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Search for "intramolecular" in Full Text gives 1394 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

An Fe(II)-catalyzed synthesis of spiro[indoline-3,2'-pyrrolidine] derivatives

  • Elizaveta V. Gradova,
  • Nikita A. Ozhegov,
  • Roman O. Shcherbakov,
  • Alexander G. Tkachenko,
  • Larisa Y. Nesterova,
  • Elena Y. Mendogralo and
  • Maxim G. Uchuskin

Beilstein J. Org. Chem. 2025, 21, 2383–2388, doi:10.3762/bjoc.21.183

Graphical Abstract
  • . For instance, an intramolecular SN2-type cyclization of β-3-indolyl ketone oximes using MsCl and Et₃N affords spiro[indoline-3,2'-pyrrolidines] (Scheme 1, path f) [13]. A subsequent Cu-catalyzed spirocyclization of β-3-indolyl ketone oxime acetates was developed. This process involves homolytic N–O
  • bond cleavage to generate an N-imidoyl radical intermediate that undergoes intramolecular cyclization to yield the spirocyclic product (Scheme 1, path g) [14]. Notably, iron is known to exhibit similar behavior in single-electron transfer (SET) processes [15][16][17]. In fact, we previously
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Published 05 Nov 2025

Synthetic study toward vibralactone

  • Liang Shi,
  • Jiayi Song,
  • Yiqing Li,
  • Jia-Chen Li,
  • Shuqi Li,
  • Li Ren,
  • Zhi-Yun Liu and
  • Hong-Dong Hao

Beilstein J. Org. Chem. 2025, 21, 2376–2382, doi:10.3762/bjoc.21.182

Graphical Abstract
  • vibralactone, a potent inhibitor of pancreatic lipase, is reported. The synthesis of the challenging all-carbon quaternary center within the cyclopentene ring was achieved through intramolecular alkylidene carbene C–H insertion. Keywords: alkylidene carbene; C–H insertion; total synthesis; vibralactone
  • and ClpP2 and it could be utilized as a probe to study the activity and structure of the ClpP1P2 complex from Listeria monocytogenes [25]. Previously, Snider and co-worker reported the first total synthesis of vibralactone (6) employing Birch reductive alkylation, intramolecular aldol reaction and
  • ketal moiety was removed and the resulting intermediate underwent Wittig olefination to yield vinyl chloride 20. Subsequent hydrolysis and intramolecular esterification furnished intermediate 21, which was then subjected to C–H insertion [42][43][44]. To our disappointment, this ring closure still did
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Published 04 Nov 2025

Rotaxanes with integrated photoswitches: design principles, functional behavior, and emerging applications

  • Jullyane Emi Matsushima,
  • Khushbu,
  • Zuliah Abdulsalam,
  • Udyogi Navodya Kulathilaka Conthagamage and
  • Víctor García-López

Beilstein J. Org. Chem. 2025, 21, 2345–2366, doi:10.3762/bjoc.21.179

Graphical Abstract
  • biomembrane-compatible rotaxanes are promising for designing artificial ion transporters to address channelopathies. Song and co-workers developed a system in which the azobenzene in the axle is encapsulated within a chiral β-cyclodextrin, affording a self-locked [1]rotaxane [15]. The intramolecular host
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Published 31 Oct 2025

Comparative analysis of complanadine A total syntheses

  • Reem Al-Ahmad and
  • Mingji Dai

Beilstein J. Org. Chem. 2025, 21, 2334–2344, doi:10.3762/bjoc.21.178

Graphical Abstract
  • these lycopodium alkaloids [12]. Lysine could be advanced to 4-(2-piperidyl)acetoacetate (7) and pelletierine (8), which would react with each other to deliver phlegmarine (9). Double oxidation of 9 would give 10 for a subsequent intramolecular Mannich-type cyclization to forge the C4–C13 bond and
  • intramolecular cyclization to afford alkyne–nitrile 19 for the first [2 + 2 + 2] cycloaddition with bis(trimethylsilyl)butadiyne (20). This transformation proceeded smoothly under thermal conditions with CpCo(CO)2 to afford 21 as the major regioisomer (rr = 25:1) [22]. Removal of the two TMS groups and
  • underwent ketone release and amine-ketone condensation to form iminium ion 27. Under the same acidic conditions, enamide 26 underwent hydrolysis and tautomerization to form enol 28. Conjugate addition of enol 28 to iminium ion 27 gave 29 for the subsequent intramolecular Mannich cyclization to deliver 30
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Published 30 Oct 2025

Recent advances in Norrish–Yang cyclization and dicarbonyl photoredox reactions for natural product synthesis

  • Peng-Xi Luo,
  • Jin-Xuan Yang,
  • Shao-Min Fu and
  • Bo Liu

Beilstein J. Org. Chem. 2025, 21, 2315–2333, doi:10.3762/bjoc.21.177

Graphical Abstract
  • singlet state, which undergoes intersystem crossing (ISC) to form the excited triplet state B. An intramolecular 1,5-hydrogen atom transfer (HAT) then ensues, producing the 1,4-diradical C, which can be converted into diverse products such as alkenes and enols (Scheme 1a). Notably, the 1,4-diradical
  • ]. In contrast to the direct radical coupling in Norrish–Yang cyclization, the distal biradical F, formed from quinone E through a pathway analogous to that of C in the photoredox process, subsequently undergoes intramolecular SET to generate a zwitterion G. This intermediate is then trapped by the
  • . This transformation proceeded via sequential regio- and stereoselective Norrish−Yang annulation, followed by intramolecular lactonization mediated by 12a. Notably, when the ethyl ester in 12 was replaced with a methyl group to form 14 with R = Et (Scheme 3), photoreaction of 14 led to 15 in 95% yield
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Published 30 Oct 2025

Enantioselective radical chemistry: a bright future ahead

  • Anna C. Renner,
  • Sagar S. Thorat,
  • Hariharaputhiran Subramanian and
  • Mukund P. Sibi

Beilstein J. Org. Chem. 2025, 21, 2283–2296, doi:10.3762/bjoc.21.174

Graphical Abstract
  • transferred to the radical. Important processes of this kind are hydrogen atom transfer (HAT) and halogen atom abstraction. An intramolecular group transfer reaction can result in the net migration of a functional group. Addition of a radical to a π-bond (carbon–carbon or carbon–heteroatom) is another common
  • radical reaction and can occur either intermolecularly or as an intramolecular cyclization reaction. Radical coupling or combination is a possible transformation that is more feasible when one of the radicals is relatively stabilized (a persistent radical). Trapping a radical with a transition metal is
  • mechanism involving single-electron oxidation of an enamine intermediate, addition of the resulting radical to the olefin, single-electron oxidation of the adduct to form a carbocationic intermediate, and intramolecular nucleophilic attack on the carbocation to form the pyrrolidine ring. The reaction
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Published 28 Oct 2025

Pathway economy in cyclization of 1,n-enynes

  • Hezhen Han,
  • Wenjie Mao,
  • Bin Lin,
  • Maosheng Cheng,
  • Lu Yang and
  • Yongxiang Liu

Beilstein J. Org. Chem. 2025, 21, 2260–2282, doi:10.3762/bjoc.21.173

Graphical Abstract
  • radical initiated intramolecular cascade cyclization of 1,n-enynes to provide structurally diverse heterocycles (Scheme 4) [11]. Solvent selection dictated divergent reaction pathways under I2/TBHP oxidation. When an acetonitrile/water mixed solvent was used, iodine radical addition to the alkyne
  • ligand-controlled Au(I)-catalyzed intramolecular hydroarylation overcame key challenges of poor regioselectivity and limited applicability to electron-deficient substrates. In 2018, a gold-catalyzed divergent cyclization to access heteropolycyclic frameworks was reported by the Shi group (Scheme 18) [26
  • constraints promoted intramolecular Friedel–Crafts cyclization via intermediate 84 to form spiro-polycycle 86 (Scheme 18, path b). The ligand-dependent gold(I)-catalyzed cyclization provided modular access to therapeutically significant fused polycyclic heterocyclic scaffolds via regioselective ring expansion
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Published 27 Oct 2025

Research towards selective inhibition of the CLK3 kinase

  • Vinay Kumar Singh,
  • Frédéric Justaud,
  • Dabbugoddu Brahmaiah,
  • Nangunoori Sampath Kumar,
  • Blandine Baratte,
  • Thomas Robert,
  • Stéphane Bach,
  • Chada Raji Reddy,
  • Nicolas Levoin and
  • René L. Grée

Beilstein J. Org. Chem. 2025, 21, 2250–2259, doi:10.3762/bjoc.21.172

Graphical Abstract
  • decided to prepare also the same molecules with hydrogen instead of the chlorine in meta position of the anilino group. Our previous work on DB18 suggested indeed that the chlorine atom is implicated in intramolecular halogen–π interaction, ending in a conformational constraint and ligand rigidity [24
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Published 24 Oct 2025

A m-quaterphenyl probe for absolute configurational assignments of primary and secondary amines

  • Yuka Takeuchi,
  • Mutsumi Kobayashi,
  • Yuuka Gotoh,
  • Mari Ikeda,
  • Yoichi Habata,
  • Tomohiko Shirai and
  • Shunsuke Kuwahara

Beilstein J. Org. Chem. 2025, 21, 2211–2219, doi:10.3762/bjoc.21.168

Graphical Abstract
  • group are planar, while the methyl group is more sterically demanding in three-dimensional space, this conformational model is supported (Table S1 in Supporting Information File 1). Although intramolecular electronic interactions should also be considered, the twist of the phenyl chromophores can be
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Published 20 Oct 2025

Synthesis of triazolo- and tetrazolo-fused 1,4-benzodiazepines via one-pot Ugi–azide and Cu-free click reactions

  • Xiaoming Ma,
  • Zijie Gao,
  • Jiawei Niu,
  • Wentao Shao,
  • Shenghu Yan,
  • Sai Zhang and
  • Wei Zhang

Beilstein J. Org. Chem. 2025, 21, 2202–2210, doi:10.3762/bjoc.21.167

Graphical Abstract
  • /bjoc.21.167 Abstract A one-pot Ugi–azide reaction followed by intramolecular Cu-free azide–alkyne cycloaddition generates a polycyclic scaffold 7 bearing polycyclic triazole, tetrazole, and benzodiazepine rings. This method could be extended for obtaining a more complicated scaffold 8 containing a
  • . After evaporation of the solvent MeOH, the residue was redissolved in 2 mL of MeCN and heated at 130 °C for 2 h in a sealed vial to give product 7a in 90% yield after purification via Cu-free intramolecular click reaction (Scheme 3C) [46]. This Cu-free intramolecular cyclization provides key practical
  • , the reaction of 0.2 mmol each of 1a and 2a led to the formation of Int-I which then reacted with 0.2 mmol each of 9 and 4 to form 1,5-DS-T 5b which consequently underwent lactamization to form 6a followed by an intramolecular click reaction to afford highly condensed polycyclic product 8a in 92
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Published 17 Oct 2025

Electrochemical cyclization of alkynes to construct five-membered nitrogen-heterocyclic rings

  • Lifen Peng,
  • Ting Wang,
  • Zhiwen Yuan,
  • Bin Li,
  • Zilong Tang,
  • Xirong Liu,
  • Hui Li,
  • Guofang Jiang,
  • Chunling Zeng,
  • Henry N. C. Wong and
  • Xiao-Shui Peng

Beilstein J. Org. Chem. 2025, 21, 2173–2201, doi:10.3762/bjoc.21.166

Graphical Abstract
  • characteristics. Electrochemical construction of five-membered rings from alkynes attracted increasing attention due to the notable advantages of electrochemical transformations and facile access of alkynes. Indole skeletons were constructed successfully through electrochemical intramolecular coupling of ethynyl
  • ]. Besides, electrochemical cyclization of alkynes is also an important access towards indoles. In 2016, Xu reported the electrochemical intramolecular coupling of urea derivatives to form substituted indoles (Scheme 1) [162]. Using [Cp2Fe] (5 mol %) as the redox catalyst, the intramolecular coupling of
  • , A proceeded an intramolecular nucleophilic attack by N and deprotonation to finish 15a. The other possible pathway was radical route, in which PhSe• dimerized to reform 14a or added to C≡C bond in 13a to afford B. The subsequent anodic oxidation of B gave C, which underwent nucleophilic cyclization
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Published 16 Oct 2025

C2 to C6 biobased carbonyl platforms for fine chemistry

  • Jingjing Jiang,
  • Muhammad Noman Haider Tariq,
  • Florence Popowycz,
  • Yanlong Gu and
  • Yves Queneau

Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165

Graphical Abstract
  • –Crafts alkylation products were then converted into an intermediate tryptaldehyde that underwent intramolecular olefination to form the targeted product [34]. Glycolic acid (GA) The growing impact of fossil fuel consumption has heightened the need for advancing renewable energy technologies. One
  • and hydroxyketones. The catalyst could be recovered and reused five times without decreasing its selectivity and activity. Mechanistically, the reaction involves a Heyns-type rearrangement and subsequent intramolecular olefination (Scheme 22) [96]. Arandia et al. reported the application of the
  • reaction involves the enantioselective organocatalyzed transfer of boronic acid to HFO followed by an intramolecular diastereoselective Passerini-type reaction. Varying the boronic acid enabled to reach high yields (Scheme 39) [124]. The tautomeric transformation of HFO to cis-β-formylacrylic acid was
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Published 15 Oct 2025
Graphical Abstract
  • steps, respectively. As shown in Scheme 6 [58], the Cu-catalyzed 1,4-conjugated addition of 71 [59] with vinylMgBr followed by intramolecular Claisen condensation furnished bicyclic diketone 72 on a gram scale. Notably, for such a bicyclic substrate, it is quite challenging to achieve desymmetric
  • intramolecular Diels–Alder reaction generated tricyclo[3.2.1.02,7]-octene 113. A two-step transformation including HAT hydrogenation and acetal C–H oxidation with RuCl3/NaIO4, 113 was converted into ketoester 114. The TFA-mediated C13–C15 bond cleavage of 114 proceed smoothly to give ring-opening products, which
  • transformations of 121 generated bromodiene 122. Next, the metal–halogen exchange/intermolecular addition of 122 with aldehyde (+)-123 and in situ PtCl2-promoted hydrolysis and hydration gave tricyclic product 124. The BnMe3NOH-mediated intramolecular Michael/aldol cascade reaction of 124 constructed the C/D
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Published 14 Oct 2025

Bioinspired total syntheses of natural products: a personal adventure

  • Zhengyi Qin,
  • Yuting Yang,
  • Nuran Yan,
  • Xinyu Liang,
  • Zhiyu Zhang,
  • Yaxuan Duan,
  • Huilin Li and
  • Xuegong She

Beilstein J. Org. Chem. 2025, 21, 2048–2061, doi:10.3762/bjoc.21.160

Graphical Abstract
  • . By analyzing the structure, we supposed that there might exist an inversed pathway in which tabertinggine could be converted into the ibogamine aza-[2.2.2] bridged skeleton through intramolecular aza-Michael addition of the enone moiety to form the C21–N bond and a subsequent C16–N bond cleavage
  • might undergo benzylic oxidations and intramolecular dehydration to access a diaryltetrahydrofuran (THF) skeleton. Then, oxidation of one aryl group through phenol oxidation would generate a putative cyclohexadienone intermediate to be further captured by the other phenol to access eupodienone through a
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Published 09 Oct 2025

α-Ketoglutaric acid in Ugi reactions and Ugi/aza-Wittig tandem reactions

  • Vladyslav O. Honcharov,
  • Yana I. Sakhno,
  • Olena H. Shvets,
  • Vyacheslav E. Saraev,
  • Svitlana V. Shishkina,
  • Tetyana V. Shcherbakova and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2021–2029, doi:10.3762/bjoc.21.157

Graphical Abstract
  • in 33–93% yields (Scheme 3; Table 3). According to the literature [31][53], this reaction proceeds through the formation of an iminophosphorane intermediate (Scheme 3), the product of a Staudinger reaction, which, however, was not isolated because it easily undergoes intramolecular cyclization on a
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Published 07 Oct 2025

Aryl iodane-induced cascade arylation–1,2-silyl shift–heterocyclization of propargylsilanes under copper catalysis

  • Rasma Kroņkalne,
  • Rūdolfs Beļaunieks,
  • Armands Sebris,
  • Anatoly Mishnev and
  • Māris Turks

Beilstein J. Org. Chem. 2025, 21, 1984–1994, doi:10.3762/bjoc.21.154

Graphical Abstract
  • rearrangements via the 1,2-silyl shift, enabled by the β-cation-stabilizing properties of silyl groups [19][20]. This phenomenon has been successfully employed in 1,3-difunctionalization events in both intermolecular [21] and intramolecular fashion [22] (Scheme 1B). Thus far such propargylsilane rearrangements
  • likely formed via the allylic cation intermediate Int-1 (Scheme 2), from where on two competing mechanistic pathways are possible. Deprotonation of the β-H and reductive elimination affords diene 10. Alternatively, an intramolecular cyclization leads to silylindenes 11. We were interested to see whether
  • described by us recently, among other possible transformations [21][22]. Interestingly, the addition of O-nucleophiles to form 1,3-carbofunctionalization products, can only be achieved in an intramolecular fashion. In the presence of an excess (5 equiv) of external an O-nucleophile R–OX (alcohol, carboxylic
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Published 26 Sep 2025

Asymmetric total synthesis of tricyclic prostaglandin D2 metabolite methyl ester via oxidative radical cyclization

  • Miao Xiao,
  • Liuyang Pu,
  • Qiaoli Shang,
  • Lei Zhu and
  • Jun Huang

Beilstein J. Org. Chem. 2025, 21, 1964–1972, doi:10.3762/bjoc.21.152

Graphical Abstract
  • proposed mechanism to 21 involved the formation of an electron-deficient, resonance-stabilized radical species, followed by intramolecular alkylation of the unactivated alkene to generate radical 29 via a diastereoselective 5-exo-trig cyclization step. Radical intermediate 29 was trapped by 2,4,6
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Published 24 Sep 2025

Enantioselective desymmetrization strategy of prochiral 1,3-diols in natural product synthesis

  • Lihua Wei,
  • Rui Yang,
  • Zhifeng Shi and
  • Zhiqiang Ma

Beilstein J. Org. Chem. 2025, 21, 1932–1963, doi:10.3762/bjoc.21.151

Graphical Abstract
  • intramolecular cyclization of 16 generated benzofuran 17 in 83% yield. After protecting the phenolic hydroxy group of 17, cross-metathesis (CM) with allylic alcohol 18 catalyzed by 13 furnished intermediate 19. Desilylation of 19 produced heliannuol G (20) and heliannuol H (21), with the structure of 21
  • in intramolecular [7-exo] and [8-endo] cyclization, furnishing the 7-membered cyclic ether 40 and 8-membered cyclic ether 41, respectively. Finally, MOM deprotection produced (−)-heliannuol D (42) and (+)-heliannuol A (43). In 2002, Chênevert and co-workers completed the total synthesis of (S)-α
  • suppress potential intramolecular acyl migration. To further improve the optical purity of monoester 53, a Pseudomonas aeruginosa lipase-mediated kinetic resolution was performed with ethoxyvinyl butyrate 54, ultimately achieving monoester 53 with 97% ee in 60% yield and the diester 53a. With
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Published 18 Sep 2025

Stereoselective electrochemical intramolecular imino-pinacol reaction: a straightforward entry to enantiopure piperazines

  • Margherita Gazzotti,
  • Fabrizio Medici,
  • Valerio Chiroli,
  • Laura Raimondi,
  • Sergio Rossi and
  • Maurizio Benaglia

Beilstein J. Org. Chem. 2025, 21, 1897–1908, doi:10.3762/bjoc.21.147

Graphical Abstract
  • Margherita Gazzotti Fabrizio Medici Valerio Chiroli Laura Raimondi Sergio Rossi Maurizio Benaglia Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, IT-20133 Milano, Italy 10.3762/bjoc.21.147 Abstract The stereoselective electroreductive intramolecular coupling of chiral
  • for different N-benzyl benzaldimines in moderate to good yields. In 1991, Shono’s research group described the electroreductive intramolecular coupling of aromatic diimines, carried out in DMF in the presence of methanesulfonic acid in a divided cell equipped with a lead cathode, a carbon rod anode
  • , and a ceramic diaphragm [44]. This method was found to be effective for synthesizing trans-2,3-diarylpiperazines through the intramolecular reductive coupling of 1,2-diimines and seven- and eight-membered heterocycles which were obtained in moderate to good yields via the cyclization of 1,3- and 1,4
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Published 12 Sep 2025

Preparation of spirocyclic oxindoles by cyclisation of an oxime to a nitrone and dipolar cycloaddition

  • Beth L. Ritchie,
  • Alexandra Longcake and
  • Iain Coldham

Beilstein J. Org. Chem. 2025, 21, 1890–1896, doi:10.3762/bjoc.21.146

Graphical Abstract
  • -containing compounds makes use of intramolecular 1,3-dipolar cycloaddition reactions [15], including examples with nitrone ylides [16][17][18][19][20][21][22]. Our research group has exploited this approach for the synthesis of alkaloids such as myrioxazine A and aspidospermidine [23][24]. With a nitrone 1,3
  • approach. This generates the desired spirooxindole connected to a bicyclic amine, with functionality related to the natural products. It is likely that unactivated dipolarophiles could be successful in related intramolecular cycloadditions [18]. Hence this approach could allow access the spirooxindole and
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Published 11 Sep 2025

Chiral phosphoric acid-catalyzed asymmetric synthesis of helically chiral, planarly chiral and inherently chiral molecules

  • Wei Liu and
  • Xiaoyu Yang

Beilstein J. Org. Chem. 2025, 21, 1864–1889, doi:10.3762/bjoc.21.145

Graphical Abstract
  • planarly chiral paracyclophanes [39]. Commenced with a macrocyclization precursor 36 featuring both a hydroxy group and an allenamide moiety, the CPA-catalyzed asymmetric intramolecular addition led to the successful construction of planarly chiral macrocycles 37 (Scheme 10). This method demonstrated broad
  • acid substrates 43 which, upon treatment with ynamide 44, yielded the vinyl acetate intermediate INT-A (Scheme 13). Subsequently, the one-pot CPA-catalyzed intramolecular esterification of this intermediate afforded the planarly chiral macrocycles 45 with good yield and high enantioselectivity
  • macrocyclization strategy [53]. Starting from the linear precursor 60 bearing two triazine moieties, the intramolecular SNAr reaction catalyzed by CPA 13 (30 mol %) led to macrocyclization, which produced the inherently chiral N3,O-calix[2]arene[2]triazines 61 with high enantioselectivity, albeit in moderate yield
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Published 10 Sep 2025

Photoswitches beyond azobenzene: a beginner’s guide

  • Michela Marcon,
  • Christoph Haag and
  • Burkhard König

Beilstein J. Org. Chem. 2025, 21, 1808–1853, doi:10.3762/bjoc.21.143

Graphical Abstract
  • the time within 50% of the metastable isomer is thermally converted to the stable one [3]. It depends on the photoswitch class, solvent, substitution pattern, and temperature. For some photoswitch classes, proton exchange and intramolecular hydrogen bonds are known to accelerate the thermal relaxation
  • bromide 47, followed by Fmoc protection of 56, Boc deprotection of 57, reduction of the NO2 group to NO and intramolecular Mills coupling to form 35h. Removal of the Fmoc protecting group under basic conditions affords the unsubstituted product 35d which, after N-alkylation or acylation affords the
  • Wiedbrauk and Dube [93]. Double-bond-substituted hemithioindigos 93 are synthesised by functionalising 87 with an aliphatic or aromatic 88 and subsequent intramolecular aldol reaction to 90. Treatment with SOCl2 and with the aromatic nucleophile or a cross-coupling partner of choice affords 93 (Scheme 27
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Published 08 Sep 2025

Fe-catalyzed efficient synthesis of 2,4- and 4-substituted quinolines via C(sp2)–C(sp2) bond scission of styrenes

  • Prafull A. Jagtap,
  • Manish M. Petkar,
  • Vaishnavi R. Sawant and
  • Bhalchandra M. Bhanage

Beilstein J. Org. Chem. 2025, 21, 1799–1807, doi:10.3762/bjoc.21.142

Graphical Abstract
  • cycloaddition, tandem annulation, intramolecular cyclization, and cross-coupling reactions are commonly employed under thermal conditions, utilizing metal catalysts based on Pd, Ru, Au, Cu, and Fe to access a wide array of substituted quinoline frameworks [29][30][31][32][33][34][35][36][37][38]. Conversely, in
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Published 05 Sep 2025

Unique halogen–π association detected in single crystals of C–N atropisomeric N-(2-halophenyl)quinolin-2-one derivatives and the thione analogue

  • Mai Uchibori,
  • Nanami Murate,
  • Kanako Shima,
  • Tatsunori Sakagami,
  • Ko Kanehisa,
  • Gary James Richards,
  • Akiko Hori and
  • Osamu Kitagawa

Beilstein J. Org. Chem. 2025, 21, 1748–1756, doi:10.3762/bjoc.21.138

Graphical Abstract
  • bromine atom and the π*-orbital of the quinoline-2-thione ring, rather than through π-type halogen bonding. Various C–N atropisomeric compounds and their intermolecular interactions in single crystals. Intramolecular associations detected in crystals of rac-1a and rac-1b. Intramolecular association
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Published 01 Sep 2025

Thermodynamics and polarity-driven properties of fluorinated cyclopropanes

  • Matheus P. Freitas

Beilstein J. Org. Chem. 2025, 21, 1742–1747, doi:10.3762/bjoc.21.137

Graphical Abstract
  • its ability to form ion complexes and self-assemble into a stacking arrangement [12][13][14]. Therefore, understanding the energetics and polarity of fluorinated cyclopropanes is crucial for elucidating the intramolecular forces that govern the stability of molecular structures. Moreover, these
  • preclude its synthesis, as the all-cis-1,2,3-trifluorocyclopropane framework has been successfully prepared in earlier studies [17]. To better understand the intramolecular interactions that govern the stability of fluorinated cyclopropanes, the sets of di-, tri-, and tetrafluorinated cyclopropane isomers
  • intramolecular forces in fluorinated systems but also provide a molecular framework for the design of advanced applications. Fluorinated cyclopropanes exhibit considerable potential in pharmaceuticals, where polarity influences drug solubility and activity, and in material sciences, particularly for the
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Published 29 Aug 2025
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