Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts

• Nils Clamor,
• Mattis Damrath,
• Thomas J. Kuczmera,
• Daniel Duvinage and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 12–16, doi:10.3762/bjoc.20.2

• optimized conditions in hand, the substrate scope was explored. The variations of amides are outlined in Scheme 2. Switching from valeramide to benzamide as a substrate gave a more advantageous yield of 85% of 2b. We tested para-substituted benzamides in the reaction to further assess the diversity of

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

• Nedra Touj,
• François Mazars,
• Guillermo Zaragoza and
• Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

• weaker basicity and greater modularity, the related 1,2,4-triazol-5-ylidene derivatives D have been mainly employed in organocatalysis [6]. Besides these four types of N-heterocyclic carbenes (NHCs), other families of cyclic compounds have been actively pursued to further expand the diversity of singlet

Studying specificity in protein–glycosaminoglycan recognition with umbrella sampling

• Mateusz Marcisz,
• Sebastian Anila,
• Margrethe Gaardløs,
• Martin Zacharias and
• Sergey A. Samsonov

Beilstein J. Org. Chem. 2023, 19, 1933–1946, doi:10.3762/bjoc.19.144

• (HA), chondroitin sulfate (CS), dermatan sulfate (DS), and keratan sulfate (KS). The structural and functional diversities of GAGs are regulated by their sequence, size of the chains, degree of sulfation, and the ability to bind proteins [1][18][19][20][21]. This structural diversity of GAGs

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

• -tosylimino substrates (Table 2). To elucidate the product diversity and to follow the progress of the reaction, a series of mass spectral analysis of the reaction mixture of 4-fluorophenyl-substituted N-tosylimine 2d and tripyrrane 1 has been conducted at 0 °C. Samples were taken from the reaction medium at

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

• Inorgânica, Universidade do Estado do Rio de Janeiro (UERJ), Rio de Janeiro, 20950-000, Brazil 10.3762/bjoc.19.125 Abstract N-Acylhydrazones are a versatile class of organic compounds with a diversity of potential applications. In this study, two new structure-related 3,4,5-trimethoxybenzoyl-containing N

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

• emerged as a promising class of heterocyclic compounds for charge transport applications, owing to two crucial factors. Firstly, their structural diversity enables precise customization of molecular structures, allowing for fine-tuning of their properties and optimization of performance for specific

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

• Xiaofeng Zhang,
• Xiaoming Ma and
• Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

• -pot, and multistep reactions in the synthesis of heterocyclic compounds. The methods have advantages of using readily available starting materials, performing streamlined reactions, producing diverse product structures, and having high pot, atom, and step economy (PASE) [79][80][81] for the diversity

Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

• Aaron H. Shoemaker,
• Elizabeth A. Foker,
• Elena P. Uttaro,
• Sarah K. Beitel and
• Daniel R. Griffith

Beilstein J. Org. Chem. 2023, 19, 1615–1619, doi:10.3762/bjoc.19.118

• amine protection – can potentially take place in one pot). We have shown that this protocol can be applied to the synthesis of several analogs bearing different substitution patterns on the alkene. The structural diversity that can be readily obtained utilizing this chemistry underscores the versatility

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

• ; endophytic fungi; hemiketal polyketide; Introduction Endophytic fungi are organisms that reside almost ubiquitously inside the fresh healthy tissue of plants, and they may increase the resistance of the host tropical trees to survive in extreme conditions [1]. As the global diversity of endophytic fungi is

• its mutagenic properties, no further beneficial effects could be expected with them. However, the isolation of these compounds further expands the understanding of the metabolic diversity of Diaporthe. Conclusion The study of the new fungal strain, Diaporthe cameroonensis isolated from a Cameroonian

• medicinal plant, Trema guineensis led to the isolation of seventeen secondary metabolites, including two previously undescribed polyketides, namely 5,7-dimethylpseudopithonone (1) and 3,9-diacetylalternariol (2). This study has contributed further to our knowledge of the metabolic diversity within Diaporthe

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• berberine variants none are as easily modulated to rapidly install substituent diversity [31][43][44][45][46][47][48]. The method deemed most amenable to varying substituents involves substituted 2-bromo-1-aminonaphthalenes which are used in subsequent palladium cross-coupling reactions [45]. As such, our

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

• diversity, low cost, and versatile applications. This article overviews applications of NHC–Cu(I) complexes as catalysts in organic synthesis over the last 12 years, which include hydrosilylation reactions, conjugate addition, [3 + 2] cycloaddition, A3 reaction, boration and hydroboration, N–H and C(sp2)–H

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

• increasingly interesting [26][27]. In addition, as one-pot processes with a huge exploratory potential and diversity-oriented character, syntheses of indoles by multicomponent reactions have aroused considerable interest [28][29][30]. As part of our program to develop heterocycle syntheses based upon

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

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

• -phenacylideneoxindoles resulted in the two different novel dispirooxindole skeletons. Conclusion In summary, we have investigated the base-promoted multicomponent reaction of 3-methyleneoxindoles, dimedone, isatins and ammonium acetate. The reaction showed very interesting molecular diversity and diastereoselectivity

Five new sesquiterpenoids from agarwood of Aquilaria sinensis

• Hong Zhou,
• Xu-Yang Li,
• Hong-Bin Fang,
• He-Zhong Jiang and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 998–1007, doi:10.3762/bjoc.19.75

• more active than alcohols or acids. Conclusion In summary, five new eudesmane-type sesquiterpenes compounds (1–5) and five known compounds (6–10) were isolated from agarwood of A. sinensis. The discovery of these new compounds enriches the structural diversity and complexity of sesquiterpenes derived

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

• Xiu-Yu Chen,
• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

• acetylenedicarboxylates and 5,6-unsubstituted 1,4-dihydropyridines. The advantages of the reaction include the use of readily available starting materials, simple reaction conditions, without using any catalyst, high molecular diversity and atomic economy. Therefore, this reaction not only successfully developed

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

• structures developed recently, and, significantly, quinoline-3-sulfonamides are frequently encountered among such pharmacologically active hybrids (Figure 1b) [31][32][33][34]. Despite these facts, the diversity of quinoline-3-sulfonamides reported in the literature is limited due to obstacles in the

• illustrates unobstructed synthetic routes [72][73][74] to sulfonamides and sulfones 2, and the diversity of reagents used to prepare the target products 5. With the reaction conditions optimized, a series of novel tertiary quinoline-3-sulfonamides and quinoline-3-sulfones was successfully generated. In case

Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• designed NGs with tailor-made sizes and structures not only show planar conformation as fragments of graphene, but also evolved with a diversity of other shapes, including bowls [10], saddles [11][12][13], helixes [14][15], belts [16], rings [17], and their hybrid conformations such as helical bilayers [18

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

• Oleksandr V. Kolomiiets,
• Alexander V. Tsygankov,
• Maryna N. Kornet,
• Aleksander A. Brazhko,
• Vladimir I. Musatov and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

• ]pyridine and peptidomimetic moieties as pharmacophores with four diversity points introduced from readily available starting materials, including scaffold diversity. A small focused compound library of 20 Ugi products was prepared and screened for antibacterial activity. Keywords: Groebke–Blackburn

• , isocyanide multicomponent reactions are the way to prepare the necessary drugs "of tomorrow", and the possibility to combine such reactions gives a powerful method to rapidly and qualitatively expand the molecular diversity of biologically active compounds. The following possible combinations of IMCR have

• attention to another isocyanide multicomponent reaction – the Ugi reaction [21], which is one of the most important methods for the synthesis not only of peptidomimetics but also of other types of complex organic compounds. The presence of several diversity points and modification of starting components for

Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates

• Bastian Jakob,
• Nico Schneider,
• Luca Gengenbach and
• Georg Manolikakes

Beilstein J. Org. Chem. 2023, 19, 719–726, doi:10.3762/bjoc.19.52

• is an improved extension of our pervious protocol with arylboronic acids and provides access to enantioenriched α-arylglycines with an improved substrate diversity. It can be used for the direct synthesis of peptide-like building blocks, which can find direct application in the total synthesis of

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

• Cécile Alleman,
• Charlène Gadais,
• Laurent Legentil and
• François-Hugues Porée

Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23

• electrophilic desilylation agents which can be used, a large diversity of compounds can be accessible through this method [51][52]. Oxidation followed by desilylation with fluoride source produces the natural product poitediol (118) in overall good yield. 2 Nozaki–Hiyama–Kishi (NHK) cyclization The Nozaki

• there described in 17 to 20 steps [71][72]. The series was later extended via a revised and improved synthetic strategy toward the tricyclic [5-8-6]-pleuromutilin platform [74], allowing access to remarkable chemical diversity for pleuromutilin derivatives which were evaluated against a panel of Gram

An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides

• Shubham Sharma,
• Dharmender Singh,
• Sunit Kumar,
• Vaishali,
• Rahul Jamra,
• Naveen Banyal,
• Deepika,
• Chandi C. Malakar and
• Virender Singh

Beilstein J. Org. Chem. 2023, 19, 231–244, doi:10.3762/bjoc.19.22

• product isolation procedures [58][59][60][61][62]. In the recent past, our group also reported two methods towards the exploration of elemental sulfur for the formation of a sulfur-containing framework; however, these methods suffer from some drawbacks such as lack of diversity in starting substrate, need

Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris

• Angelique Ladwig,
• Markus Kroll and
• Stefan Schulz

Beilstein J. Org. Chem. 2023, 19, 167–175, doi:10.3762/bjoc.19.16

• by Taber and Gunn [13], using a Diels–Alder reaction as the key step, as it would allow access to several cadinol diastereomers, in line with a diversity-oriented synthetic plan. The synthesis began with enamine formation of isovaleraldehyde (1) and piperidine (2) to give enamine 3 that was reacted

• synthesis and characterization showed that this compound is the opposite enantiomer of 14 known from plants. This may indicate biosynthesis in the frog, but more work has to be performed to establish this. Furthermore, a short diversity-oriented synthesis based on the work of Taber and Gunn [13] enabled

Combining the best of both worlds: radical-based divergent total synthesis

• Kyriaki Gennaiou,
• Antonios Kelesidis,
• Maria Kourgiantaki and
• Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

• libraries. But how big should this chemical space be, so as to actually address our needs? A general consensus has emerged, supporting that “it is not actually the library size but rather the library diversity in terms of molecular structure and function which is fundamental for a successful drug discovery

• of divergent synthesis, common synthetic scaffolds, which are regarded as the points of diversity of the synthetic plan, lie at the heart of retrosynthetic design. Radical disconnections on common scaffolds, in accordance to the trends of green chemistry [11] and the concepts of atom economy [12] and

• ], psychotropic activity, and antiplasmodic activity [64]. Their structural diversity, consisting of different connectivities between piperidine and decalin domains, is especially difficult to be divergently accessed. Shenvi’s group recognized that an aromatic congener within this class could be traced back to

Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B

• Adwoa P. Nartey,
• Aboagye K. Dofuor,
• Kofi B. A. Owusu,
• Anil S. Camas,
• Hai Deng,
• Marcel Jaspars and
• Kwaku Kyeremeh

Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185

• point away from us resulting in an S configuration at C-39 as opposed to and R configuration. Subsequently, we propose the 3D structure of compound 1 as shown in Figure 5. Structurally, compound 1 belongs to the surfactin group of lipopeptides that exhibit huge chemical diversity through the alternate