Copper-catalyzed N-arylation of amines with aryliodonium ylides in water

• Kasturi U. Nabar,
• Bhalchandra M. Bhanage and
• Sudam G. Dawande

Beilstein J. Org. Chem. 2023, 19, 1008–1014, doi:10.3762/bjoc.19.76

• ylide; sustainable; Introduction Arylamines are among the most privileged structural motifs appearing in various natural products, and bioactive molecules [1][2] as well as offer widespread applications in pharmaceuticals, agrochemicals, dyes, and materials science [3][4]. Particularly the

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

• Haritha Sindhe,
• Malladi Mounika Reddy,
• Karthikeyan Rajkumar,
• Akshay Kamble,
• Amardeep Singh,
• Anand Kumar and
• Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

• containing bioactive molecules (Scheme 10). To attain enantioselectivity a chiral phosphine oxide (43)-ligated Ni–Al bimetallic catalyst was used that was critical in improving the reactivity and controlling the selectivity of the reaction. Further, based on deuterium labelling experiments, KIE studies, and

NaI/PPh₃-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles

• Dan Liu,
• Yue Zhao and
• Frederic W. Patureau

Beilstein J. Org. Chem. 2023, 19, 57–65, doi:10.3762/bjoc.19.5

• attention due to their propensity to build important oxindole scaffolds. These are broadly found in natural products, pharmaceuticals, and bioactive molecules (Figure 1) [7][8][9][10][11][12][13]. Although a number of synthetic approaches have already been explored [14][15][16][17][18][19][20], these

Synthetic study toward tridachiapyrone B

• Morgan Cormier,
• Florian Hernvann and
• Michaël De Paolis

Beilstein J. Org. Chem. 2022, 18, 1741–1748, doi:10.3762/bjoc.18.183

• ; Introduction The α’-methoxy-γ-pyrone motif is present in natural products and bioactive molecules [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Amidst these targets, a number contains a quaternary carbon vicinal to the scaffold, such as crispatene and photodeoxytridachione (Scheme 1a) [15]. These molecules

Functionalization of imidazole N-oxide: a recent discovery in organic transformations

• Koustav Singha,
• Imran Habib and
• Mossaraf Hossain

Beilstein J. Org. Chem. 2022, 18, 1575–1588, doi:10.3762/bjoc.18.168

• -saving drugs and medicines. Imidazole is one of the pharmacologically important heterocyclic motifs found in widely used and well-known medicines and bioactive molecules. The applications of imidazole derivatives displaying various biological activities, motivated researchers for the development of more

• improvements in this research area and that there will be growing interest to work in this domain of research. This would provide more exceptional and versatile literature reports with innovative research procedures to make this research field prosperous. Selected imidazole-based bioactive molecules. Formation

Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry

• Koji Kubota,
• Emiru Baba,
• Tamae Seo,
• Tatsuo Ishiyama and
• Hajime Ito

Beilstein J. Org. Chem. 2022, 18, 855–862, doi:10.3762/bjoc.18.86

• mill; borylation; cross-coupling; mechanochemistry; solid-state reaction; Introduction Arylboronic acid and its derivatives are indispensable reagents in modern synthetic chemistry because they have been frequently used for the preparation of many bioactive molecules, natural products, and functional

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

• functionalization enabled the de novo assembly of bioactive molecules [9]. The full potential of the mild nature of C–H functionalization is unlocked by the merger with modern photochemistry and electrocatalysis manifolds. In this context, recent advances were realized by the combination of photoredox catalysis and

Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

• Shun Saito,
• Kanji Indo,
• Naoya Oku,
• Hisayuki Komaki,
• Masashi Kawasaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203

• within the class Actinomycetales, have provided many important clinical drugs [1][2], agrochemicals [3], food additives [4][5], and biochemical reagents [6][7][8][9], and continue to be a core source of bioactive molecules [10]. While most of the actinomycetes-derived compounds have been reported from

Photophysical, photostability, and ROS generation properties of new trifluoromethylated quinoline-phenol Schiff bases

• Inaiá O. Rocha,
• Yuri G. Kappenberg,
• Wilian C. Rosa,
• Clarissa P. Frizzo,
• Nilo Zanatta,
• Marcos A. P. Martins,
• Isadora Tisoco,
• Bernardo A. Iglesias and
• Helio G. Bonacorso

Beilstein J. Org. Chem. 2021, 17, 2799–2811, doi:10.3762/bjoc.17.191

• electron-withdrawing group that enhances the effects of many bioactive molecules due to a significant improvement in stability, lipophilicity, and resistance to enzymatic degradation [17][18]. Also, it has been widely applied as a special alkyl substituent for ligands of phosphorescent heavy metal

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

• construction of axial chirality [7][8][9][10][11][12][13][14]. Axially chiral biaryl and heterobiaryl units are widely used as basic building blocks for chiral ligands [14], chiral catalysts [14][15][16][17] (Figure 1), various natural products, drugs and bioactive molecules [18][19], pharmaceutical agents [20

• synthesis of atropisomeric heterobiaryls 2.1. Synthesis of atropisomeric arylindoles The indole scaffold is found in many natural products, drugs, and bioactive molecules. Moreover, the introduction of axial chirality into the indole scaffold is receiving attention due to its widespread use [45][52]. In

• bioactive molecules and chiral catalysts [62][63][64], the construction of this scaffold has recently become valuable and attracted the attention of chemists [2][64]. In this context, Shi and co-workers reported a new strategy for the enantioselective synthesis of axially chiral naphthylindoles via the

Electrocatalytic C(sp³)–H/C(sp)–H cross-coupling in continuous flow through TEMPO/copper relay catalysis

• Bin Guo and
• Hai-Chao Xu

Beilstein J. Org. Chem. 2021, 17, 2650–2656, doi:10.3762/bjoc.17.178

• ]. In this context, few methods have been developed for the dehydrogenative cross-coupling of tetrahydroisoquinolines with terminal alkynes because of the prevalence of the tetrahydroisoquinoline moiety in natural products and bioactive molecules [3][4][5][6][7][8][9][10]. These methods proceed through

Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions

• Akhil K. Dubey and
• Raghunath Chowdhury

Beilstein J. Org. Chem. 2021, 17, 2642–2649, doi:10.3762/bjoc.17.177

• ]. In addition, the C–Si bond can be oxidized to a hydroxy group by Tamao–Fleming oxidation [3][4] or to an alkene unit via protodesilylation [5][6]. Many complex natural products, bioactive molecules, and drug molecules have been synthesized on exploitation of the above-mentioned properties of

Copper-catalyzed monoselective C–H amination of ferrocenes with alkylamines

• Zhen-Sheng Jia,
• Qiang Yue,
• Ya Li,
• Xue-Tao Xu,
• Kun Zhang and
• Bing-Feng Shi

Beilstein J. Org. Chem. 2021, 17, 2488–2495, doi:10.3762/bjoc.17.165

• , including bioactive molecules, were successfully installed to the ortho-position of ferrocene amides with high efficiency under mild conditions. A range of functionalized ferrocenes were compatible to give the aminated products in moderate to good yields. The gram-scale reaction was smoothly conducted and

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

• in many natural products, pharmaceuticals, and bioactive molecules. For instance, some pyridine derivatives have been used for therapy of HIV, cancer, inflammation, microbial infection and so on [1][2][3][4][5]. In addition, it is also an important synthetic unit, which is frequently used as catalyst

• the synthesis of five- or six-membered cyclic compounds [54]. Various efficient synthetic methods have been developed for the synthesis of halogenated pyrroles, which are widely presented in many pharmacologically active natural products, bioactive molecules, and organic building blocks. Based on the

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

• Li Liu,
• Yue Li,
• Tiao Huang,
• Dulin Kong and
• Mingshu Wu

Beilstein J. Org. Chem. 2021, 17, 2321–2328, doi:10.3762/bjoc.17.150

• industrial application. Representation of bioactive molecules and applications. Synthetic methodologies for 3-monohalooxindoles. Substrate scope of the acidolysis of isatin-derived phosphates 2 with hydrochloric acid. Standard reaction conditions: 2a–r (0.5 mmol), respectively, hydrochloric acid (7.5 mmol

Photoredox catalysis in nickel-catalyzed C–H functionalization

• Lusina Mantry,
• Rajaram Maayuri,
• Vikash Kumar and
• Parthasarathy Gandeepan

Beilstein J. Org. Chem. 2021, 17, 2209–2259, doi:10.3762/bjoc.17.143

• optimal to furnish the desired cross-coupled products 37 in satisfactory yields. Furthermore, the method proved applicable to the late-stage diversification of bioactive molecules, pharmaceuticals, and agrochemicals as aryl coupling partners (Scheme 21) [77]. The authors proposed a catalytic cycle that

Catalyzed and uncatalyzed procedures for the syntheses of isomeric covalent multi-indolyl hetero non-metallides: an account

• Ranadeep Talukdar

Beilstein J. Org. Chem. 2021, 17, 2102–2122, doi:10.3762/bjoc.17.137

• heterocycles, because of its diverse presence in bioactive molecules [1][2][3][4][5][6][7][8], coupled with the distinct nucleophilic chemistry revolving its aromatic benzo-fused pyrrole system as encountered throughout the bibliography [9][10][11][12][13][14][15]. It is therefore obvious that a non-metal

• synthesis of bis(indol-2-yl)sulfides which are the precursors of potent bioactive molecules [71][72][73]. The simple synthetic strategies for the molecular units 82 were first reported by Barbier in 1989. The condensation of tryptamine monoacetate (81a) or indole oxime (81b) with sulfur dichloride in a

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• bioactive molecules. They are also known to present valuable biological activities, such as anti-HBV (1) [44], anti-HIV (2) [45], antitumor (3) [46] and even antiplasmodial activities (4) [47] (Scheme 2A). Although these studied bioactive compounds do not directly represent the structural moieties obtained

• . The photo-electro methodology allowed the late-stage functionalization of valuable bioactive molecules, and the structures of a adapalene precursor (65) and ibuprofen derivative (66) were successfully azidated in moderate yields (Scheme 23C). Some silylated compounds like 67 have proven to be

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

• biologically active small molecules and complex peptides. Keywords: bioactive molecules; 3d transition metals; late-stage functionalization; manganese catalyst; sustainable catalysis; Introduction Manganese, a 3d transition metal, allows for a potentially ideal sustainable catalytic system because of the

• solution obtained by the nuclear reaction using a cyclotron, and manganese–salen complex 7 was used as a fluoride transfer catalyst, which facilitated late-stage C–H radiofluorination, affording the corresponding radiofluorinated bioactive molecules 8a–h. In general, the regioselectivity of fluorination

• the tertiary position using the manganese–salen catalyst. Furthermore, this Mn-catalyzed azidation protocol is highly robust in air, highlighting the practical simplicity of late-stage C–H azidation of bioactive molecules. A plausible reaction pathway was proposed, as illustrated in Figure 3. Similar

Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center

• Thanigaimalai Pillaiyar,
• Masoud Sedaghati,
• Andhika B. Mahardhika,
• Lukas L. Wendt and
• Christa E. Müller

Beilstein J. Org. Chem. 2021, 17, 1464–1475, doi:10.3762/bjoc.17.102

• -fluorinated analogs [25]. Considering the ever-growing demand for organofluorine compounds, the development of new methodologies that allow the incorporation of fluorine atoms into bioactive molecules is highly desired and will also be addressed herein. Recently, the use of indol-3-ylmethanols as

• investigate these bioactive molecules and their targets in future studies. Diindolylmethanes and reported biological activities. Synthetic strategies toward trifluoromethylated unsymmetrical quaternary DIMs. Reactions performed to study the scope of the method. Gram-scale synthesis of unsymmetrical DIMs 3a

Design, synthesis and photophysical properties of novel star-shaped truxene-based heterocycles utilizing ring-closing metathesis, Clauson–Kaas, Van Leusen and Ullmann-type reactions as key tools

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2021, 17, 1374–1384, doi:10.3762/bjoc.17.96

• medicinally active as well as smart functional materials possessing the pyrrole as a fundamental subunit [28][29][30]. Additionally, 3,4-disubstituted pyrrole derivatives are versatile building blocks for the production of diverse bioactive molecules like co-enzyme, alkaloids, porphyrins and other related

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

• provided an easy access to the synthesis of complex bioactive molecules with multiple point diversity incorporating up to eight components in one-pot [8]. The pharmaceutical industry has witnessed a considerable surge in drug synthesis via multicomponent strategies [9][10][11], including the synthesis of

Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines

• Geetanjali S. Sontakke,
• Rahul K. Shukla and
• Chandra M. R. Volla

Beilstein J. Org. Chem. 2021, 17, 485–493, doi:10.3762/bjoc.17.42

• purified by column chromatography (ethyl acetate/petroleum ether 1:9) to get the desired product 3a in 92% yield (50 mg, 0.18 mmol). Bioactive molecules containing the 2-aminoquinoline motif. C2-selective C–N bond formation of N-oxides. Substrate scope of N-sulfonyl-1,2,3-triazoles. Reaction conditions: 1a

Progress in the total synthesis of inthomycins

• Bidyut Kumar Senapati

Beilstein J. Org. Chem. 2021, 17, 58–82, doi:10.3762/bjoc.17.7

• synthetic efforts toward neooxazolomycin (4), oxazolomycin A (5a), and related antibiotics [17]. The recent review of Lee has mainly focused on the application of copper(I) salt and fluoride-promoted Stille coupling reactions in the synthesis of bioactive molecules including inthomycins A–C (1–3) [18]. The

Bifurcated synthesis of methylene-lactone- and methylene-lactam-fused spirolactams via electrophilic amide allylation of γ-phenylthio-functionalized γ-lactams

• Tetsuya Sengoku,
• Koki Makino,
• Ayumi Iijima,
• Toshiyasu Inuzuka and
• Hidemi Yoda

Beilstein J. Org. Chem. 2020, 16, 2769–2775, doi:10.3762/bjoc.16.227

• -butyrolactone; spirolactams; Introduction α-Methylene-γ-butyrolactone is a pharmaceutically important motif which is found in a wide variety of bioactive molecules including natural products (Scheme 1a) [1][2][3]. For example, sesquiterpene lactones represented by parthenolide and helenalin have attracted