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Search for "N-sulfonyl" in Full Text gives 35 result(s) in Beilstein Journal of Organic Chemistry.

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

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  • the synthesis of 2,3-dihydro-N-sulfonyl-1,2-thiazoles was developed based on the optimized reaction of acrylic acid thioamides containing aryl- and hetarylidene fragments with N-tosyl and N-mesyliminoiodinanes (Scheme 1D). Results and Discussion The reaction of thioamide 1a with PhINTs (2a) was chosen
  • as a model for searching the optimal synthesis conditions (Table 1). We found that when processing thioamide 1a with PhINTs (2a, 1.5 equiv) in chloroform at 50 °C in the presence of Rh2(Piv)4 (0.5 equiv), 2,3-dihydro-N-sulfonyl-1,2-thiazole 3aa is formed with a 48% yield (Table 1, entry 1). When
  • used for the synthesis of a number of 2,3-dihydro-N-sulfonyl-1,2-thiazoles 3 (Scheme 2, method A). The conditions described in entry 12 (Table 1; Scheme 2, method B) are also noteworthy, since they do not require the preliminary synthesis of iodonium salts 2, which saves time and effort, however, the
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Published 10 Jul 2025

Entry to 2-aminoprolines via electrochemical decarboxylative amidation of N‑acetylamino malonic acid monoesters

  • Olesja Koleda,
  • Janis Sadauskis,
  • Darja Antonenko,
  • Edvards Janis Treijs,
  • Raivis Davis Steberis and
  • Edgars Suna

Beilstein J. Org. Chem. 2025, 21, 630–638, doi:10.3762/bjoc.21.50

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  • under constant current conditions in aqueous acetonitrile and provides access to N-sulfonyl, N-benzoyl, and N-Boc-protected 2-aminoproline derivatives. Keywords: anodic oxidation; decarboxylation; electrosynthesis; Hofer–Moest reaction; non-proteinogenic amino acids; Introduction Non-proteinogenic
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Published 19 Mar 2025

Advances in radical peroxidation with hydroperoxides

  • Oleg V. Bityukov,
  • Pavel Yu. Serdyuchenko,
  • Andrey S. Kirillov,
  • Gennady I. Nikishin,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

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Published 18 Nov 2024

Hydrogen-bond activation enables aziridination of unactivated olefins with simple iminoiodinanes

  • Phong Thai,
  • Lauv Patel,
  • Diyasha Manna and
  • David C. Powers

Beilstein J. Org. Chem. 2024, 20, 2305–2312, doi:10.3762/bjoc.20.197

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  • -pyridinium substituent. Based on those observations, we reasoned that similarly enhanced reactivity might be accessed by Lewis acid or H-bond activated iminoiodinanes. Here, we describe the HFIP-promoted aziridination of unactivated olefins with N-sulfonyl iminoiodinane reagents, which are among the most
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Published 11 Sep 2024

Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins

  • Ke Jiang,
  • Cheng Pan,
  • Limin Wang,
  • Hao-Yang Wang and
  • Jianwei Han

Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76

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  • -trifluoroborate-substituted diaryliodonium salts furnished iodonium zwitterions as bifunctional reagents [22][23][24][25]. Additionally, ortho-trifluoromethanesulfonate, N-sulfonyl, or tosylmethylene-substituted diaryliodonium salts can undergo intramolecular aryl migrations [26][27][28]. More recently, we
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Published 18 Apr 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
  • field [4][5][6]. Pyridazine drugs have also shown high pharmaceutical activity. Many types of pyridazine drugs have been listed for antibacterial, anti-inflammatory, and other purposes [7][8][9][10]. Nowadays, a range of transformations to spirobenzosultams have been established using N-sulfonyl
  • ketimines as suitable three-carbon synthons in [3 + 2] and [3 + 3] annulations [11][12][13][14][15]. However, methods using N-sulfonyl ketimines as dienophiles in [4 + 2] annulation reactions to afford biologically important spiro compounds are still limited to date [16]. 1,2-Diaza-1,3-dienes [17][18][19
  • benzoisothiazole 1,1-dioxides with 1,2-diaza-1,3-dienes (Scheme 1). Results and Discussion To initiate our studies, 3-ethylbenzo[d]isothiazole 1,1-dioxide (1a) and α-halogeno hydrazone 2a were selected as the model substrates. Our aim was to explore the possibility of enamine–iminium tautomerism of N-sulfonyl
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Published 14 Feb 2024

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

  • Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

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  • building blocks offers another mainstream approach to introducing fluorine. Among these, di/trifluorodiazoethane [19][20][21][22], trifluoromethyl aldimines [23][24][25], trifluoroacetimidoyl halides [26], and fluoroalkyl N-sulfonyl hydrazones [27] have emerged as powerful nitrogen-containing fluorinated
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Published 15 Nov 2023
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  • aza-Friedel–Crafts process between indoles 4 and cyclic N-sulfonyl ketimines 5. The authors employed the BINOL-based chiral phosphoric acid P2 bearing two imidazoline moieties at the ortho-positions as the catalyst which activates both reactants through H-bonding where the NH group of the nucleophile
  • Brønsted acid catalyst to execute a straightforward aza-Friedel–Crafts reaction between 3-substituted indoles 4 and N-sulfonyl-substituted aldimines 128. The reaction successfully installed an aza-tertiary stereocenter at the C2 position of the heterocyclic ring. A broad substrate scope was investigated by
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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

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  • solvent at 100 °C (Scheme 6). Finally, compounds 13 were used to prepare various arylpyrrolo- and pyrazolopyrrolizinones for diverse biological activity. In 2007, Török and co-workers [60] reported a convenient one-pot synthesis of N-sulfonyl-substituted pyrroles, indoles, and carbazole via a modified
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Published 27 Jun 2023

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

  • Austin Pounder,
  • Eric Neufeld,
  • Peter Myler and
  • William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

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  • naphthylation of oxabenzonorbornadienes 30 with N-sulfonyl 2-aminobenzaldehydes 172 (Scheme 30) [76]. This reaction was amenable to a variety of EDG, EWG, as well as a broad scope of sulfonyl groups. Surprisingly, this reaction also proceeded smoothly with nitro substituents on the benzene ring which are
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Published 24 Apr 2023

Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold

  • Dmitry Dar’in,
  • Grigory Kantin,
  • Alexander Bunev and
  • Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1070–1078, doi:10.3762/bjoc.18.109

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  • homophthalimides 8 [10][11][12]. We reasoned that a similar strategy could be adopted for the preparation of 1,2,4-trisubstituted 1,4-DHIQs 9 if access to their diazo precursors 10 was gained. N-Sulfonyl analogs of compounds 10 have recently been synthesized via an innovative Dimroth rearrangement of 4
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Published 22 Aug 2022

Recent advances in organocatalytic asymmetric aza-Michael reactions of amines and amides

  • Pratibha Sharma,
  • Raakhi Gupta and
  • Raj K. Bansal

Beilstein J. Org. Chem. 2021, 17, 2585–2610, doi:10.3762/bjoc.17.173

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  • high enantioselectivities (up to 65–91%) [40]. Rajasekar et al. developed an efficient one-pot tandem rhodium(II)/chiral squaramide relay catalysis for the enantioselective construction of dihydro-β-carbolines 37 from the Michael reaction of suitably substituted indole derivatives 34 with N-sulfonyl
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Published 18 Oct 2021

Catalyzed and uncatalyzed procedures for the syntheses of isomeric covalent multi-indolyl hetero non-metallides: an account

  • Ranadeep Talukdar

Beilstein J. Org. Chem. 2021, 17, 2102–2122, doi:10.3762/bjoc.17.137

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  • 149 of the N-sulfonyl-protected indole 1o with metallic Te in four steps including desulfonylation (Scheme 19) [99]. The treatment with base followed by the addition of elemental tellurium to N-protected indole 1o generates lithium telluride 150. Telluride 150 is then oxidized to ditelluride 151 by
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Published 19 Aug 2021

Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes

  • Olga Bakhanovich,
  • Viktor Khutorianskyi,
  • Vladimir Motornov and
  • Petr Beier

Beilstein J. Org. Chem. 2021, 17, 504–510, doi:10.3762/bjoc.17.44

Graphical Abstract
  • of pyrroles to the 3,4-disubstituted derivatives is challenging because an electrophilic aromatic substitution of pyrroles or the metalation of N-substituted pyrroles and the subsequent reaction with electrophiles take place in position two of the ring [6][7]. Recently, N-sulfonyl-1,2,3-triazoles
  • , agrochemicals, and functional materials. Transformation of N-sulfonyl-1,2,3-triazoles to pyrroles via metal iminocarbenes. Transannulation of triazoles 2 with phenylacetylene. Transannulation of N-perfluoroalkyl-1,2,3-triazoles with aliphatic alkynes. Reaction of 1a with hex-5-ynenitrile. Metalation and
  • electrophilic metal-bound iminocarbenes form. These iminocarbenes undergo a variety of intriguing reactions, such as a cycloaddition and a C–H functionalization, among others, leading mostly to nitrogen heterocycles [8][9][10]. Using this chemistry, a variety of pyrroles have been prepared starting from N
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Published 18 Feb 2021

Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines

  • Geetanjali S. Sontakke,
  • Rahul K. Shukla and
  • Chandra M. R. Volla

Beilstein J. Org. Chem. 2021, 17, 485–493, doi:10.3762/bjoc.17.42

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  • isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and
  • -catalyzed “Click” chemistry, N-sulfonyl-1,2,3-triazoles have become useful precursors for accessing a variety of heterocyclic moieties [55][56]. In spite of the above methods for the C2-amination, the establishment of a simple, efficient and atom-economical method for the synthesis of 2-triazolylquinoline
  • derivatives is highly desired. The continuous interest and efforts of our group for the derivatization of quinoline moieties [57] and use of N-sulfonyl-1,2,3-triazoles as heterocyclic precursors encouraged us to develop a new strategy for the regioselective C2-triazolylation of quinoline N-oxide under mild
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Published 17 Feb 2021

Pentannulation of N-heterocycles by a tandem gold-catalyzed [3,3]-rearrangement/Nazarov reaction of propargyl ester derivatives: a computational study on the crucial role of the nitrogen atom

  • Giovanna Zanella,
  • Martina Petrović,
  • Dina Scarpi,
  • Ernesto G. Occhiato and
  • Enrique Gómez-Bengoa

Beilstein J. Org. Chem. 2020, 16, 3059–3068, doi:10.3762/bjoc.16.255

Graphical Abstract
  • rearrangement (specially the TS1-like first step). is rate determining with a low activation barrier of 10.0 kcal⋅mol−1 and that the Nazarov-cyclization is an extremely easy process (ΔΔG‡ = 5.1 kcal⋅mol−1) [16]. To homogenize with our results in Figure 1, we computed the corresponding N-sulfonyl-protected
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Published 15 Dec 2020

Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides

  • Vladimir Ilkin,
  • Vera Berseneva,
  • Tetyana Beryozkina,
  • Tatiana Glukhareva,
  • Lidia Dianova,
  • Wim Dehaen,
  • Eugenia Seliverstova and
  • Vasiliy Bakulev

Beilstein J. Org. Chem. 2020, 16, 2937–2947, doi:10.3762/bjoc.16.243

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  • , Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium 10.3762/bjoc.16.243 Abstract N-Sulfonyl amidines bearing 1,2,3-triazole, isoxazole, thiazole and pyridine substituents were successfully prepared for the first time by reactions of primary, secondary and tertiary heterocyclic
  • thioamides with alkyl- and arylsulfonyl azides. For each type of thioamides a reliable procedure to prepare N-sulfonyl amidines in good yields was found. Reactions of 1-aryl-1,2,3-triazole-4-carbothioamides with azides were shown to be accompanied with a Dimroth rearrangement to form 1-unsubstituted 5
  • , antibiotics and in many types of synthetic drugs [1][2][3][4][5][6][7][8][9][10][11][12]. N-Sulfonyl amidines have received considerable attention because they exhibit various types of pharmaceutical properties and biological activities [13][14][15][16][17][18][19][20][21] and also have been used as
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Published 01 Dec 2020

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

  • Lucas Guillemard and
  • Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

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  • excellent yields. Remarkably, a high functional group tolerance was observed, including heterocyclic substrates. In contrast, the N-substitution pattern clearly impacted the efficiency of the reaction. Indeed, exchanging the N-sulfonyl or N-acetyl protecting group with other functionalities, such as
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Published 21 Jul 2020

Recent advances in Cu-catalyzed C(sp3)–Si and C(sp3)–B bond formation

  • Balaram S. Takale,
  • Ruchita R. Thakore,
  • Elham Etemadi-Davan and
  • Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

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  • types of aldimines 47 to give both good chemical yields and enantioselectivities associated with products 48–51 (Scheme 12). However, these additions were not applicable to neutral imines or ketimines – they are best performed on activated imines (e.g., N-sulfonyl imines) [38]. The same year, Sato and
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Published 15 Apr 2020

Installation of -SO2F groups onto primary amides

  • Jing Liu,
  • Shi-Meng Wang,
  • Njud S. Alharbi and
  • Hua-Li Qin

Beilstein J. Org. Chem. 2019, 15, 1907–1912, doi:10.3762/bjoc.15.186

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  • aromatic amines with SO2F2 or the fluorosulfurylimidazolium salt have been achieved for assembly of N-sulfonyl fluorides [1][30], which have served as important active precursors for the development of noncovalent inhibitors (Scheme 1, (1)) [1][30][31]. Amides are the key connections in proteins, amides
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Published 09 Aug 2019

DABCO- and DBU-promoted one-pot reaction of N-sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives

  • Soumitra Guin,
  • Raman Gupta,
  • Debashis Majee and
  • Sampak Samanta

Beilstein J. Org. Chem. 2018, 14, 2771–2778, doi:10.3762/bjoc.14.254

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  • -Michael reaction between MBH carbonates derived from an acrylate/acrylonitrile and N-sulfonyl ketimines as C,N-binucleophiles catalyzed by DABCO, followed by elimination of SO2 under the influence of base and subsequent aromatization in an open atmosphere. Keywords: MBH carbonates; metal-free; N-sulfonyl
  • cyclic sulfamidate imines and MBH acetates of acrylate as coupling partners [68]. Herein, we further present a DABCO-catalyzed and DBU-promoted sequential one-pot procedure for the access to the interesting class of (2-hydroxyaryl)nicotinates/nicotinonitriles from N-sulfonyl ketimines and MBH adducts as
  • useful synthons [72][73] in the presence of open atmosphere (Scheme 1b). Results and Discussion We have commenced the model reaction between cyclic N-sulfonyl imine 1a as interesting C,N-binucleophiles [74] and MBH carbonate of acrylate 2a using 20 mol % of DABCO in toluene at room temperature for 14 h
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Published 02 Nov 2018

Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide

  • Lu Yang,
  • Yuwei Wu,
  • Yiming Yang,
  • Chengping Wen and
  • Jie-Ping Wan

Beilstein J. Org. Chem. 2018, 14, 2348–2353, doi:10.3762/bjoc.14.210

Graphical Abstract
  • , Figure 1). Moreover, it is notable that no N-sulfonyl-1,2,3-triazole was isolated from any of the above experiments, indicating the excellent chemoselectivity of the present synthetic method. In order to illustrate the potential application of this authentically green synthetic method, a gram scale
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Published 07 Sep 2018

A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N-chloramines

  • Katherine E. Jolley,
  • Michael R. Chapman and
  • A. John Blacker

Beilstein J. Org. Chem. 2018, 14, 2220–2228, doi:10.3762/bjoc.14.196

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  • generates and immediately reacts N-chloramines directly, avoiding purification and isolation steps. 2-Chloramines were produced from the reaction of styrenes with N-alkyl-N-sulfonyl-N-chloramines, whilst N-alkyl or N,N’-dialkyl-N-chloramines reacted with anisaldehyde in the presence of t-BuO2H oxidant to
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Published 24 Aug 2018

Anodic oxidation of bisamides from diaminoalkanes by constant current electrolysis

  • Tatiana Golub and
  • James Y. Becker

Beilstein J. Org. Chem. 2018, 14, 861–868, doi:10.3762/bjoc.14.72

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  • cyclization via anodic oxidation of an eneamide. Anodic bond cleavages in amides of type Ph2CHCONHAr. Type of products obtained (n = 0, 1, 2). Synthesized cyclic N-acyl and N-sulfonyl piperidines for electrolysis. Type of bisamides (derived from diamines) studied (n = 2, 3, 4). Type of products obtained from
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Published 16 Apr 2018

CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF3SO2Cl

  • Hélène Chachignon,
  • Hélène Guyon and
  • Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2800–2818, doi:10.3762/bjoc.13.273

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  • -arylacrylamides para-substituted on their aryl moiety by electron-donating or electron-withdrawing groups were converted into the corresponding oxindoles with similarly good yields. However, the reaction was compatible only with acrylamides bearing methyl or phenyl as R1 and R2 groups; for example, N-acyl and N
  • -sulfonyl amides failed to react. Interestingly, Zhang and co-workers demonstrated that this reaction could be performed as well using bismuth oxybromide (BiOBr) nanosheets instead of a ruthenium complex as the photocatalyst (Scheme 5) [12]. The reaction unfortunately suffered from the same limitations
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Published 19 Dec 2017
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