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Search for "cascade reactions" in Full Text gives 82 result(s) in Beilstein Journal of Organic Chemistry.

Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols

  • Jie Zheng,
  • Shuyu Meng and
  • Quanrui Wang

Beilstein J. Org. Chem. 2021, 17, 1481–1489, doi:10.3762/bjoc.17.104

Graphical Abstract
  • stereostructures of compound cis-14aa and trans-14aa. Crystal structure of the tosylate 21. The displacement ellipsoids are drawn at the 30% probability level. Reported strategies for the synthesis of tetralin-2-ol ring systems. Designed cascade reactions to 4-substituted tetralin-2-ols. The documented synthesis
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Published 22 Jun 2021

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

  • Premansh Dudhe,
  • Mena Asha Krishnan,
  • Kratika Yadav,
  • Diptendu Roy,
  • Krishnan Venkatasubbaiah,
  • Biswarup Pathak and
  • Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

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  • purification reduce the efforts in the synthesis of complex molecular architectures. Therefore, cascade reactions are essential in synthetic organic chemistry, even with moderate yields [26]. Recently, such reactions have claimed their much deserving place in drug design and natural product synthesis [27]. In
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Published 17 Jun 2021

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

  • Zhonglie Yang,
  • Yutong Liu,
  • Kun Cao,
  • Xiaobin Zhang,
  • Hezhong Jiang and
  • Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

Graphical Abstract
  • -radical cascade reactions could efficiently construct various carbocycles and heterocycles with multifarious structures and complexity [59][60][61]. Centered on this context, we give a clear overview on a variety of novel cyclization reactions initiated by EDA complexes from the recent years. In 2016
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Published 06 Apr 2021

Pentannulation of N-heterocycles by a tandem gold-catalyzed [3,3]-rearrangement/Nazarov reaction of propargyl ester derivatives: a computational study on the crucial role of the nitrogen atom

  • Giovanna Zanella,
  • Martina Petrović,
  • Dina Scarpi,
  • Ernesto G. Occhiato and
  • Enrique Gómez-Bengoa

Beilstein J. Org. Chem. 2020, 16, 3059–3068, doi:10.3762/bjoc.16.255

Graphical Abstract
  • reactions, which allow for structural modifications on the organic compounds by forming several chemical bonds in one pot. To this end, gold catalysis [1][2][3][4][5][6][7] has been widely exploited to construct various cyclic and heterocyclic frameworks through cascade reactions triggered by the activation
  • substrates. Keywords: DFT calculations; gold catalysis; Nazarov reaction; N-heterocycles; Introduction In the development of new and effective catalysts, step economy is surely one of the major goals. A reduction of the number of steps in the synthesis of complex compounds can be attained by cascade
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Published 15 Dec 2020

Recent developments in enantioselective photocatalysis

  • Callum Prentice,
  • James Morrisson,
  • Andrew D. Smith and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

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Published 29 Sep 2020

Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes

  • Thomas Schneider,
  • Michael Keim,
  • Bianca Seitz and
  • Gerhard Maas

Beilstein J. Org. Chem. 2020, 16, 2064–2072, doi:10.3762/bjoc.16.173

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  • even anthracene. At higher temperature, the cycloadducts undergo an intramolecular SE(Ar) reaction leading to condensed carbocycles incorporating a 1-(trifluoromethyl)-1-(dimethylamine)indene ring system. With styrenes and some substituted styrenes, cascade reactions take place, which likely include
  • consider the reactivity of the electrophilic (“electron-poor”) acetylenic bond toward 1,3-dienes, and show how the expected [4 + 2] or [2 + 2] cycloaddition products can enter subsequent cascade reactions toward carbocycles which incorporate a C(CF3)NMe2 structural unit. Results and Discussion The Diels
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Published 24 Aug 2020

An overview on disulfide-catalyzed and -cocatalyzed photoreactions

  • Yeersen Patehebieke

Beilstein J. Org. Chem. 2020, 16, 1418–1435, doi:10.3762/bjoc.16.118

Graphical Abstract
  • of vinylcyclopropanes with olefins [8]. The reaction mechanism of this cycloaddition process was similar to other thiyl radical-catalyzed cycloaddition cascade reactions. The alkylthiyl radical generated by the homolysis of a disulfide-bridged peptide precatalyst under UV-light irradiation triggers
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Published 23 Jun 2020

Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones

  • Valeria Nori,
  • Antonio Arcadi,
  • Armando Carlone,
  • Fabio Marinelli and
  • Marco Chiarini

Beilstein J. Org. Chem. 2020, 16, 1084–1091, doi:10.3762/bjoc.16.95

Graphical Abstract
  • stereoselective Pd-catalyzed cascade reactions, consisting of the addition of in situ-generated arylpalladium complexes over a proximate carbon–carbon triple bond, followed by cross-coupling reactions, have been reported [26][27][28][29][30][31]. Our continuing interest in the palladium-catalyzed reactions of
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Published 20 May 2020

Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles

  • Ming-Xi Bi,
  • Shuai Liu,
  • Yangen Huang,
  • Xiu-Hua Xu and
  • Feng-Ling Qing

Beilstein J. Org. Chem. 2020, 16, 657–662, doi:10.3762/bjoc.16.62

Graphical Abstract
  • )propioloyl]indole and N-propargylindoles, respectively. Inspired by these elegant results, we became interested in the preparation of SCF3-substituted pyrrolo[1,2-a]indol-3-ones, which might be potentially useful in medicinal chemistry. Radical cascade reactions constitute highly efficient strategies for the
  • strategy in the synthesis of a series of CH2SCF3-substituted heterocycles. For the construction of SCF3-substituted cyclic compounds, normally proper alkynes are chosen as the substrates for cascade reactions [28][29][30][31][32]. In 2015, Wang developed an oxidative radical cyclization of aryl alkynoate
  • converted to the mono(trifluoromethylthiolated) products in moderate yields. Further studies on applying radical cascade reactions to the construction of fluorine-containing heterocyclic scaffolds are in progress in our laboratory. Representative examples of biologically active pyrrolo[1,2-a]indol-3-one
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Published 08 Apr 2020

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

  • Eric J. N. Helfrich,
  • Geng-Min Lin,
  • Christopher A. Voigt and
  • Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

Graphical Abstract
  • the leaving pyrophosphate group and the nucleophilic alkenes in proximity to initiate the C–C-bond forming, carbocation-mediated cascade reactions [10]. The hydrophobic binding pocket stabilizes the reaction intermediates and tames the propagation of carbocations through cation–π and other
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Published 29 Nov 2019

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

Graphical Abstract
  • to a pentacyclic ketone. A similar cyclization reaction was developed by our group some years ago for ester substrates [18], and an analogous cyclization of nitriles was described by Kristensen in ring-closing cascade reactions [34]. The new cyclization method was first tested with ester 20a
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Published 26 Sep 2019

Genome mining in Trichoderma viride J1-030: discovery and identification of novel sesquiterpene synthase and its products

  • Xiang Sun,
  • You-Sheng Cai,
  • Yujie Yuan,
  • Guangkai Bian,
  • Ziling Ye,
  • Zixin Deng and
  • Tiangang Liu

Beilstein J. Org. Chem. 2019, 15, 2052–2058, doi:10.3762/bjoc.15.202

Graphical Abstract
  • recently reported type III TPSs, UbiA-related TPSs, also catalyse cascade reactions by diphosphate elimination [8]. In addition, each type of TPS is characterised by a unique aspartate-rich motif; most type I TPSs have a DDXXD/E motif and an NSE/DTE motif, whereas type II TPSs have the DXDD motif [9][10
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Published 28 Aug 2019

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

  • Piyali Sarkar,
  • Sayan Sarkar and
  • Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

Graphical Abstract
  • nanoreactor which is a single molecule as catalyst in the earliest steps of the mechanistic pathway (Figure 6). This multicomponent reaction is expected to comprise a series of condensations and subsequent ring-closure cascade reactions (Scheme 3). To demonstrate the mechanistic pathway, dimedone (2), isatin
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Published 08 Jul 2019

Mechanistic investigations on multiproduct β-himachalene synthase from Cryptosporangium arvum

  • Jan Rinkel and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2019, 15, 1008–1019, doi:10.3762/bjoc.15.99

Graphical Abstract
  • or multiple compounds, are terpene synthases (TSs). These enzymes are able to guide complex cascade reactions from structurally simple oligoprenyl diphosphates to often complex, polycyclic products [4][5][6] circumventing the low selectivity observed for carbocationic reactions by a defined active
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Published 02 May 2019

The LANCA three-component reaction to highly substituted β-ketoenamides – versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives

  • Tilman Lechel,
  • Roopender Kumar,
  • Mrinal K. Bera,
  • Reinhold Zimmer and
  • Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2019, 15, 655–678, doi:10.3762/bjoc.15.61

Graphical Abstract
  • -ketoenamide and the pyridin-4-ol has been discussed earlier [21][22][23], but the essentials of the involved cascade reactions have to be presented again in order to understand the formation of the crucial β-ketoenamide intermediates (Scheme 2). The protonation of the primarily formed allenylimine A by the
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Published 13 Mar 2019

Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide

  • Lu Yang,
  • Yuwei Wu,
  • Yiming Yang,
  • Chengping Wen and
  • Jie-Ping Wan

Beilstein J. Org. Chem. 2018, 14, 2348–2353, doi:10.3762/bjoc.14.210

Graphical Abstract
  • , including those reactions involving valuable C–C [7][8][9][10][11], C–heteroatom [12][13][14][15][16], heteroatom–heteroatom [17][18] bond formation as well as divergent cascade reactions [19][20][21][22][23], are presently taking place to guide the progress of sustainable organic synthesis. 1,2,3-Triazole
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Published 07 Sep 2018

DFT calculations on the mechanism of copper-catalysed tandem arylation–cyclisation reactions of alkynes and diaryliodonium salts

  • Tamás Károly Stenczel,
  • Ádám Sinai,
  • Zoltán Novák and
  • András Stirling

Beilstein J. Org. Chem. 2018, 14, 1743–1749, doi:10.3762/bjoc.14.148

Graphical Abstract
  • ][37][38][39][40][41][42][43][44]. The mechanistic details of these cascade reactions are not clear as evidenced by the different mechanistic proposals (see, e.g., [18][30][40][44]). These mechanisms suggest the presence and existence of vinyl cation 7, alkynyl–Cu(III) 5, or alkenyl–Cu(III) complexes 6
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Published 12 Jul 2018

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

  • Eirinaios I. Vrettos,
  • Gábor Mező and
  • Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

Graphical Abstract
  • ]. This type of linkers/spacers offers the capability to release the active drug after simultaneous cascade reactions, as shown in Figure 5. Para-amino benzyl alcohol (PABC; colored in red) is a representative example that can be connected in the amino group via an amide bond to an enzyme-hydrolyzable
  • overexpressed in the targeted tumor microenvironment (i.e cathepsin B). Once EHU will be recognized by these enzymes it is cleaved off resulting in the consequent release of the active drug through rapid cascade reactions (Figure 5). The most representative examples of various types of linkers are summarized in
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Published 26 Apr 2018

Nanoreactors for green catalysis

  • M. Teresa De Martino,
  • Loai K. E. A. Abdelmohsen,
  • Floris P. J. T. Rutjes and
  • Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

Graphical Abstract
  • systems include: 1) the site isolation of reactive components (enabling cascade reactions), 2) the ability to convert hydrophobic substrates in water (under green conditions), and 3) the facile catalyst recovery. All these attractive features are covered in this review. Moreover, in this review we have
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Published 29 Mar 2018

Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry

  • Katharina Hiebler,
  • Georg J. Lichtenegger,
  • Manuel C. Maier,
  • Eun Sung Park,
  • Renie Gonzales-Groom,
  • Bernard P. Binks and
  • Heidrun Gruber-Woelfler

Beilstein J. Org. Chem. 2018, 14, 648–658, doi:10.3762/bjoc.14.52

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  • sacubitril. In addition, successful implementation of heterogeneous Pd catalysts in Pickering emulsions is a first promising step towards the aimed combination of chemo- and biocatalysis for the continuous formation of valsartan and sacubitril via multistep catalytic cascade reactions. Finally, it could be
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Published 19 Mar 2018

CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF3SO2Cl

  • Hélène Chachignon,
  • Hélène Guyon and
  • Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2800–2818, doi:10.3762/bjoc.13.273

Graphical Abstract
  • , regenerating the trifluoromethyl radical in the process, was also considered. Intermediate 2 was ultimately converted into the final product after liberating an acetyl cation, which was captured by a chloride anion to give acetyl chloride (Scheme 3). Trifluoromethylation of olefins with cascade reactions: The
  • most widely described type of reactions in which CF3SO2Cl and molecules carrying a C=C double bond are involved are actually cascade reactions that include a cyclisation or a group migration step. In this context, the acrylamide motif was a notably popular object of research, and served in several
  • acrylamides were also investigated for the realisation of cascade reactions including a trifluoromethylation step. This was notably the case of unactivated alkenes: Dolbier and co-workers showed that such compounds could be involved in photoredox-catalysed trifluoromethylation reactions, followed by a 6-exo
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Published 19 Dec 2017

Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

  • Layal Hariss,
  • Kamal Bou Hadir,
  • Mirvat El-Masri,
  • Thierry Roisnel,
  • René Grée and
  • Ali Hachem

Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208

Graphical Abstract
  • demonstrate the regiochemistry of the reaction. These cascade reactions proceed first through a Michael addition of the primary amine on the enone, followed by an intramolecular cyclization by the pyridine/pyrimidine nucleus. Unfortunately, no crystal structure could be obtained for the imidazopyrimidines and
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Published 10 Oct 2017

Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions

  • Yonglei Du,
  • Jian Li,
  • Kerong Chen,
  • Chenglin Wu,
  • Yu Zhou and
  • Hong Liu

Beilstein J. Org. Chem. 2017, 13, 1342–1349, doi:10.3762/bjoc.13.131

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  • spirocyclopentaneoxindoles. Keywords: asymmetric synthesis; four consecutive stereocenters; Michael–Henry cascade reactions; spirocyclopentaneoxindoles; thioureas; Introduction The spirocyclic oxindole core represents an important scaffold that is encountered frequently in many biologically active molecules and natural
  • functionalized nitrovinylacetamides are rare. Chiral thioureas [28][38][39] have evolved as powerful hydrogen bonding catalysts for the asymmetric synthesis of spirocyclopentaneoxindoles, which have been demonstrated as acceptable but still considerably limited. Organocatalytic iminium–enamine cascade reactions
  • [35] (Scheme 1, reaction 1A) and Michael–Henry cascade reactions [25] (Scheme 1, reaction 1B) reported by Barbas III's group involve the cyclization between α,β-unsaturated aldehydes and nitrostyrenes with 3-substituted oxindoles to generate the corresponding CHO- or NO2-substituted spirooxindole
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Published 07 Jul 2017

Development of a continuous process for α-thio-β-chloroacrylamide synthesis with enhanced control of a cascade transformation

  • Olga C. Dennehy,
  • Valérie M. Y. Cacheux,
  • Benjamin J. Deadman,
  • Denis Lynch,
  • Stuart G. Collins,
  • Humphrey A. Moynihan and
  • Anita R. Maguire

Beilstein J. Org. Chem. 2016, 12, 2511–2522, doi:10.3762/bjoc.12.246

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  • -chloroacrylamides; cascade reactions; flow chemistry; Introduction Since the efficient and highly stereoselective transformation of α-thioamides to the corresponding α-thio-β-chloroacrylamides derivatives was first reported [1][2], the considerable synthetic utility of these heavily functionalized acrylamide
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Published 24 Nov 2016

Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

  • Bin Yu,
  • Hui Xing,
  • De-Quan Yu and
  • Hong-Min Liu

Beilstein J. Org. Chem. 2016, 12, 1000–1039, doi:10.3762/bjoc.12.98

Graphical Abstract
  • enantioselectivities (>95:5 dr, up to 98:1 er). Very recently, Shi et al. revealed an unprecedented acid-promoted intermediate-dependent unusual [4 + 3], [3 + 2] and cascade reactions of 3-indolylmethanols with Nazarov reagents, leading to the construction of diverse indole derivatives (Scheme 56) [73]. 3
  • enantioselectivities (90–98% ee, Scheme 57) [74]. Following above success, Shi et al. developed other CPA-catalyzed cascade reactions of 3-indolylmethanols with 7-vinylindoles, affording C7-functionalized indoles and constructing the cyclopenta[b]indole and spirooxindole frameworks with excellent
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Published 18 May 2016
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