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Search for "macrocycles" in Full Text gives 173 result(s) in Beilstein Journal of Organic Chemistry.

Switchable molecular tweezers: design and applications

  • Pablo Msellem,
  • Maksym Dekthiarenko,
  • Nihal Hadj Seyd and
  • Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

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Published 01 Mar 2024

Active-metal template clipping synthesis of novel [2]rotaxanes

  • Cătălin C. Anghel,
  • Teodor A. Cucuiet,
  • Niculina D. Hădade and
  • Ion Grosu

Beilstein J. Org. Chem. 2023, 19, 1776–1784, doi:10.3762/bjoc.19.130

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  • beautiful structures and intriguing properties. We present herein a new synthetic strategy to access [2]rotaxanes, namely active-metal template clipping. We discuss the design of the target [2]rotaxanes, synthesis and characterization of the axle, macrocycle precursors and macrocycles as well as preparation
  • CuAAC click chemistry [38][39][40]. The choice of CuAAC as key step to accomplish the synthesis of the [2]rotaxanes was motivated by its high efficiency [41]. In addition, this reaction proved its versatility for rotaxanes synthesis [15], including chiral [2]rotaxanes [42]. The macrocycles M1 and M2
  • -functonalized stopper 3 after substitution of bromine with azide. The dialkyne-decorated pyridine 5 was prepared starting from 2,6-bis(bromomethyl)pyridine that was reacted with compound 4, under phase transfer catalysis (Scheme 1). Finally, the axle 6, as well as the reference macrocycles M1 and M2 [44], were
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Published 20 Nov 2023

Tying a knot between crown ethers and porphyrins

  • Maksym Matviyishyn and
  • Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

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  • materials science [10]. These two classes of molecules seem particularly remarkable among the endless family of macrocyclic compounds due to their unique features and easy accessibility. The popularity of porphyrins and crown ethers has been so extensive that the whole range of these macrocycles is even
  • macrocycles is shown. As several topics were reviewed earlier, we did not intend to present an exhaustive overview but instead focused on presenting selected examples of molecules of fundamental importance in this research area. The more interested readers are referred to excellent review articles focused on
  • specific classes of macrocycles, such as crowned porphyrins [22], calixpyrroles [26][27][28][29], Schiff porphyrinoids [30], expanded porphyrinoids [31][32], or carbaporphyrinoids [33][34], and a selection of articles dedicated to crown ether chemistry [17][20][35][36][37]. Historical Perspective Various
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Published 27 Oct 2023

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

  • Chandra Sekhar Tekuri,
  • Pargat Singh and
  • Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

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  • ; multicomponent synthesis; one-pot reaction; trichloroacetic acid; Introduction π-Conjugated porphyrin macrocycles are known for their applications in numerous areas ranging from oxygen transport, photosynthesis, catalysis and medicine [1][2][3]. In the past several years, diverse organic scaffolds have been
  • incorporated at the porphyrin periphery and different metal ions in the porphyrin core to modulate ground-state and excited-state characteristics of easily accessible meso-tetraarylporphyrins. Some of these π-extended tetrapyrrolic macrocycles have emerged as potential candidates in photodynamic therapy and
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Published 11 Aug 2023

Cyclodextrins as building blocks for new materials

  • Miriana Kfoury and
  • Sophie Fourmentin

Beilstein J. Org. Chem. 2023, 19, 889–891, doi:10.3762/bjoc.19.66

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  • publications carried out on cyclodextrins (CDs) and their market growth are clear evidence of the undying interest in these macrocycles discovered in 1891 [1]. It seems that these supramolecules still have not revealed all their secrets and are still stimulating curiosity in fundamental and applied research
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Published 19 Jun 2023

Light-responsive rotaxane-based materials: inducing motion in the solid state

  • Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

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  • supramolecular gels (Figure 2a) [52]. Upon irradiation using a UV-light-emitting diode (LED) and a visible LED as sources, the reversible cleavage of the trithiocarbonate stoppers was accomplished, thus allowing the dethreading [53] of the wheels to take place by the shuttling of the macrocycles along the thread
  • cyclobutanes (Figure 4b). Interestingly, the changes in the crystalline array as a consequence of this photodimerization within the cucurbituril macrocycles also induced a macroscopic deformation of the metal-organic material, promoting a photomechanical bending of the crystals. This photomechanical
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Published 14 Jun 2023

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

  • Nan Yang,
  • Yi-Yan Zhu,
  • Wei-Xiu Lin,
  • Yi-Long Lu and
  • Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

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  • supramolecular systems derived from water-soluble macrocycles, including cyclodextrins (CDs), calix[n]arenes (CXs), cucurbiturils (CBs), and pillararenes have been widely studied [2][6][7][8]. Similar to those macrocyclic acceptors, tribenzotriquinacene (TBTQ) derivatives, a class of versatile host molecules
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Published 08 May 2023

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

  • Péter Kisszékelyi and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

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Published 04 May 2023

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

  • Jorge de Lima Neto and
  • Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

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  • Jorge de Lima Neto Paulo Henrique Menezes Universidade Federal de Pernambuco, Departamento de Química Fundamental, Recife-PE, 50740-560, Brazil 10.3762/bjoc.19.31 Abstract The combretastatin D series and its analogues, corniculatolides and isocorniculatolides belong to a class of macrocycles
  • ; macrocycles; Introduction Conceptually, cyclic molecules containing more than 12 covalently connected atoms are called macrocycles and this class comprises several structurally distinct compounds [1]. Due to their structural characteristics and their different biological activities, the isolation of new
  • macrocycles and their synthesis finds several examples described in the literature and has already been the subject of review articles [2][3][4]. More recently, cyclic diaryl ether heptanoids (DAEH) [5], another class of macrocycles has been attracting attention not only because of their structural and
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Published 29 Mar 2023

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

  • Cécile Alleman,
  • Charlène Gadais,
  • Laurent Legentil and
  • François-Hugues Porée

Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23

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Published 03 Mar 2023

Supramolecular approaches to mediate chemical reactivity

  • Pablo Ballester,
  • Qi-Qiang Wang and
  • Carmine Gaeta

Beilstein J. Org. Chem. 2022, 18, 1463–1465, doi:10.3762/bjoc.18.152

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  • supramolecular catalysts were based on covalent hosts, typically cyclodextrin macrocycles [1], which had an interior hydrophobic cavity decorated with catalytically useful functional groups. Recently, increased emphasis has been placed on catalysis that takes use of noncovalent hosts, including self-assembled
  • of novel supramolecular catalysts. In their contribution Wang and co-workers [17] reported an interesting example of chalcogen bonding catalysis approach for the synthesis of calix[4]pyrrole macrocycles. The Se···O=C chalcogen bonding interactions between a selenide-based catalyst and the carbonyl
  • tetraaminobisthiourea chiral macrocycles as catalysts in decarboxylative Mannich reactions. Low macrocycle loading was used to catalyze the decarboxylative addition of malonic acid half thioesters to isatin-derived ketimines with excellent yields and good enantioselectivity. It was reported that effective activation
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Published 14 Oct 2022

Synthesis of meso-pyrrole-substituted corroles by condensation of 1,9-diformyldipyrromethanes with pyrrole

  • Baris Temelli and
  • Pinar Kapci

Beilstein J. Org. Chem. 2022, 18, 1403–1409, doi:10.3762/bjoc.18.145

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  • amount of pyrrole is presented for the first time. This procedure is a simple and efficient way for the preparation of corroles with a polymerizable substituent on meso-positions. Keywords: corrole; dipyrromethane; macrocycles; metal triflates; pyrrole; Introduction Corroles, a member of contracted
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Published 06 Oct 2022

Synthesis of odorants in flow and their applications in perfumery

  • Merlin Kleoff,
  • Paul Kiler and
  • Philipp Heretsch

Beilstein J. Org. Chem. 2022, 18, 754–768, doi:10.3762/bjoc.18.76

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  • can be highly beneficial. Therefore, Skowerski and co-workers constructed a tube-in-tube reactor for the ring-closing metathesis of dienes 62 and 63 to macrocycles 65 or 66, respectively, mediated by ruthenium catalyst 64 (Scheme 15) [53]. The substrate and the catalyst are mixed in a Q-piece and
  • temperature of 70 °C and a residence time of 30 min, macrocycles 65 and 66 are obtained in excellent yields with a preference for the E-isomers as determined by GC/MS analysis. Although, macrocycles 65 and 66 are, to the best of our knowledge, not used as musks in perfumery, this work demonstrates the value
  • cyclohexanone in flow. Synthesis of macrocyclic olefine 60 by ring-closing metathesis of diene 58 in a continuously stirred tank reactor (CSTR). Synthesis of macrocycles 65 and 66 by ring-closing metathesis of dienes 62 or 63, respectively, in a tube-in-tube reactor removing the formed ethylene. Z-Selective
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Published 27 Jun 2022

Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

  • Conrad Kuhwald,
  • Sibel Türkhan and
  • Andreas Kirschning

Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70

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  • is a three-step flow-through protocol leading to macrocycles with musk-like olfactoric properties, which was realized under extreme conditions. These include the use of safety-hazardous reaction mixtures, the handling of explosive intermediates, and their pyrolysis at high temperatures (Scheme 17
  • . Inductively heated continuous flow protocol for the synthesis of Iso E Super (88) [91][92]. Three-step continuous flow synthesis of macrocycles 89 and 90 with musk-like olfactoric properties. Acknowledgements We thank Dr. J. Panten (Symrise AG, Holzminden, Germany) and Dr. H. Herzog (EVONIK Degussa GmbH
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Published 20 Jun 2022

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

  • Prodip Howlader and
  • Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

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  • differently sized triangles (S)-40 and (S)-41 depending on the length of the organic spacer in the acceptor unit (Figure 9) [75]. Since the interior cavity of the homochiral macrocycles was equipped with BINOL units, they were utilized as catalysts for the asymmetric conjugate addition of chalcone 42 with
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Published 27 May 2022

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

  • Man-Ping Li,
  • Nan Yang and
  • Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

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  • , supramolecular chemotherapy has received considerable attention by utilizing a supramolecular strategy to decrease the cytotoxicity of anticancer drugs to normal cells while preserving their cytotoxicity against cancer cells [11]. Supramolecular systems derived from macrocycles [12][13], such as calix[n]arenes
  • ) derivatives are a class of molecules possessing a rigid bowl-shaped structure and a C3v-symmetric skeleton [21]. Bearing similarity with macrocycles in general, they can act as versatile hosts for encapsulating guest molecules. Over the past two decades, host–guest interactions and self-assembly based on TBTQ
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Published 12 May 2022

BINOL as a chiral element in mechanically interlocked molecules

  • Matthias Krajnc and
  • Jochen Niemeyer

Beilstein J. Org. Chem. 2022, 18, 508–523, doi:10.3762/bjoc.18.53

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  • thread also leads to a desymmetrization of the BINOL-based macrocycle (loss of C2 symmetry), as seen by 13C NMR spectroscopy. Stoddart and co-workers also used their π–π-recognition approach for the synthesis of BINOL-containing cationic catenanes [47][48]. They employed BINOL-based macrocycles
  • containing electron-rich hydroquinone or 1,5-dioxynaphthalene units (macrocycles 15/21/23), together with suitable dicationic bis-bipyridinium precursors (16/19). Self-assembly of the corresponding pseudorotaxanes by π–π stacking, following by capping with dibromo-p-xylene 17 gave rise to a series of chiral
  • ). Next, the authors showed that the application of the chiral BINOL-based bisbipyridinium precursor 19 (in combination with 15 and 17) leads to the corresponding catenane 20, which contains two BINOL-based macrocycles (see Figure 5b). When using (rac)-15 and (R)-19, the (S,R)-diastereomer of the product
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Published 06 May 2022

Bioinspired tetraamino-bisthiourea chiral macrocycles in catalyzing decarboxylative Mannich reactions

  • Hao Guo,
  • Yu-Fei Ao,
  • De-Xian Wang and
  • Qi-Qiang Wang

Beilstein J. Org. Chem. 2022, 18, 486–496, doi:10.3762/bjoc.18.51

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  • 10.3762/bjoc.18.51 Abstract A series of tetraamino-bisthiourea chiral macrocycles containing two diarylthiourea and two chiral diamine units were synthesized by a fragment-coupling approach in high yields. Different chiral diamine units, including cyclohexanediamines and diphenylethanediamines were
  • readily incorporated by both homo and hetero [1 + 1] macrocyclic condensation of bisamine and bisisothiocyanate fragments. With the easy synthesis, gram-scale of macrocycle products can be readily obtained. These chiral macrocycles were applied in catalyzing bioinspired decarboxylative Mannich reactions
  • tertiary amine sites were found to be crucial for achieving efficient activation and stereocontrol. As shown in control experiments, catalysis with the acyclic analogues having the same structural motifs were non-selective. Keywords: chiral macrocycles; cooperative asymmetric catalysis; decarboxylative
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Published 02 May 2022

Diametric calix[6]arene-based phosphine gold(I) cavitands

  • Gabriele Giovanardi,
  • Andrea Secchi,
  • Arturo Arduini and
  • Gianpiero Cera

Beilstein J. Org. Chem. 2022, 18, 190–196, doi:10.3762/bjoc.18.21

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  • the bonded metal. This crucial aspect prompted their application in supramolecular chemistry as well. Thus, a recent evolution of their chemistry concerns the development of novel architectures in which P(III) compounds are incorporated in cavity-shaped macrocycles [5][6][7][8]. In this scenario
  • macrocycles are less exploited in catalysis [28]. The larger macrocycle size, its conformational adaptability, and the possibility to selectively functionalize the macrocycle offered several opportunities to design synthetic receptors and prototypes of nanodevices, instead [29]. In this context, we recently
  • via conventional protocols using (Me2S)AuCl. Notably, the organometallic macrocycles A,B,C(AuCl)2 could be isolated via column chromatography separation. Gold(I) catalysts were subsequently fully characterized by NMR analysis and high-resolution mass spectrometry. The conformation of the catalysts, in
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Published 10 Feb 2022

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

  • Hendrik Gruß,
  • Rebecca C. Feiner,
  • Ridhiwan Mseya,
  • David C. Schröder,
  • Michał Jewgiński,
  • Kristian M. Müller,
  • Rafał Latajka,
  • Antoine Marion and
  • Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

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  • of macrocycles [49]. The macrocyclisation technique by tryptophan C2–H activation has been further improved showing structurally constrained peptides bearing a side chain connection of tryptophan and phenylalanine or tyrosine [50]. Moreover, a similar Pd-mediated approach for C(sp3)–H activation of
  • shown to be a highly effective tool to sample the conformational space of polypeptides made of sequences of 10 to 30 amino acids [87][88] and of macrocycles [89]. Our simulation strategy, mainly adapted from the latter references, made use of 15 independent 700 ns-long aMD simulation runs for each
  • the macrocycles was analysed via principal component analysis (PCA) of the non-hydrogen atoms forming the cycle, and the structure of the peptide backbone was investigated via secondary structure analysis and backbone root mean square deviation (RMSD) clustering including amino acids Pro3 to Met15
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Published 03 Jan 2022

Synthesis of a novel aminobenzene-containing hemicucurbituril and its fluorescence spectral properties with ions

  • Qingkai Zeng,
  • Qiumeng Long,
  • Jihong Lu,
  • Li Wang,
  • Yuting You,
  • Xiaoting Yuan,
  • Qianjun Zhang,
  • Qingmei Ge,
  • Hang Cong and
  • Mao Liu

Beilstein J. Org. Chem. 2021, 17, 2840–2847, doi:10.3762/bjoc.17.195

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  • Macrocycles with converging binding sites and functional groups hold a key position in supramolecular chemistry, which has been repeatedly confirmed by classic macrocyclic molecules, such as crown ethers, cyclodextrins, calixarenes, cucurbiturils and their homologues [1]. For the past decades, numerous
  • intriguing macrocycles have come into our sight, cycloparaphenylenes [2][3][4][5][6][7][8], pillararenes [9][10][11][12], tiaraarenes [13][14], coronaarenes [15][16][17], heteracalixaromatics [18][19], and hemicucurbiturils [20] for instance, and these modified macrocycles have been applied into practical
  • . These adverse properties have impeded the development of hemicucurbit[n]urils to some extent. Introducing aromatic fragments into macrocycles which have no chromophore is a viable strategy to expand the scope of their application. Ganin et al. [34] reported the synthesis and formation of several
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Published 06 Dec 2021

A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines

  • Zsanett Benke,
  • Attila M. Remete and
  • Loránd Kiss

Beilstein J. Org. Chem. 2021, 17, 2051–2066, doi:10.3762/bjoc.17.132

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  • of natural products (especially macrocycles) [12], alkaloids [13], amino acids and functionalized biomolecules such as peptides [14][15][16][17][18][19][20] or various drugs [21]. Due to the ring strain, bicyclic systems and derivatives, such as norbornadiene derivatives can easily be converted
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Published 13 Aug 2021

Recent advances in the syntheses of anthracene derivatives

  • Giovanni S. Baviera and
  • Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

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  • activity for iodoethynyl groups [63]. Intramolecular cyclization In 2009, Swager’s research group published the synthesis of fluorescent macrocycles based on 1,3-butadiyne-bridged dibenzo[a,j]anthracene subunits via a multistep route (Scheme 30) [64]. They synthesized substituted dibenzo[a,j]anthracenes
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Published 10 Aug 2021
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  • macrocycles [31][32]. Moreover, polypyrrolic systems are of extensive interest in numerous areas namely optics, medicine, and supramolecular chemistry in addition to the materials sciences and technology. Fascinatingly, in luminescence as well as fluorescence-based sensors, pyrrole derivatives play a vital
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Published 02 Jun 2021

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

  • Guido Gambacorta,
  • James S. Sharley and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

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Published 18 May 2021
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