Light-responsive rotaxane-based materials: inducing motion in the solid state

• Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

• light-responsive intertwined materials and the industrial scale-up production usually hindered by the low yield of the interlocked molecules. Thus, future research efforts should be focused on the development of novel synthetic methodologies to access to such interlocked architecture, as well as the use

Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones

• Ksenia Malkova,
• Andrey Bubyrev,
• Stanislav Kalinin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 800–807, doi:10.3762/bjoc.19.60

• through a range of synthetic methodologies suggested recently. Cyclization strategies [35][36][37][38][39][40][41][42][43][44][45] as well as cycloaddition/cyclocondensation techniques [46][47][48][49][50][51] represent those with hetero-ring construction. Alternative approaches rely on a peripheral

Total synthesis: an enabling science

• Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 474–476, doi:10.3762/bjoc.19.36

• Bastien Nay Laboratoire de Synthèse Organique, École Polytechnique, CNRS, ENSTA, Institut Polytechnique de Paris, 91128 Palaiseau, France 10.3762/bjoc.19.36 Keywords: chemical complexity; natural products; synthetic methodologies; total synthesis; Total synthesis is a topic strongly related to

• enabling science. Total synthesis is the science of constructing molecules from simple starting materials. It often deals with complex molecular architectures that require a thorough retrosynthetic problem-solving analysis [7]. Total synthesis and the discovery of new synthetic methodologies have always

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

• Bram Ryckaert,
• Ellen Demeyere,
• Frederick Degroote,
• Hilde Janssens and
• Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

• , should open up many more possibilities. Moreover, as the synthetic access to these sulfur-based heterocycles is now more straightforward, the importance of 1,4-dithianes and related heterocycles in new synthetic methodologies can be expected. An area where these C2-synthons have so far been less

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

• Elena R. Lopat’eva,
• Igor B. Krylov,
• Dmitry A. Lapshin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

• stoichiometric oxidants. The development of organic chemistry is strongly affected by rising “green” demands to synthetic methodologies, including reduction of waste formation, low trace-metal content in drug compounds, high energy-efficiency and selectivity of processes. In the last decade researchers proposed

Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

• Emine Salamci and
• Ayse Kilic Lafzi

Beilstein J. Org. Chem. 2022, 18, 1539–1543, doi:10.3762/bjoc.18.163

• antibiotic activities. Therefore, synthetic methodologies for the preparation of the aziridinyl system have attracted attention in recent decades. Opening of the aziridine ring by using different nucleophiles gives the corresponding amino alcohols, amino esters, azido amines, amines, and other derivatives [9

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

• character – have been harnessed in a plethora of applications in modern life: Teflon in non-stick pans, fire-fighting foams, stain-resistant and weatherproof fabrics, etching of circuit boards, and even imaging agents [1]. Given their importance, multiple synthetic methodologies for the introduction of long

Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives

• Sayan Pramanik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 469–478, doi:10.3762/bjoc.18.49

• ][10][11][12][13][14]. Among the known synthetic methodologies, the domino cycloaddition reaction of benzimidazolium salts with two molecules of 2-(2-oxoindolin-3-ylidene)acetates provided as an important tool for the construction of dispirooxindoles [15]. In particular, most of the dispirooxindole

• . Again, in 2018, Yang et al. [26] synthesized functionalized dispiro[indoline-3,1-cyclopentane-3,3-indolines] via cyclodimerization of 3-phenacylideneoxindolines with benzoyl hydrazides and arylhydrazines. Encouraged by these synthetic methodologies and in continuation to our efforts towards the

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

Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents

• Rodolfo H. V. Nishimura,
• Thiago dos Santos,
• Valter E. Murie,
• Luciana C. Furtado,
• Leticia V. Costa-Lotufo and
• Giuliano C. Clososki

Beilstein J. Org. Chem. 2021, 17, 2968–2975, doi:10.3762/bjoc.17.206

• antitumor agents, several synthetic methodologies have been developed to prepare these compounds. Amination using primary [6][8][9][10][11][12][13] or secondary [14][15][16] amines and 4-chloroquinazolines is among the most employed procedures. Electron-rich amines (e.g., primary aliphatic amines or hydroxy

DABCO-promoted photocatalytic C–H functionalization of aldehydes

• Bruno Maia da Silva Santos,
• Mariana dos Santos Dupim,
• Cauê Paula de Souza,
• Thiago Messias Cardozo and
• Fernanda Gadini Finelli

Beilstein J. Org. Chem. 2021, 17, 2959–2967, doi:10.3762/bjoc.17.205

• interchanging steps, often required in traditional synthetic methodologies [1][2]. The development of photocatalysis enabled inexpensive access to C–H activation methodologies under mild conditions, with hydrogen atom transfer (HAT) reactions standing out as a main strategy [1][3][4]. The hydrogen abstractor is

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• has set a milestone as a new and effective method for the synthesis of macromolecules [11]. Initiation of this reaction photocatalytically provides many advantages for the synthetic methodologies including bioconjugation, labeling, surface functionalization, dendrimer synthesis, polymer synthesis, and

Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

• Ren-Jie Fang,
• Chen Yan,
• Jing Sun,
• Ying Han and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2021, 17, 2425–2432, doi:10.3762/bjoc.17.159

• hand, carbazole derivatives also have potential applications in optoelectronic materials, conducting polymers, and synthetic dyes [9][10][11]. Over the past decades, many efficient synthetic methodologies for functionalized carbazole derivatives have been successfully developed [12][13][14][15][16][17

Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• human cancer cell lines and inhibition of the chemokine receptor CCR5, make them attractive synthetic targets. This review article highlights the recent synthetic methodologies and briefly summarizes their biological activities. Keywords: brevipolides; 5,6-dihydro-α-pyrone; Furukawa-modified Simmons

• design new synthetic methodologies for reproducing these natural products and their analogues as well as to develop new pharmaceuticals from them. Structures of brevipolides A–O (1 – 15). Retrosynthetic analysis of brevipolide H (8) by Kumaraswamy. Attempt to synthesize brevipolide H (8) by Kumaraswamy

Synthesis and antimicrobial activity of 1H-1,2,3-triazole and carboxylate analogues of metronidazole

• Satya Kumar Avula,
• Syed Raza Shah,
• Khdija Al-Hosni,
• Muhammad U. Anwar,
• Rene Csuk,
• Biswanath Das and
• Ahmed Al-Harrasi

Beilstein J. Org. Chem. 2021, 17, 2377–2384, doi:10.3762/bjoc.17.154

• develop new synthetic methodologies toward the 1H-1,2,3-triazole group containing organic entities. However, earlier methods of the synthesis of aliphatic and aromatic esters of metronidazole are associated with different drawbacks such as long conversion times, low yields and preparation of their

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

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

• few of them become approved, due to their toxicity or other issues related to their applicability. Therefore, synthetic methodologies that facilitate the successful production of potential biologically active molecules have a relevant role in the organic synthesis research field. One of the key

• synthetic methodologies is the C–H bond activation process that enables a straightforward access to several important and innovative compounds [14][15][16][17][18]. In the last few years, metals such as ruthenium [19][20][21], rhodium [22][23][24], palladium [25][26][27], and iridium [28][29][30] have been

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli,
• Noureddine Chaaben,
• Kamel Alimi,
• Stefan Jopp and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

• ][38][39] and were reported to be promising candidates for potential use as organic light emitting diodes [40]. Thus, various synthetic methodologies for the preparation of acridine-based molecules have been developed [41][42][43][44][45][46][47]. Tetrahydroacridine, containing a partially hydrogenated

Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances

• Thiago S. Silva and
• Fernando Coelho

Beilstein J. Org. Chem. 2021, 17, 1565–1590, doi:10.3762/bjoc.17.112

• activation. The use of metals in which the protodemetalation step of the σ-alkylmetal complex occurs preferentially to the β-hydride elimination arose as an alternative for the development of new methodologies. During the early 2000s, several synthetic methodologies flourished that employed gold catalysis to

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

• pentofuranosyl sugar moiety. Various synthetic methodologies have been developed for the introduction of the additional nucleobase/heterocyclic system directly or via a linker at the C-2′/C-3′/C-4′/C-5′ position of the pentofuranosyl moieties. We have categorized the double-headed furanosyl-nucleosides depending

• , Bose Institute, P1/12 CIT Scheme VIIM, Kolkata-700 054, India 10.3762/bjoc.17.98 Abstract Double-headed nucleoside monomers have immense applications for studying secondary nucleic acid structures. They are also well-known as antimicrobial agents. This review article accounts for the synthetic

• methodologies and the biological applications of double-headed nucleosides. Keywords: acyclic double-headed nucleosides; bicyclic double-headed nucleosides; furanosyl double-headed nucleosides; modified nucleosides; pyranosyl double-headed nucleosides; Introduction Nucleosides are the constructional subunits

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

• metathesis, Ullmann-type coupling, Clauson–Kaas, and Van Leusen reactions as crucial transformations. Synthetic Strategy Basically, our endeavor toward the synthesis of truxene-based systems has been rooted in the development of new synthetic methodologies to assemble diverse polycyclic as well as

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

• . Asymmetric synthesis of pyrrolidines The pyrrolidine ring is more represented within natural products than the 3- and 4-membered nitrogen-containing heterocycles. This molecular array is also found in drugs and other biologically active molecules. For this reason, there are numerous examples of synthetic

• methodologies for these compounds in the literature. In most cases, the pyrrolidine ring is formed from an amine with a hydrocarbon chain that also carries a functional group at the appropriate distance that allows the cyclization process to take place. In the case of substituted pyrrolidines, the

Synthetic accesses to biguanide compounds

• Oleksandr Grytsai,
• Cyril Ronco and
• Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

• critical overview of the synthetic accesses to biguanide compounds, as well as their comparative advantages and limitations. It also underlines the need of developing new synthetic methodologies to reach a wider variety of biguanides and to overcome the underrepresentation of these compounds. Keywords

Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

• Emine Salamci and
• Yunus Zozik

Beilstein J. Org. Chem. 2021, 17, 705–710, doi:10.3762/bjoc.17.59

• inhibitors of α-glycosidases [11][19]. Recent reviews report on the latest synthetic methodologies for aminocyclitols and related compounds [1][2][3][16]. Many methods have been previously reported for the synthesis of aminocyclitols containing five- and six-membered rings, along with their diverse

A new and efficient methodology for olefin epoxidation catalyzed by supported cobalt nanoparticles

• Lucía Rossi-Fernández,
• Viviana Dorn and
• Gabriel Radivoy

Beilstein J. Org. Chem. 2021, 17, 519–526, doi:10.3762/bjoc.17.46

• heterogeneous catalysts [27] that are wide in substrate scope, active enough and highly selective. As part of our continuing interest in the development of new synthetic methodologies based on the use of catalysis by non-noble transition metal nanoparticles (MNPs) for their application in a wide range of