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Search for "acid chlorides" in Full Text gives 61 result(s) in Beilstein Journal of Organic Chemistry.

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
  • in Table 1. The yield of compounds 1 after flash chromatography on silica gel under modified conditions (B) are significantly higher than under standard conditions (A). The results demonstrate the broad applicability of the optimized reaction conditions. Acid chlorides with electron-withdrawing (-CN
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Published 20 Jun 2025

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

  • Seungmin Lee,
  • Minsuk Kim,
  • Hyewon Han and
  • Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

Graphical Abstract
  • approaches. Despite the synthetic strategies to generate the copper nitrenoid intermediates are gaining more attention [104][105], several limitations still remain. First, multiple steps are required to prepare dioxazolones, synthesized conventionally from carboxylic acids or acid chlorides over two steps
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Published 22 Jan 2025

Synthesis of 2H-azirine-2,2-dicarboxylic acids and their derivatives

  • Anastasiya V. Agafonova,
  • Mikhail S. Novikov and
  • Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2024, 20, 3191–3197, doi:10.3762/bjoc.20.264

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  • derivatives, were synthesized using two reaction sequences (Table 1). The first sequence involved the chloroformylation of isoxazolones 3 to 5-chloroisoxazole-4-carbaldehydes 4 by POCl3/DMF [20][21][22][23], followed by radical chlorination of 4 with SO2Cl2/AIBN [24]. The alternative route to acid chlorides 1
  • included oxidation of aldehydes 4 with Oxone to acids 5 and the conversion of the latter into acid chlorides with thionyl chloride. The first reaction sequence was suitable for obtaining compounds 1a–c,e,f with substituents tolerant to radical reaction conditions. A significant advantage of the method is
  • the conversion of the latter to the acid chlorides 1 with thionyl chloride proceeded with yields of 77–92%. This made it possible to synthesize the target isoxazoles 1b,d,g–j with fairly high yields. Having in hand a set of isoxazoles 1a–i containing aryl substituents at the 3-position of the
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Published 05 Dec 2024

Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction

  • Yuta Kabumoto,
  • Eiichiro Yoshimoto,
  • Bing Xiaohuan,
  • Masato Morita,
  • Motohiro Yasui,
  • Shigeyuki Yamada and
  • Tsutomu Konno

Beilstein J. Org. Chem. 2024, 20, 2776–2783, doi:10.3762/bjoc.20.233

Graphical Abstract
  • ]-proton shift reaction of various tetrafluoroethylenated imines. Results and Discussion The preparation of substrates used in this study was as outlined in Scheme 3. Namely, the zinc reagent was prepared from commercially available 3,3,4,4-tetrafluoro-1-butene (18) [33] and reacted with various acid
  • chlorides in the presence of a copper catalyst to afford the corresponding tetrafluoroethylenated ketones 19. The ketones were then condensed with (R)-1-phenylethylamine under the influence of TiCl4 [34][35] to prepare various optically active imines (R)-16 in high yields (Scheme 3). Based on the result of
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Published 01 Nov 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

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  • -dicarbonyl compounds and their one-pot transformation pave the way for MCR syntheses of pyrazoles. 1,3-Dicarbonyl compounds can, for example, be generated in situ from enolates and carboxylic acid chlorides. They can be converted to the corresponding pyrazoles 1 in a consecutive multicomponent reaction with
  • necessary [73]. Most advantageously, this methodology tolerates many polar functional groups and allows access to pyrazole libraries from simple starting materials (alkynes, acid chlorides, hydrazines) in good to excellent yield. Notably, pyrazoles 102 and 103 demonstrate intense luminescence both in
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Published 16 Aug 2024

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

  • Xiaofeng Zhang,
  • Xiaoming Ma and
  • Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

Graphical Abstract
  • could also be applied for the synthesis of pyrrolobenzodiazepines when using 2-bromoketones instead of the acid chlorides affording products 24a–g in 59–77% yields with 3:1 to 6:1 dr (Scheme 15). The pyrroloquinazolines and pyrrolobenzodiazepines made by this route have structure similarity with
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Published 06 Nov 2023

Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity

  • Swagat K. Mohapatra,
  • Khaled Al Kurdi,
  • Samik Jhulki,
  • Georgii Bogdanov,
  • John Bacsa,
  • Maxwell Conte,
  • Tatiana V. Timofeeva,
  • Seth R. Marder and
  • Stephen Barlow

Beilstein J. Org. Chem. 2023, 19, 1651–1663, doi:10.3762/bjoc.19.121

Graphical Abstract
  • , for example through hydride abstraction by Ph3C+ [13]. Alternatively, they can also be obtained by condensation of N,N'-dimethylphenylene-1,2-diamine derivatives with acid chlorides, YCOCl, or through the methylation of 2-substituted benzoimidazoles [24], which in turn can be obtained from
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Published 01 Nov 2023

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

Graphical Abstract
  • example, the sequential hydrozirconation/carbonylation of propargylic ethers 18 reported by Donato [58] yielded α,β-unsaturated lactones 19. Beside the hydrozirconation/acylation sequence of nitriles utilizing acid chlorides published by Majoral/Floreancig [59][60], Cox revealed that terminal alkynes 16
  • sequential reaction, different enynes 25 and acid chlorides 26 were studied (Table 4). Fortunately, all desired products 27 were formed in ≥95% (2E,4E)-configuration (via 1H NMR). First, phenylenyne 25a (R1 = Ph) was chosen as the starting material and reacted with different acid chlorides 26a–s (Table 4
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Published 17 Feb 2023

Menadione: a platform and a target to valuable compounds synthesis

  • Acácio S. de Souza,
  • Ruan Carlos B. Ribeiro,
  • Dora C. S. Costa,
  • Fernanda P. Pauli,
  • David R. Pinho,
  • Matheus G. de Moraes,
  • Fernando de C. da Silva,
  • Luana da S. M. Forezi and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

Graphical Abstract
  • the reaction of menadione (10) with formaldehyde in the presence of gaseous HCl bubbled into the reaction medium [129][130]. Then, the chloromethyl derivative 84 was treated with diselenides, generated in situ from the reaction between Se0, NaBH4 and different acid chlorides, to form conjugates 86 in
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Published 11 Apr 2022

Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes

  • Nicolai Wippert,
  • Martin Nieger,
  • Claudine Herlan,
  • Nicole Jung and
  • Stefan Bräse

Beilstein J. Org. Chem. 2021, 17, 2773–2780, doi:10.3762/bjoc.17.187

Graphical Abstract
  • characterization impossible. Therefore, the crude aminomethyl compounds 17a–g were directly converted to the corresponding amides 9a–i using different anhydrides or acid chlorides 11a–c. The resulting amides were stable and gained mediocre to good yields except for amides 9a and 9d (Table 2). The yield of 9d was
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Published 22 Nov 2021

Synthesis and antimicrobial activity of 1H-1,2,3-triazole and carboxylate analogues of metronidazole

  • Satya Kumar Avula,
  • Syed Raza Shah,
  • Khdija Al-Hosni,
  • Muhammad U. Anwar,
  • Rene Csuk,
  • Biswanath Das and
  • Ahmed Al-Harrasi

Beilstein J. Org. Chem. 2021, 17, 2377–2384, doi:10.3762/bjoc.17.154

Graphical Abstract
  • respective acid chlorides by using thionyl chlorides and these acid chlorides were then made to react with the -OH functionality of metronidazole to get different esters [7]. Here we report a convenient method for the synthesis of aliphatic and aromatic esters of metronidazole. Furthermore, derivatives of
  • analogues of metronidazole Compound 1 reacted with different acid chlorides (6a–e) in the presence of pyridine, a catalytic amount of DMAP and in dry DCM at room temperature. The reaction proceeded smoothly to give the desired metronidazole carboxylate derivatives 7a–e in 86–93% yields [21][22]. The
  • compounds 5a–i and 7a–e. Reagents and conditions: (a) TsCl, Et3N, dry DCM, DMAP, 0 °C to room temperature, 5 h, 96%; (b) NaN3, DMF, 70 °C, 3 h, 88%; (c) alkyne derivative (4a–i), CuI, Et3N, CH3CN, room temperature, 3 h, (5a–i) 85–94%. Reagents and conditions: (a) acid chlorides 6a–e, pyridine, dry DCM, DMAP
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Published 09 Sep 2021

Photoredox catalysis in nickel-catalyzed C–H functionalization

  • Lusina Mantry,
  • Rajaram Maayuri,
  • Vikash Kumar and
  • Parthasarathy Gandeepan

Beilstein J. Org. Chem. 2021, 17, 2209–2259, doi:10.3762/bjoc.17.143

Graphical Abstract
  • iridium photocatalysis/nickel catalysis enabled the α-C(sp3)–H acylation of ethers 9 with acid chlorides 45 (Scheme 38) [121]. The optimized catalytic conditions were not limited to acid chlorides as acyl sources, and an acid anhydride proved as viable substrate, albeit in a somewhat lower yield. Based on
  • high yields. Based on the detailed computational and experimental mechanistic studies, the authors proposed a catalytic cycle which involves the C–H cleavage prior to the oxidative addition of N-acylsuccinimide (Figure 19) [125]. The acylation of benzylic C‒H bonds with acid chlorides 45 by means of
  • aliphatic acid chlorides 45 were well tolerated under the catalytic conditions to offer the ketone products 79. The authors also showed that acid anhydrides could also be used as viable acylating reagents under the optimized reaction conditions, however, with less efficacy than acid chlorides. A related
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Published 31 Aug 2021

Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

  • David Weinzierl and
  • Mario Waser

Beilstein J. Org. Chem. 2021, 17, 800–804, doi:10.3762/bjoc.17.68

Graphical Abstract
  • transformation into diastereomers by esterification with chiral acid chlorides [19][20] as well as the kinetic resolution (KR) of racemic esters of 2 via an enzymatic hydrolysis [25][26][27] were very successfully used to access enantioenriched 2. Recently, Akiyama and co-workers reported the kinetic resolution
  • of the most significant results obtained in this screening). Anhydride 4a was chosen in a first instance as it proved successful in previous acylative resolutions reported by others [28][33][34][36][37] but we later on also tested other anhydrides and acid chlorides (vide infra, Scheme 2). First
  • catalyst loading from 10 to 5 mol % allowed for a similar conversion, but resulted in a slightly reduced selectivity (Table 1, entry 10). At this point, we decided to screen other anhydrides and acid chlorides 4, but, as outlined in Scheme 2, the initially used isobutyric anhydride 4a clearly outperformed
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Published 08 Apr 2021

Valorisation of plastic waste via metal-catalysed depolymerisation

  • Francesca Liguori,
  • Carmen Moreno-Marrodán and
  • Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

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Published 02 Mar 2021

Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction

  • Lukáš Marek,
  • Lukáš Kolman,
  • Jiří Váňa,
  • Jan Svoboda and
  • Jiří Hanusek

Beilstein J. Org. Chem. 2021, 17, 527–539, doi:10.3762/bjoc.17.47

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  • pyridine–P4S10 as sulfurization agent. The tertiary thiobenzamides 4a–c were synthetized by a one-pot acylation/thionation from the corresponding acid chlorides and dimethylamine [55]. Other chemicals and solvents were purchased from Acros Organics, Sigma-Aldrich, or Fluorochem and were used as received
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Published 23 Feb 2021

Copper-promoted/copper-catalyzed trifluoromethylselenolation reactions

  • Clément Ghiazza and
  • Anis Tlili

Beilstein J. Org. Chem. 2020, 16, 305–316, doi:10.3762/bjoc.16.30

Graphical Abstract
  • acid chlorides (Scheme 6) [23]. Therein, the key was the addition of a catalytic amount of iron powder as the Lewis acid to foster C–Cl bond cleavage and to access the desired products with high yields. The reaction encompassed a broad range of functional groups, including acetate, halides, and
  • carbonyl compounds with [(bpy)CuSeCF3]2 by the group of Weng. Trifluoromethylselenolation of α,β-unsaturated ketones with [(bpy)CuSeCF3]2 by the group of Weng. Trifluoromethylselenolation of acid chlorides with [(bpy)CuSeCF3]2 by the group of Weng. Synthesis of 2-trifluoromethylselenylated benzofused
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Published 03 Mar 2020

Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

  • Natascha Breuer,
  • Irina Gruber,
  • Christoph Janiak and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 2684–2703, doi:10.3762/bjoc.15.262

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  • -pyrones from acid chlorides, terminal alkynes and dialkyl malonates. Consecutive pseudo-four-component alkynylation–Michael addition–cyclocondensation (AMAC) synthesis of 1H-pyridines 5a and an aniline derivative. Consecutive pseudo-four-component alkynylation–Michael addition–cyclocondensation (AMAC
  • ) synthesis of 1H-pyridines 5a from acid chlorides 1, terminal alkynes 2 and ethyl cyanoacetate (4). Model system for the optimization of the Michael addition–cyclocondensation reaction step to 1H-pyridine 5a or/and α-pyrone 6a. Formation of α-pyrone 6a and 1H-pyridine 5a at 20 °C. Formation of α-pyrone 6a
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Published 12 Nov 2019

1,5-Phosphonium betaines from N-triflylpropiolamides, triphenylphosphane, and active methylene compounds

  • Vito A. Fiore,
  • Chiara Freisler and
  • Gerhard Maas

Beilstein J. Org. Chem. 2019, 15, 2603–2611, doi:10.3762/bjoc.15.253

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  • in transamidation reactions with nucleophilic amines [18][22]. Therefore, it was interesting to know the performance of propiolic acid chlorides in the same betaine syntheses. We found that acid chlorides 4 indeed underwent the three-component reaction with N,N’-dimethylbarbituric acid and furnished
  • betaines 3b, 3j and 3k, respectively, with about the same E/Z ratios as in Figure 1 (Scheme 5). However, the products were obtained in low yield, because unidentified side-reactions occurred and purification was cumbersome. Thus, propiolic acid chlorides are not well suited for these three-component
  • acid chlorides. Two mechanistic scenarios for the formation of betaines 3. Resonance structures describing the bonding in 1,2-oxaphospholes/1,5-betaines 8. Bond distances and torsion angles in betaines E-3a, E-3b, E-3e, and Z-3e based on XRD data.a Selected NMR data of betaines 3a. Supporting
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Published 01 Nov 2019

2,3-Dibutoxynaphthalene-based tetralactam macrocycles for recognizing precious metal chloride complexes

  • Li-Li Wang,
  • Yi-Kuan Tu,
  • Huan Yao and
  • Wei Jiang

Beilstein J. Org. Chem. 2019, 15, 1460–1467, doi:10.3762/bjoc.15.146

Graphical Abstract
  • base. The butoxy groups were introduced to positioning the aminomethyl groups. Under pseudo-high dilution conditions, the diamine S3 and the acid chlorides were added dropwise through a syringe pump to a flask containing Et3N and CH2Cl2 at room temperature. The tetralactam macrocycles 1 and 2 were
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Published 02 Jul 2019

Steroid diversification by multicomponent reactions

  • Leslie Reguera,
  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

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  • yields. Overall, five different components are incorporated in the reaction sequence, whereas acid chlorides, anhydrides, hydrazine, etc., could also be employed in the post-MCR cyclization [44]. The library of steroidal heterocycles was tested against oxidative stress and neuroinflammation due to
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Published 06 Jun 2019

Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives

  • Mikhail V. Makarov and
  • Marie E. Migaud

Beilstein J. Org. Chem. 2019, 15, 401–430, doi:10.3762/bjoc.15.36

Graphical Abstract
  • conditions used pyridine as solvent. The patent publication of Szczepankiewicz et al. [34] describes the preparation of 5′-alkanoate and 2′,3′,5′-alkanoate derivatives of NR+ synthesized by the direct acylation of NR+Cl− or NR+OTf− with the corresponding acid anhydrides or acid chlorides (Scheme 20). Thus
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Published 13 Feb 2019

Cross metathesis-mediated synthesis of hydroxamic acid derivatives

  • Shital Kumar Chattopadhyay,
  • Subhankar Ghosh and
  • Suman Sil

Beilstein J. Org. Chem. 2018, 14, 3070–3075, doi:10.3762/bjoc.14.285

Graphical Abstract
  • CM-mediated synthesis of functionalized alkenes of various kinds continue to appear. For example, cross metathesis with acrylates [8][9][10], α,ß-unsaturated acid chlorides [11], acrylamides [12][13][14], vinyl sulfones [15], vinylphosphine oxides [16], vinyl phosphonates [17], enones [18], and
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Published 17 Dec 2018

Synthesis of functionalised β-keto amides by aminoacylation/domino fragmentation of β-enamino amides

  • Pavel Yanev and
  • Plamen Angelov

Beilstein J. Org. Chem. 2018, 14, 2602–2606, doi:10.3762/bjoc.14.238

Graphical Abstract
  • scope [21]. A contribution of ours in this area is the application of ethylenediamine-derived β-enamino amides as synthetic equivalents of primary and secondary amide enolate synthons in reactions with acid chlorides [22]. To extend the scope of the methodology, we now have explored the acylation of
  • improve the yields of 3k,l to 77% and 60%, respectively, only by using the corresponding N-phthaloyl amino acid chlorides [35][36] as acylating reagents. The increased yield however came at the expense of chiral integrity, with nearly full racemisation. After the series of α-aminoacyl (3) and ω-aminoacyl
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Published 10 Oct 2018

Synthesis of dihydroquinazolines from 2-aminobenzylamine: N3-aryl derivatives with electron-withdrawing groups

  • Nadia Gruber,
  • Jimena E. Díaz and
  • Liliana R. Orelli

Beilstein J. Org. Chem. 2018, 14, 2510–2519, doi:10.3762/bjoc.14.227

Graphical Abstract
  • , affording 2d in good yield (Table 1, entry 15). A further increase in the reaction temperature, however, was unfavorable due to decomposition of the substrate (Table 1, entry 16). Next, N-aryl-2-aminobenzylamines 2 were selectively acylated to yield compounds 3, using acid chlorides or anhydrides. No N,N
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Published 26 Sep 2018

Practical tetrafluoroethylene fragment installation through a coupling reaction of (1,1,2,2-tetrafluorobut-3-en-1-yl)zinc bromide with various electrophiles

  • Ken Tamamoto,
  • Shigeyuki Yamada and
  • Tsutomu Konno

Beilstein J. Org. Chem. 2018, 14, 2375–2383, doi:10.3762/bjoc.14.213

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  • synthetic tool for producing functional molecules with a CF2CF2 fragment. Keywords: acid chlorides; cross-coupling; iodoarenes; tetrafluoroethylene fragment; thermally stable zinc reagent; Introduction Recently, much attention has been paid to organic compounds containing a perfluoroalkylene unit, e.g
  • lowered the yield of 6a (Table 3, entry 9). With the optimized conditions (Table 3, entry 8), various kinds of acid chlorides 5b–k could be converted to the corresponding CF2CF2-substituted products 6b–k (Figure 4). Benzoyl chloride derivatives with an electron-donating (5b–d) and an electron-withdrawing
  • temperature, significantly improved the yield of 6g. Acid chlorides with a heteroaromatic moiety, e.g., 5h and 5i, could also readily participate in the coupling reaction, leading to 6h and 6i in 83% and 87% isolated yields, respectively. Additionally, cinnamoyl chloride (5j) and n-octanoyl chloride (5k) were
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Published 11 Sep 2018
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