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Search for "multicomponent" in Full Text gives 324 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple

  • Alexander S. Filatov,
  • Olesya V. Khoroshilova,
  • Anna G. Larina,
  • Vitali M. Boitsov and
  • Alexander V. Stepakov

Beilstein J. Org. Chem. 2022, 18, 769–780, doi:10.3762/bjoc.18.77

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  • azomethine ylides generated from primary or secondary α-amino acids and carbonyl compounds such as alloxan, isatin, tryptanthrin, and 11H-indeno[1,2-b]quinoxalin-11-one were performed in a multicomponent fashion [19][20][21][24]. In these reactions, the azomethine ylides generated in situ are highly reactive
  • cyclopropenes with azomethine ylides from ninhydrin were also successfully carried out in a multicomponent fashion [23]. Mention should also be made of the recent advances in developing enantioselective approaches to the synthesis of 3-azabicyclo[3.1.0]hexane derivatives. Deng and co-workers reported the first
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Published 29 Jun 2022

A trustworthy mechanochemical route to isocyanides

  • Francesco Basoccu,
  • Federico Cuccu,
  • Federico Casti,
  • Rita Mocci,
  • Claudia Fattuoni and
  • Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 732–737, doi:10.3762/bjoc.18.73

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  • , they are often used in heterocycles formation [8][9], multicomponent strategies [10][11], polymers production [12][13], and metal complexation [14][15]. The molecular structure is composed of an N–C planar triple bond where the nitrogen atom assumes a positive charge due to the fourth bond with a
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Published 22 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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  • electromagnetic field. Other comparisons include the Pd-mediated transfer hydrogenations using ethanol in cyclohexene (Scheme 9, case A), multicomponent reactions (Scheme 9, case B), pericyclic reactions (Scheme 10, case A) and Pd-catalyzed reactions (Scheme 10, case B) [53]. Noteworthy, packed bed fillings used
  • for the transfer hydrogenations (Pd) are reusable for several reductions without the need to adjust the overall reaction conditions (flow rate and residence time, temperature etc.). Multicomponent reactions (MCRs) are of particular interest in the field of flow chemistry because this enabling
  • consisting of O-allylation and Claisen rearrangement for the continuous synthesis of 2-allyl-4,6-difluorophenol (SiC = silicon carbide) [52]. Continuous flow reactions and comparison with batch reaction (oil bath). A. Pd-catalyzed transfer hydrogenations using ethanol in cyclohexene [53], B. multicomponent
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Published 20 Jun 2022

DDQ in mechanochemical C–N coupling reactions

  • Shyamal Kanti Bera,
  • Rosalin Bhanja and
  • Prasenjit Mal

Beilstein J. Org. Chem. 2022, 18, 639–646, doi:10.3762/bjoc.18.64

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  • ten innovative technologies that IUPAC recognized [7]. To perform organic transformations in a greener way, the mechanochemical methods can also be considered as one of the alternative approaches [8][9][10]. The one-pot multicomponent synthesis of important heterocycles can be the state of art
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Published 01 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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  • allows, as demonstrated by Nature by the multicomponent ATP synthase motor, a more detailed and refined configuration of purposeful machinery. Furthermore, (metallo)supramolecular catalysis is shown to extend beyond the single "supramolecular unit" and to reach far into the field and concepts of systems
  • multicomponent ATP synthase motor [23], a more detailed and refined configuration of purposeful machinery [24]. For the preparation of heteroleptic aggregates, one must differentiate between dynamic (rapidly exchanging) and kinetically inert heteroleptic metal–ligand interactions. While the inert heteroleptic
  • of the guest molecule was proven by UV–vis and IR spectroscopy. The multicomponent prism (Figure 3) was finally utilized as a heterogeneous catalyst for Michael and Diels–Alder (DA) reactions in water, representing an uncommon hydrogen-bond donating heterogeneous catalyst [59]. Intrigued by the
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Published 27 May 2022

New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence

  • Long Zhao,
  • Mao-Lin Yang,
  • Min Liu and
  • Ming-Wu Ding

Beilstein J. Org. Chem. 2022, 18, 286–292, doi:10.3762/bjoc.18.32

Graphical Abstract
  • polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines under mild reaction conditions is still of high demand in the discovery of biologically active compounds. The Passerini reaction is an isocyanide-based multicomponent reaction, which has been used in preparing various α-acyloxy adducts starting
  • ]. Continuing our interest in the synthesis of N-heterocycles via the aza-Wittig reaction and multicomponent reactions [36][37][38], we wish to report herein a facile synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines via sequential Passerini/Staudinger/aza-Wittig/addition
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Published 04 Mar 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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  • ], disulfide- [13], thioether- [14][15][16][17][18][19][20], triazole- [21][22], oxime- [23] and hydrazone formation [24] as well as multicomponent reactions such as the Ugi- or Petasis reaction [25][26][27][28][29][30][31][32]. The content of helicity can moreover be changed by the introduction of a photo
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Published 03 Jan 2022

Iron-catalyzed domino coupling reactions of π-systems

  • Austin Pounder and
  • William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

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Published 07 Dec 2021

Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

  • Chuanhua Qu,
  • Run Huang,
  • Yong Li,
  • Tong Liu,
  • Yuan Chen and
  • Guiting Song

Beilstein J. Org. Chem. 2021, 17, 2822–2831, doi:10.3762/bjoc.17.193

Graphical Abstract
  • important C1 synthon. Its special reactivity, such as the ability to react with electrophilic, nucleophilic, and radical reagents [25][26][27][28], determines that it can participate in many types of reactions such as multicomponent reactions [29][30][31][32], tandem reactions [33][34], and insertion
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Published 02 Dec 2021

Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure

  • Agnieszka Grajewska,
  • Maria Chrzanowska and
  • Wiktoria Adamska

Beilstein J. Org. Chem. 2021, 17, 2511–2519, doi:10.3762/bjoc.17.168

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  • ; cyclization; multicomponent reactions; synthetic methods; tetrahydroisoquinoline; Introduction The tetrahydroisoquinoline moiety is the key structure in large number of natural and synthetic biologically important molecules. Among them, isoquinoline alkaloids constitute a large family of natural products
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Published 07 Oct 2021

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

  • Yi Liu,
  • Puying Luo,
  • Yang Fu,
  • Tianxin Hao,
  • Xuan Liu,
  • Qiuping Ding and
  • Yiyuan Peng

Beilstein J. Org. Chem. 2021, 17, 2462–2476, doi:10.3762/bjoc.17.163

Graphical Abstract
  • condensation of α-halogenated carbonyl compounds, β-dicarbonyl compounds and amines; and iv) the latest developed multicomponent tandem reactions and transition metal-catalyzed coupling reactions [30][31][32][33][34][35][36][37][38][39]. Recently, substantial achievements have been made using azides as a
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Published 22 Sep 2021

Constrained thermoresponsive polymers – new insights into fundamentals and applications

  • Patricia Flemming,
  • Alexander S. Münch,
  • Andreas Fery and
  • Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

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  • guidelines for the use of UCST-type polymer topologies especially within multicomponent systems. The present review will be limited exclusively to stimuli-responsive polymer layers bonded to flat and particulate inorganic surfaces as well as to star polymers and polymer micelles. Only polymer layers that are
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Published 20 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

Graphical Abstract
  • (diphenylphosphino)ethane (DPPE) as ligand improved the yield of the anthraquinones. Representative examples included anthraquinones 179a and 179b obtained from terminal alkynes and 179c and 179d from internal alkynes [75]. Multicomponent reactions In 2009, Singh and co-workers reported a solvent-free methodology to
  • synthesize tetrahydrobenzo[a]xanthene-11-ones 184 and diazabenzo[a]anthracene-9,11-dione derivatives 185 in good yields via a multicomponent reaction (Scheme 42) [76]. This methodology was based on the cyclocondensation of aromatic aldehydes 180, β-naphthol (181), and cyclic 1,3-dicarbonyl compounds 182 or
  • -workers [77] provided better results. In a related approach, Estévez-Braun and co-workers synthesized dibenzo[a,h]anthracene-12,13-diones 188 from 2-hydroxy-1,4-naphthoquinone (186), β-naphthol (181), and aromatic aldehydes 187 through a multicomponent reaction that used InCl3 as catalyst under solvent
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Published 10 Aug 2021

Correction: One-pot multicomponent green Hantzsch synthesis of 1,2-dihydropyridine derivatives with antiproliferative activity

  • Giovanna Bosica,
  • Kaylie Demanuele,
  • José M. Padrón and
  • Adrián Puerta

Beilstein J. Org. Chem. 2021, 17, 2026–2027, doi:10.3762/bjoc.17.130

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  • 10.3762/bjoc.17.130 Keywords: antiproliferative activity; 1,2-dihydropyridines; green Hantzsch synthesis; heterogeneous catalysis; one-pot multicomponent reaction; The authors noticed that the E-factor (E) was calculated using a wrong Equation 2 in the original publication: The correct Equation 2 should
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Published 10 Aug 2021

Asymmetric organocatalyzed synthesis of coumarin derivatives

  • Natália M. Moreira,
  • Lorena S. R. Martelli and
  • Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

Graphical Abstract
  • as harsh reaction conditions, has become paramount in the field of organic synthesis in recent years [19]. In this sense, Molnar et al. published a review on green chemistry approaches to the synthesis of coumarin derivatives [20] and Chandrakar et al. reviewed the developments of multicomponent
  • multicomponent reaction (IMCR) [31]. The enantioenriched hemiacetals 5 were obtained using the Jørgensen catalyst 7 as previously described by Rueping et al. [32]. This approach enables the rapid assembly of complex natural product hybrids 6 including up to four different molecular fragments, such as
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Published 03 Aug 2021

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

  • Pezhman Shiri,
  • Ali Mohammad Amani and
  • Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

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  • 1,2,3-triazoles through multicomponent reactions and the relevant mechanistic aspects have been surveyed by Chen, Ren, et al. [27]. The 1,3-dipolar cycloaddition reaction between azides and alkynes is the most efficient pathway for the preparation of disubstituted 1,2,3-triazole derivatives. The copper
  • aniline (Scheme 5) [40]. A one-pot and multicomponent route to 1,4,5-trisubstituted 1,2,3-triazoles 11 containing a carboxylic ester group on the triazole ring was reported by Zhao et al. This strategy generates desired products from the reaction of readily available primary amines 10, 1,3-dicarbonyl
  •  24) [52]. A one-pot and multicomponent protocol for the synthesis of 5-selanyltriazoles 85 from the reaction of ethynylstibanes 82, organic azides 83, and diaryl diselenides 84 using catalytic amounts of CuI and 1,10-phenanthroline in DMSO at 60 °C under air with good to high yield was presented by
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Published 13 Jul 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

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

  • Joseane A. Mendes,
  • Paulo R. R. Costa,
  • Miguel Yus,
  • Francisco Foubelo and
  • Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

Graphical Abstract
  • addition of HMPA and imine 14 in the multicomponent coupling. When the bulky TBS group was used, and HMPA was added to the reaction mixture before the imine 14, aziridines 36 were formed. The addition of lithium metaloenamine took place through and open transition state to the Re face of the imine (RS)-14
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Published 12 May 2021

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

  • Shivani Gulati,
  • Stephy Elza John and
  • Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

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  • Shivani Gulati Stephy Elza John Nagula Shankaraiah Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad 500 037, India 10.3762/bjoc.17.71 Abstract Microwave-assisted (MWA) multicomponent reactions (MCRs) have successfully emerged as one
  • -MCRs and their mechanistic insights over the past decade and shed light on its advantage over the conventional approach. Keywords: cycloaddition; Knoevenagel condensation; Michael addition; microwave; multicomponent reactions; Introduction Recently, organic chemists are focussed to develop
  • economic perspective due to increased amounts of waste generation, toxic solvents, and no real-time control of pollution generated, etc. [4]. Therefore, in this connection, the multicomponent reaction (MCR) is one such approach where three or more reactants combine to form a single product retaining the
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Published 19 Apr 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
  • 22 can be afforded easily (Scheme 7). This procedure offers a novel cyclization method with bifunctionalization, causing a multicomponent reaction of vinylaniline, halide, and sulfonylate to give corresponding indole derivatives. Furthermore, a wide variety of applicable substrates and good
  • successfully applied to the gram scale, providing a step towards assorted aryl sulfide structural units with medicinal value. In 2019, Yang and colleagues [52] developed a method for preparing S-aryl dithiocarbamates 135 by a multicomponent reaction of an EDA complex under visible-light irradiation (Scheme 47
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Published 06 Apr 2021

Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition

  • Maryna O. Mazur,
  • Oleksii S. Zhelavskyi,
  • Eugene M. Zviagin,
  • Svitlana V. Shishkina,
  • Vladimir I. Musatov,
  • Maksim A. Kolosov,
  • Elena H. Shvets,
  • Anna Yu. Andryushchenko and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2021, 17, 678–687, doi:10.3762/bjoc.17.57

Graphical Abstract
  • harder while the microwave-assisted catalyst-free conditions were effective for both terminal and non-terminal alkynes. Keywords: click chemistry; microwave chemistry; multicomponent reactions; triazolobenzodiazepines; Ugi reaction; Introduction Benzannulated heterocycles are among the most important
  • a few steps and constitutes one of the most actual and promising synthetic routes of modern organic chemistry. Among a wide variety of tandem strategies combination of an isocyanide-based multicomponent Ugi reaction with secondary transformations is one of the most powerful tools and provides access
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Published 08 Mar 2021

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

  • Zbigniew Malinowski,
  • Emilia Fornal,
  • Agata Sumara,
  • Renata Kontek,
  • Karol Bukowski,
  • Beata Pasternak,
  • Dariusz Sroczyński,
  • Joachim Kusz,
  • Magdalena Małecka and
  • Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

Graphical Abstract
  • phthalazinone derivatives 5 and 6 (Scheme 1, route B). In the literature, the number of reported synthetic methods for 4-aminophthalazin-1(2H)-ones is limited to a few examples and they usually involve two main approaches: 1) the application of multicomponent reactions starting from, e.g., the available o
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Published 25 Feb 2021

Synthetic strategies of phosphonodepsipeptides

  • Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

Graphical Abstract
  • reviewed, including the phosphonylation of hydroxy esters with phosphonochloridates, the condensation of phosphonic monoesters and hydroxy esters, the alkylation of phosphonic monoesters with 1-(alkoxycarbonyl)alkyl halides or sulfonates, multicomponent condensation of amides, aldehydes, and
  • phosphonodepsipeptides with C-1-hydroxyalkylphosphonic acids. Keywords: alkylation; mimetic; multicomponent condensation; peptide; phosphonopeptide; phosphonodepsipeptide; phosphonylation; Introduction Both, phosphonopeptides and phosphonodepsipeptides are phosphorus analogues of peptides [1][2][3][4][5]. The
  • -hydroxyglutarate (84) in a Mitsunobu reaction to generate the γ-phosphonodepsipeptide 79 in a high yield of 66% (Scheme 27) [28]. Synthesis of phosphonodepsipeptides via the multicomponent condensation of amides, aldehydes, and phosphites followed by alcoholysis with hydroxy esters Previously, the Mannich-type
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Published 16 Feb 2021

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

  • Vladislav A. Budevich,
  • Sergei V. Voitekhovich,
  • Alexander V. Zuraev,
  • Vadim E. Matulis,
  • Vitaly E. Matulis,
  • Alexander S. Lyakhov,
  • Ludmila S. Ivashkevich and
  • Oleg A. Ivashkevich

Beilstein J. Org. Chem. 2021, 17, 385–395, doi:10.3762/bjoc.17.34

Graphical Abstract
  • -generator and blowing agent [1][2]. Moreover, it is a useful building block in organic synthesis, including various multicomponent reactions opening the way to diverse fused heterocycles [3]. Salts with anionic tetrazole, i.e., aminotetrazolates 2, and cationic ones, i.e., aminotetrazolium salts 3, are
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Published 08 Feb 2021

Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams

  • Michał M. Więcław and
  • Bartłomiej Furman

Beilstein J. Org. Chem. 2021, 17, 115–123, doi:10.3762/bjoc.17.12

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  • Schwartz’s reagent-mediated reductive amide functionalization followed by a variant of the Ugi–azide multicomponent reaction. The anomeric configurations of two products were unambiguously confirmed by X-ray analysis. This work also describes examples of interesting further transformations of the title
  • one-pot Mannich/Michael sequence leading to oligocyclic compounds [24], and employment in subsequent Joulié–Ugi multicomponent reactions [25]. This work is an extension of these efforts and seeks to investigate the possibility of incorporating the Ugi–azide multicomponent reaction in this workflow. A
  • first example of using Schwartz’s reagent-mediated partial reduction of lactams and the Ugi–azide multicomponent reaction in a tandem process. Yields of the described products are moderate to good, a satisfying result for such a multistep process. We have shown that such a reaction does not necessarily
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Published 13 Jan 2021
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