Ring opening of photogenerated azetidinols as a strategy for the synthesis of aminodioxolanes

• Henning Maag,
• Daniel J. Lemcke and
• Johannes M. Wahl

Beilstein J. Org. Chem. 2024, 20, 1671–1676, doi:10.3762/bjoc.20.148

• promising starting point for pursuing this ring-opening attempt [41]. We hypothesized that this approach would allow the synthesis of 3-amino-1,2-diols, a motif commonly found in pharmaceuticals such as, e.g., β-blockers [42]. Our envisioned one-pot protocol features protonation of the azetidine from

Regio- and stereochemical stability induced by anomeric and gauche effects in difluorinated pyrrolidines

• Ana Flávia Candida Silva,
• Francisco A. Martins and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2024, 20, 1572–1579, doi:10.3762/bjoc.20.140

• stereochemical behavior. Consequently, various molecular properties, such as polarity, viscosity, and intra- and intermolecular interactions, are impacted by the C‒F bond. These features underlie the important role of selective fluorination in pharmaceuticals and agrochemicals development [1]. For instance

Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor

• Koichi Mitsudo,
• Atsushi Osaki,
• Haruka Inoue,
• Eisuke Sato,
• Naoki Shida,
• Mahito Atobe and
• Seiji Suga

Beilstein J. Org. Chem. 2024, 20, 1560–1571, doi:10.3762/bjoc.20.139

• pharmaceuticals, and the reductive syntheses of these heterocycles from pyridines and quinolines have been well studied [12]. Although these transformations have been studied intensively, such reductive reactions usually require harsh reaction conditions such as high reaction temperatures and high pressure of

Electrophotochemical metal-catalyzed synthesis of alkylnitriles from simple aliphatic carboxylic acids

• Yukang Wang,
• Yan Yao and
• Niankai Fu

Beilstein J. Org. Chem. 2024, 20, 1497–1503, doi:10.3762/bjoc.20.133

• synthesis; electrophotocatalysis; radical decarboxylation; Introduction Alkylnitriles and their derivatives are widely found in pharmaceuticals and biologically active compounds [1][2][3]. In addition, within the field of synthetic organic chemistry, nitriles are synthetically useful handles that can be

Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

• Lu Li,
• Na Li,
• Xiao-Tian Mo,
• Ming-Wei Yuan,
• Lin Jiang and
• Ming-Long Yuan

Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130

• ; primary amine; Introduction Aniline derivatives possessing arylmethyl substituents at the ortho position are an important class of amines. They have a wide variety of practical applications, ranging from anti-depression [1], being δ receptor stimulants in analgesic pharmaceuticals [2], to antioxidant

Challenge N- versus O-six-membered annulation: FeCl₃-catalyzed synthesis of heterocyclic N,O-aminals

• Giacomo Mari,
• Lucia De Crescentini,
• Gianfranco Favi,
• Fabio Mantellini,
• Diego Olivieri and
• Stefania Santeusanio

Beilstein J. Org. Chem. 2024, 20, 1412–1420, doi:10.3762/bjoc.20.123

• natural products, pharmaceuticals, and functional materials (Figure 1) [1][2][3]. It has been assessed that almost one-third of the best-selling therapeutics contains fused heterocyclic structures [4]. Among the N-heterocycles, imidazopyrazine structures [5][6], derived from amalgamation of privileged

• a new example of cyclic N,O-aminals and carbinolamine derivatives, an interesting class of organic compounds that are common structural motifs embedded within diverse biologically important natural products and pharmaceuticals [32][33][34][35][36][37]. On the other hand, the N,O-aminals are stable

Synthetic applications of the Cannizzaro reaction

• Bhaskar Chatterjee,
• Dhananjoy Mondal and
• Smritilekha Bera

Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120

• desymmetrization of crown ether dialdehydes (Scheme 17) [84]. Synthesis of natural products and pharmaceuticals Exploring intramolecular Cannizzaro reaction: The Cannizzaro reaction is a versatile synthetic tool with applications in the synthesis of natural products, fine chemicals, and pharmaceuticals. Its

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

• Mithu Roy,
• Bitan Sardar,
• Itu Mallick and
• Dipankar Srimani

Beilstein J. Org. Chem. 2024, 20, 1348–1375, doi:10.3762/bjoc.20.119

• the SET transfer process of PPh3 and quenching of photoexcited *[Ir(dF(CF3)ppy)2(bpy)]PF6 by PPh3. Fluorinated organic compounds are widely used in pharmaceuticals and pesticides. Therefore, it is crucial to diversify organic scaffolds by addition of fluorinated groups or by defluorination. In 2020

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

• are of substantial importance for the fine chemical industry, pharmaceuticals, agrochemicals, dyes, and natural products [25]. The synthesis of amine derivatives can be accomplished using many powerful techniques, including Buchwald–Hartwig and Ullmann cross-coupling reactions, hydroamination

A Diels–Alder probe for discovery of natural products containing furan moieties

• Alyssa S. Eggly,
• Namuunzul Otgontseren,
• Carson B. Roberts,
• Amir Y. Alwali,
• Haylie E. Hennigan and
• Elizabeth I. Parkinson

Beilstein J. Org. Chem. 2024, 20, 1001–1010, doi:10.3762/bjoc.20.88

• , Indiana 47906, United States 10.3762/bjoc.20.88 Abstract Natural products (NPs) are fantastic sources of inspiration for novel pharmaceuticals, oftentimes showing unique bioactivity against interesting targets. Specifically, NPs containing furan moieties show activity against a variety of diseases

• -based probes; Introduction To date, natural products and their derivatives have served as the foundation of many pharmaceuticals used today. These compounds have activity against various diseases such as cancer, bacterial infections, and fungal infections, as well as other indications [1]. Specifically

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

• ring. It was discovered in 1866 by Baeyer and Knop as the basic structure of the natural dye indigo, from which it is derived [1]. The indole ring is a common structural element found in both natural and synthetic products, including pharmaceuticals, agrochemicals, dyes, herbicides, and materials [2][3

Innovative synthesis of drug-like molecules using tetrazole as core building blocks

• Jingyao Li,
• Ajay L. Chandgude,
• Qiang Zheng and
• Alexander Dömling

Beilstein J. Org. Chem. 2024, 20, 950–958, doi:10.3762/bjoc.20.85

• blocks. Its implications for future drug discovery and development are profound, with the potential to streamline the process of creating new and effective pharmaceuticals. We hope the methodologies and findings described herein will inspire further research and innovation. As the exploration of the

(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

• well as the impact they have on the physiochemical and biological properties of pharmaceuticals and agrochemicals. Keywords: bioisosteres; drug discovery; meta-benzene; ortho-benzene; Introduction The logical and iterative modification of the structure of a drug candidate is a critical part of the

Confirmation of the stereochemistry of spiroviolene

• Yao Kong,
• Yuanning Liu,
• Kaibiao Wang,
• Tao Wang,
• Chen Wang,
• Ben Ai,
• Hongli Jia,
• Guohui Pan,
• Min Yin and
• Zhengren Xu

Beilstein J. Org. Chem. 2024, 20, 852–858, doi:10.3762/bjoc.20.77

• would be potentially applied as fragrances, pharmaceuticals etc. Until now, more than 80,000 terpenoid structures have been reported, which are found in all domains of life [1][2][3]. Despite their remarkable chemodiversity, the biosynthetic logic of terpenes is straightforward [4]. All terpenes are

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

• Martyn Jevric,
• Julian Klepp,
• Johannes Puschnig,
• Oscar Lamb,
• Christopher J. Sumby and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

• cyrene (2) allows for its use as a chiral solvent [4]. This product is emerging as a promising platform chemical for the construction of chiral small molecules for pharmaceuticals [5][6][7][8], as a building block for catalysts and auxiliaries [9][10][11], and in materials applications [12][13][14]. New

Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

• Victoria M. Alpatova,
• Evgeny G. Rys,
• Elena G. Kononova and
• Valentina A. Ol'shevskaya

Beilstein J. Org. Chem. 2024, 20, 767–776, doi:10.3762/bjoc.20.70

• compounds in drug development [34][35][36][37]. Owing to their stability, carboranes also may increase the in vivo stability and bioavailability of pharmaceuticals that might otherwise rapidly metabolize [38]. The functionalization of porphyrins with carborane clusters provides dual-action photo(radio

Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization

• Senze Qiao,
• Zhongyu Cheng and
• Fuzhuo Li

Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66

• polyketides; thioesterase; Introduction Nonribosomal peptides, polyketides, and their hybrids exhibit significant diversity and a broad spectrum of bioactivities [1][2][3]. Particularly, macrocycles from these three categories of natural products are vital resources for developing pharmaceuticals and drug

• candidates [4]. Many clinical pharmaceuticals with high market value, including the immunosuppressants cyclosporin and rapamycin, the antibiotics daptomycin and erythromycin, and the antitumor agent epothilone, all belong to these categories. Therefore, the rising demand for corresponding therapeutics

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

• dance process using a more electron-rich quinazoline. The commercially available 2,4-dichloro-6,7-dimethoxyquinazoline (7) was chosen for this purpose (Scheme 3). The common dimethoxy motif is also found in a variety of quinazoline-based pharmaceuticals [2][3][8][23]. We commenced our study with the

Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

• Alexander S. Hampton,
• David R. W. Hodgson,
• Graham McDougald,
• Linhua Wang and
• Graham Sandford

Beilstein J. Org. Chem. 2024, 20, 460–469, doi:10.3762/bjoc.20.41

• significant pharmaceuticals [lubiprostone (constipation), maraviroc (HIV), tafluproct (anti-inflamatory), ledipasvir (hepatitis-C)] and agrochemicals [isopyrazam (fungicide), riodipine (calcium channel blocker), primisulfuron-methyl (pesticide)] owe their enhanced bioactivity, in part, to the presence of

(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

• important synthons, which are widely used in agrochemicals, pharmaceuticals and other fields [24][25][26]. Fluoroorganic lithium and Grignard reagents have been obtained by the metalation reactions of organofluorine compounds containing bromine and iodine atoms with alkyllithium and Grignard reagents

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

• highest fungicidal activity [11]. Brønsted or Lewis acid catalysis – conventional synthetic methods The indole moiety is part of many natural products, agrochemicals, and pharmaceuticals. In medicinal chemistry, indole and its derivatives are considered important compounds, since they exhibit valuable

Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters

• Youlong Du,
• Haibo Mei,
• Ata Makarem,
• Ramin Javahershenas,
• Vadim A. Soloshonok and
• Jianlin Han

Beilstein J. Org. Chem. 2024, 20, 212–219, doi:10.3762/bjoc.20.21

• over 50% of agricultural chemicals contain at least one fluorine atom, among which architectural motifs containing fluorine and amino acid residues are a fast-growing segment of modern pharmaceuticals [10][11][12][13]. Fluoroalkyldiazo compounds belong to the most versatile and valuable reagents in

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

• Over the past decades, the 8-aminoquinoline motif that could be found in several natural products [1] has attracted significant attention for its widespread usage in pharmaceuticals [2], agrochemicals [3], and functional materials [4]. In particular, the aminoquinoline scaffold has emerged as an

Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates

• Xing Liu,
• Wenjing Shi,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1923–1932, doi:10.3762/bjoc.19.143

• motif, which is frequently found in natural products, bioactive molecules, and pharmaceuticals [1][2][3][4]. 1,2-Diazepine derivatives exhibit promising biological activities such as anticonvulsant, antibacterial, and antiproliferative effects [5][6][7][8][9][10][11][12][13]. Thus, the development of

• [22][23][24][25][26][27]. In addition, spirooxindole is also a privileged structural scaffold, which has been recognized as key structural unit in many bioactive natural products and pharmaceuticals with broad biological activities [28][29][30]. The development of elegant synthetic methodologies for

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

• of mild reaction conditions allowed for the application of this method in the modification of complex natural products or pharmaceuticals. Moreover, this photoinduced decarboxylative approach demonstrated the potential for broader utilization in the construction of diverse C(sp3)–N and C(sp3)–X bonds

• 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

• emphasized their significance in facilitating the synthesis of diverse compounds and paving the way for further advancements in the field of photocatalysis. The highly efficient construction of carbon–heteroatom (C–X) bonds is of significant importance in the fields of natural products, pharmaceuticals, and