Search results

Search for "hydrolysis" in Full Text gives 818 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

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

Graphical Abstract
  • first attempts in iPrOH did not provide the starting material conversion. The reaction in THF resulted in the full conversion of the starting material, but the analysis of the crude product revealed the quantitative formation of hydrolysis product 5a. Assuming the instability of intermediate 2a, a one
  • -pot reaction was performed by adding sodium 4-methylphenylsulfinate in the first step which was followed by NaN3. As the result, the formation of hydrolysis product 5a and 2,4-diazidoquinazoline (6a) was observed. Next, the reaction 1a → 4a in DMSO yielded diazidoquinazoline 6a as a major product and
  • hydrolysis product 5a. In MeCN the conversion to derivative 2a was stopped at 50% and was not facilitated by an extra addition of sulfinate. To our delight, in MeOH we observed the formation of intermediate 2a over 5 hours, and after the subsequent addition of sodium azide product 4a was isolated in 31
PDF
Album
Supp Info
Full Research Paper
Published 28 Mar 2024

Production of non-natural 5-methylorsellinate-derived meroterpenoids in Aspergillus oryzae

  • Jia Tang,
  • Yixiang Zhang and
  • Yudai Matsuda

Beilstein J. Org. Chem. 2024, 20, 638–644, doi:10.3762/bjoc.20.56

Graphical Abstract
  • spectrometry (HRMS) analysis revealed the molecular formula of 1 to be C25H36O5, corresponding to the 4-desmethyl form of (6R,10′R)-epoxyfarnesyl-DMOA methyl ester (Figure 2C). Furthermore, the molecular formula of 2 was determined to be C25H38O6, indicating that 2 is formed by the hydrolysis of the epoxide
PDF
Album
Supp Info
Letter
Published 20 Mar 2024

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

  • Andrew D. Gillie,
  • Matthew G. Wakeling,
  • Bethan L. Greene,
  • Louise Male and
  • Paul W. Davies

Beilstein J. Org. Chem. 2024, 20, 621–627, doi:10.3762/bjoc.20.54

Graphical Abstract
  • -diisopropylphenylamine, could not be converted into the desired imidazolium salt (Scheme 1a, path b). Applying a range of conditions, including those successful on other annulated systems, led to unreacted starting material or hydrolysis products after work-up (see Supporting Information File 1) [5][18][19][23][24][25
PDF
Album
Supp Info
Letter
Published 18 Mar 2024

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

Graphical Abstract
  • cruciferous vegetables, as hydrolysis products from the metabolism of glucosinolates [1]. In 2017, Müller and her research team showcased the ability of BIMs to operate as anti-inflammatory drugs by acting as GPR84 agonists [2]. GPR84 is a protein-coupled receptor found in immune cells, which regulates a
PDF
Album
Review
Published 22 Feb 2024

Synthesis of spiropyridazine-benzosultams by the [4 + 2] annulation reaction of 3-substituted benzoisothiazole 1,1-dioxides with 1,2-diaza-1,3-dienes

  • Wenqing Hao,
  • Long Wang,
  • Jinlei Zhang,
  • Dawei Teng and
  • Guorui Cao

Beilstein J. Org. Chem. 2024, 20, 280–286, doi:10.3762/bjoc.20.29

Graphical Abstract
  • 4aa [35] was isolated in 62% yield (Scheme 4). On the basis of the transformation of 3aa to 4aa, a tentative reaction mechanism is proposed. As shown in Scheme 5, the spiropyridazine-benzosultam 3aa was firstly oxidized to intermediate A. Next, an aziridine was formed with the hydrolysis of the amide
PDF
Album
Supp Info
Full Research Paper
Published 14 Feb 2024

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

Graphical Abstract
  • amounts of 2a were observed (Table 1, entry 1). The predominant side products were 2,2'-diiodobiphenyl and 9H-carbazole. The formation of free carbazole indicated the formation and subsequent hydrolysis of 2a. The presence of 2,2'-diiodobiphenyl suggests the reaction of 1a with iodide released by each
PDF
Album
Supp Info
Letter
Published 04 Jan 2024

1-Butyl-3-methylimidazolium tetrafluoroborate as suitable solvent for BF3: the case of alkyne hydration. Chemistry vs electrochemistry

  • Marta David,
  • Elisa Galli,
  • Richard C. D. Brown,
  • Marta Feroci,
  • Fabrizio Vetica and
  • Martina Bortolami

Beilstein J. Org. Chem. 2023, 19, 1966–1981, doi:10.3762/bjoc.19.147

Graphical Abstract
  • 1 (after drying the IL under vacuum for 16 h), there was a significant increase in product yield from 53% to 87%. Then, we investigated addition of water to BMIm-BF4, as the literature reports that the hydrolysis of the anion of this IL is quite slow in the presence of excess water (less than 5% BF4
  • hydrolysis in a 1:1 in volume IL/water solution kept at 45 °C for 24 h) [105]. It should be noted that the same treatment carried out on 1-methyl-3-octylimidazolium tetrafluoroborate (OMIm-BF4) evidenced a much higher extent of BF4‒ hydrolysis. This is probably due to the weaker interaction between cation
  • and anion of the IL as the length of the side alkyl chain increases, which makes the BF4‒/water interaction more effective. Although Saihara and co-workers demonstrated that BF4‒ hydrolysis generates HF, which reacts with the surrounding glass container yielding SiF62‒ (signal at −130 ppm in 19F NMR
PDF
Album
Supp Info
Full Research Paper
Published 28 Dec 2023

N-Boc-α-diazo glutarimide as efficient reagent for assembling N-heterocycle-glutarimide diads via Rh(II)-catalyzed N–H insertion reaction

  • Grigory Kantin,
  • Pavel Golubev,
  • Alexander Sapegin,
  • Alexander Bunev and
  • Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 1841–1848, doi:10.3762/bjoc.19.136

Graphical Abstract
  • including the degradation of lymphoid transcription factors [15][16][17] IKZF1, IKZF3, and SALL4 where the latter's degradation could result in a significant teratogenic effect [18]. In addition, these glutarimide derivatives are highly susceptible to hydrolysis and enzymatic cleavage under physiological
PDF
Album
Supp Info
Full Research Paper
Published 07 Dec 2023

Selectivity control towards CO versus H2 for photo-driven CO2 reduction with a novel Co(II) catalyst

  • Lisa-Lou Gracia,
  • Philip Henkel,
  • Olaf Fuhr and
  • Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

Graphical Abstract
  • -dimethylacetamide (DMA) as the major component. Although this solvent has very similar properties as the mostly used N,N-dimethylformamide (DMF), it is highly stable and does not produce formate upon hydrolysis [49]. In the solvent system DMA/TEOA 3:1 (v/v), we could observe that carbon monoxide was formed, however
PDF
Album
Supp Info
Full Research Paper
Published 17 Nov 2023

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

Graphical Abstract
  • physiological conditions since the presence of this substituent significantly affects the pKa of the phenol: an apparent value of 5.68 ± 0.02 was obtained. This also impacts the basicity of the azomethine nitrogen and, as a consequence, increases the hydrazone’s susceptibility to hydrolysis. Nevertheless, both
  • species (ROS) in vitro, which may be another mechanism through which the compound exerts its protective effects in the brain. From a drug development perspective, however, INHHQ has some pharmacological limitations, such as low solubility and certain susceptibility to hydrolysis in a water-rich medium
  • (hdz-NO2). It is expected that those substituents impact the chemical (e.g., acidity and hydrolysis susceptibility) as well as the structural and spectroscopic properties of the compounds. Results and Discussion The methyl-substituted hdz-CH3 and its nitro-containing analogue hdz-NO2 were isolated as
PDF
Album
Supp Info
Full Research Paper
Published 10 Nov 2023

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

  • Ken-ichi Nakashima,
  • Naohito Abe,
  • Masayoshi Oyama,
  • Hiroko Murata and
  • Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

Graphical Abstract
  • by acid hydrolysis of 1 using the method developed by Tanaka et al. [16], in which the hydrolysates are derivatized with ʟ-cysteine methyl ester and o-tolyl isothiocyanate followed by HPLC analysis. For compound 1, peaks were observed at retention times of 13.96, 20.83, and 22.16 min. The peaks at
PDF
Album
Supp Info
Full Research Paper
Published 19 Oct 2023

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

  • Stéphanie Hesse

Beilstein J. Org. Chem. 2023, 19, 1537–1544, doi:10.3762/bjoc.19.110

Graphical Abstract
  • classical organic solvents were used. The expected compounds are recovered by a simple filtration after hydrolysis and no purification is required. Those derivatives were studied for their antioxidant activities and the results are consistent with those reported in the literature indicating that phenolic
  • hydrolysis (Table 2, entry 1). The same compound was synthesized by Molnar et al. in 53% yield after reaction in ChCl/urea at 90 °C [3]. When increasing the reaction temperature to 60 °C, product 3a was obtained with 94% yield after 1 h of reaction in Pro/Gly (1:2) (Table 2, entry 2). For comparison purposes
PDF
Album
Supp Info
Full Research Paper
Published 04 Oct 2023

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

Graphical Abstract
  • through the use of additional NaOH and refluxing the crude alkylation mixture. After heating for 3 h, the desired intermediates were recovered in acceptable yields over this two-step one-pot sequence. The amide hydrolysis of 7 and 8 to the desired free naphthylamines 9 and 10 proved challenging, but was
  • nevertheless successful, albeit in low yields after an extended reaction time. We explored KOH and NH3 as alternatives to NaOH for this amide cleavage, and found the resulting yields less satisfactory. We also explored the amide hydrolysis under acidic conditions as well, though this resulted to almost
PDF
Album
Supp Info
Full Research Paper
Published 29 Sep 2023

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

Graphical Abstract
  • oxidation with Br2 and hydrolysis, the bromoethyl phosphate 5.4. Finally, the quaternarization with trimethylamine produced 5.5 and the acetylation produced 5.6 PAF. The intermediate compounds like 6.2 (1-O-alkylglycerol) or the protected secondary alcohol 6.6, either as enantiopure or racemic forms, are
  • deprotonation of solketal in DMF followed by the addition of oleyl alcohol tosylate. 9.3 was isolated after the hydrolysis in acidic conditions of the acetal protecting group. The protection of the primary alcohol required a protecting group that can be deprotected without affecting the C=C double bond of the
  • hypotensive effects. First, Wissner et al. reported the synthesis of racemic sn-1-deoxy-PAF 11.8 (Figure 11) [91]. First, n-octadecanoic acid chloride (11.1) reacted with tris[(trimethylsilyl)oxy]ethylene (11.2) [92] to produce, after acidic hydrolysis and subsequent decarboxylation, compound 11.3. Then, the
PDF
Album
Review
Published 08 Sep 2023

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp3)–H to construct C–C bonds

  • Hui Yu and
  • Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

Graphical Abstract
  • extract a hydrogen from the ether C (sp3)–H bond to form radicals. Subsequently, a single electron transfer (SET) leads to the oxonium species. Then, the enamine generated in situ from methyl aryl ketone and pyrrolidine undergoes a nucleophilic reaction with the oxonium species followed by hydrolysis to
  • ]. This pathway involves the presence of methanesulfonic acid and a large amount of metal oxide to obtain the target product with moderate to good yield. In 2015, a MnO2-catalyzed sequential oxidative alkylation of C(sp3)–H/C(sp2)–H CDC and hydrolysis of enamides with ethers was reported by Xu et al
  • . (Scheme 34) [99]. The CDC reaction was initiated by a radical oxidative addition of C(sp2)–H and the final product was obtained by amide hydrolysis. The strategy provides a simple and practical method for synthesizing β-oxoketones. In 2015, Cai et al. reported a novel CDC of C(sp3)–H and C(sp2)–H bonds in
PDF
Album
Review
Published 06 Sep 2023

Acetaldehyde in the Enders triple cascade reaction via acetaldehyde dimethyl acetal

  • Alessandro Brusa,
  • Debora Iapadre,
  • Maria Edith Casacchia,
  • Alessio Carioscia,
  • Giuliana Giorgianni,
  • Giandomenico Magagnano,
  • Fabio Pesciaioli and
  • Armando Carlone

Beilstein J. Org. Chem. 2023, 19, 1243–1250, doi:10.3762/bjoc.19.92

Graphical Abstract
  • intercepts the nitroalkene 3 in a Michael-type addition forming intermediate B. Hydrolysis regenerates catalyst 1 that can then selectively condense with the α,β-unsaturated aldehyde 4 to form chiral iminium ion intermediate C. Iminium ion C reacts with intermediate B in a further Michael-type reaction. The
  • developed in our previous work [17], we tried to introduce 6 as an acetaldehyde equivalent, adding water in the reaction system and Amberlyst-15 as a catalyst to accelerate the hydrolysis process (Scheme 2). To our delight, 6 as an acetaldehyde surrogate allows a slightly better yield with doubled
PDF
Album
Supp Info
Full Research Paper
Published 24 Aug 2023

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

  • Winnie Chemutai Sum,
  • Sherif S. Ebada,
  • Didsanutda Gonkhom,
  • Cony Decock,
  • Rémy Bertrand Teponno,
  • Josphat Clement Matasyoh and
  • Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

Graphical Abstract
  • potency against cancer cells in the presence of a 3-OH group. Notably, hydrolysis of the C3-acetoxy group in pachymic acid to tumulosic acid increased the activity of the compound compared to the positive control (cisplatin), in some instances [36]. Concomitantly, the oxidation of the hydroxy group at C-3
  • effects of compound 1 and related analogues could be realized by C-3 hydrolysis. In 2010, Liu et al. also demonstrated the major role played by changes at C-16 on antibacterial effects of F. pinicola steroids [33]. The acetylation at C-16 reduced the potency compared to the corresponding congener with a
PDF
Album
Supp Info
Full Research Paper
Published 02 Aug 2023

Photoredox catalysis harvesting multiple photon or electrochemical energies

  • Mattia Lepori,
  • Simon Schmid and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

Graphical Abstract
PDF
Album
Review
Published 28 Jul 2023

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

  • Dmitry B. Vinogradov,
  • Alexei N. Izmest’ev,
  • Angelina N. Kravchenko,
  • Yuri A. Strelenko and
  • Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

Graphical Abstract
  • [2,3-c][1,2,4]triazines was synthesized via a cascade sequence of hydrolysis and skeletal rearrangement of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazin-7(8H)-ylidene)acetic acid esters in methanol upon treatment with excess KOH. Imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazin-6(7H)-ylidene)acetic acid
  • esters are also suitable substrates for the reaction. In this case hydrolysis and thiazole ring expansion were accompanied with the change of the thiazolotriazine junction type from thiazolo[3,2-b][1,2,4]triazine to thiazino[2,3-c][1,2,4]triazine. Keywords: N,S-heterocycles; ring expansion; skeletal
  • ][1,3]thiazino[2,3-c][1,2,4]triazines 3a–i as a result of ester group hydrolysis and thiazolidine ring expansion to the corresponding thiazine (Scheme 3). The potassium salts 3a,b were isolated in 81 and 63% yield, respectively. Compounds 3c–i were used in further transformations without isolation. 1H
PDF
Album
Supp Info
Full Research Paper
Published 28 Jul 2023

Synthesis of tetrahydrofuro[3,2-c]pyridines via Pictet–Spengler reaction

  • Elena Y. Mendogralo and
  • Maxim G. Uchuskin

Beilstein J. Org. Chem. 2023, 19, 991–997, doi:10.3762/bjoc.19.74

Graphical Abstract
  • of some of the products was investigated and selected synthetic transformations of the obtained tetrahydrofuro[3,2-c]pyridines were shown. Keywords: acid hydrolysis; 1,4-diketone; tetrahydrofuro[3,2-c]pyridines; Paal–Knorr reaction; Pictet–Spengler reaction; Introduction Hydrogenated furo[3,2-c
  • hydrolysis of 4a was observed in most cases in trace amounts; an exception is entry 18 (Table 1), in which the 1,4-diketone 5a was isolated in 10% yield. With the optimized reaction conditions in hand, we investigated the scope of the developed tetrahydrofuro[3,2-c]pyridine synthesis. We found that a wide
  • hydrolysis could be a convenient tool for the synthesis of substituted 3-(2-oxopropyl)piperidin-4-ones 5. Using tetrahydrofuro[3,2-c]pyridine 4a as the model compound, we studied the effect of various Brønsted acids, temperature, concentrations, and the nature of the solvent on the efficiency of the reaction
PDF
Album
Supp Info
Full Research Paper
Published 30 Jun 2023
Graphical Abstract
  • hydrolysis, (−)-fumimycin (146) was obtained (Scheme 36) [66]. Conclusion The aza-Friedel–Crafts reaction is a powerful reaction that allows the incorporation of an aminoalkyl functionality in aromatic systems through C–C bond formation. This C–H bond functionalization methodology of aromatic systems also
PDF
Album
Review
Published 28 Jun 2023

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

  • Dileep Kumar Singh and
  • Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

Graphical Abstract
  • synthesis of various acid- or heat-sensitive N-substituted pyrrole derivatives 27. In this method, 2,5-dimethoxytetrahydrofuran undergoes mild hydrolysis in water to provide an activated species that reacts with various primary amines 26 in the presence of acetate buffer solution at ambient temperature to
  • hydrolysis of 2,5-DMTHF (2), which provide intermediate C after the removal of methanol in the presence of CuCl2. In the next steps, nucleophilic addition reaction of amines 34 with intermediate C, dehydration, and intramolecular aromatization affords N-substituted pyrroles 35. In 2018, Patil and Kumar [70
PDF
Album
Review
Published 27 Jun 2023

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine

  • Alessio Regni,
  • Francesca Bartoccini and
  • Giovanni Piersanti

Beilstein J. Org. Chem. 2023, 19, 918–927, doi:10.3762/bjoc.19.70

Graphical Abstract
  • ]. Regioselective palladium-catalyzed prenylation of 2 with prenylboronic acid pinacol ester and subsequent hydrolysis with LiOH provided the linear prenylated acid 4 in good yield. Coupling acid 4 with N-hydroxyphthalimide using DCC and a catalytic amount of DMAP afforded the key intermediate 5 in 59% yield. With
  • interconvertible to each other by hydration or dehydration, i.e., a plausible precursor of the allylic alcohol would be the diene, and vice versa [90]. Since both 8 and 10 are easily obtainable from 2 by Mozoroki–Heck coupling with commercially available 2-methyl-3-buten-2-ol, ester hydrolysis (LiOH in THF/H2O
PDF
Album
Supp Info
Full Research Paper
Published 26 Jun 2023

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

  • Till Steinmetz,
  • Blaise Kimbadi Lombe and
  • Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

Graphical Abstract
  • reactions (e.g., hydrolysis, esterification, oxidation) might be due to the isolation conditions or they could be attributed to unspecific enzymatic biotransformations. For compound 1, no spontaneous conversion to the ester 2 was observed, even after storage in methanol for two months. In contrast, the
PDF
Album
Supp Info
Full Research Paper
Published 23 Jun 2023

Pyridine C(sp2)–H bond functionalization under transition-metal and rare earth metal catalysis

  • Haritha Sindhe,
  • Malladi Mounika Reddy,
  • Karthikeyan Rajkumar,
  • Akshay Kamble,
  • Amardeep Singh,
  • Anand Kumar and
  • Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

Graphical Abstract
  • migratory insertion of the alkene into the metal–C bond of 23 gives the intermediate 24a on reaction with styrene 18 and intermediate 24b in the presence of alkene 20. The intermediates 24a and 24b then undergo further hydrolysis to give the desired linear products 19 and branched products 21, respectively
PDF
Album
Review
Published 12 Jun 2023
Other Beilstein-Institut Open Science Activities