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Search for "SNAr" in Full Text gives 74 result(s) in Beilstein Journal of Organic Chemistry.

1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

  • Dace Cīrule,
  • Irina Novosjolova,
  • Ērika Bizdēna and
  • Māris Turks

Beilstein J. Org. Chem. 2021, 17, 410–419, doi:10.3762/bjoc.17.37

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  • . A series of substituted products was obtained in SNAr reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C–O and C–C bond forming reactions clearly show the ability of the 1,2,3-triazolyl
  • ][3][4][5][6]. They are often used as antiviral, anticancer and antibacterial agents. Such intensive medicinal chemistry applications demand for constant development of novel synthetic methodologies. Frequently, the purine structure is modified in SNAr reactions with N- [7][8][9][10][11] and S
  • -nucleophiles [12][13][14] and in metal catalyzed reactions of halopurine derivatives [15][16][17][18][19][20]. Modifications of purines with O-nucleophiles are based on SNAr reactions between 6-halopurine derivatives and alcohols [21][22][23][24][25][26][27][28] in the presence of a base. Alcohols are used in
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Published 11 Feb 2021

1,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

  • Kārlis-Ēriks Kriķis,
  • Irina Novosjolova,
  • Anatoly Mishnev and
  • Māris Turks

Beilstein J. Org. Chem. 2021, 17, 193–202, doi:10.3762/bjoc.17.19

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  • new method for C–N bond transformations into C–P bonds was developed using 1,2,3-triazoles as leaving groups in SNAr–Arbuzov reactions. A series of C6-phosphonated 2-triazolylpurine derivatives was synthesized for the first time, with the isolated yields reaching up to 82% in the C–P-bond-forming
  • event. The SNAr–Arbuzov reaction of 2,6-bistriazolylpurines follows the general regioselectivity pattern of the C6-position being more reactive towards substitution, which was unambiguously proved by X-ray analysis of diethyl (9-heptyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purin-6-yl)phosphonate
  • development of this topic [8][9][10][11]. On the contrary, only a few examples can be found in the literature where a phosphorus-containing substituent is directly attached to the purine ring [12][13]. In 2008, an SNAr–Arbuzov reaction was developed for 6-chloropurine derivatives under microwave irradiation
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Published 20 Jan 2021

Novel library synthesis of 3,4-disubstituted pyridin-2(1H)-ones via cleavage of pyridine-2-oxy-7-azabenzotriazole ethers under ionic hydrogenation conditions at room temperature

  • Romain Pierre,
  • Anne Brethon,
  • Sylvain A. Jacques,
  • Aurélie Blond,
  • Sandrine Chambon,
  • Sandrine Talano,
  • Catherine Raffin,
  • Branislav Musicki,
  • Claire Bouix-Peter,
  • Loic Tomas,
  • Gilles Ouvry,
  • Rémy Morgentin,
  • Laurent F. Hennequin and
  • Craig S. Harris

Beilstein J. Org. Chem. 2021, 17, 156–165, doi:10.3762/bjoc.17.16

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  • library building block acid chloride 2. The libraries were prepared in a 3-step manner: 1) amide coupling; 2) deprotection of the 2-methoxypyridine through hydrolysis at elevated temperatures; and 3) the final SNAr or Ullman step to introduce the amine vector with variable yields and chromatographic
  • morpholine amide 7. The synthesis started by selective SNAr reaction with 4 and tert-butyl ((cis)-4-aminocyclohexyl)carbamate affording the intermediate nicotinic acid 5 in 70% yield without the need for chromatography. Subsequent amide coupling using TBTU afforded 2-chloro precursor 6 in excellent yield
  • ). No product was observed via direct SNAr using KOH (Table 1, entry 1) [3]. Acidic conditions (Table 1, entries 2–5) [4], where we can expect protonation thus activation of the pyridine ring towards nucleophilic attack, resulted in only traces of product along with hydrolysis of the amide moiety at C-3
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Published 18 Jan 2021

Et3N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

  • Dharmender Singh,
  • Vipin Kumar and
  • Virender Singh

Beilstein J. Org. Chem. 2020, 16, 1740–1753, doi:10.3762/bjoc.16.146

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  • presence of the electron-withdrawing substituents in B seemed to favor the anticipated SNAr mechanism by stabilizing the negatively charged intermediate 10 (Figure 2). Overall, it was noted that the 1-formyl-β-carbolines 1a–m reacted faster and afforded the corresponding products in higher yields as
  • nucleophilic substitution reaction (SNAr) by transit the sulfur anion in 9 followed by dismissal of the nitrite ion may result in the formation of the β-carboline-tethered benzothiophenone derivative 2bA. It is anticipated that the role of DMSO is to stabilize the ionic intermediates, specifically 10 and to
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Published 20 Jul 2020

Heterogeneous photocatalysis in flow chemical reactors

  • Christopher G. Thomson,
  • Ai-Lan Lee and
  • Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

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Published 26 Jun 2020

In silico rationalisation of selectivity and reactivity in Pd-catalysed C–H activation reactions

  • Liwei Cao,
  • Mikhail Kabeshov,
  • Steven V. Ley and
  • Alexei A. Lapkin

Beilstein J. Org. Chem. 2020, 16, 1465–1475, doi:10.3762/bjoc.16.122

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  • . Both selectivity and mechanism were correctly identified by the algorithm applying the previously set threshold to the SnAr intermediate stability (intermediates 5), which is shown in Table 4. Conclusion A computational algorithm rationalising the existing palladium catalysed C–H activation reactions
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Published 25 Jun 2020

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

  • Stephanie G. E. Amos,
  • Marion Garreau,
  • Luca Buzzetti and
  • Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

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  • fragmentation is not favored, these charged radicals can be intercepted and lead to different selectivities when compared to a traditional two-electron chemistry (e.g., anti-Markovnikov vs Markovnikov or ipso-SNAr reactions). Heteroatom-containing radical anions, such as ketyl radicals, constitute a special
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Published 29 May 2020

Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids

  • Benedikt C. Melzer,
  • Alois Plodek and
  • Franz Bracher

Beilstein J. Org. Chem. 2019, 15, 2304–2310, doi:10.3762/bjoc.15.222

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  • magnesiation with N,N-dimethylformamide did not lead to the expected bromoaldehyde 15 but provided surprisingly the aminoaldehyde 16. Probably, the intermediate aminoalkoxide delivers dimethylamine during aqueous work-up, followed by SNAr reaction at C-4. Related nucleophilic substitutions have been reported
  • for 4-chlorobenzo[c][2,7]naphthyridine (9a) previously [10]. Alternatively, this SNAr could have taken place under anhydrous conditions directly from the aminoalkoxide. This latter mechanism is in analogy to an intramolecular reaction of a hydrazone derivative proposed by Guillier et al. [12
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Published 26 Sep 2019

Synthesis and properties of sulfur-functionalized triarylmethylium, acridinium and triangulenium dyes

  • Marco Santella,
  • Eduardo Della Pia,
  • Jakob Kryger Sørensen and
  • Bo W. Laursen

Beilstein J. Org. Chem. 2019, 15, 2133–2141, doi:10.3762/bjoc.15.210

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  • -substituted triarylmethylium salts as simple precursors allowing both introduction of dialkylamino donor groups and formation of the heterocyclic triangulenium ring systems. These characteristic types of aromatic nucleophilic substitution (SNAr) reactions are exemplified by the synthesis of A3-ADOTA+ (Figure
  • conditions and intramolecular SNAr replacement of ortho-methoxy groups [18][32]. The SNAr approach to the synthesis of triangulenium dyes [14][18][19] has been extremely successful and expanded the family greatly from the single derivative (TOTA+, Figure 1b) first synthesized by Martin and Smith in 1964 [32
  • ], and also includes the family of helicenium dyes [33][34][35]. However, the introduction of groups other than nitrogen and oxygen has so far not been performed by the SNAr approach. Thus in the preparation of the sulfur-bridged triangulenium ions DOTTA+ and AOTTA+ (Figure 1b) Lacour and co-workers
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Published 09 Sep 2019

Synthesis of benzo[d]imidazo[2,1-b]benzoselenoazoles: Cs2CO3-mediated cyclization of 1-(2-bromoaryl)benzimidazoles with selenium

  • Mio Matsumura,
  • Yuki Kitamura,
  • Arisa Yamauchi,
  • Yoshitaka Kanazawa,
  • Yuki Murata,
  • Tadashi Hyodo,
  • Kentaro Yamaguchi and
  • Shuji Yasuike

Beilstein J. Org. Chem. 2019, 15, 2029–2035, doi:10.3762/bjoc.15.199

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  • probably deprotonation of the heterocyclic rings with a base. Moreover, nucleophilic aromatic substitution (SNAr) reactions between an aryl halide and a selenium reagent such as aryl selenide anion or diaryl diselenide for C(Ar)–Se bond formation using a base have been reported [20][21][22]. However, the
  • mechanism is as depicted in Scheme 3. The base deprotonates the imidazole ring giving an anion at the 2-position, which reacts with selenium by nucleophilic attack, resulting in C(Het)–Se bond formation. Next, the ring closure proceeds via the SNAr reaction by attack of the selenide anion on the phenyl
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Published 26 Aug 2019

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

  • Gagandeep Kour Reen,
  • Ashok Kumar and
  • Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

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Published 19 Jul 2019

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

  • Emeline Benoit,
  • Ahmed Fnaiche and
  • Alexandre Gagnon

Beilstein J. Org. Chem. 2019, 15, 1162–1171, doi:10.3762/bjoc.15.113

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  • thiophenols 14 through SN2 reaction with cyclopropyl bromide (15, Scheme 2a) [2][4] or by SNAr reaction between aryl fluorides 16 and cyclopropanethiol (17, (Scheme 2b) [6]. Although simple and attractive, these approaches usually require harsh conditions such as the presence of a strong base and high
  • temperatures [18]. In addition, an electron-withdrawing group (EWG) must be present on the aryl fluoride 16 for the SNAr reaction to proceed. Aryl cyclopropyl sulfides can also be accessed by the addition of thiophenols 14 to cyclopropenes 18 (Scheme 2c) [19][20] or to exo-methylenecyclopropanes 20 (Scheme 2d
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Published 27 May 2019

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

  • Andrejs Šišuļins,
  • Jonas Bucevičius,
  • Yu-Ting Tseng,
  • Irina Novosjolova,
  • Kaspars Traskovskis,
  • Ērika Bizdēna,
  • Huan-Tsung Chang,
  • Sigitas Tumkevičius and
  • Māris Turks

Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41

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  • % for N(9)-alkylated products. Both methodologies produced a mixture of N(9)- and N(7)-alkylated isomers from which the major N(9) product was easily separated by column chromatography [42][43][44][45][46][47]. Alkylated products were used in SNAr reactions with NaN3 in acetone or DMF, giving good to
  • deprotonated starting material 1b was methylated with MeI and further submitted to SNAr reaction with NaN3 according to a previously published procedure [39]. The expected 2,6-diazido-7-deazapurine (3) was obtained in 78% yield. It should be noted that the medium size alkyl chains at N(9) were chosen for
  • →4) followed by a SNAr process (4→5) which showcases the use of 1,2,3-triazoles as leaving groups. It is well established during our previous research in the purine nucleoside series that such an approach provides 6-amino-2-(1,2,3-triazol-1-yl) derivatives [25]. On the other hand, it was also
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Published 15 Feb 2019

Synthesis and biological evaluation of 1,2-disubstituted 4-quinolone analogues of Pseudonocardia sp. natural products

  • Stephen M. Geddis,
  • Teodora Coroama,
  • Suzanne Forrest,
  • James T. Hodgkinson,
  • Martin Welch and
  • David R. Spring

Beilstein J. Org. Chem. 2018, 14, 2680–2688, doi:10.3762/bjoc.14.245

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  • , entry 1). Meanwhile, use of base-induced SNAr-type conditions allowed a small amount of product to be isolated (Table 1, entry 2) [21], but copper-catalysed conditions offered a higher yield (Table 1, entry 3) [12]. This behaviour stands in contrast to that noted for substrates bearing an alkyl
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Published 19 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

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  • by cyclodehydration allowed for a straightforward and efficient synthesis of 3,4-dihydroquinazolines with N-aryl substituents bearing electron-withdrawing groups. The sequence involves an initial SNAr displacement, N-acylation and MW-assisted ring closure. Remarkably, the uncatalyzed N-arylation of 2
  • reaction promoted by trimethylsilyl polyphosphate (PPSE) is also proposed on the basis of literature data and our experimental observations. Keywords: cyclodehydrations; dihydroquinazolines; microwaves; nitrilium ions; PPSE; SNAr; Introduction Dihydroquinazolines (DHQs) represent heterocyclic cores of
  • others, and involve a reduction step which would be incompatible with the presence of nitro or cyano groups [5][13][14][39][68][69][70][71]. The synthetic sequence towards compounds 1 requires the chemoselective arylation of the benzylic amino group of the precursor with active haloaryl derivatives. SNAr
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Published 26 Sep 2018

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

  • Michael K. Bogdos,
  • Emmanuel Pinard and
  • John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

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  • how this protocol translates seamlessly to drug discovery in the LSF strategy. In a method that is complementary to their C–H amination strategy, Nicewicz et al. have reported the SNAr-type addition of nucleophiles to methoxybenzene derivatives at the ipso position, as opposed to the C–H amination
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Published 03 Aug 2018

Imide arylation with aryl(TMP)iodonium tosylates

  • Souradeep Basu,
  • Alexander H. Sandtorv and
  • David R. Stuart

Beilstein J. Org. Chem. 2018, 14, 1034–1038, doi:10.3762/bjoc.14.90

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  • , transition metals feature prominently in such methods, but even recent examples employ stoichiometric metal mediators [4]. Metal-free methods by classic SNAr are also attractive, but only possible on very electron-deficient arene substrates [5]. Diaryliodonium salts are useful reagents for metal-free aryl
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Published 11 May 2018

Synthesis and stability of strongly acidic benzamide derivatives

  • Frederik Diness,
  • Niels J. Bjerrum and
  • Mikael Begtrup

Beilstein J. Org. Chem. 2018, 14, 523–530, doi:10.3762/bjoc.14.38

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  • stability under acidic and basic conditions are also reported. Keywords: benzoic acid; cross-coupling; hydrolysis; SNAr; trifluoromethanesulfonamide; Introduction Very strong organic acids are interesting as catalysts for chemical reactions [1][2] and for facilitation of proton conduction [3]. In order to
  • (SNAr) [6][7]. Benzoic acids (e.g., 2) are relatively weak acids, even with highly electron-withdrawing substituents on the aromatic core [8]. Very strong benzoic acid derivatives (e.g., 4 and 6) have been synthesized by replacing one or both of the oxygens of the carboxylate group with the
  • of the corresponding imidoyl chlorides 10 with PCl5 in POCl3, followed by the additional reaction with trifluoromethanesulfonamide (1) and protonation by sulfuric acid (Scheme 1) [10]. In recent years, we have reported high yielding catalyst-free N-arylation by SNAr reaction of mono- or
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Published 27 Feb 2018

Stereochemical outcomes of C–F activation reactions of benzyl fluoride

  • Neil S. Keddie,
  • Pier Alexandre Champagne,
  • Justine Desroches,
  • Jean-François Paquin and
  • David O'Hagan

Beilstein J. Org. Chem. 2018, 14, 106–113, doi:10.3762/bjoc.14.6

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  • carbon–halogen bond known [1]. Its low reactivity, in comparison to other C–X bonds, means that it is inert to all but the most harsh reaction conditions, and fluorine can generally be carried through multistep syntheses without concern over side reactions (the exception being SNAr reactions). In recent
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Published 09 Jan 2018

A concise flow synthesis of indole-3-carboxylic ester and its derivatisation to an auxin mimic

  • Marcus Baumann,
  • Ian R. Baxendale and
  • Fabien Deplante

Beilstein J. Org. Chem. 2017, 13, 2549–2560, doi:10.3762/bjoc.13.251

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  • . Results and Discussion In order to generate the core indole unit through a robust synthetic sequence we decided to investigate the treatment of a 2-chloronitrobenzene 9 with ethyl cyanoacetate (10) as the nucleophile in a base-mediated SNAr reaction (Scheme 1). The resulting adduct 11 would then be
  • coil reactor maintained at 50 °C (Scheme 2). The intensely red coloured solution (anion of the SNAr adduct) [8] which quickly formed was quenched after the incubation period (35–108 min) using a third flow stream of hydrochloric acid (1 M) blended via a dedicated mixer chip before the combined mixture
  • product 8 with yields and throughputs. Optimisation experiments for SNAr with ethyl cyanoacetate (10).a Selected optimisation experiments for reductive cyclisation to compound 12.a Supporting Information Supporting Information File 474: Reproductions of 1H and 13C NMR spectra for the reported compounds
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Published 29 Nov 2017

Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

  • Roman A. Irgashev,
  • Nikita A. Kazin,
  • Gennady L. Rusinov and
  • Valery N. Charushin

Beilstein J. Org. Chem. 2017, 13, 1396–1406, doi:10.3762/bjoc.13.136

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  • through a conventional mechanism of nucleophilic aromatic substitution (SNAr). On the other hand, conversion of the second nitro group, as well as a similar transformation of compound 10b, can possibly be explained in terms of the radical-nucleophilic aromatic substitution (SRN1), since no other electron
  • -withdrawing groups, facilitating the SNAr reactions, are present in these aromatics [51]. Such type of nitro–thiolate substitution is a rare phenomenon; only a few reports on this topic are available in the literature [52][53][54]. Some N-nucleophiles are also able to react with 6,12-dinitro-substituted ICZs
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Published 14 Jul 2017

Studies directed toward the exploitation of vicinal diols in the synthesis of (+)-nebivolol intermediates

  • Runjun Devi and
  • Sajal Kumar Das

Beilstein J. Org. Chem. 2017, 13, 571–578, doi:10.3762/bjoc.13.56

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  • Sharpless asymmetric dihydroxylation as the sole source of chirality [27]. For the synthesis of chroman derivative 2, first a base-mediated intramolecular SNAr reaction was envisioned for the aryl C–O bond formation under transition-metal-free conditions [28][29][30]. The additional benefit of this strategy
  • (±)-14 we were in a position to investigate the key cyclization involving an intramolecular SNAr to deliver 2. Unfortunately, all attempts of cyclizing (±)-14 to obtain chroman derivative (±)-2 under various SNAr reaction conditions were not successful. Treatment of (±)-14 with KOt-Bu/THF (65 °C), NaH
  • /DMF (80 °C), NaH/DMSO (100 °C) and KOt-Bu/toluene (110 °C) did not lead to any conversion. However, more forcing conditions such as NaH/NMP (130 °C) resulted in a to partial decomposition of the starting material. These results indicated that an intramolecular SNAr reaction of triol (±)-14 to form
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Published 21 Mar 2017

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

  • Constantin Mamat,
  • Marc Pretze,
  • Matthew Gott and
  • Martin Köckerling

Beilstein J. Org. Chem. 2016, 12, 2478–2489, doi:10.3762/bjoc.12.242

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  • and [18F]5b was accomplished using the SNAr concept. The appropriate precursors and reference compounds were prepared in two steps from simple commercially available starting materials in high yields, but at this stage the building blocks are not appropriate for further labeling purposes. Experimental
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Published 21 Nov 2016

Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene

  • Javier Ajenjo,
  • Martin Greenhall,
  • Camillo Zarantonello and
  • Petr Beier

Beilstein J. Org. Chem. 2016, 12, 192–197, doi:10.3762/bjoc.12.21

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  • , nitro(pentafluorosulfanyl)benzenes are widely-available primary industrial products and starting materials to other SF5-benzenes which were prepared by reduction followed by condensation or diazotization chemistry [8][14][15][16], SEAr [17], SNAr [18][19][20][21][22][23][24], or metal-catalyzed cross
  • -coupling reactions [25][26][27]. Synthetic methods to novel SF5-containing building blocks are sought after and drive the development of applications of these compounds. In this work, we explore SNAr chemistry of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene which was initially obtained as a minor
  • ; redistillation afforded 2 in 99% purity (detected by GC). However, for investigations of SNAr of 2, a more efficient process for its synthesis was required. With higher excess of fluorine, the 2:1 ratio increased. Therefore, the synthesis of 2 by the direct fluorination of 1 was investigated (Scheme 2 and Figure
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Published 03 Feb 2016

An efficient synthesis of N-substituted 3-nitrothiophen-2-amines

  • Sundaravel Vivek Kumar,
  • Shanmugam Muthusubramanian,
  • J. Carlos Menéndez and
  • Subbu Perumal

Beilstein J. Org. Chem. 2015, 11, 1707–1712, doi:10.3762/bjoc.11.185

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  • , these compounds were available only through multistep sequences, most notably one involving as the final step an SNAr reaction with the amine and having the serious limitation of requiring the presence of an additional strong electron-withdrawing group at C-5 [42][43][44]. Our protocol requires only two
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Published 22 Sep 2015
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