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Search for "sulfonamides" in Full Text gives 99 result(s) in Beilstein Journal of Organic Chemistry.

Regio- and stereoselective carbometallation reactions of N-alkynylamides and sulfonamides

  • Yury Minko,
  • Morgane Pasco,
  • Helena Chechik and
  • Ilan Marek

Beilstein J. Org. Chem. 2013, 9, 526–532, doi:10.3762/bjoc.9.57

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Published 13 Mar 2013

Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides

  • Silvia M. Soria-Castro and
  • Alicia B. Peñéñory

Beilstein J. Org. Chem. 2013, 9, 467–475, doi:10.3762/bjoc.9.50

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  • ] and sulfonamides [49]. Thioacetate and thiobenzoate derivatives have been synthesized by the reactions of thioacetate and thiobenzoate anions with arenediazonium tetrafluoroborates [50]. However, this methodology implies moderate overall yields and the handling of usually unstable diazonium salts
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Published 04 Mar 2013

Acylsulfonamide safety-catch linker: promise and limitations for solid–phase oligosaccharide synthesis

  • Jian Yin,
  • Steffen Eller,
  • Mayeul Collot and
  • Peter H. Seeberger

Beilstein J. Org. Chem. 2012, 8, 2067–2071, doi:10.3762/bjoc.8.232

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  • glycosylated linker 21 (major product) rather than the desired product 22 were found (Scheme 3). N-Glycosidic sulfonamides were previously used during the synthesis of inhibitors of hepatocellular carcinoma cells [26]. This observation illustrates a limitation of the linker system since these undesired
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Letter
Published 26 Nov 2012

Synthesis of chiral sulfoximine-based thioureas and their application in asymmetric organocatalysis

  • Marcus Frings,
  • Isabelle Thomé and
  • Carsten Bolm

Beilstein J. Org. Chem. 2012, 8, 1443–1451, doi:10.3762/bjoc.8.164

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  • was known for chiral bifunctional amine-based sulfonamides that two hydrogen bond donors were not strictly required in the enantioselective organocatalytic ring opening of meso-anhydrides [48][54], this particular transformation was chosen as initial test reaction. Cyclic anhydride 4 served as
  • good yield (66%) within 24 h. Disappointingly, however, the product was racemic. In general, two concomitant events are discussed for bifunctional organocatalysts such as amino group-containing sulfonamides or thioureas: One is the activation of the anhydride carbonyl group by hydrogen bonding to the
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Published 03 Sep 2012

Exploring chemical diversity via a modular reaction pairing strategy

  • Joanna K. Loh,
  • Sun Young Yoon,
  • Thiwanka B. Samarakoon,
  • Alan Rolfe,
  • Patrick Porubsky,
  • Benjamin Neuenswander,
  • Gerald H. Lushington and
  • Paul R. Hanson

Beilstein J. Org. Chem. 2012, 8, 1293–1302, doi:10.3762/bjoc.8.147

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  • (cyclic sulfonamides) represent a class of compounds with a non-natural chemotype [5][6] that have gained enormous interest in recent years due to their extensive range of biological activities [7][8][9][10][11][12][13][14]. In particular, benzofused sultams, possessing a rich content of sp3 amine
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Published 15 Aug 2012

Hybrid super electron donors – preparation and reactivity

  • Jean Garnier,
  • Douglas W. Thomson,
  • Shengze Zhou,
  • Phillip I. Jolly,
  • Leonard E. A. Berlouis and
  • John A. Murphy

Beilstein J. Org. Chem. 2012, 8, 994–1002, doi:10.3762/bjoc.8.112

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  • ] afforded aryl anions from the same substrates by transfer of two electrons at room temperature, and also cleaved selected sulfonamides [19], bis-sulfones [19], Weinreb amides [22], acyloin derivatives [24], triflate esters and triflamides [26]. Most recently, we announced the synthesis of the unstable
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Published 03 Jul 2012

An intramolecular inverse electron demand Diels–Alder approach to annulated α-carbolines

  • Zhiyuan Ma,
  • Feng Ni,
  • Grace H. C. Woo,
  • Sie-Mun Lo,
  • Philip M. Roveto,
  • Scott E. Schaus and
  • John K. Snyder

Beilstein J. Org. Chem. 2012, 8, 829–840, doi:10.3762/bjoc.8.93

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  • refluxed for 24 h. After removal of the solvent in vacuo, the residue was dried by the addition and evaporation of toluene three times, and used directly in the next step without any further purification. General procedure B, preparation of sulfonamides 8: The isatin-derived triazine 9 was suspended in THF
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Published 06 Jun 2012

Equilibrium constants and protonation site for N-methylbenzenesulfonamides

  • José A. Moreira,
  • Ana M. Rosa da Costa,
  • Luis García-Río and
  • Márcia Pessêgo

Beilstein J. Org. Chem. 2011, 7, 1732–1738, doi:10.3762/bjoc.7.203

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  • above spectra is the absolute lack of isosbestic points, which arises from the shift in the n → π* absorption bands of the sulfonamides as the acid concentration increases. In order to eliminate this effect, the spectra must be treated by the characteristic vectors analysis (CVA) method [39]. This
  • -benzisothiazoline 1,1-dioxide in fluorosulfonic acid protonated on the nitrogen atom, Chardin and co-workers [44] showed that protonation of sulfonamides occurred on the oxygen atom. Still, a possibility that should not be discarded is the existence of a tautomeric equilibrium between the N- and O-protonated
  • structures, the latter having a greater relevance for the sulfonamides with electron-donor groups (Scheme 3). Conclusion The protonation equilibrium constants (pKBH+) for the para-substituted N-methylbenzenesulfonamides 3a–d in aqueous sulfuric acid were obtained from spectrophotometric measurements
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Published 27 Dec 2011

Development of the titanium–TADDOLate-catalyzed asymmetric fluorination of β-ketoesters

  • Lukas Hintermann,
  • Mauro Perseghini and
  • Antonio Togni

Beilstein J. Org. Chem. 2011, 7, 1421–1435, doi:10.3762/bjoc.7.166

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  • -sulfonamides supported the reaction, but electron-withdrawing groups on nitrogen were needed to induce a fast reaction (Table 5, entries 3, 7 and 8). N-fluoropyridinium salts (Table 5, entries 4–6) gave rise to slow catalyses. With the exception of the dicationic N,N'-difluorobipyridinium salt (Table 5, entry
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Published 17 Oct 2011

Amines as key building blocks in Pd-assisted multicomponent processes

  • Didier Bouyssi,
  • Nuno Monteiro and
  • Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

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  • series of benzo-fused sultams. A range of α-bromobenzenesulfonyl chlorides 40 were first coupled with various amines in DMF at room temperature in the presence of Et3N to generate intermediate sulfonamides 41. Subsequent in situ addition of a Michael acceptor in large excess together with Et3N, Bu4NCl
  • . Synthesis of pyrroles by cyclization of propargyl amines. Isoindolone and phthalazone synthesis by cyclization of acylhydrazides. Sultam synthesis by cyclization of sulfonamides. Synthesis of sulfonamides by aminosulfonylation of aryl iodides. Pyrrolidine synthesis by carbopalladation of allylamines
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Published 10 Oct 2011

Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays

  • Ian Cumpstey,
  • Jens Frigell,
  • Elias Pershagen,
  • Tashfeen Akhtar,
  • Elena Moreno-Clavijo,
  • Inmaculada Robina,
  • Dominic S. Alonzi and
  • Terry D. Butters

Beilstein J. Org. Chem. 2011, 7, 1115–1123, doi:10.3762/bjoc.7.128

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  • investigations into this area [6] we found that the installation of amine linkages between primary–primary carbons of monosaccharides was relatively straightforward; this was achieved by Mitsunobu coupling between carbohydrate C-6 alcohols and carbohydrate C-6 sulfonamides. Primary–secondary linkages were more
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Published 16 Aug 2011

Intramolecular hydroamination of alkynic sulfonamides catalyzed by a gold–triethynylphosphine complex: Construction of azepine frameworks by 7-exo-dig cyclization

  • Hideto Ito,
  • Tomoya Harada,
  • Hirohisa Ohmiya and
  • Masaya Sawamura

Beilstein J. Org. Chem. 2011, 7, 951–959, doi:10.3762/bjoc.7.106

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  • Hideto Ito Tomoya Harada Hirohisa Ohmiya Masaya Sawamura Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan 10.3762/bjoc.7.106 Abstract The gold-catalyzed, seven-membered ring forming, intramolecular hydroamination of alkynic sulfonamides has been
  • heterocyclic seven-membered rings, and we applied the triethynylphosphine–gold(I) catalytic systems to the synthesis of azepine derivatives through intramolecular hydroamination of alkynic sulfonamides. This article describes the results of the optimization of reaction conditions, exploration of substrate
  • that the 7-exo-dig intramolecular hydroamination of ω-alkynic N-alkyl-N-sulfonamides is efficiently catalyzed by a gold(I) complex coordinated with the semihollow-shaped triethynylphopshine ligand L1, and that the cyclization protocol provides a new efficient route to N-containing seven-membered ring
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Published 08 Jul 2011

Synthetic applications of gold-catalyzed ring expansions

  • David Garayalde and
  • Cristina Nevado

Beilstein J. Org. Chem. 2011, 7, 767–780, doi:10.3762/bjoc.7.87

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  • in the presence of sulfonamides [24]. Phenylcyclopropylalcohol 21 was efficiently transformed into sulfonyl pyrrolidine 23 in the presence of 5 mol % of the cationic complex AuOTf (Scheme 7). The reaction was applicable to a wide range of activated and non-activated cyclopropylmethanols, sulfonamides
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Published 07 Jun 2011

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

  • Marcus Baumann,
  • Ian R. Baxendale,
  • Steven V. Ley and
  • Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

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  • and decarboxylation then affords sumatriptan [14]. All the reported methods for the synthesis of sumatriptan begin with the sulfonamide group already present on the aromatic ring and several routes are possible to introduce this functional group. The scalable route to the sulfonamides inevitably
  • sulfonamides, all prepared in high yields. As this route employs sulfonamide-stabilised anions the preparation and handling of unstable sulfonyl chloride intermediates is therefore circumvented (Scheme 14) [17]. An analogous Heck reaction approach has also been employed to introduce a homologous side chain as
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Published 18 Apr 2011

Approaches towards the synthesis of 5-aminopyrazoles

  • Ranjana Aggarwal,
  • Vinod Kumar,
  • Rajiv Kumar and
  • Shiv P. Singh

Beilstein J. Org. Chem. 2011, 7, 179–197, doi:10.3762/bjoc.7.25

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  • starting from substituted sulfonamides 71. Sulfonamides 71 after diazotization undergo a coupling reaction with malononitrile to generate the hydrazones 72, which on cycloaddition with hydrazine hydrate give the corresponding pyrazoles (Scheme 19). Reaction of ketenes, particularly those with a cyano group
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Published 09 Feb 2011

Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds

  • Carolin Fischer and
  • Burkhard Koenig

Beilstein J. Org. Chem. 2011, 7, 59–74, doi:10.3762/bjoc.7.10

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  • ], benzimidazoles [40][41], sulfonamides [38], pyrroles [42] and lactams [43]. The three typical methods for N-arylation have been extensively reviewed concerning scope and limitation of these reactions [4][44][45][46][47][48]. However, the application of palladium- and copper-mediated N-arylation reactions in the
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Published 14 Jan 2011

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

  • Vladimir N. Boiko

Beilstein J. Org. Chem. 2010, 6, 880–921, doi:10.3762/bjoc.6.88

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  • disulfides under irradiation or on mild heating to give the corresponding trifluoromethyl sulfides (Scheme 54). The N- trifluoromethylnitrososulfonamide of trifluoromethane sulfonic acid reacts similarly with aliphatic disulfides [214]. Interaction of CF3NO with aryl sulfonamides generates relatively stable
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Published 18 Aug 2010

Recent advances in carbocupration of α-heterosubstituted alkynes

  • Ahmad Basheer and
  • Ilan Marek

Beilstein J. Org. Chem. 2010, 6, No. 77, doi:10.3762/bjoc.6.77

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  • centers. Carbocupration of alkynyl sulfonamide. Tandem carbocupration-sigmatropic rearrangement. Silylcupration of alkynyl sulfonamides. Carbocupration of P-substituted alkynes. Carbocupration of alkynylphosphonates. Carbocupration of thioalkynes. Tandem carbocupration-1,2-metalate rearrangement
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Published 15 Jul 2010

Anion receptors containing thiazine-1,1-dioxide heterocycles as hydrogen bond donors

  • Hong-Bo Wang,
  • James A. Wisner and
  • Michael C. Jennings

Beilstein J. Org. Chem. 2010, 6, No. 50, doi:10.3762/bjoc.6.50

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  • anions can be attributed to greater steric demand in the cleft formed, in part, by its terminal phenyl rings; an effect that is absent in the comparison receptor. Keywords: anions; hydrogen bonds; receptors; sulfonamides; supramolecular chemistry; Introduction The synthesis of neutral hosts and study
  • of nitrogen-based hydrogen bond donor groups such as amides [3][4], ureas [5], pyrroles/indoles/carbazoles [6][7] and sulfonamides [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] to complex the anionic targets in a topologically complementary fashion. Sulfonamides are an interesting
  • case as the hydrogen bond donor is often significantly more acidic (pKa approx. 11 for simple N-phenylaryl sulfonamides such as 3 (see below)) than that presented by other groups typically incorporated in these frameworks. The greater acidity of such a subunit can be an advantage by providing greater
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Published 19 May 2010

Diastereoselective functionalisation of benzo-annulated bicyclic sultams: Application for the synthesis of cis-2,4-diarylpyrrolidines

  • Susan Kelleher,
  • Pierre-Yves Quesne and
  • Paul Evans

Beilstein J. Org. Chem. 2009, 5, No. 69, doi:10.3762/bjoc.5.69

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  • place to afford cis-2,4-diaryl-substituted pyrrolidines 35–37. Keywords: cyclic sulfonamides; diastereoselective alkene functionalisation; double reduction; Pd-mediated cross coupling; Introduction Substituted pyrrolidine ring systems represent a common structural motif in a range of biologically
  • active compounds, including pharmaceutical agents and natural products. In relation to these general targets, we have recently developed a method that enables the construction of aryl-substituted pyrrolidines, featuring the double reduction of cyclic aromatic sulfonamides [1][2][3][4]. As illustrated in
  • preparation of 2,4-diaryl-substituted pyrrolidines from more readily available, albeit racemic, substrates. Results and Discussion Bicyclic aromatic cyclic sulfonamides 5a and 5b were formed according to the 3-step sequence previously described [1][2][3][10]. Originally, inclusion of triphenylphosphine was
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Published 25 Nov 2009

Enantiospecific synthesis of [2.2]paracyclophane- 4-thiol and derivatives

  • Gareth J. Rowlands and
  • Richard J. Seacome

Beilstein J. Org. Chem. 2009, 5, No. 9, doi:10.3762/bjoc.5.9

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  • ]paracyclophane compounds; aryl sulfonylation and the related sulfenylation facilitates the synthesis of sulfonic acids, sulfonamides and protected thiols [24][25][26] whilst directed metallation has allowed the formation of various sulfides [27][28][29][30]. Very few methodologies allow the synthesis of simple
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Published 12 Mar 2009

N-Arylation of amines, amides, imides and sulfonamides with arylboroxines catalyzed by simple copper salt/EtOH system

  • Zhang-Guo Zheng,
  • Jun Wen,
  • Na Wang,
  • Bo Wu and
  • Xiao-Qi Yu

Beilstein J. Org. Chem. 2008, 4, No. 40, doi:10.3762/bjoc.4.40

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  • , imides and sulfonamides catalyzed by a copper salt/EtOH system has been developed. In the absence of a base or additive the corresponding N-arylation products were obtained in moderate to excellent yields. Keywords: N-arylation; arylboroxine; copper salt; cross-coupling; ethanol; Introduction The
  • ). Furthermore, we expand the substrate scope of this reaction: a variety of amines, amides, imides and sulfonamides with arylboroxine can also participate in this catalytic system to give the corresponding N-arylation products in moderate to excellent yields. To the best of our knowledge, N-arylation of NH
  • reaction. In an endeavor to expand the scope of the above methodology, the catalytic system was also applied to imides, amines, amides and sulfonamides. Such coupling was found to give the desired N-arylation products in moderate yields, as shown in Table 5, except for sulfonamide, which afforded the
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Preliminary Communication
Published 07 Nov 2008

The enantiospecific synthesis of (+)-monomorine I using a 5-endo- trig cyclisation strategy

  • Malcolm B. Berry,
  • Donald Craig,
  • Philip S. Jones and
  • Gareth J. Rowlands

Beilstein J. Org. Chem. 2007, 3, No. 39, doi:10.1186/1860-5397-3-39

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  • tosyl moiety as the nitrogen-protecting group (PG) and resulted in a succinct synthesis of alkenes of the type 4 (X = NTs; Scheme 1). [15] Disappointingly, all attempts to ring-close the sulfonamides proved fruitless, and it was found that desulfonylation was necessary before cyclisation could be
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Published 08 Nov 2007

Synthesis of sulfonimidamides from sulfinamides by oxidation with N-chlorosuccinimide

  • Olga García Mancheño and
  • Carsten Bolm

Beilstein J. Org. Chem. 2007, 3, No. 25, doi:10.1186/1860-5397-3-25

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  • % yield. Conclusion A convenient alternative procedure for the synthesis of sulfonimidamides from sulfinamides and various amines and sulfonamides using N-chlorosuccinimide as halogenating agent has been developed. Introduction Sulfonimidamides 3 are derivatives of sulfonic acid and analogous of
  • sulfonamides, in which one oxygen has been replaced by a nitrogen group. They are known since 1962,[1] and a number of recent investigations focussed on both their reactivity and application in organic synthesis, such as nitrogen sources for metal-catalyzed nitrene transfer reactions, [2][3][4][5] and their
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Published 25 Sep 2007
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