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

• pathway to 2-alkoxyquinolines. a) Conventional drugs containing either a sulfonamide fragment or a quinoline core; b) biologically active quinoline sulfonamides. Knoevenagel condensation/aza-Wittig reaction cascade for the quinoline core formation. Key reaction steps during the synthesis of 3-sulfonyl

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

• –Bienaymé reaction; imidazo[1,2-a]pyridine; isocyanide; multicomponent reaction; peptidomimetic; Ugi reaction; Introduction The use of isocyanide multicomponent reactions (IMCR) to prepare biologically active compounds is one of the most promising tools in modern organic and medicinal chemistry. Therefore

• , 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

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

• slow release of the boronic acid from the aryltrifluoroborates and enables to enantioselectively synthesize of a broader variety of arylglycines, including a common building block for several biologically active compounds. Results and Discussion During our previous studies, we observed that the

• arylglycine-containing natural products. Currently, we are performing a detailed mechanistic study in order to overcome still existing limitations of the method and to provide a truly general approach to arylglycines with uniformly high yields and enantioselectivities. Biologically active molecules containing

Strategies in the synthesis of dibenzo[b,f]heteropines

• David I. H. Maier,
• Barend C. B. Bezuidenhoudt and
• Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

• dibenzo[b,f]heteropine template is an important feature in several commercial and lead active pharmaceutical ingredients, biologically active natural products, dyes in OLEDs and dye sensitive solar cells, and in certain ligands. This review provides an overview of the different synthetic strategies

Synthesis of medium and large phostams, phostones, and phostines

• Jiaxi Xu

Beilstein J. Org. Chem. 2023, 19, 687–699, doi:10.3762/bjoc.19.50

• /bjoc.19.50 Abstract Phostams, phostones, and phostines are a series of 1,2-azaphosphaheterocycle and 1,2-oxaphosphaheterocycle 2-oxide derivatives. They are phosphorus analogues of lactams and lactones and important biologically active compounds. The strategies for the synthesis of medium and large

• phostine derivatives, less attention has been paid to the synthesis of medium and large phostam, phostone, and phostine derivatives. They are also biologically active compounds, such as inhibitors of the human farnesyl pyrophosphate synthase [21][22], antitumor agents [23], and hapten for the production of

• chemical synthesis of macrocyclic lactones which are the key structural motifs in some biologically active compounds, 14-methyl-2-phenoxy-1-oxa-2-phosphacyclotetradecane 2-oxide (74) was synthesized as the hapten from phenyl hydrogen (12-hydroxytridecyl)phosphonate (73) via Mitsunobu reaction. The

Nucleophile-induced ring contraction in pyrrolo[2,1-c][1,4]benzothiazines: access to pyrrolo[2,1-b][1,3]benzothiazoles

• Ekaterina A. Lystsova,
• Maksim V. Dmitriev,
• Andrey N. Maslivets and
• Ekaterina E. Khramtsova

Beilstein J. Org. Chem. 2023, 19, 646–657, doi:10.3762/bjoc.19.46

• popular in medicinal chemistry and pharmacology as potential biologically active compounds. In particular, PBTAs were found to be promising inhibitors of centromere-associated protein E (CENP-E) (Figure 1), which is demanded for the development of targeted cancer therapy [1]. Furthermore, candidate

• proceeds through a different pathway from the one to pyrrolobenzothiazoles 3, 7, and 12. Biologically active PBTAs. Electrophilic centers in FPDs. Approaches to PBTAs via annulation of benzothiazoles. Approaches to PBTAs via annulation of o-aminothiophenols. Approach to PBTAs via radical substitution

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

• Péter Kisszékelyi and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

• successfully treated by artemisinin combination therapy (ACT). Artemisinin can be isolated from the Artemisia annua (sweet wormwood) plant. This sesquiterpene lactone bearing a peroxide is a prodrug of the biologically active dihydroartemisinin. In 2012, Zhu and Cook developed a gram-scale asymmetric total

Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups

• Ita Hajdin,
• Romana Pajkert,
• Mira Keßler,
• Jianlin Han,
• Haibo Mei and
• Gerd-Volker Röschenthaler

Beilstein J. Org. Chem. 2023, 19, 541–549, doi:10.3762/bjoc.19.39

• closely linked to the substitution pattern of the cyclopropane unit [2]. The prevalence of the biologically active cyclopropyl derivatives, either isolated from natural sources or rationally designed as pharmaceutical agents, has inspired chemists to find efficient methods for their preparation. Among

• fluorinated moieties within cyclopropyl rings imparts useful properties to these molecules. Thus, it is not surprising that difluoromethyl- or trifluoromethyl-substituted cyclopropanes serve as important structural motifs in many biologically active molecules as well as in special materials [4][5][6

Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones

• Manuel Pedrón,
• Jana Sendra,
• Irene Ginés,
• Tomás Tejero,
• Jose L. Vicario and
• Pedro Merino

Beilstein J. Org. Chem. 2023, 19, 477–486, doi:10.3762/bjoc.19.37

• ; Introduction Transannular cycloaddition reactions (TCRs) are useful for the synthesis of complex natural products and other biologically active compounds with high efficiency and stereoselectivity [1][2][3][4]. There are several different ways in which TCRs can occur, depending on the nature of the starting

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• biologically active molecules on CD-coated polymers used in chromatography [62]. PCA was used for the evaluation of the similarity/dissimilarity of some pesticides, especially fungicides and herbicides, using the effect of a water-soluble β-CD polymer on the apparent pesticide’s lipophilicity [63]. Also

• above-mentioned biologically active compounds and its content varies in complexes at 1:1:1 and 3:1:1 molar ratios. In the FTIR spectra of β-CD as a host, besides the wavenumbers corresponding to characteristic bands of β-CD, their intensities are relevant for the discrimination of the ternary complexes

• thermal/oxidative stability of ternary complexes is similar to β-CD hydrate, as was evaluated by TG and DSC. Moreover, the formation of the molecular inclusion complexes is supported by thermal analysis (partial replacing of the hydration water by biologically active molecules and disappearance of the DSC

Sequential hydrozirconation/Pd-catalyzed cross coupling of acyl chlorides towards conjugated (2E,4E)-dienones

• Benedikt Kolb,
• Daniela Silva dos Santos,
• Sanja Krause,
• Anna Zens and
• Sabine Laschat

Beilstein J. Org. Chem. 2023, 19, 176–185, doi:10.3762/bjoc.19.17

• by a hydrozirconation/acylation sequence. Examples of biologically active compounds with (2Ε,4E)-unsaturated ketone units. Selected examples for the synthesis of conjugated dienones from the literature [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21]. Previous work of hydrozirconations

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

• [81]. Miglustat is a biologically active analog of the natural product deoxynojirimycin, and its enantiomer also shows a promising profile in early biological activity studies. In future applications of 1,4-dithiane or -dithiin building blocks, the recently described zincation protocol by Knochel and

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

• Christian Schumacher,
• Jas S. Ward,
• Kari Rissanen,
• Carsten Bolm and
• Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

• -azidocholest-5-ene (5) in high yield. The same product was recently obtained by direct dehydroxyazidation of cholesterol upon treatment with N-acetyl azidobenziodazolone (ABZ) and PPh3 in THF [19], Table 1. While synthesizing new potential biologically active probes with cholesterol scaffolds in the Port Said

NaI/PPh₃-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles

• Dan Liu,
• Yue Zhao and
• Frederic W. Patureau

Beilstein J. Org. Chem. 2023, 19, 57–65, doi:10.3762/bjoc.19.5

• investigations revealed that this cyclization reaction proceeds via a cascade radical pathway. We expect these results to encourage the further development of NaI/PPh3-catalyzed and related synthetic methods. Representative natural products and biologically active molecules containing an oxindole moiety [7][8][9

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

• environment and their ability to be biologically active across different species. Keywords: Leishmania; lipopeptides; molecular networking; sequence tagging; trypanosomes; Introduction Microbes belonging to the genus Bacillus are mainly Gram-positive with only a few examples characterized as Gram-negative

• , since it promotes the ability of these ubiquitous cyclic lipopeptides to be effective and biologically active across different organism types. Hence, cyclic lipopeptides have been previously reported to possess antimicrobial, antifungal, antiviral, anticancer, and cytotoxic biological activities, but

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

• proceeds with the preservation of stereocenters. It is tolerant to a wide range of functional groups, which makes it compatible with natural substances and complex biologically active compounds. TEMPO and its derivatives are successfully used as electrocatalysts. 4-Acetamido-2,2,6,6-tetramethylpiperidin-1

A novel bis-triazole scaffold accessed via two tandem [3 + 2] cycloaddition events including an uncatalyzed, room temperature azide–alkyne click reaction

• Ksenia Malkova,
• Andrey Bubyrev,
• Vasilisa Krivovicheva,
• Dmitry Dar’in,
• Alexander Bunev and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1636–1641, doi:10.3762/bjoc.18.175

• -tetrahydro-4H-[1,2,3]triazolo[1,5-d][1,4]diazepine (A) and 5,6,7,8-tetrahydro-4H-[1,2,3]triazolo[1,5-a][1,4]diazepine (B) scaffolds are of high medicinal importance, as evident from the literature. The range of biologically active compounds based on these two closely related scaffolds (both incorporated as

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• natural product chemists have shifted their attention to marine-derived microorganisms such as bacteria and fungi over the past 10 years [2], sponges continue to be a source of novel and biologically active metabolites and remain an important taxonomic phylum for the discovery of new and bioactive natural

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

• and they are important building blocks in the synthesis as well as substructures of a number of biologically active natural and unnatural products [1][2][3][4][5][6][7][8]. Aziridines are valuable synthetic intermediates for the preparation of structurally complex molecules because of their

• aziridine-fused derivatives. Some biologically active aziridine-bearing compounds 1, 2 and aminocyclitol 3. Synthesis of dimesylate 8. Synthesis of aminocyclooctanetriol 13. Synthesis of aziridinecyclooctanediol 16. Supporting Information Supporting Information File 344: Experimental section, 1H and 13C

A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4 + 1] annulation reaction of fused 1H-pyrrole-2,3-diones with diazooxindoles

• Pavel A. Topanov,
• Anna A. Maslivets,
• Maksim V. Dmitriev,
• Irina V. Mashevskaya,
• Yurii V. Shklyaev and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2022, 18, 1532–1538, doi:10.3762/bjoc.18.162

• first example of a catalyst-free formal [4 + 1] cycloaddition reaction of enones and complex diazo compounds. The synthesized compounds 3 have a pharmaceutically interesting fungal metabolites-like structure with a spiro[dihydrofuran-2,3'-oxindole] moiety. Selected examples of biologically active

One-pot synthesis of 2-arylated and 2-alkylated benzoxazoles and benzimidazoles based on triphenylbismuth dichloride-promoted desulfurization of thioamides

• Arisu Koyanagi,
• Yuki Murata,
• Shiori Hayakawa,
• Mio Matsumura and
• Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 1479–1487, doi:10.3762/bjoc.18.155

• benzazole derivatives is of interest as they are biologically active substances. Herein, a simple method for the synthesis of 2-aryl- and 2-alkyl-substituted benzazoles is described. The reaction of 2-aminophenols with thioamides at 60 °C in the presence of triphenylbismuth dichloride in 1,2-dichloroethane

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• for simplified analogues, hopefully retaining the function of the biologically active compound, is very relevant when considering its potential in medicinal chemistry [279][280][281]. Start from leads obtained from previous research A second research direction for chemists is to start from previously

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

• Péter Kisszékelyi,
• Tibor Peňaška,
• Klára Stankovianska,
• Mária Mečiarová and
• Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 1195–1202, doi:10.3762/bjoc.18.124

• protease inhibitors. Given the potential usefulness of the benzothiazine scaffold as a biologically active unit and the peptidomimetic nature of many SARS-CoV-2 protease inhibitors [35], we decided to investigate the viability of attaching a 4H-benzo[b][1,4]thiazine-3-carboxylic core to amino acids

Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Nguyen Ngoc Tri,
• Luc Van Meervelt,
• Nguyen Tien Trung and
• Wim Dehaen

Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118

• to obtain structurally complicated and biologically active products containing substantial portions of all starting materials [27]. Recently, polysubstituted 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones have been synthesized via eco-friendly multicomponent reactions of aromatic aldehydes, amines, and

Electrochemical formal homocoupling of sec-alcohols

• Kosuke Yamamoto,
• Kazuhisa Arita,
• Masashi Shiota,
• Masami Kuriyama and
• Osamu Onomura

Beilstein J. Org. Chem. 2022, 18, 1062–1069, doi:10.3762/bjoc.18.108

• ]. Such scaffolds are widely utilized as versatile building blocks in the synthesis of biologically active compounds [3][4][5][6][7], chiral auxiliaries [8][9], and chiral ligands [10][11][12][13]. Traditional pinacol coupling reactions are performed with a stoichiometric or even excess amount of low