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Search for "amine" in Full Text gives 1173 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

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
  • compared to compounds 5, which can be clearly seen in the spectrum of compound 8h with both substituted ortho-positions of the amine moiety. In our opinion, this indicates the presence of rotamerism [59][60] caused by the restricted rotation of the sterically hindered amide group. The 1H NMR spectra of
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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
  • selectively degraded and the pure product (E)-8v could be isolated with 47% yield. On the other hand, if the amine group was too nucleophilic, as in the case of N-(4-(tert-butyldimethylsilyl)hex-5-yn-1-yl)aniline (7h), the amine N–H was arylated instead of the alkyne, resulting in the formation of N-(4-(tert
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Published 26 Sep 2025

Photochemical reduction of acylimidazolium salts

  • Michael Jakob,
  • Nick Bechler,
  • Hassan Abdelwahab,
  • Fabian Weber,
  • Janos Wasternack,
  • Leonardo Kleebauer,
  • Jan P. Götze and
  • Matthew N. Hopkinson

Beilstein J. Org. Chem. 2025, 21, 1973–1983, doi:10.3762/bjoc.21.153

Graphical Abstract
  • reactions have been developed. Employing the simple amine, DIPEA, as the terminal reductant, products resulting from overall 2-electron or 4-electron-reduction processes could be obtained using either a photocatalytic approach under blue light irradiation or directly under UV-A light irradiation without an
  • substrate (Figure 1b). This led to the successful development of a novel dual NHC/light-mediated reduction process using either the simple tertiary amine, NEt(iPr)2 (DIPEA) or the widely available silane HSiEt3, as the only reductant. Moreover, interesting insights into the reaction mechanism supported by
  • = 4,4′-di-tert-butyl-2,2′-dipyridine) as a photocatalyst and the simple tertiary amine diisopropylethylamine (DIPEA, 5 equiv) in MeCN (0.05 M). After 24 h under irradiation with light from blue LEDs (λmax = 440 nm), the crude mixture was concentrated under reduced pressure and analyzed by 1H NMR
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Published 25 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
  • 139, epoxide 136 was first prepared from (R)-130 in two steps. Parikh–Doering oxidation of 136 followed by addition with Et2Zn in the presence of ligand 137 afforded alcohol 138, which was subsequently converted into amine 139 via a seven-step sequence. With the fragments 135 and 139 in hand
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Review
Published 18 Sep 2025

Rhodium-catalysed connective synthesis of diverse reactive probes bearing S(VI) electrophilic warheads

  • Scott Rice,
  • Julian Chesti,
  • William R. T. Mosedale,
  • Megan H. Wright,
  • Stephen P. Marsden,
  • Terry K. Smith and
  • Adam Nelson

Beilstein J. Org. Chem. 2025, 21, 1924–1931, doi:10.3762/bjoc.21.150

Graphical Abstract
  • amine (→ 4-18); cyclopropanation (→ 2-7); and formal C–H insertion into an indole (→ 1-15a and 2-15a) or naphthol (→ 2-4 and 3-4b). In the case of 4 (2-naphthol) and 15 (5-methoxyindole), co-substrates containing functional groups with more than one potentially reactive site, two regioisomeric products
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Published 17 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
  • -dipole, access to 1,3-amino-alcohol functionality is possible. This arrangement is present in many Alstonia alkaloids, and we envisaged using this cycloaddition chemistry to set up the bridged amine ring system found in these natural products. Bridged and spirocyclic ring systems are known to be
  • 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
  • directly used as a planarly chiral primary amine catalyst in the asymmetric electrophilic amination reaction of aldehyde 34, which yielded the α-amination product 35 with high enantioselectivity. In 2022, our group disclosed an enantioselective macrocyclization protocol for the asymmetric synthesis of
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Published 10 Sep 2025

Systematic pore lipophilization to enhance the efficiency of an amine-based MOF catalyst in the solvent-free Knoevenagel reaction

  • Pricilla Matseketsa,
  • Margret Kumbirayi Ruwimbo Pagare and
  • Tendai Gadzikwa

Beilstein J. Org. Chem. 2025, 21, 1854–1863, doi:10.3762/bjoc.21.144

Graphical Abstract
  • Pricilla Matseketsa Margret Kumbirayi Ruwimbo Pagare Tendai Gadzikwa Department of Chemistry, Kansas State University, Manhattan, Kansas 66506, United States 10.3762/bjoc.21.144 Abstract We systematically lipophilized an amine-based metal-organic framework (MOF) catalyst and applied the
  • functionalized MOFs to the Knoevenagel condensation reaction. A well-defined MOF material composed of both amine- and hydroxy-bearing linkers was reacted with a series of aliphatic isocyanates (isopropyl, tert-butyl, n-hexyl, and tetradecyl) and, incongruously, was found to preferentially react at the hydroxy
  • preventing its interference with the Lewis acidic catalyst surface sites, but we wondered, if similar reaction acceleration of a condensation reaction could be achieved by the lipophilization of the internal surfaces of an amine-based MOF catalyst. The majority of studies of lipophilic MOFs applied to
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Published 09 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
  • -triazoles 28 can be obtained by click chemistry (Scheme 6B) via one-pot deprotection of 26 and Cu(I)-catalysed reaction with an azide [43][44]. Heteroarylimines 31a,b can be easily obtained by condensation of a (hetero)aromatic aldehyde 30a,b with a (hetero)aromatic amine 29a,b [36][37][38] (Scheme 7). The
  • choice of aldehyde and amine will determine the direction of the imine bond and the geometry of the Z-isomer. Examples Non-ionic bithienylpyrrole push–pull azo dye 32 was successfully introduced in liquid-crystalline matrices with thermal relaxation in the µs order, making them among the fastest liquid
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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
  • during GC–MS analysis) and formaldehyde (2a′′) via C–C bond scission of styrene in the presence of FeIII/O2, possibly through a 1,2-addition of O2 to styrene [49][58][59][60]. This in-situ generated aldehyde species then undergoes condensation with the amine 1a, leading to the formation of the
  • formation of intermediates III and III′. Subsequent electrophilic cyclization/C–H annulation of the aromatic amine, followed by aromatization, afford intermediates V and V′. The oxidative dehydrogenation of intermediates V and V′ then results in the formation of products 3a and 3a′ and the regeneration of
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Published 05 Sep 2025

Research progress on calixarene/pillararene-based controlled drug release systems

  • Liu-Huan Yi,
  • Jian Qin,
  • Si-Ran Lu,
  • Liu-Pan Yang,
  • Li-Li Wang and
  • Huan Yao

Beilstein J. Org. Chem. 2025, 21, 1757–1785, doi:10.3762/bjoc.21.139

Graphical Abstract
  • solubility, this can be improved through derivatization. Water-soluble calixarene derivatives can be obtained through functional modifications, including the introduction of sulfonic acid, amine, and carboxylic acid groups [57][58][59]. These water soluble macrocycle derivatives can be used to increase the
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Published 03 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
  • diverse C–N atropisomeric compounds possessing carboxamide, imide, lactam, sulfonamide, indole, pyrrole, imidazole, carbazole and amine skeletons have been reported by many groups [1][2][3][4][5][6][7][8][9]. C–N atropisomers are attractive compounds from the viewpoint of not only synthetic organic
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Published 01 Sep 2025

Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides

  • Tsun-Yi Chiang,
  • Mei-Huei Lin,
  • Chun-Wei Chang,
  • Jinq-Chyi Lee and
  • Cheng-Chung Wang

Beilstein J. Org. Chem. 2025, 21, 1671–1677, doi:10.3762/bjoc.21.131

Graphical Abstract
  • position of the galactoside using 1.3 equivalents of bis(trimethylsilyl)amine (HMDS), concurrently leaving the 3-OH group at the non-reducing end available for glycosylation with the ᴅ-Galf donor 12 [47]. After the in situ activation with TolSCl/AgOTf, product 13 was obtained with a 76% yield and exclusive
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Published 21 Aug 2025

Influence of the cation in hypophosphite-mediated catalyst-free reductive amination

  • Natalia Lebedeva,
  • Fedor Kliuev,
  • Olesya Zvereva,
  • Klim Biriukov,
  • Evgeniya Podyacheva,
  • Maria Godovikova,
  • Oleg I. Afanasyev and
  • Denis Chusov

Beilstein J. Org. Chem. 2025, 21, 1661–1670, doi:10.3762/bjoc.21.130

Graphical Abstract
  • the water content in the reaction medium did not exceed 0.7 equiv. In case of LiH2PO2 or NaH2PO2 the model amine formed with similar high yields of the target product (65–70%) (Table 1, lines 2 and 3) both in the presence and in the absence of H3PO2. On the contrary, Rb, K and Cs in the absence of
  • the further study. Using the optimal K2CO3/H3PO2 ratio 0.125/0.5, it was found that 78% yield of the model amine could be reached at lower temperature (110 °C) under prolonged reaction time (Scheme 2). The water content in the system had a crucial influence on the reaction outcome: an excess of the
  • media. Finally, the combination of H3PO2 and KH2PO2 1:1 with the ratio of H2PO2− to amine 1:2 is optimal balance between solubility of reductant, acidity of the medium and stability of the reducing system providing the highest efficiency of the interaction. Under optimized reaction conditions, the
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Published 20 Aug 2025

Catalytic asymmetric reactions of isocyanides for constructing non-central chirality

  • Jia-Yu Liao

Beilstein J. Org. Chem. 2025, 21, 1648–1660, doi:10.3762/bjoc.21.129

Graphical Abstract
  • of the resulting products in developing chiral organocatalysts was investigated as well. For instance, 28a was converted to a thiourea-tertiary amine 29 through a four-step procedure in an overall 36% yield. This compound was then utilized as the catalyst in the electrophilic amination reaction
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Published 19 Aug 2025

Chemical synthesis of glycan motifs from the antitumor agent PI-88 through an orthogonal one-pot glycosylation strategy

  • Shaokang Yang,
  • Xingchun Sun,
  • Hanyingzi Fan and
  • Guozhi Xiao

Beilstein J. Org. Chem. 2025, 21, 1587–1594, doi:10.3762/bjoc.21.122

Graphical Abstract
  • of polar groups, including phosphoryl acid and amine groups [62]. After several optimizations, the following sequence was adopted to remove all Bn, Bz, and Cbz groups: 1) global hydrogenolysis of Bn and Cbz groups in 12 with Pd(OH)2/C in a mixed solvent (THF/MeOH/AcOH/H2O) and 2) saponification of
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Published 06 Aug 2025

Facile synthesis of hydantoin/1,2,4-oxadiazoline spiro-compounds via 1,3-dipolar cycloaddition of nitrile oxides to 5-iminohydantoins

  • Juliana V. Petrova,
  • Varvara T. Tkachenko,
  • Victor A. Tafeenko,
  • Anna S. Pestretsova,
  • Vadim S. Pokrovsky,
  • Maxim E. Kukushkin and
  • Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 1552–1560, doi:10.3762/bjoc.21.118

Graphical Abstract
  • synthesis of hydantoin/1,2,4-oxadiazoline spiro-compounds using two different methods for introducing a tertiary amine into the reaction mixture containing the dipolarophile and precursor of the 1,3-dipole (chloro oxime), either by dropwise addition or by diffusion mixing. By varying the substituents on N1
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Published 31 Jul 2025

General method for the synthesis of enaminones via photocatalysis

  • Paula Pérez-Ramos,
  • Raquel G. Soengas and
  • Humberto Rodríguez-Solla

Beilstein J. Org. Chem. 2025, 21, 1535–1543, doi:10.3762/bjoc.21.116

Graphical Abstract
  • -bromochromones via a Michael reaction of an amine with an electron-deficient alkene moiety and subsequent photocatalyzed debromination. With this dual catalytic system, a range of structurally diverse enaminone derivatives have been achieved in good yields with total trans selectivity. Mechanistic studies
  • enaminones. This transformation is simple, straightforward, and proceeds under mild conditions. Results and Discussion The initial challenge in achieving the desired reactivity was the activation of the unsaturated system towards the nucleophilic addition of the amine. The most common strategy to increase
  • electrophilicity of the β-carbon due to the electron-donating nature of the methyl group. Subsequently, we turned our attention to investigate a range of amine derivatives 8 under the standard conditions. When morpholine was replaced by piperidine, the expected enaminone 9g was provided, albeit in lower yield
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Published 29 Jul 2025

Photoredox-catalyzed arylation of isonitriles by diaryliodonium salts towards benzamides

  • Nadezhda M. Metalnikova,
  • Nikita S. Antonkin,
  • Tuan K. Nguyen,
  • Natalia S. Soldatova,
  • Alexander V. Nyuchev,
  • Mikhail A. Kinzhalov and
  • Pavel S. Postnikov

Beilstein J. Org. Chem. 2025, 21, 1480–1488, doi:10.3762/bjoc.21.110

Graphical Abstract
  • DIPEA as an organic base but the yield of 2aa was very low and we observed a range of byproducts, mainly amine addition instead of water (see Supporting Information File 1, 2.2 Preliminary and Additional Experiments, Figures S5 and S6). Afterwards, we evaluated the other crucial parameters for
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Published 21 Jul 2025

Microwave-enhanced additive-free C–H amination of benzoxazoles catalysed by supported copper

  • Andrei Paraschiv,
  • Valentina Maruzzo,
  • Filippo Pettazzi,
  • Stefano Magliocco,
  • Paolo Inaudi,
  • Daria Brambilla,
  • Gloria Berlier,
  • Giancarlo Cravotto and
  • Katia Martina

Beilstein J. Org. Chem. 2025, 21, 1462–1476, doi:10.3762/bjoc.21.108

Graphical Abstract
  • ][44] and sulfamoyl chlorides [32] can perform the coupling under basic conditions, the need for the activation of the amine as an electrophilic agent generates additional waste. This reduces atom economy and indicates lower reaction efficiency. Acid-catalysed protocols have also been specifically
  • , that still required high temperatures, but the excess of amine (2 equiv) was lowered and only a catalytic amount of acid was utilised. Similar acidic protocols were subsequently developed by Li et al. [46], in which benzoxazoles were reacted with secondary amines and amides, with higher temperature
  • being applied when reacting amides to achieve their decarbonylation. In 2014, Cao et al. [47] reported the amination of benzoxazole with a secondary amine either in air or an O2 atmosphere, lowering the catalyst amount and the reaction temperature. In 2020, a study by De Vos and co-workers [48] focused
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Published 15 Jul 2025

Reactions of acryl thioamides with iminoiodinanes as a one-step synthesis of N-sulfonyl-2,3-dihydro-1,2-thiazoles

  • Vladimir G. Ilkin,
  • Pavel S. Silaichev,
  • Valeriy O. Filimonov,
  • Tetyana V. Beryozkina,
  • Margarita D. Likhacheva,
  • Pavel A. Slepukhin,
  • Wim Dehaen and
  • Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2025, 21, 1397–1403, doi:10.3762/bjoc.21.104

Graphical Abstract
  • , pyridinyl, furyl, isopropyl, and cyclohexyl substituents were introduced into position 3; cyano and various carbonyl groups were added to position 4 and cyclic amine residues were added to position 5 which increase the solubility of the synthesized compounds 3 (Scheme 2). An analysis of the yields of
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Published 10 Jul 2025

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

Graphical Abstract
  • highly cytotoxic agent inhibiting IDO1 (indole-amine 2,3-dioxygenase) which possesses an excellent pharmacokinetic profile and is suitable for both oral and parenteral dosing [16]. Compound 3, called ziresovir, is a promising candidate for treatment of the respiratory syncytial virus (RSV) infection in
  • -aminooxetanes 169 through a defluorosulphonylative coupling of sulphonyl fluorides 168 (Scheme 41) [92]. Because this novel methodology mimics the classical amide coupling strategy, it allows for a direct use of the established amine libraries and thus provides a rapid access to benzamide bioisosteres. The
  • , the synthesis starts with the preparation of a reactive amine species 170 which is then reacted with a Grignard or, in case of ester-containing substrates, with an organozinc reagent. Because this method involves only two simple steps and is not limited to aryl groups, it provides a more rapid access
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Published 27 Jun 2025

Optimized synthesis of aroyl-S,N-ketene acetals by omission of solubilizing alcohol cosolvents

  • Julius Krenzer and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2025, 21, 1201–1206, doi:10.3762/bjoc.21.97

Graphical Abstract
  • of an amine base in a binary 1,4-dioxane/ethanol mixture. Ethanol was used as a cosolvent to ensure solubility of the polar intermediate according to the mechanistic rationale (Scheme 2) [5][6]. Although, a broad scope of diversely substituted (hetero)aroyl-S,N-ketene acetals 8 was obtained (111
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Published 20 Jun 2025

Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C–H activation with directing groups

  • Julius Seumer,
  • Nicolai Ree and
  • Jan H. Jensen

Beilstein J. Org. Chem. 2025, 21, 1171–1182, doi:10.3762/bjoc.21.94

Graphical Abstract
  • reactions, the regioselectivity is not only determined by the activation energy for the rate-determining step but also by the proximity of an intramolecular reaction partner, here the secondary amine. From this in-depth analysis, we conclude that our QM workflow only predicted the wrong reaction site for
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Published 16 Jun 2025

A multicomponent reaction-initiated synthesis of imidazopyridine-fused isoquinolinones

  • Ashutosh Nath,
  • John Mark Awad and
  • Wei Zhang

Beilstein J. Org. Chem. 2025, 21, 1161–1169, doi:10.3762/bjoc.21.92

Graphical Abstract
  • reaction followed by the cleavage of the alkyl group to give intermediate II as a free amine. Annulation of II with CDI gave product B which is an HIV reverse transcriptase inhibitor (Scheme 1B) [17]. We have reported a three-component [3 + 2] cycloaddition followed by IMDA reaction for making heterocyclic
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Published 13 Jun 2025
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