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Search for "naphthalene" in Full Text gives 204 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Coordination chemistry and photoswitching of dinuclear macrocyclic cadmium-, nickel-, and zinc complexes containing azobenzene carboxylato co-ligands

  • Jennifer Klose,
  • Tobias Severin,
  • Peter Hahn,
  • Alexander Jeremies,
  • Jens Bergmann,
  • Daniel Fuhrmann,
  • Jan Griebel,
  • Bernd Abel and
  • Berthold Kersting

Beilstein J. Org. Chem. 2019, 15, 840–851, doi:10.3762/bjoc.15.81

Graphical Abstract
  • physicochemical properties of the bound guest molecules are also greatly affected. Thus, complexation of naphthalene diimide carboxylato ligands leads to a substantial (>95%) quenching of the diimide fluorescence [5], and incorporation of a Fe(CpCO2H)2 unit leads to a significant anodic shift of the metallocene’s
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Published 03 Apr 2019

Azologization of serotonin 5-HT3 receptor antagonists

  • Karin Rustler,
  • Galyna Maleeva,
  • Piotr Bregestovski and
  • Burkhard König

Beilstein J. Org. Chem. 2019, 15, 780–788, doi:10.3762/bjoc.15.74

Graphical Abstract
  • properties of direct azologization to azo-extension, two additional derivatives of the in vitro most promising naphthalene azopurine 16c were synthesized either by keeping the original thioether (Scheme 5) or replacing it by an amide bond (Scheme 6) known as common structural feature of 5-HT3R antagonists
  • , two azo-extended purine derivatives 23 and 28 were synthesized resulting in excellent photochromic properties. Figure 1 compares exemplarily the UV–vis absorption spectra of the naphthalene-azo-purine 16c (left) and its azo-extended azobenzene thioether purine 23 (right). The determination of the
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Published 25 Mar 2019

Selective benzylic C–H monooxygenation mediated by iodine oxides

  • Kelsey B. LaMartina,
  • Haley K. Kuck,
  • Linda S. Oglesbee,
  • Asma Al-Odaini and
  • Nicholas C. Boaz

Beilstein J. Org. Chem. 2019, 15, 602–609, doi:10.3762/bjoc.15.55

Graphical Abstract
  • aromatization was observed, suggesting that monooxygenated products are able to react further. We propose that acetoxylated tetrahydronaphthalene eliminates acetic acid to yield dihydronaphthalene, which can be further oxidized by two electrons to yield the stable naphthalene ring. Minisci and co-workers also
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Published 05 Mar 2019

Oxidative radical ring-opening/cyclization of cyclopropane derivatives

  • Yu Liu,
  • Qiao-Lin Wang,
  • Zan Chen,
  • Cong-Shan Zhou,
  • Bi-Quan Xiong,
  • Pan-Liang Zhang,
  • Chang-An Yang and
  • Quan Zhou

Beilstein J. Org. Chem. 2019, 15, 256–278, doi:10.3762/bjoc.15.23

Graphical Abstract
  • different amount of NBS (N-bromosuccinimide). The corresponding CF3-substituted naphthalene 32 could be obtained in 69% yield when the product 31a was oxidized by 3 equiv of NBS (Scheme 9, reaction a). When the amount of NBS was increased to 6 equiv under identical conditions, the CF3-substituted
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Published 28 Jan 2019

Adhesion, forces and the stability of interfaces

  • Robin Guttmann,
  • Johannes Hoja,
  • Christoph Lechner,
  • Reinhard J. Maurer and
  • Alexander F. Sax

Beilstein J. Org. Chem. 2019, 15, 106–129, doi:10.3762/bjoc.15.12

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Published 11 Jan 2019

1,8-Bis(dimethylamino)naphthyl-2-ketimines: Inside vs outside protonation

  • A. S. Antonov,
  • A. F. Pozharskii,
  • P. M. Tolstoy,
  • A. Filarowski and
  • O. V. Khoroshilova

Beilstein J. Org. Chem. 2018, 14, 2940–2948, doi:10.3762/bjoc.14.273

Graphical Abstract
  • -arylketimines of 1,8-bis(dimethylamonio)naphthalene with a different number of methoxy groups in an aromatic substituent were investigated in solution by NMR (acetone, DMSO, MeCN), in solid state by X-ray analysis and in the gas phase by DFT calculations. Both mono- and diprotonated species were considered. It
  • rotation of the NH2+ fragment in dications. Keywords: hydrogen bond; imine; NMR; proton sponge; superbase; Introduction It is well known that the extremely high basicity of 1,8-bis(dimethylamino)naphthalene (1, DMAN; pKa = 12.1 in H2O [1][2], 18.62 in MeCN [3], 7.5 in DMSO [4]) and its derivatives
  • of the Z-form through formation of a stronger hydrogen bond between the DMSO molecule and the NHb proton [11], which is sterically unhindered and accessible for the solvent. Indeed, X-ray data and quantum chemical calculations show that phenyl and naphthalene rings are almost perpendicular (Figure 2
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Published 28 Nov 2018
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  • strength, the high surface area may play a role in catalysis. The catalyst was reused up to five cycles [69]. Pourmousavi et al. [70] found that sulfonated polynaphthalene 121 synthesized from naphthalene (119) shows high catalytic activities in the one-pot preparation of amidoalkyl naphthols 50. The
  • sulfonated polynaphthalene can be achieved in two steps: (a) polymerization of naphthalene (119) in nitrobenzene using FeCl3 as reagent (b) sulfonation of polynaphthalene (120) with chlorosulfonic acid in dichloromethane (Scheme 22). Amidoalkylnaphthol derivatives 50 were synthesized using catalyst 121 under
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Published 01 Nov 2018

Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers

  • Christian Schütz and
  • Martin Empting

Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241

Graphical Abstract
  • benzimidazole moiety (compound not shown) [80]. In a follow-up patent they generated PqsR inhibitor 45 as a front-runner compound [81], in which the benzimidazole headgroup was replaced by a substituted naphthalene bearing a carboxamide, in analogy to a fragment 44 of Zender et al. [82] and similar to the
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Published 15 Oct 2018

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

  • Sambasivarao Kotha,
  • Milind Meshram and
  • Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

Graphical Abstract
  • precursor 9 to [Ru-2] catalyst 5 gave the ring-closure product 10 in quantitative yield (Scheme 1). A sequential usage of SM cross coupling and RCM was responsible to construct various naphthalene derivatives such as 15 [31]. The SM coupling product 3,4-diallylbenzene derivative 13 (90%) was obtained from
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Published 21 Sep 2018

Tetrathiafulvalene – a redox-switchable building block to control motion in mechanically interlocked molecules

  • Hendrik V. Schröder and
  • Christoph A. Schalley

Beilstein J. Org. Chem. 2018, 14, 2163–2185, doi:10.3762/bjoc.14.190

Graphical Abstract
  • possibility of orthogonal switching (redox and light) enables an electrochemical “writing” of data which can be subsequently locked by a light stimulus. The TTF-based doubly interlocked crown/ammonium rotaxane 19 recently reported by us consists of a divalent axle with a π-electron-poor central naphthalene
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Published 20 Aug 2018

Cobalt-catalyzed peri-selective alkoxylation of 1-naphthylamine derivatives

  • Jiao-Na Han,
  • Cong Du,
  • Xinju Zhu,
  • Zheng-Long Wang,
  • Yue Zhu,
  • Zhao-Yang Chu,
  • Jun-Long Niu and
  • Mao-Ping Song

Beilstein J. Org. Chem. 2018, 14, 2090–2097, doi:10.3762/bjoc.14.183

Graphical Abstract
  • provide the intermediate B. Subsequently, the transfer of ligand OR from the coordinated CoIII to the naphthalene ring led to the formation of intermediate C. Finally, the alkoxylated product 3aa was released accompanied with the deprotonation and the CoII species was transformed into the CoIII species by
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Published 09 Aug 2018

A conformationally adaptive macrocycle: conformational complexity and host–guest chemistry of zorb[4]arene

  • Liu-Pan Yang,
  • Song-Bo Lu,
  • Arto Valkonen,
  • Fangfang Pan,
  • Kari Rissanen and
  • Wei Jiang

Beilstein J. Org. Chem. 2018, 14, 1570–1577, doi:10.3762/bjoc.14.134

Graphical Abstract
  • macrocycles possess multiple conformers due to the naphthalene flipping in analogy with the phenyl-ring flipping seen in the more common calixarenes. The conformers so formed undergo quick interconversion and each one has a slightly different cavity. Thus, these conformers consist of a complex conformational
  • guests and the four naphthalene rings of the host should still be the major driving force as mentioned above. However, it was noticed that the distances between diagonal linker oxygen atoms in the backbone of the host are slightly different for the four complexes. These interactions may be tuned by the
  • = −0.13, R2 = 0.9956) and TΔS (right, slope = 0.93, R2 = 0.9976). (a) Chemical structures of ZB4 and the guests involved in this research. The counterions are PF6−. (b) The four representative conformers of ZB4 resulting from naphthalene flipping. Numberings on the structures are used to assign NMR
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Published 27 Jun 2018

Hyper-reticulated calixarene polymers: a new example of entirely synthetic nanosponge materials

  • Alberto Spinella,
  • Marco Russo,
  • Antonella Di Vincenzo,
  • Delia Chillura Martino and
  • Paolo Lo Meo

Beilstein J. Org. Chem. 2018, 14, 1498–1507, doi:10.3762/bjoc.14.127

Graphical Abstract
  • (bromocresol green, 8), a bis-indole (indigo carmine, 9) and a naphthalene-bis-diazoic (naphthol blue-black, 10), in order to evaluate the outcome of molecular size, shape and electric charge. Dyes can be considered suitable and easily detectable models of pollutants [43][44][45][46][47], for the removal of
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Published 20 Jun 2018

A survey of chiral hypervalent iodine reagents in asymmetric synthesis

  • Soumen Ghosh,
  • Suman Pradhan and
  • Indranil Chatterjee

Beilstein J. Org. Chem. 2018, 14, 1244–1262, doi:10.3762/bjoc.14.107

Graphical Abstract
  • new kind of binaphthyl-based chiral I(III) prereagent 19 with the 8 and 8′ positions of the naphthalene substituents being occupied by iodide. Here they have observed that this chiral hypervalent iodine reagent 19 in the presence of co-oxidant m-CBPA is very useful for the dearomatizing
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Published 30 May 2018

One hundred years of benzotropone chemistry

  • Arif Dastan,
  • Haydar Kilic and
  • Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

Graphical Abstract
  • reported that the oxidative amination of 2,3-benzotropone (12) with methylcopperamine sulfate in aqueous methylamine at room temperature afforded 4-methylamino-1-naphthalene carbaldehyde (215) with a trace amount of 4-methylamino-2,3-benzotropone (214) via reaction paths including the dishing of Michael
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Published 23 May 2018

Synthetic avenues towards a tetrasaccharide related to Streptococcus pneumonia of serotype 6A

  • Aritra Chaudhury,
  • Mana Mohan Mukherjee and
  • Rina Ghosh

Beilstein J. Org. Chem. 2018, 14, 1095–1102, doi:10.3762/bjoc.14.95

Graphical Abstract
  • ). Subsequently, 10 was subjected to naphthylmethylation/p-methoxybenzylation [32] with 2-(bromomethyl)naphthalene (NapBr)/p-methoxybenzyl chloride in DMF to afford 6a/11 [32] in 90% and 80% yields, respectively. These derivatives were next subjected to thioglycoside hydrolysis using trichloroisocyanuric acid
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Published 17 May 2018

An overview of recent advances in duplex DNA recognition by small molecules

  • Sayantan Bhaduri,
  • Nihar Ranjan and
  • Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

Graphical Abstract
  • and its cytotoxicity was attributed to DNA minor groove binding ability [105]. Recently, Schmuck et al. have developed a first prototype of cationic oligopeptide-based molecular beacon (conjugate 43) coupled with a FRET pair, a naphthalene donor and a dansyl acceptor, for ratiometric detection of ds
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Published 16 May 2018

Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

  • Fabiana Pandolfi,
  • Isabella Chiarotto and
  • Marta Feroci

Beilstein J. Org. Chem. 2018, 14, 891–899, doi:10.3762/bjoc.14.76

Graphical Abstract
  • Fabiana Pandolfi Isabella Chiarotto Marta Feroci Deptartment of Fundamental and Applied Sciences for Engineering (SBAI), Sapienza University of Rome, via Castro Laurenziano, 7, 00161, Rome, Italy 10.3762/bjoc.14.76 Abstract The electrochemical reduction of 2-(2,2-dibromovinyl)naphthalene in a DMF
  • solution (Pt cathode) yields selectively 2-ethynylnaphthalene or 2-(bromoethynyl)naphthalene in high yields, depending on the electrolysis conditions. In particular, by simply changing the working potential and the supporting electrolyte, the reaction can be directed towards the synthesis of the terminal
  • alkyne (Et4NBF4) or the bromoalkyne (NaClO4). This study allowed to establish that 2-(bromoethynyl)naphthalene can be converted into 2-ethynylnaphthalene by cathodic reduction. Keywords: arylalkyne; carbon–bromine bond cleavage; cathodic reduction; Corey–Fuchs reaction; 2-(2,2-dibromovinyl)naphthalene
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Published 23 Apr 2018

Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: synthesis of axitinib

  • Jingbo Yu,
  • Zikun Hong,
  • Xinjie Yang,
  • Yu Jiang,
  • Zhijiang Jiang and
  • Weike Su

Beilstein J. Org. Chem. 2018, 14, 786–795, doi:10.3762/bjoc.14.66

Graphical Abstract
  • coupling product 3oa (70%). Besides, N-unsubstituted indazole 1n could also be tolerated in this reaction giving 3na (52%) and 3nf (49%) in moderate yield by using 1,8-bis(dimethylamino)naphthalene as a base. To our delight, 3-chloroindazole could also be activated in this reaction, giving the
  • 207 stainless-steel balls (dMB = 6 mm, ФMB = 0.293), milling at 800 rpm for 90 min. aN-Boc-3-bromoindazole was used as substrate. b150 min. c700 rpm. d3-chloro-1-methyl-1H-indazole was used as substrate, νrot = 900 rpm. e1,8-Bis(dimethylamino)naphthalene was used as base. Synthesis of axitinib by
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Published 06 Apr 2018

An air-stable bisboron complex: a practical bidentate Lewis acid catalyst

  • Longcheng Hong,
  • Sebastian Ahles,
  • Andreas H. Heindl,
  • Gastelle Tiétcha,
  • Andrey Petrov,
  • Zhenpin Lu,
  • Christian Logemann and
  • Hermann A. Wegner

Beilstein J. Org. Chem. 2018, 14, 618–625, doi:10.3762/bjoc.14.48

Graphical Abstract
  • yields of the substituted naphthalene 5e were comparable between the two bidentate Lewis acid catalysts (Table 1, entry 5). The binding of pyridazine (1j) with bisboron compound A, seems to be too strong to engage a fast ligand exchange with phthalazine (3). Recently we have demonstrated that catalyst A
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Published 13 Mar 2018

The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives

  • Shunsuke Kuribayashi,
  • Tomoyuki Kurioka,
  • Shinsuke Inagi,
  • Ho-Jung Lu,
  • Biing-Jiun Uang and
  • Toshio Fuchigami

Beilstein J. Org. Chem. 2018, 14, 389–396, doi:10.3762/bjoc.14.27

Graphical Abstract
  • , Rozhkov and Laurent reported an electrochemical partial fluorination of naphthalene and olefins about 30 years ago [5][6]. However, at that time, there has been no report on the anodic fluorination of heteroatom-containing compounds. At almost the same time, we found that the anodic α-methoxylation of
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Published 12 Feb 2018
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  • naphthalene-derived natural product plumbagin. In fact, trapping 1-metalated isoquinoline 3 with Eschenmoser’s salt gave the aminomethyl derivative 5 in 37% yield. Chromatographic separation from starting material 3 (recovered yield: 32%) was unproblematic. Surprising results were obtained in our
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Published 11 Jan 2018

Fluorescent nucleobase analogues for base–base FRET in nucleic acids: synthesis, photophysics and applications

  • Mattias Bood,
  • Sangamesh Sarangamath,
  • Moa S. Wranne,
  • Morten Grøtli and
  • L. Marcus Wilhelmsson

Beilstein J. Org. Chem. 2018, 14, 114–129, doi:10.3762/bjoc.14.7

Graphical Abstract
  • ). Notable recent examples of fluorescent base analogues. For cnA and dnA the attachment point to the substituted naphthalene moiety has been varied. Absorption and emission of tC (dashed line) and tCO (solid line) in dsDNA. The absorption below 300 nm is divided by three to emphasize the absorption spectral
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Published 10 Jan 2018

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

  • Markéta Bláhová,
  • Sergey K. Filippov,
  • Lubomír Kováčik,
  • Jiří Horský,
  • Simona Hybelbauerová,
  • Zdenka Syrová,
  • Tomáš Křížek and
  • Jindřich Jindřich

Beilstein J. Org. Chem. 2017, 13, 2509–2520, doi:10.3762/bjoc.13.248

Graphical Abstract
  • complexation of the alkylation agent to the CD cavity and orientation of the agent´s reactive center towards the 3-OH group [11][12][13]. Here, we report the preparation of regioisomers of novel mononaphthylallyl γ-CD (NA-CD), i.e., 3-(naphthalene-2-yl)prop-2-en-1-yl γ-CD, which is interesting for several
  • based on a direct alkylation of γ-CD with 2-(3-chloroprop-1-enyl)naphthalene. Cross-metathesis Mono 2I-O-, 3I-O- and 6I-O-naphthylallyl-γ-CDs (2-O-NA-γ-CD, 2a, 3-O-NA-γ-CD, 2b, 6-O-NA-γ-CD, 2c) were prepared from peracetylated O-allyl derivatives [14] by cross-metathesis with 2-vinylnaphthalene (Scheme
  • allyl esters was described before by Tanaka et al. [26][27]. Naphthylallylation The same naphthylallyl derivatives of γ-CD 2a–c were also prepared by direct alkylation of γ-CD with 2-(3-chloroprop-1-enyl)naphthalene [28] as the alkylation reagent (Scheme 2). This reagent is easy to prepare on a large
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Published 27 Nov 2017

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P® activation of 3-arylpropiolic acids

  • Melanie Denißen,
  • Alexander Kraus,
  • Guido J. Reiss and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231

Graphical Abstract
  • are often prepared by condensation of acid anhydrides and amines [34]. Their applications are widespread, ranging from pharmaceutically active compounds [35] to agrochemicals [36] and fluorophores [37]. The characteristic photophysical properties of 1,8- and 2,3-naphthalene imides render the substance
  • can be detected and monitored by absorption and emission spectroscopy. Furthermore, the investigation of a substance library of various 2,3- and 1,8-naphthalene imides has shown that the electronic nature of the ground and the excited state is decisively influenced by variation of the substitution
  • pattern of the naphthalene scaffold. Even the smallest polarity change in the solvent system effects their absorption and emission behavior [34][40]. Very recent investigations on naphthaleneimide derivatives revealed enormous phosphorescence lifetimes that are particularly interesting for imaging
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Published 03 Nov 2017
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