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Search for "phthalimide" in Full Text gives 105 result(s) in Beilstein Journal of Organic Chemistry.

Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes

  • Igor B. Krylov,
  • Stanislav A. Paveliev,
  • Mikhail A. Syroeshkin,
  • Alexander A. Korlyukov,
  • Pavel V. Dorovatovskii,
  • Yan V. Zubavichus,
  • Gennady I. Nikishin and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2018, 14, 2146–2155, doi:10.3762/bjoc.14.188

Graphical Abstract
  • imide-N-oxyl radicals are used as effective mediators for CH-functionalization with formation of C–C, C–O, C–S, and C–N bonds [11][16][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42]. Phthalimide-N-oxyl (PINO) is one of the most known imide-N-oxyl
  • on the literature data describing the formation of the phthalimide-N-oxyl radical (PINO) from NHPI under the action of PhI(OAc)2 [34][55][59][76][77], and based on information about the reaction of the PINO radical with styrenes [45] and interaction of benzyl radicals with iodine [78][79], a
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Published 16 Aug 2018

β-Hydroxy sulfides and their syntheses

  • Mokgethwa B. Marakalala,
  • Edwin M. Mmutlane and
  • Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

Graphical Abstract
  • few years ago, Denmark and co-workers revealed an impressive catalytic asymmetric thiofunctionalization of unactivated alkenes 102 with the commercially available arylsulfenylating agent N-(phenylthio)phthalimide (103) using selenophosphoramide 104 as a catalyst in the presence of methanesulfonic acid
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Published 05 Jul 2018

Anomeric modification of carbohydrates using the Mitsunobu reaction

  • Julia Hain,
  • Patrick Rollin,
  • Werner Klaffke and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

Graphical Abstract
  • with simple alcohols (Scheme 20) [81][82]. In this case, of course, the sugar thioglycoside takes the role of the nucleophile rather than of the alcohol component in the Mitsunobu reaction. Reactions with NH acids to achieve N-glycosides Early on, phthalimide was regarded as a good Mitsunobu reagent
  • -dialkoxycarbonylhydrazines [84]. This anomeric N-phthalimidation was later implemented by Nishimura et al. for the iminosugar 114 with phthalimide to give 115 in a high yield, en route to a new family of α-L-fucosidase inhibitors (Scheme 21) [85]. More generally, the preparation of modified glycosylamines under Mitsunobu
  • (6.3), N-hydroxyphthalimide was early considered in Mitsunobu reactions, for example by Grochowski and Jurczak to form an anomeric phthalimide–oxy bond as shown in several sugar series [109][110][111]. This gives access to new O-glycosylhydroxylamines, namely for the construction of glycosidic N–O
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Published 29 Jun 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

Graphical Abstract
  • Souradeep Basu Alexander H. Sandtorv David R. Stuart Department of Chemistry, Portland State University, Portland OR 97201, United States 10.3762/bjoc.14.90 Abstract Herein, we describe the synthesis of N-aryl phthalimides by metal-free coupling of potassium phthalimide with unsymmetrical aryl
  • )iodonium salts [12][13][14] and describe here the development of a C–N coupling of a phthalimide anion with non-sterically biased aryl groups. The protocol is compatible with ortho-, meta-, and para-substitution on the aryl group and the phthalimide moiety may also provide access to anilines. Results and
  • Discussion We initiated our optimization of the arylation of the potassium phthalimide nucleophile with diaryliodonium electrophiles by surveying several reaction conditions: dummy ligand (Aux), counter anion, solvent and volume, reaction temperature, and stoichiometry (Table 1). Consistent with an
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Published 11 May 2018

Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"

  • Karolina Tiara,
  • Mykhaylo A. Potopnyk and
  • Sławomir Jarosz

Beilstein J. Org. Chem. 2018, 14, 634–641, doi:10.3762/bjoc.14.50

Graphical Abstract
  • alternative way to the desired amine 12a, based on the SN2 reaction of the activated alcohol 13 [34][35] with benzylamine, also failed (Scheme 2). The Mitsunobu approach to convert the hydroxy group into an amine function was also unsuccessful. Although 13 reacted with phthalimide gave the desired product 13a
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Published 15 Mar 2018

The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones

  • Ommid Anamimoghadam,
  • Saira Mumtaz,
  • Anke Nietsch,
  • Gaetano Saya,
  • Cherie A. Motti,
  • Jun Wang,
  • Peter C. Junk,
  • Ashfaq Mahmood Qureshi and
  • Michael Oelgemöller

Beilstein J. Org. Chem. 2017, 13, 2833–2841, doi:10.3762/bjoc.13.275

Graphical Abstract
  • ; arylmethylenedihydroisoindolinones; photochemistry; photodecarboxylation; phthalimide; Introduction Phthalimides and their related 3-alkyl- and 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones play an important role in medicinal chemistry due to their biological activities for a wide range of therapeutic applications [1][2][3][4
  • [41], followed by amination [42] furnishes the desired target compounds. The amino group is introduced in the final step as it would otherwise interfere with the desired photoreaction. In fact, amines are very potent electron donors and are easily oxidized by the excited phthalimide chromophore [43
  • ][44][45][46]. Results and Discussion Initial irradiation experiments were conducted with N-(2-bromoethyl)phthalimide (1a) and potassium phenylacetate (2a) as a model system (Scheme 2 and Table 1). The salt 2a, generated from the corresponding phenylacetic acid and potassium carbonate, was used in
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Published 20 Dec 2017

Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides

  • Tao Fan,
  • Wei-Dong Meng and
  • Xingang Zhang

Beilstein J. Org. Chem. 2017, 13, 2610–2616, doi:10.3762/bjoc.13.258

Graphical Abstract
  • , aldehyde, and phthalimide (4e, 4f, 4j and 4k), were all applicable to the reaction, thus offering good opportunities for downstream transformations and highlighting the utility of the current process further. (3-Bromo-4,4,4-trifluorobutyl)benzene and 4-bromo-5,5,5-trifluoropentyl benzoate were also
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Published 06 Dec 2017

Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis

  • Raju Cheerlavancha,
  • Ahmed Ahmed,
  • Yun Cheuk Leung,
  • Aggie Lawer,
  • Qing-Quan Liu,
  • Marina Cagnes,
  • Hee-Chan Jang,
  • Xiang-Guo Hu and
  • Luke Hunter

Beilstein J. Org. Chem. 2017, 13, 2316–2325, doi:10.3762/bjoc.13.228

Graphical Abstract
  • the electrophilic fluorination reagent NFSI (compared with nucleophilic fluorination reagents such as DeoxoFluor). Accordingly, two aldehyde substrates (7a and 7b) were prepared [21][22], containing either a phthalimide or a Boc protecting group. Electrophilic fluorination was attempted according to
  • 7a (containing the phthalimide protecting group) suggested that the undesired difluorinated compound 12 was formed as the major product. An additional complication was that the phthalimide protecting group of 12 seemed to be at least partially sensitive to sodium borohydride [23]. In contrast, the
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Published 01 Nov 2017

Phosphonic acid: preparation and applications

  • Charlotte M. Sevrain,
  • Mathieu Berchel,
  • Hélène Couthon and
  • Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

Graphical Abstract
  • dealkylation and compatible with the presence of other groups such as allyl, ketone, primary alcohol, phthalimide, ester or thioether as illustrated with the transformation of the phosphonate 79 to the phosphonic acid 80 (Figure 23). The best results were obtained when 0.9 equivalents of BBr3 per phosphonate
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Published 20 Oct 2017

Mechanochemical synthesis of small organic molecules

  • Tapas Kumar Achar,
  • Anima Bose and
  • Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

Graphical Abstract
  • reaction time, hazardous organic solvent, and tedious isolation procedure are implemented. Dekamin and co-workers have demonstrated the synthesis of pyrans using potassium phthalimide (POPI) as a catalyst under ball-milling which is found to be advantageous over solution phase synthesis [158]. Malonitrile
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Published 11 Sep 2017

Mechanochemical N-alkylation of imides

  • Anamarija Briš,
  • Mateja Đud and
  • Davor Margetić

Beilstein J. Org. Chem. 2017, 13, 1745–1752, doi:10.3762/bjoc.13.169

Graphical Abstract
  • organic solvents. Ex situ IR spectroscopy (ATR) of milling of imides 11–17 with K2CO3 was used for monitoring the reaction progress, which showed for instance, that potassium phthalimide [29] was formed after one hour of grinding (Figure 2). This salt was, without isolation, subjected to further milling
  • deprotonation of the imides with pKa values at least within the range of 8.3–9.9 units [30] under ball milling conditions. Deprotonation of phthalimide in solution is usually carried out with the use of bases stronger than K2CO3 [31] and this difference in reactivity in comparison to solvent free conditions has
  • need for tetrabutylammonium iodide as phase-transfer catalyst to increase the limited solubility of 14. The selectivity was observed for certain substrates. For example, the alkylation of phthalimide 12 with 1,4-bis(bromomethyl)benzene led to the formation of two products, namely 28 and 29. By keeping
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Published 22 Aug 2017

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

  • Santanu Hati,
  • Ulrike Holzgrabe and
  • Subhabrata Sen

Beilstein J. Org. Chem. 2017, 13, 1670–1692, doi:10.3762/bjoc.13.162

Graphical Abstract
  • phthalimide-N-oxyl radical (PINO) via transfer of hydrogen from NHPI to O2. Co2+-assisted this step by associating with oxygen to generate a Co3+–oxygen complex. It then abstracts the hydrogen from NHPI. Next, PINO abstracted a hydrogen from the DHP produced to generate radical X which aromatizes via hydrogen
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Published 15 Aug 2017

1-Imidoalkylphosphonium salts with modulated Cα–P+ bond strength: synthesis and application as new active α-imidoalkylating agents

  • Jakub Adamek,
  • Roman Mazurkiewicz,
  • Anna Węgrzyk and
  • Karol Erfurt

Beilstein J. Org. Chem. 2017, 13, 1446–1455, doi:10.3762/bjoc.13.142

Graphical Abstract
  • )imide 7 with triarylphosphonium tetrafluoroborate was melted at 85–140 °C in the presence of NaBr as a catalyst under reduced pressure (0.1–0.2 mmHg) for 0.5–10 h (Table 2). Phthalimide-derived phosphonium salts 5 (A = o-C6H4) were usually obtained in good to excellent yields, whereas the yields of
  • reaction product. It seems that the steric congestion caused by two methoxy groups in ortho positions to the attacking carbon caused the displacement of a phthalimide anion by triarylphosphine in the primary reaction product and thus leading to the phosphonium salt 10 as an unexpected side product (Scheme
  • isomers was obtained only in the case of 1-imidoalkylphosphonium salts derived from succinimide, with a relatively small imide ring (Table 3, entries 14 and 15). On the other hand, phosphonium salts derived from phthalimide gave in all cases some excess of the para isomers. Bulky phenyl or isobutyl
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Published 24 Jul 2017

Exploring endoperoxides as a new entry for the synthesis of branched azasugars

  • Svenja Domeyer,
  • Mark Bjerregaard,
  • Henrik Johansson and
  • Daniel Sejer Pedersen

Beilstein J. Org. Chem. 2017, 13, 644–647, doi:10.3762/bjoc.13.63

Graphical Abstract
  • phthalimide-protected compounds were synthesised as UV active analogues that would facilitate analysis. Aminoalcohols 1 and 2 were Boc- and Pht-protected under standard conditions to provide alcohols 3–6 in good yield. Oxidation of alcohol 3 to aldehyde 7 was achieved in moderate yield using standard Parikh
  • to the phthalimide-protected dienes 15,16. When the same reaction was performed with rose bengal on diene 16 a very low yield of endoperoxide 19 was obtained and most starting material was recovered (78%) even after prolonged reaction time (40 h). However, the reaction outcome was greatly improved by
  • was encouraging and gave access to a variety of novel protected azasugar precursors. We conclude that the choice of amine and dihydroxy protecting groups can have an impact on the success of the endoperoxide synthesis and its thermal stability, and that employing phthalimide and acetonide groups for N
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Published 03 Apr 2017

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

  • Nikolay V. Lukashev,
  • Gennadii A. Grabovyi,
  • Dmitry A. Erzunov,
  • Alexey V. Kazantsev,
  • Gennadij V. Latyshev,
  • Alexei D. Averin and
  • Irina P. Beletskaya.

Beilstein J. Org. Chem. 2017, 13, 564–570, doi:10.3762/bjoc.13.55

Graphical Abstract
  • (6a) is readily aminated by phthalimide using classical Ullmann conditions (15% Cu powder, quinoline, 200 °C in PhNO2) [41]. However, the reaction of 3c with 6a using the same conditions, as well as the addition of stronger bases (DABCO, DIPEA, DBU) afforded extremely low yields (7–12%) of aminated
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Published 20 Mar 2017

A versatile route to polythiophenes with functional pendant groups using alkyne chemistry

  • Xiao Huang,
  • Li Yang,
  • Rikard Emanuelsson,
  • Jonas Bergquist,
  • Maria Strømme,
  • Martin Sjödin and
  • Adolf Gogoll

Beilstein J. Org. Chem. 2016, 12, 2682–2688, doi:10.3762/bjoc.12.265

Graphical Abstract
  • -bromoterephthalate and 2-bromo-4,4’-bipyridine were prepared according to reported procedures [38][39]. The electron acceptor phthalimide (PT) was attached to EDOT via cycloaddition between the alkyne and an alkylazide to produce derivative 13 (Scheme 4). Regioselective formation of 13 involved the Cu(I)-catalyzed
  • Huisgen 1,3-dipolar cycloaddition between N-(2-azidoethyl)phthalimide and the alkyne terminal of pyEDOT under ultrasound conditions in 73% yield. Detailed synthetic routes are presented in Supporting Information File 1. Figure 1a shows the cyclic voltammograms (CVs) for electrochemical polymerization of
  • phthalimide-EDOT derivative 13 failed to polymerize. A plausible reason could be an interference of the electron rich aromatic moieties with the thiophene radical cations formed during polymerization, in analogy to previous suggestions from Bäuerle et al. for triazolomethyl-substituted EDOT. Post
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Published 09 Dec 2016

Conjugate addition–enantioselective protonation reactions

  • James P. Phelan and
  • Jonathan A. Ellman

Beilstein J. Org. Chem. 2016, 12, 1203–1228, doi:10.3762/bjoc.12.116

Graphical Abstract
  • enantioselective synthesis of β-amino esters 62 via the addition of arylboronic acids 47 to α-methylaminoacrylates 61 (Scheme 14) [35]. The authors identified (S)-difluorphos (44, Figure 2) and phthalimide as the optimal ligand and proton source combination, respectively. Additionally, the bulky tert-butyl ester
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Published 15 Jun 2016

Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

  • Shino Manabe and
  • Yukishige Ito

Beilstein J. Org. Chem. 2016, 12, 328–333, doi:10.3762/bjoc.12.35

Graphical Abstract
  • phthalimide group in the 2-position, was converted to α-glycoside 4, by introducing an N-acetyl 2,3-trans-carbamate group (Scheme 3) and by conducting an anomerization reaction. The glycosylation reaction of phthalimido-protected glucosamine thioglycoside 5 with inositol 6 [24] afforded β-linked pseudo
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Published 22 Feb 2016

Copper-catalyzed intermolecular oxyamination of olefins using carboxylic acids and O-benzoylhydroxylamines

  • Brett N. Hemric and
  • Qiu Wang

Beilstein J. Org. Chem. 2016, 12, 22–28, doi:10.3762/bjoc.12.4

Graphical Abstract
  • Liu reported a palladium-catalyzed introduction of phthalimide (HNPhth) and acetate functionalities to terminal allylic and homoallylic ethers in the presence of an iodine oxidant (Scheme 1B) [13]. The Yoon lab also developed copper- and iron-catalyzed olefin difunctionalization reactions with
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Published 07 Jan 2016

Copper-catalyzed aminooxygenation of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives

  • Yan Li,
  • Xue Zhou,
  • Guangfan Zheng and
  • Qian Zhang

Beilstein J. Org. Chem. 2015, 11, 2721–2726, doi:10.3762/bjoc.11.293

Graphical Abstract
  • aminooxygenation reaction of alkenes with phthalimide and (diacetoxyiodo)benzene through cis-aminopalladation and SN2 C–O bond formation [34]. In 2013, Zhu and co-workers described an n-Bu4NI-catalyzed aminooxygenation of inactive alkenes with benzotriazole and water which underwent a nitrogen-centred radical
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Published 24 Dec 2015

Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates

  • Takamichi Wakamatsu,
  • Kazunori Nagao,
  • Hirohisa Ohmiya and
  • Masaya Sawamura

Beilstein J. Org. Chem. 2015, 11, 2444–2450, doi:10.3762/bjoc.11.265

Graphical Abstract
  • accessible through the hydroboration–conjugate addition one-pot protocol with excellent syn stereoselectivities (Table 2). This protocol tolerated functional groups such as methoxy, ester, phthalimide, fluoro, cyano and aldehyde moieties in the alkylboranes and alkynoates (Table 2, entries 1–3, 6–9 and 11
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Published 04 Dec 2015

Recent advances in copper-catalyzed C–H bond amidation

  • Jie-Ping Wan and
  • Yanfeng Jing

Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240

Graphical Abstract
  • products 49 or 50 by incorporating phthalimide/saccharin 46. Under the standard conditions, however, the reaction of benzamide with 2-phenylpyridine provided product 51 with low yield (Scheme 14). As a special aromatic system, quinoline N-oxides were well investigated in their reactivity for metal
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Published 17 Nov 2015

Preparative semiconductor photoredox catalysis: An emerging theme in organic synthesis

  • David W. Manley and
  • John C. Walton

Beilstein J. Org. Chem. 2015, 11, 1570–1582, doi:10.3762/bjoc.11.173

Graphical Abstract
  • )phthalimide was employed by the Overman group in their synthesis of (−)-aplyviolene [11]. Heterogeneous PRCs form a second class consisting of semiconductor materials. These are generally metal oxides or sulfides in the form of fine particles that consequently have the additional advantage of easily being
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Published 09 Sep 2015

The enantioselective synthesis of (S)-(+)-mianserin and (S)-(+)-epinastine

  • Piotr Roszkowski,
  • Jan. K. Maurin and
  • Zbigniew Czarnocki

Beilstein J. Org. Chem. 2015, 11, 1509–1513, doi:10.3762/bjoc.11.164

Graphical Abstract
  • phthalimide proposed by Moffett [15] may be used for this step with comparable results. The imine 6 was then transformed to the enantiomerically enriched amine 7 with the aid of asymmetric transfer hydrogenation (ATH) process [8][10][11]. As in our synthesis of aptazepine [8], we initially used the chiral
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Published 28 Aug 2015

Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8–DMSO: application to the synthesis of vernakalant

  • Dnyaneshwar N. Garad,
  • Subhash D. Tanpure and
  • Santosh B. Mhaske

Beilstein J. Org. Chem. 2015, 11, 1008–1016, doi:10.3762/bjoc.11.113

Graphical Abstract
  • phthalimide was obtained in very good yield (Table 3, entry 6). Furthermore, the scope of the protocol to obtain imides from aliphatic amines and saturated anhydride was explored (Table 4). Primary aliphatic amines with short and long alkyl chains were treated with succinic anhydride and they were found to
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Published 12 Jun 2015
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