J. Org. Chem. 2017, 13, 1866–1870, doi:10.3762/bjoc.13.181

• that are the key motif of many natural products and pharmaceuticals. Consequently, new and straightforward methods to access indoles are highly desirable [35][36]. We chose a propargyl phosphite rearrangement to achieve allenyl intermediates and aimed to synthetize indoles via allenyl phosphonates

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

• Jihen Ati,
• Pierre Lafite and
• Richard Daniellou

Beilstein J. Org. Chem. 2017, 13, 1857–1865, doi:10.3762/bjoc.13.180

• published roadmap for glycosciences in Europe, carbohydrates are expected, both by academics and industrials, to become key players in a near future in tremendous fields such as pharmaceuticals and personalized biomedicine, food, materials and renewable resources, and bioenergy for examples [2]. To achieve

Mechanochemical synthesis of thioureas, ureas and guanidines

• Vjekoslav Štrukil

Beilstein J. Org. Chem. 2017, 13, 1828–1849, doi:10.3762/bjoc.13.178

• application as organocatalysts and sensors. On the other hand, the specific and unique nature of each of these functionalities render (thio)ureas and guanidines as the key constituents of pharmaceuticals and other biologically active compounds. Keywords: guanidines; mechanochemistry; solid state synthesis

Iodoarene-catalyzed cyclizations of N-propargylamides and β-amidoketones: synthesis of 2-oxazolines

• Somaia Kamouka and
• Wesley J. Moran

Beilstein J. Org. Chem. 2017, 13, 1823–1827, doi:10.3762/bjoc.13.177

• -oxazolines, which are valuable heterocycles found in ligand scaffolds, natural products such as the leupyrrins [18][19], and potential pharmaceuticals (Figure 1) [20][21][22]. Traditional routes to this heterocycle include the dehydration of amino alcohols with carboxylic acids, however, this process

An efficient Pd–NHC catalyst system in situ generated from Na₂PdCl₄ and PEG-functionalized imidazolium salts for Mizoroki–Heck reactions in water

• Nan Sun,
• Meng Chen,
• Liqun Jin,
• Wei Zhao,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 1735–1744, doi:10.3762/bjoc.13.168

• -catalyzed cross-coupling reactions to form C–C bonds are very powerful synthetic tools in modern organic synthesis [7]. With their increasing applications in the synthesis of pharmaceuticals, natural products and functional materials [8][9][10], moving these useful transformations to occurring in aqueous

Encaging palladium(0) in layered double hydroxide: A sustainable catalyst for solvent-free and ligand-free Heck reaction in a ball mill

• Wei Shi,
• Jingbo Yu,
• Zhijiang Jiang,
• Qiaoling Shao and
• Weike Su

Beilstein J. Org. Chem. 2017, 13, 1661–1668, doi:10.3762/bjoc.13.160

• Wei Shi Jingbo Yu Zhijiang Jiang Qiaoling Shao Weike Su National Engineering Research Center for Process Development of Active Pharmaceutical Ingredients, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, 310014

Sustainable synthesis of 3-substituted phthalides via a catalytic one-pot cascade strategy from 2-formylbenzoic acid with β-keto acids in glycerol

• Lina Jia and
• Fuzhong Han

Beilstein J. Org. Chem. 2017, 13, 1425–1429, doi:10.3762/bjoc.13.139

• Lina Jia Fuzhong Han College of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, China 10.3762/bjoc.13.139 Abstract Background: Phthalides are privileged constituents of numerous pharmaceuticals, natural products and agrochemicals and exhibit several biological and

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

• purity of a chemical synthesis. Reprinted with permission from [36]; copyright 2016 Macmillan Publishers Ltd. (Top) Photograph of a small-molecule synthesizer comprised of three modules for deprotection, coupling, and purification steps. (Bottom) Natural products, materials, pharmaceuticals, and

Sugar-based micro/mesoporous hypercross-linked polymers with in situ embedded silver nanoparticles for catalytic reduction

• Qing Yin,
• Qi Chen,
• Li-Can Lu and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 1212–1221, doi:10.3762/bjoc.13.120

• good catalytic activity, which takes on important implications for the conversion of nitro compound precursors or intermediates to the corresponding amino or amine compounds in the preparation of pharmaceuticals and agrochemicals [42][43]. 4-Nitrophenol (4-NP) can cause water pollution, which has

• precursors for the preparation of pharmaceuticals and agrochemicals. Experimental Synthesis of perbenzyl phenyl β-D-glucopyranoside (Sug-2) Sodium hydride (60%, 0.43 g, 10.85 mmol) was added portionwise to a solution of phenyl β-D-glucopyranoside (93 mg, 0.36 mmol) in DMF (5.0 mL) over 40 min under nitrogen

Characterization of non-heme iron aliphatic halogenase WelO5* from Hapalosiphon welwitschii IC-52-3: Identification of a minimal protein sequence motif that confers enzymatic chlorination specificity in the biosynthesis of welwitindolelinones

• Qin Zhu and
• Xinyu Liu

Beilstein J. Org. Chem. 2017, 13, 1168–1173, doi:10.3762/bjoc.13.115

• engineering and evolution of these proteins for biocatalyst application. Keywords: alkaloid biogenesis; biosynthetic divergency; C–H activation; halogenase; non-heme iron enzyme; Introduction Carbon–halogen (C–X) bonds are prevalent structural motifs in modern agrochemicals, pharmaceuticals and bioactive

An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks

• Sushil K. Maurya and
• Rohit Rana

Beilstein J. Org. Chem. 2017, 13, 1106–1118, doi:10.3762/bjoc.13.110

• with many functional groups found application in pharmaceuticals, agrochemicals, cosmetics and materials science [1][2][3][4]. Carbohydrate-embedded macrocycles represent an important class of macrocyclic compounds in which at least two bonds from a monosaccharide residue form a part of the macrocyclic

α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones

• Liquan Tan,
• Cui Chen and
• Weibing Liu

Beilstein J. Org. Chem. 2017, 13, 1079–1084, doi:10.3762/bjoc.13.107

• products and pharmaceuticals, and α-acetoxyaryl ketones are widely used as synthetic intermediates [1][2][3][4][5]. Traditional methods for the preparation of α-acyloxy ketones focus on the substitution reactions of α-halo carbonyl compounds with alkaline carboxylates or carboxylic acids [6][7], and