Diameter-selective extraction of single-walled carbon nanotubes by interlocking with Cu-tethered square nanobrackets

• Guoqing Cheng and
• Naoki Komatsu

Beilstein J. Org. Chem. 2024, 20, 1298–1307, doi:10.3762/bjoc.20.113

• can calculate larger system (>500 atoms) containing transition metals more precisely [16][17]. Result and Discussion Synthesis of Cu-tethered square nanobrackets 1b A pyrene-based nanobracket 4b was synthesized via a one-pot Suzuki coupling followed by the formation of dipyrrin from the dialdehyde 3

Synthesis and physical properties of tunable aryl alkyl ionic liquids based on 1-aryl-4,5-dimethylimidazolium cations

• Stefan Fritsch and
• Thomas Strassner

Beilstein J. Org. Chem. 2024, 20, 1278–1285, doi:10.3762/bjoc.20.110

• formation of N-oxides, which were then reduced using iron powder. The imidazoles were synthesized in a one-pot procedure on a scale of up to 400 mmol. Quaternization of the imidazoles using bromoalkanes with different chain lengths provided the bromide salts 10–36. Conversion to the NTf2 ionic liquids 37–63

Domino reactions of chromones with activated carbonyl compounds

• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 1256–1269, doi:10.3762/bjoc.20.108

• triethylamine in methanol afforded benzocoumarines 18a–ac (Scheme 4) [33][34]. The formation of the product, which was obtained in a two-step one-pot reaction, can be explained by a mechanism similar to the one discussed for the formation of 17. 1,4-Addition gave intermediate D which was isolated, but used in

• of DBU afforded furo[3,2-b]chromen-9-one 36a in 32% yield. Based on this observation, the two-step one-pot reaction of ketoamides 34a–f with 3-halochromones 15a–c was studied which afforded furo[3,2-b]chromen-9-ones 36a–f, albeit, in only low to moderate yields (Scheme 19) [41]. The formation of

• . Similarly to products 35, relatively low yields were observed for reactions of methoxy-substituted 3-halochromones. The two-step one-pot reaction of N-unsubstituted ketoamide 33a with 3-halochromones 29a and 31a afforded spirocycles 36a,b, albeit, in only moderate yields (Scheme 20) [41]. The formation of

The Ugi4CR as effective tool to access promising anticancer isatin-based α-acetamide carboxamide oxindole hybrids

• Carolina S. Marques,
• Aday González-Bakker and
• José M. Padrón

Beilstein J. Org. Chem. 2024, 20, 1213–1220, doi:10.3762/bjoc.20.104

• , 38200, La Laguna, Spain 10.3762/bjoc.20.104 Abstract Considering early-stage drug discovery programs, the Ugi four-component reaction is a valuable, flexible, and pivotal tool, facilitating the creation of two new amide bonds in a one-pot fashion to effectively yield the desired α-aminoacylamides. Here

• aspects. Multicomponent reactions (MCRs) are remarkable tools which demonstrated great potential for more sustainable production of active pharmaceutical ingredients (API’s). These flexible and versatile one-pot transformations in which three or more reagents are combined to access a new complex scaffold

Introduction of peripheral nitrogen atoms to cyclo-meta-phenylenes

• Koki Ikemoto and
• Hiroyuki Isobe

Beilstein J. Org. Chem. 2024, 20, 1207–1212, doi:10.3762/bjoc.20.103

• achieved with one-pot Suzuki–Miyaura coupling to arrange phenylene rings and pyridinylene rings in an alternating fashion. Analyses with UV–vis spectroscopy showed changes in the photophysical properties with nitrogen doping, and X-ray crystallographic analyses experimentally revealed the presence of

• -doped [n]CMPs, 3a and 3b, were synthesized via one-pot Suzuki–Miyaura coupling [12] (Scheme 1). Previously, we synthesized [n]CMPs with inward-focused nitrogen dopants by using Suzuki–Miyaura coupling with Pd(PPh3)4 as the catalyst [13] and applied this method to outward-radiated congeners in this work

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

• Mohd Farhan Ansari,
• Atul Kumar Maurya,
• Abhishek Kumar and
• Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

• regeneration of complex Mn7-a (Scheme 14). In 2020, Morrill's group reported the one-pot synthesis of N-methylarylamines from nitroarenes using methanol as a methylating agent and reductant [44]. When substituted nitroarenes were methylated with methanol under optimal conditions (5 mol % Mn3, 2 equiv of KOH at

• ) as a base in toluene at 140 °C for 36 h that gave up to 84% yield (Scheme 29A). More interestingly, double alkylation also occurred in one pot using acetophenone and 4-methoxyacetophenone with different benzyl alcohols under the optimized conditions. In the first step, monoalkylation of the methyl

Synthesis of 1,4-azaphosphinine nucleosides and evaluation as inhibitors of human cytidine deaminase and APOBEC3A

• Maksim V. Kvach,
• Stefan Harjes,
• Harikrishnan M. Kurup,
• Geoffrey B. Jameson,
• Elena Harjes and
• Vyacheslav V. Filichev

Beilstein J. Org. Chem. 2024, 20, 1088–1098, doi:10.3762/bjoc.20.96

• experiments with human CDA (hCDA), we used deprotected nucleoside Va as a mixture of anomers and converted it to Vb through a four-step one-pot synthesis involving silylation, treatment with oxalyl chloride, ammonolysis and removal of silyl groups. Purified phosphinamide Vb was obtained as a mixture of

Light on the sustainable preparation of aryl-cored dibromides

• Fabrizio Roncaglia,
• Alberto Ughetti,
• Nicola Porcelli,
• Biagio Anderlini,
• Andrea Severini and
• Luca Rigamonti

Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95

• then telescoped, resulting in a one-pot, two-step synthesis of 3c from 3, with improved operativity and yield (see experimental part). The same strategies were followed for the preparation of 1c (from 1b or from 1), as well as for 4c (from 4b or from 4). The preparation of the tetrabromo compound 2c

• issues observed during the benzylic bromination of 4. As a result, 4c was obtained from 4 (in a one-pot, two-step process) with an 85% isolated yield. The particular cleanliness of the conversion of 4b into 4c, featuring negligible formation of gem dihalides, could arise from the useful steric hindrance

• given by the halogen bound to the core. Figure 4 collects the results obtained in the preparation of aryl-cored halides of Figure 3, by means of the peroxide-bromide process. For products featuring bromine on both the aromatic core and the side chain, the “direct” one-pot two-stage and the “indirect

Carbonylative synthesis and functionalization of indoles

• Alex De Salvo,
• Raffaella Mancuso and
• Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

• complexes are important for the synthesis of heterocyclic and non-heterocyclic compounds. In 2009, Arthuis and co-workers developed a new process for the synthesis of 2-aroylindoles and 2-heteroaroylindoles by a one-pot palladium-catalyzed domino reaction that involves an initial C,N-coupling followed by

Direct synthesis of acyl fluorides from carboxylic acids using benzothiazolium reagents

• Lilian M. Maas,
• Alex Haswell,
• Rory Hughes and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2024, 20, 921–930, doi:10.3762/bjoc.20.82

• Kingdom 10.3762/bjoc.20.82 Abstract 2-(Trifluoromethylthio)benzothiazolium triflate (BT-SCF3) was used as deoxyfluorinating reagent for the synthesis of versatile acyl fluorides directly from the corresponding carboxylic acids. These acyl fluorides were reacted with amines in a one-pot protocol to form

• acyl fluoride products directly from carboxylic acids. Here, we report the results of this study, which led to the development of a practical and high yielding methodology for the synthesis of acyl fluorides and their subsequent one-pot conversion into amides. Moreover, by virtue of BT-SCF3’s ability

• unreliable isolation of acyl fluoride intermediates, we next considered whether BT-SCF3-mediated deoxyfluorination of carboxylic acids could be coupled with a subsequent acylation in an overall one-pot process. Selecting amines as nucleophilic coupling partners, a short optimisation study was carried out to

One-pot Ugi-azide and Heck reactions for the synthesis of heterocyclic systems containing tetrazole and 1,2,3,4-tetrahydroisoquinoline

• Jiawei Niu,
• Yuhui Wang,
• Shenghu Yan,
• Yue Zhang,
• Xiaoming Ma,
• Qiang Zhang and
• Wei Zhang

Beilstein J. Org. Chem. 2024, 20, 912–920, doi:10.3762/bjoc.20.81

• Chemistry and Center for Green Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd, Boston, MA 02125, USA 10.3762/bjoc.20.81 Abstract A new method for the synthesis of heterocyclic systems containing tetrazole and tetrahydroisoquinoline is developed via the performance of one-pot Ugi-azide

• and Heck cyclization reactions. The integration of the multicomponent and post-condensation reactions in one-pot maximizes the pot-, atom-, and step-economy (PASE). Keywords: Heck reaction; one-pot; tetrahydroisoquinoline; tetrazolo-pyrazino[2,1-a]isoquinolin-6(5H)-ones; tetrazole; Ugi-azide reaction

• fused imidazotetrazolodiazepinones (Scheme 2A) [37]. The Gámez-Montaño group introduced a one-pot synthesis of Ugi-azide/N-acylation/Diels–Alder/dehydration reactions for isoindolin-1-one and 1,5-DS-T in a linked manner (Scheme 2B) [41]. The Ding group developed sequential Ugi-azide/Ag-catalyzed

(Bio)isosteres of ortho- and meta-substituted benzenes

• H. Erik Diepers and
• Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

• carbene insertion into bicyclobutane was reported in 2022 by Bychek and Mykhailiuk [74]. Previously the same group had also reported the synthesis of BCPs containing a difluorinated bridge by CF2 carbene insertion into bicyclobutanes [75]. More recently Davies and co-worker reported the one-pot synthesis

Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins

• Ke Jiang,
• Cheng Pan,
• Limin Wang,
• Hao-Yang Wang and
• Jianwei Han

Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76

• salts is an efficient tool for the construction of two or more chemical bonds in a one-pot process. Ortho-functionalized diaryliodonium salts have showcased distinct reactivity in the exploration of benzocyclization or arylocyclization. With this strategy of ortho-ester-substituted diaryliodonium salts

• the low yield of 3al. We subsequently turned our attention to explore the effect of structural diversity of the ortho-ester-substituted diaryliodonium salts. Firstly, a family of substituted diaryliodonium salts were synthesized in a one-pot procedure. These ortho-substituted diaryliodonium salts were

• protocol enables the efficient formation of two chemical bonds in one pot, representing a valuable tool for the synthesis of polycyclic benzocoumarins. Our ongoing research endeavours are dedicated to explore the detailed reaction mechanism with the ultimate aim of broadening the scope and applicability of

Advancements in hydrochlorination of alkenes

• Daniel S. Müller

Beilstein J. Org. Chem. 2024, 20, 787–814, doi:10.3762/bjoc.20.72

• reported. In surface-mediated reactions, the proton donor is typically Si–OH or Al–OH. For clarity in discussing subsequent reactions, we have separated the in situ HCl gas synthesis from the hydrochlorination. It is important to note that these reactions are one-pot processes rather than two-pot reactions

Regioselective quinazoline C2 modifications through the azide–tetrazole tautomeric equilibrium

• Dāgs Dāvis Līpiņš,
• Andris Jeminejs,
• Una Ušacka,
• Anatoly Mishnev,
• Māris Turks and
• Irina Novosjolova

Beilstein J. Org. Chem. 2024, 20, 675–683, doi:10.3762/bjoc.20.61

• product. Compounds 12 did not tolerate aqueous conditions or high temperatures and have also been observed to degrade under direct sunlight. Next, a stepwise one-pot approach was investigated to increase the overall yield (Scheme 6). The reaction in anhydrous DMF yielded a mixture of the desired product

• the aromatic nucleophilic substitution of 2-azido-4-sulfonylquinazoline 12a or by performing three subsequent SNAr reactions starting from 2,4-dichloroquinazoline 7 in a one-pot procedure [28] (Scheme 9, Table 2). The resulting products exist in an azide–tetrazole equilibrium in solution, but in solid

• . Synthesis of 6,7-dimethoxyquinazoline derivatives 16, 17a and 18. Synthesis of 2-amino-4-azido-6,7-dimethoxyquinazolines 17. Synthesis of terazosin and prazosin hydrochlorides 19a and 19b. Modifications of derivatives 17. Conditions for one-pot synthesis of 4-azido-6,7-dimethoxy-2-sulfonylquinazolines 12

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

• Luan A. Martinho and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2024, 20, 628–637, doi:10.3762/bjoc.20.55

• ][21][22]. Multicomponent reactions (MCRs) provide one-pot reactions, simple synthetic procedures, less waste being produced, fewer purification steps, and a high atom economy [23]. The GBB three-component reaction is carried out in the presence of Lewis or Brønsted acid catalysis to increase the

Entry to new spiroheterocycles via tandem Rh(II)-catalyzed O–H insertion/base-promoted cyclization involving diazoarylidene succinimides

• Alexander Yanovich,
• Anastasia Vepreva,
• Ksenia Malkova,
• Grigory Kantin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 561–569, doi:10.3762/bjoc.20.48

• data. Further syntheses of spirobutenolides 2 were performed under the one-pot conditions: after completion of the first O–H insertion step, a base was added to the reaction mixture and kept at room temperature until completion of the cyclization step, controlled by TLC. The results of the syntheses

• also in the alpha position of the furanone ring. Reactions with allenic acids 11 were carried out according to a similar scheme, in the one-pot mode, without isolation of OH-insertion intermediates 12 (Scheme 4). In order to accelerate the cyclization step in this case, moderate heating was used after

• monitor the progress of the reaction and the formation of the OH-insertion product 14. An attempt to carry out the second step in a one-pot format with the addition of 1.2 equiv of base (DIPEA or DBU) was unsuccessful and the formation of the spirocyclic product was not observed. Replacing DCM with a more

(E,Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene

• Nataliia V. Kirij,
• Andrey A. Filatov,
• Yurii L. Yagupolskii,
• Sheng Peng and
• Lee Sprague

Beilstein J. Org. Chem. 2024, 20, 452–459, doi:10.3762/bjoc.20.40

• -1,1,1,4,4,4-hexafluorobut-2-enes have been investigated. A simple, one-pot procedure for the preparation of a new allene (1,1,4,4,4-pentafluorobuta-1,2-diene) and some of its transformations is presented. Keywords: allenes; dehydrohalogenation; halogenation; 1,1,1,4,4,4-hexafluorobut-2-enes; isomerization

Mono or double Pd-catalyzed C–H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives

• Nahed Ketata,
• Linhao Liu,
• Ridha Ben Salem and
• Henri Doucet

Beilstein J. Org. Chem. 2024, 20, 427–435, doi:10.3762/bjoc.20.37

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• his research group developed a novel sulfonic graphitic carbon nitride (g-C3N4-SO3H) as a nanosheet ionic liquid for the one-pot synthesis of BIMs [125]. Graphitic carbon nitride is a non-metal and non-toxic chemically stable nanostructure, which is obtained through a facile pyrolysis process that has

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

• Eugeny Ivakhnenko,
• Vasily Malay,
• Pavel Knyazev,
• Nikita Merezhko,
• Nadezhda Makarova,
• Oleg Demidov,
• Gennady Borodkin,
• Andrey Starikov and
• Vladimir Minkin

Beilstein J. Org. Chem. 2024, 20, 336–345, doi:10.3762/bjoc.20.34

• -di-tert-butyl-2-(arylamino)-3H-phenoxazin-3-ones 4. 6,8-Di-tert-butyl-2-(arylamino)-3H-phenoxazin-3-ones 4 prepared by the one-pot reaction between 6,8-di-tert-butyl-3H-phenoxazin-3-one (1) and aromatic amines 2b (the yield is given in parentheses). Synthesis of 14H-quinoxaline[2,3-b]phenoxazines 5

Catalytic multi-step domino and one-pot reactions

• Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25

• ; multi-step reactions; multicomponent reactions; one-pot synthesis; organocatalysis; tandem reactions; transition-metal-catalysis; The synthesis of pharmaceutical ingredients, natural products, agrochemicals, ligand systems, and building blocks for materials science has reached a high level of

• atom efficiency, step and pot economies, decreased number of purification steps, or protecting-group-free synthesis. Multi-step domino [1][2] and one-pot [3] reactions represent a new powerful toolbox in organic synthesis to install molecular complexity economically and sustainably, starting from

• simple compounds. In particular, catalytic domino reactions and one-pot processes with excellent selectivity and functional-group tolerance are of significant interest to industrial and academic research. In the so-called domino reactions, all of the required reagents, the catalyst, and a solvent are

Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target

• Milandip Karak,
• Cian R. Cloonan,
• Brad R. Baker,
• Rachel V. K. Cochrane and
• Stephen A. Cochrane

Beilstein J. Org. Chem. 2024, 20, 220–227, doi:10.3762/bjoc.20.22

• disaccharide synthesis alongside C6-protected acceptors (2a or 2b in Figure 2) [10][11][14][15][37][38]. More recently, an innovative one-pot glycosylation approach using a (2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)-protected glycosyl acceptor has been developed, demonstrating satisfactory stability

• , followed by in situ re-acetylation of the C2-amino group and C6-alcohol with acetic anhydride, resulting in the formation of disaccharide 4 in a one-pot fashion. The anomeric benzyl protecting group in disaccharide 4 was then removed via a Pd/C-catalyzed hydrogenation reaction, producing a mixture of α/β

Metal-catalyzed coupling/carbonylative cyclizations for accessing dibenzodiazepinones: an expedient route to clozapine and other drugs

• Amina Moutayakine and
• Anthony J. Burke

Beilstein J. Org. Chem. 2024, 20, 193–204, doi:10.3762/bjoc.20.19

• ; carbonylative cyclization; Chan–Lam; nitrogen heterocycle; one-pot; Introduction Dibenzodiazepine units are without doubt highly privileged structures, endowed with numerous medicinally relevant properties, and notably include anti-anxiolytic and antidepressant activities. These scaffolds have received much

• occurs first at the amide position. This approach enabled the successful synthesis of a broad spectrum of dibenzodiazepinone units in a one-pot fashion. The synthetic utility of Laha’s approach was highlighted by preparing the corresponding dibenzodiazepinone which was further reacted with N

• driving forces for the development of the work discussed in this report. Results and Discussion Synthesis of o-(2-bromophenyl)aminoaniline via Buchwald–Hartwig C–N coupling One-pot synthesis of dibenzodiazepinones Our preliminary attempt to synthesize DBDAPs via B–H amination and carbonylation was carried

Synthesis of the 3’-O-sulfated TF antigen with a TEG-N₃ linker for glycodendrimersomes preparation to study lectin binding

• Mark Reihill,
• Hanyue Ma,
• Dennis Bengtsson and
• Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

• [24][25]. Interestingly, Jacquemard et al. outlined a useful, mild method for removing a range of carbamates using Bu4NF in an article from 2004 [26]. As 7 contained a DTBS group, the possibility of removing both Troc and DTBS groups in a one-pot procedure was tested. Disaccharide 7 was therefore