Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

• Christina Schøttler,
• Kasper Lund-Rasmussen,
• Line Broløs,
• Philip Vinterberg,
• Ema Bazikova,
• Viktor B. R. Pedersen and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

• expanded by pyrrolo annelation. The optical and redox properties of these compounds, in some cases carbon-rich, were studied by UV–vis absorption spectroscopy and cyclic voltammetry. Synthetically, the work explores IF diones or fluorenone as central building blocks by subjecting the carbonyl groups to a

• other end of the IF core with electron-accepting moieties. An overview of general motifs targeted in this work is shown in Figure 1. Results and Discussion Synthesis The synthetic building blocks 1–8 used in this work are shown in Figure 2. The dione 1 and the ketones 4 and 6 were synthesized according

• to literature procedures [14][19][20], as were the 1,3-dithiole-2-thiones 2 and 3 [21]. Fluorenone 5 is commercially available. The new building blocks 7 and 8 were prepared according to related literature procedures [21], as described in Supporting Information File 1. Our first objective was to

Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

• Pavel S. Silaichev,
• Tetyana V. Beryozkina,
• Vsevolod V. Melekhin,
• Valeriy O. Filimonov,
• Andrey N. Maslivets,
• Vladimir G. Ilkin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3

• -diaminoacrylonitriles 1 and azides 2 can serve as three atom building blocks (Figure 1), affording 5-amino-1,2,3-triazole-4-carbimidamides A (Scheme 1C), which could be suitable precursors for the desired compounds 3. With the starting 3,3-diaminoacrylonitriles 1 and azides 2 at hands they were subjected to the

• and elaboration of a novel tandem process, synthesis of starting building blocks and 21-st target compounds was made by chemistry team and founded by Russian Science Foundation, project number 23-13-00248. The study of cytotoxic effect of 7 compounds was financially supported by the Ministry of

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

• understanding the correlations between structure and electronic properties, as these units serve as fundamental building blocks in graphite and carbon nanotubes [3]. The limited stability of this particular class of PAHs arises as a key challenge, primarily attributed to their extended conjugation. The longer

N-Boc-α-diazo glutarimide as efficient reagent for assembling N-heterocycle-glutarimide diads via Rh(II)-catalyzed N–H insertion reaction

• Grigory Kantin,
• Pavel Golubev,
• Alexander Sapegin,
• Alexander Bunev and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 1841–1848, doi:10.3762/bjoc.19.136

• heterocyclic fragment into the glutarimide core, creating potential CRBN ligands and crucial building blocks for assembling PROTACs. In this paper, a more convenient diazo reagent 5 is introduced and its effectiveness in reacting with a broad variety of NH-heterocycles and in providing N-Boc-protected

Substituent-controlled construction of A₄B₂-hexaphyrins and A₃B-porphyrins: a mechanistic evaluation

• Seda Cinar,
• Dilek Isik Tasgin and
• Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

• building blocks in the fields of near-infrared (NIR) dyes [5], nonlinear optical (NLO) materials [2], and photosensitizers in photodynamic therapy [1], however, their synthesis is still a challenge for chemists. Hexaphyrins are one of the most investigated structures among expanded porphyrins owing to

GlAIcomics: a deep neural network classifier for spectroscopy-augmented mass spectrometric glycans data

• Thomas Barillot,
• Baptiste Schindler,
• Baptiste Moge,
• Elisa Fadda,
• Franck Lépine and
• Isabelle Compagnon

Beilstein J. Org. Chem. 2023, 19, 1825–1831, doi:10.3762/bjoc.19.134

• building blocks with distinct molecular structures, carbohydrates feature hundreds of building blocks – many of them coming in groups of closely related isomers with ambiguous molecular structures – and they form complex, branched arrangements due to the versatility of the glycosidic bond (position and

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• ), specifically by extracting a hydrogen atom from the α-position of benzyl radicals A. The process described above led to the formation of the corresponding olefins 11, eliminating the need for a carbon–iodine bond formation step. Alkylation Diaziridines are highly versatile building blocks in synthesis, with

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

• Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

• Zhang Dongxu Department of Fire Protection Engineering, China Fire and Rescue Institute, Beijing 102202, P. R. of China 10.3762/bjoc.19.127 Abstract Nitrogen-containing organofluorine derivatives, which are prepared using fluorinated building blocks, are among the most important active fragments

• . Keywords: acylhydrazones; difluoromethylation; dihydropyridazine; fluorinated building blocks; hydrazones; imidazolidines; pyrazoles; pyrazolidines; pyrazolines; trifluoromethylation; Introduction The introduction of fluorine into pharmaceuticals, agrochemicals, and materials can significantly enhance

• building blocks offers another mainstream approach to introducing fluorine. Among these, di/trifluorodiazoethane [19][20][21][22], trifluoromethyl aldimines [23][24][25], trifluoroacetimidoyl halides [26], and fluoroalkyl N-sulfonyl hydrazones [27] have emerged as powerful nitrogen-containing fluorinated

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• high electron mobility and efficient charge transfer. In particular, Qx derivatives find use as non-fullerene acceptors (NFAs) in OSCs and as essential building blocks in sensitizers for DSSCs. The significance of Qx extends beyond to thermally activated delayed fluorescence (TADF) emitters and

• absorption, good dye regeneration, and promising NLO properties underscored the multifunctional nature of Qx derivatives as auxiliary acceptors [49]. Figure 5 depicts molecular structures of Qx derivatives used as building blocks of dyes and sensitizers. The device properties of such prominent materials are

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• . It has been reported that the performance of HLCT fluorophores greatly depends on the strength of donors, acceptors, and π spacers and the building blocks of HLCT should be carefully selected to regulate appropriate electron push–pull strength [32][35][47][48]. Here, a novel chromophore, 4,9-bis(9-(4

Morpholine-mediated defluorinative cycloaddition of gem-difluoroalkenes and organic azides

• Tzu-Yu Huang,
• Mario Djugovski,
• Sweta Adhikari,
• Destinee L. Manning and
• Sudeshna Roy

Beilstein J. Org. Chem. 2023, 19, 1545–1554, doi:10.3762/bjoc.19.111

• with an organic azide. A relatively wide range of 1,4,5-trisubstituted-1,2,3-triazoles was obtained in 30–70% yields with high regioselectivity and modest functional group tolerability. This work demonstrates that gem-difluoroalkenes can serve as versatile fluorinated building blocks in lieu of alkynes

One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives

• Hans-Ulrich Reissig and
• Fei Yu

Beilstein J. Org. Chem. 2023, 19, 1399–1407, doi:10.3762/bjoc.19.101

• -catalyzed version can generally be executed at room temperature and it affords exclusively 1,4-disubstituted 1,2,3-triazole derivatives, thus allowing a controlled and highly efficient connection of a variety of molecular building blocks. This “Lego-approach” found countless applications and the bestowal of

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

• Nadia Ledermann,
• Alae-Eddine Moubsit and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

• prior to terminal alkylation could provide a straightforward entry to trisubstituted 3-iodoindoles, which are valuable building blocks for accessing highly decorated (aza)indoles (Scheme 1). Here, we report the concise consecutive four-component synthesis of trisubstituted 3-iodoindoles. Results and

• N-iodosuccinimide prior to N-alkylation to give substituted 3-iodoindoles in a concise consecutive four-component fashion in modest to good yields. These target compounds are versatile building blocks for instance for a Suzuki coupling to give 1-alkyl-2,3-diarylindoles that can be of particular

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

• Feng Chen,
• Xiu-Hua Xu,
• Zeng-Hao Chen,
• Yue Chen and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2023, 19, 1372–1378, doi:10.3762/bjoc.19.98

• ; Introduction Acyloins (also known as α-hydroxy ketones) are widely found as structural motif in natural products [1][2][3][4][5][6][7] and bioactive molecules [8][9][10][11] (Figure 1). They can also be used as building blocks in organic synthesis [12][13][14], involved in numerous transformations to other

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• ). The review of Lemaire et al., dedicated to the synthesis of glycerol ether, is complemental to this review article [57]. Of note, the review of Godfroid and Braquet attempted to decipher the binding site of PAF via a QSAR study [58]. 1.1 Synthesis of PAF and some building blocks The platelet

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp³)–H to construct C–C bonds

• Hui Yu and
• Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

• are widespread as essential building blocks in various drugs, natural products, agrochemicals, and materials. Modern economy requires developing green strategies with improved efficiency and reduction of waste. Due to its atom and step-economy, the cross-dehydrogenative coupling (CDC) reaction has

• CDC reaction to be a new generation method for the construction of C–C bonds and it has received extensive attention and in-depth research [16][17][18][19][20][21][22][23][24]. The building blocks of ethers are widely found in biomass, chemical feedstocks, biologically active drugs, and natural

Acetaldehyde in the Enders triple cascade reaction via acetaldehyde dimethyl acetal

• Alessandro Brusa,
• Debora Iapadre,
• Maria Edith Casacchia,
• Alessio Carioscia,
• Giuliana Giorgianni,
• Giandomenico Magagnano,
• Fabio Pesciaioli and
• Armando Carlone

Beilstein J. Org. Chem. 2023, 19, 1243–1250, doi:10.3762/bjoc.19.92

• condensation coproducts, such as water, hydrogen chloride or other small molecules [1][2][3]. MCRs have a great advantage over the classical two-component reactions; they allow the construction of complex molecular motifs in only one synthetic operational step starting from simpler building blocks. For this

Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction

• Ziying Xiao,
• Fengshun Xu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1234–1242, doi:10.3762/bjoc.19.91

• methodologies for diverse spirooxindoles have become one of the hottest research fields in organic and pharmaceutical chemistry [10][11]. In order to synthesize diverse spirooxindole derivatives, commercially available isatins and easily obtainable 3-methyleneoxindolines were the most employed building blocks

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

Linker, loading, and reaction scale influence automated glycan assembly

• Marlene C. S. Dal Colle,
• Manuel G. Ricardo,
• Nives Hribernik,
• José Danglad-Flores,
• Peter H. Seeberger and
• Martina Delbianco

Beilstein J. Org. Chem. 2023, 19, 1015–1020, doi:10.3762/bjoc.19.77

• purification steps. Keywords: automated glycan assembly; photocleavable linker; polysaccharides; solid-phase synthesis; Introduction Automated glycan assembly (AGA) is a solid-phase method that enables the rapid synthesis of complex oligo- and polysaccharides from protected monosaccharide building blocks

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

• Till Steinmetz,
• Blaise Kimbadi Lombe and
• Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

• ] and the photoxenobactins [32]. A unifying theme in the biosynthesis of these natural products is the use of a thiotemplate-based assembly strategy [33]. The molecular building blocks that are needed for the biosynthesis are covalently bound via thioester bonds to multi-domain enzymes. The domains

• fulfill specific functions, ranging from the selection and linkage of building blocks to their chemical modification. A plausible scenario for the formation of compounds 1–6 involves the enzymatic machinery for massiliachelin biosynthesis, namely the protein RS02200 [18]. According to our proposal (Figure

Cyclodextrins as building blocks for new materials

• Miriana Kfoury and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2023, 19, 889–891, doi:10.3762/bjoc.19.66

• Miriana Kfoury Sophie Fourmentin Université du Littoral Côte d'Opale, Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV, UR 4492), 59140 Dunkerque, France 10.3762/bjoc.19.66 Keywords: building blocks; cyclodextrins; new materials; The continuous increase in the number of

• , and catalysis [2][5][12]. Molecular encapsulation is not the only application area for these macrocyclic components at present. CDs are versatile molecules. Their 3D structure makes them exceptional building blocks for the design of innovative supramolecular architectures due to the differential

Asymmetric tandem conjugate addition and reaction with carbocations on acylimidazole Michael acceptors

• Brigita Mudráková,
• Renata Marcia de Figueiredo,
• Jean-Marc Campagne and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 881–888, doi:10.3762/bjoc.19.65

• its applications in the total syntheses of complex natural products and other molecules of biological relevance [13][14]. Acylimidazoles proved to be versatile building blocks broadly applicable in asymmetric catalysis and organic synthesis. Today, acylimidazoles are used as ester/amide surrogates

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

• struts and the photoresponsive linkers. The use of ditopic interlocked building blocks, such as that employed to form mainly a cyclic hetero[4]pseudorotaxane from a self-complementary [2]rotaxane [73], is also envisioned as a strategy that will be employed in the future to dynamically change 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

• (0)/PR3-catalyzed C3 or C4-arylation of nicotinic and isonicotinic acids using amide as a directing group (Scheme 27) [97]. This method provides a way for arylated nicotinic acid derivatives which serve as building blocks for biologically important molecules. This was the first report for a directing