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

• have successfully optimized a modular approach for the synthesis of lipid II and its analogues, including variants with distinct prenyl-chain lengths. The key to this methodology lies in the optimization of glycosylation conditions, utilizing readily available glycosyl donors, which is a pivotal step

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

• Tsvelikhovsky introduced an efficient synthetic strategy to construct diverse dibenzodiazepinones through a sequential methodology consisting of a B–H coupling between o-carbonylanilines and 1,2-dihaloarene derivatives providing access to key precursors that undergo a tandem amination–intramolecular cyclization

• surrogate through the in situ formation of an o-(2-bromophenyl)aminoaniline intermediate (Scheme 1d). It should be noted these target compounds have been of great interest to our group and in 2015 we reported a proposed novel methodology for the synthesis of dibenzodiazepines [18], however, upon later

• good yield (this represented a formal synthesis to clozapine [26], if the procedure of Rao [27] is used, which entails heating 4e with 1-methylpiperidine and Ti(IV)Cl4, Scheme 4). Also compound 4a can be transformed to Hügel's 1,2,3-triazole-DBDAP using the methodology described in their report (Scheme

Copper-promoted C5-selective bromination of 8-aminoquinoline amides with alkyl bromides

• Changdong Shao,
• Chen Ma,
• Li Li,
• Jingyi Liu,
• Yanan Shen,
• Chen Chen,
• Qionglin Yang,
• Tianyi Xu,
• Zhengsong Hu,
• Yuhe Kan and
• Tingting Zhang

Beilstein J. Org. Chem. 2024, 20, 155–161, doi:10.3762/bjoc.20.14

• were obtained in high yields (92‒99%), which demonstrated the practical value of this methodology. Moreover, the reaction showed a good tolerance to sterically hindered substrates like trimethylbenzamide, affording the corresponding brominated product in 70% yield (3la). Also the substrate derived from

• primary alkyl bromides is higher than that of secondary alkyl bromides, while the reactivity of tertiary alkyl bromides is the lowest (2a–c, 2g–i). Finally, dibromomethane (2j) proceeded well in the reaction, furnishing 3aa in 65% yield. As showcased in Scheme 4, this methodology is also applicable to

• , we have developed an efficient and practical method for the synthesis of C5-brominated 8-aminoquinoline amides in good to excellent yields via a copper-promoted selective bromination using alkyl bromides as the bromide source. This methodology is scalable, proceeds well with various aromatic and

Visible-light-induced radical cascade cyclization: a catalyst-free synthetic approach to trifluoromethylated heterocycles

• Chuan Yang,
• Wei Shi,
• Jian Tian,
• Lin Guo,
• Yating Zhao and
• Wujiong Xia

Beilstein J. Org. Chem. 2024, 20, 118–124, doi:10.3762/bjoc.20.12

• derivatives. UV–vis spectra of substrates; [1a] 0.33 M, [2a] 0.11 M. Selected works for the construction of dihydropyrido[1,2-a]indolones and current methodology. Substrate scope of the cascade reaction. Radical trapping experiment. Plausible reaction mechanism. Optimization of reaction conditions.a

Electron-beam-promoted fullerene dimerization in nanotubes: insights from DFT computations

• Laura Abella,
• Gerard Novell-Leruth,
• Josep M. Ricart,
• Josep M. Poblet and
• Antonio Rodríguez-Fortea

Beilstein J. Org. Chem. 2024, 20, 92–100, doi:10.3762/bjoc.20.10

• + 2] cycloaddition in phase 1 We analyzed in detail the energy profile for the first step in the dimerization process, that is, the reversible [2 + 2] cycloaddition to obtain dimers 1-Cs and 1-D2h. We initially considered dimerization in the gas phase to check the reliability of our methodology

• of dimer 1-Cs•+ (see Supporting Information File 1, Figure S9). However, TS-2 is significantly lower in energy. Therefore, in gas phase, dimer 1-D2h•+ is predicted to be the thermodynamic and the kinetic product. Once our methodology was validated, the energy profile for the formation of dimer 1-Cs

NMRium: Teaching nuclear magnetic resonance spectra interpretation in an online platform

• Luc Patiny,
• Hamed Musallam,
• Alejandro Bolaños,
• Michaël Zasso,
• Julien Wist,
• Metin Karayilan,
• Eva Ziegler,
• Johannes C. Liermann and
• Nils E. Schlörer

Beilstein J. Org. Chem. 2024, 20, 25–31, doi:10.3762/bjoc.20.4

• ; structure elucidation; Introduction For the validation of molecular structures, nuclear magnetic resonance (NMR) spectroscopy is an indispensable methodology in the daily routine of synthetic chemistry laboratories. Arguably, NMR experiments serve as the ‘eye of the synthetic chemist’ because they allow a

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

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

• developed for the synthesis of biphenylene-containing azaacene structures [47] (Scheme 13). The methodology used in this study closely resembled their previous work (Scheme 9) [43]. The method used offered a distinct advantage compared to previous approaches [45], as it enabled the synthesis of not only

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

• have been obtained. Glutarimide-based immunomodulatory drugs (IMiDs) and CRBN ligands. Examples of α-carbonyl NH-heterocycles for which N–H insertion products could not be obtained. Main literature approaches towards α-hetaryl glutarimides 1 (routes A and B) and new “diazo” methodology based on Rh(II

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

• probabilistic deep neural network (Bayesian deep neural networks [12]) to support automated monosaccharide recognition for carbohydrate sequencing. We obtained a highly performing algorithm that we called "GlAIcomics", specifically trained on carbohydrates. Methodology Data production Our carbohydrate analysis

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

• substituents at the C-2 position. As a way of expanding the scope of this methodology, we resorted to the α-C-acylation of β-enamino amides, a reliable reaction, the utility of which we have already demonstrated in other contexts [62][63]. Results and Discussion As the starting point of our synthetic

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

• catalysis has risen to prominence as an incredibly effective methodology, establishing itself as a powerful tool for crafting various C–X (X = C, N, O, F, Cl…) bonds owing to its advantageous traits, such as sustainability, practicality, and environmental compatibility [5]. Despite its broad synthetic

• readily accessible redox-active esters 3 and cost-effective NaI/PPh3 photoactivators under mild reaction conditions (Scheme 8) [14]. The methodology exhibited remarkable efficacy when applied to a wide range of natural products and pharmaceuticals, significantly expanding the synthetic utility of this

• replenished the NaI/PPh3 catalyst, completing the catalytic cycle. Very recently, Zhong and his colleagues proposed a decarboxylative alkylation method for vinylcyclopropanes 46 using alkyl N-(acyloxy)phthalimide esters 3. This methodology enabled the synthesis of variously substituted 2-alkylated 3,4

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• -Aldrich and Vetec in the highest purity available and used without further purification. Syntheses of the compounds Compounds were synthesized by modifying the existing methodology in the literature [50]. The compounds were prepared by condensation between 3,4,5-trimethoxybenzoic acid hydrazide (TMP, 1.0

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• porphyrins was investigated, resulting in the formation of lead(II), zinc(II), and copper(II) binuclear coordination compounds [54]. The synthetic methodology developed by Sessler allowed to generate a variety of expanded Schiff porphyrinoids [30][128] and texaphyrins [57][60][129]. The group has also

• geometry with the cobalt(II) positioned slightly above the N4 donor plane. The X-ray structure of 18b-Co exhibited a similar Pacman motif as its palladium analogue, with the cobalt(II) cation residing in a square-planar environment. The exploitation of a similar synthetic methodology allowed for preparing

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis

• Bel Youssouf G. Mountessou,
• Élodie Gisèle M. Anoumedem,
• Blondelle M. Kemkuignou,
• Yasmina Marin-Felix,
• Frank Surup,
• Marc Stadler and
• Simeon F. Kouam

Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112

• National Herbarium of Cameroon, Yaoundé, where a voucher specimen was deposited under the number 42166/HNC. The isolation of fungi from the plant material was carried out following the previously described methodology [6]. The fungus was recently introduced as the new species Diaporthe cameroonensis by

• -1121341), the AvH Research Hub project CECANAPROF (3.4-CMR-Hub) and the International Foundation for Science (grant I1-F-6554-1). Author Contributions Conceptualization, S.F.K. and M.S.; methodology, B.Y.G.M., E.G.M.A. and Y.M.-F.; validation, S.F.K. and M.S.; collection of the plant material and

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• according to the different positions of the OMe group. The preparation of α,α-bisthiofunctionalized butenolides through a bis-sulfenylation methodology was reported by Zhou and Yuan et al. [49]. For this purpose, they applied N-(alkyl(aryl)sulfanyl)succinimides or N-(phenylsulfanyl)phthalimides using a

α-(Aminomethyl)acrylates as acceptors in radical–polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping

• Angel Palillero-Cisneros,
• Paola G. Gordillo-Guerra,
• Fernando García-Alvarez,
• Olivier Jackowski,
• Franck Ferreira,
• Fabrice Chemla,
• Joel L. Terán and
• Alejandro Perez-Luna

Beilstein J. Org. Chem. 2023, 19, 1443–1451, doi:10.3762/bjoc.19.103

• ). Asymmetric variants of these transformations are possible using the tert-butanesulfinyl chiral auxiliary on the nitrogen atom. The levels of 1,4-stereoinduction are significant but a convincing model to account for it cannot be put forward at this point. Nonetheless, from a synthetic methodology point of

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

• Nosheen Beig,
• Varsha Goyal and
• Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

• and co-workers (Scheme 72) [94]. Some of the characteristic features of this methodology are: enantioselective formation of the quaternary stereocenters, broad substrate scope, high enantioselectivity, and branched:linear selectivity. Furthermore, the NHC–Cu complex incorporating the chelating N-2

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 scientific community for different reasons: 1) to have an overview on the methods already available, 2) to invite scientists that are working on synthesis methodology to apply their works to the design of ELs analogues, 3) the methods reported in this review can be useful tools for the scientific

• have done a selection, which is based on the methodology employed in order to have an overview of the most useful methods employed for the synthesis of PAF and PAF-analogues. The synthesis of alkyl EL involves the chemistry of glycerol or its direct precursors (e.g., glycidol, solketal, epichlorohydrin

• time before the discovery of the structure of PAF, Arnold, Weltzien and Westphal reported the synthesis of lyso-PAF starting from 1,3-benzylideneglycerol (3.1) [69] (Figure 3). 3.2 was prepared from 3.1 following the methodology reported by West et al. [70]. Then, 3.2 was deprotonated with sodium and

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

• simple flash chromatography. Conclusion An unprecedented methodology for the synthesis of 4,6-disubstituted 5-nitrocyclohexene carbaldehydes with three contiguous stereogenic centers using acetaldehyde as one of the reaction components of an Enders cascade reaction has been developed. The masked form of

• enantiomeric excesses. Unfortunately, the developed methodology is currently limited to aromatic substrates and the formation of one stereocenter is difficult to control, leading to a mixture of two diastereomers. Current efforts in our laboratories are addressing these challenges. Approaches based on the

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• Chandra Sekhar Tekuri Pargat Singh Mahendra Nath Department of Chemistry, Faculty of Science, University of Delhi, Delhi 110 007, India 10.3762/bjoc.19.89 Abstract A facile one-pot four-component synthetic methodology is evolved to construct novel copper(II) benzo[f]chromeno[2,3-h

Exploring the role of halogen bonding in iodonium ylides: insights into unexpected reactivity and reaction control

• Carlee A. Montgomery and
• Graham K. Murphy

Beilstein J. Org. Chem. 2023, 19, 1171–1190, doi:10.3762/bjoc.19.86

• was first reported in 2010 [133], the subsequent collection of works by Vasdev and Liang led to an improved methodology appropriate for the time and temperature requirements of radiofluorination reactions, and led to a mechanistic proposal dependent on σ-hole selective halogen bonding [134]. Vasdev

Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light

• Damiano Diprima,
• Hannes Gemoets,
• Stefano Bonciolini and
• Koen Van Aken

Beilstein J. Org. Chem. 2023, 19, 1146–1154, doi:10.3762/bjoc.19.82

• negligible depending on the concentration of water. Conclusion A catalyst-free methodology for the selective oxygenation of heteroatoms (S, P, Se) has been developed using only air, water, and light. The protocol allows high conversion and excellent selectivity for a wide scope of substrates, with relative

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

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

• Dmitry B. Vinogradov,
• Alexei N. Izmest’ev,
• Angelina N. Kravchenko,
• Yuri A. Strelenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

• ][1,2,4]triazine or imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine and the expansion of the thiazolidine ring to a thiazine core. The methodology proved to be effective for the preparation of a series of target compounds with different substituents in the tricyclic fragment. Examples of natural and

Aromatic C–H bond functionalization through organocatalyzed asymmetric intermolecular aza-Friedel–Crafts reaction: a recent update

• Anup Biswas

Beilstein J. Org. Chem. 2023, 19, 956–981, doi:10.3762/bjoc.19.72

• 2004. In this methodology, a 1,1’-bi-2-naphthol (BINOL)-derived chiral phosphoric acid P1 was used as the catalytic reagent to couple 2-methoxyfuran (1) and N-Boc-protected aldimines 2 to incorporate an aza-tertiary stereocenter into the 2’ position of the heteroaromatic products 3 (Scheme 1) [24

• -substituted indoles which effectively attacked the electrophile through the C2 position. The reaction was even compatible with pyrroles (Scheme 7a). The utility of this methodology was successfully demonstrated by the synthesis of product 23a, the key intermediate of natural product (+)-trigonoliimine (Scheme

• in the aryl ring of the imines whereas amenability of this methodology was narrow for ring-substituted pyrroles and indoles (Scheme 15a) [40]. In the next year, the same research group reported another aza-Friedel–Crafts reaction between 4,7-dihydroindole (55) and N-unsubstituted trifluoromethylated