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Search for "[3 2]-cycloaddition reactions" in Full Text gives 26 result(s) in Beilstein Journal of Organic Chemistry.

Catalytic multi-step domino and one-pot reactions

  • Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25

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  • . Zhang, Ma, and W. Zhang reflects the state of the art in the α-amino acid-based [3 + 2] cycloaddition reactions of N–H-type azomethine ylides in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse bioactive heterocyclic compounds and natural products [9]. Computational studies
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Editorial
Published 08 Feb 2024

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

  • Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

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  • presence of Brønsted acid. In their pioneering research, Tanaka et al. reported the [3 + 2] cycloaddition reactions of trifluoroacetaldehyde hydrazones and glyoxals to give 4-hydroxy-3-trifluoromethylpyrazoles. The resultant pyrazoles containing a free 4-hydroxy group were easily converted to a variety of
  • group has attracted a significant level of attention, and many trifluoromethylated pyrazoles have been used in medicinal products or in pesticides [66]. The [3 + 2] cycloaddition reactions are considered among the most powerful tools for the synthesis of versatile fluoroalkylated pyrazoles. Enol ethers
  • trifluoromethylated 1,2,4-triazoles were synthesized with excellent regioselectivities in [3 + 2] cycloaddition reactions of trifluoromethylated hydrazonoyl chlorides with imidates, amidine and 1H-benzo[d]imidazole-2-thiols, all of which were individually reported by Wang, Deng and Cai, respectively [77][78][79
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Review
Published 15 Nov 2023

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

  • Xiaofeng Zhang,
  • Xiaoming Ma and
  • Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

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  • with arylaldehydes are much less explored. The [3 + 2] adducts of α-amino acids could be used for a second [3 + 2] cycloaddition as well as for other post-condensation modifications. This article highlights our recent work on the development of α-amino acid-based [3 + 2] cycloaddition reactions of N–H
  • anionic charge on the α-carbon connecting to the EWG. They are popular AMYs for 1,3-diploar [3 + 2] cycloaddition reactions with alkenes to generate pyrrolidines 1a–d with high regio- and stereoselectivities. They have been reported in a huge number (1,000+) of publications [18][19][20][21][22][23][24][25
  • trifluoromethylated pyrrolidines As mentioned above, the unexpected double cycloaddition and low stereoselectivity are the major challenges for [3 + 2] cycloaddition reactions of semi- and non-stabilized AMYs derived from the condensation of amino acids with aldehydes. However, the reactions of amino acids with
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Perspective
Published 06 Nov 2023

Morpholine-mediated defluorinative cycloaddition of gem-difluoroalkenes and organic azides

  • Tzu-Yu Huang,
  • Mario Djugovski,
  • Sweta Adhikari,
  • Destinee L. Manning and
  • Sudeshna Roy

Beilstein J. Org. Chem. 2023, 19, 1545–1554, doi:10.3762/bjoc.19.111

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  • defluorinative processes in gem-difluoroalkenes. NiCl2(PCy3)2 and NiCl2(dppp)2 were chosen for our initial investigations since they have been used in both the defluorination of gem-difluoroalkenes and the coordination with the azides to promote [3 + 2] cycloaddition reactions [2][31][32]. Based on our
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Letter
Published 05 Oct 2023

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

  • Nosheen Beig,
  • Varsha Goyal and
  • Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

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  • catalyst when products were obtained with excellent enantioselectivity (92% ee) (Scheme 46). 2.3 [3 + 2] Cycloaddition reactions In a [3 + 2] cycloaddition reaction, a three atoms dipolar moiety (1,3-dipole) adds across two atoms of an alkene or alkyne (1,3-dipolarophile) (Scheme 47). It is also known as
  • -donors on the catalytic activity of NHC–Cu(I) complexes for azide–alkyne [3 + 2] cycloaddition reactions [67]. They determined binding constants of four NHC–CuCl complexes with two N-donors, which revealed that addition of phenanthroline to the NHC–CuCl enhanced the catalytic activity manifold. In fact
  • explored the application of a thiazolylidene-based Cu(I) complex as catalyst for [3 + 2] cycloaddition reactions. They prepared an ethylene-linked bisthiazol-2-ylidene dicopper(I) complex 136 which showed high catalytic activity (Scheme 53). The activity increased upon addition of acetic acid, particularly
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Published 20 Sep 2023

Nucleophile-induced ring contraction in pyrrolo[2,1-c][1,4]benzothiazines: access to pyrrolo[2,1-b][1,3]benzothiazoles

  • Ekaterina A. Lystsova,
  • Maksim V. Dmitriev,
  • Andrey N. Maslivets and
  • Ekaterina E. Khramtsova

Beilstein J. Org. Chem. 2023, 19, 646–657, doi:10.3762/bjoc.19.46

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  • -benzothiazol-2-yl(diazo)acetates (Scheme 1, entry 3) [12], dearomative [3 + 2] cycloaddition reactions of benzothiazoles with cyclopropanes (Scheme 1, entry 4) [13][14][15], multicomponent reactions (MCRs) of benzothiazoles, isocyanides and 2-methylidenemalonates (Scheme 1, entry 5) [16], 1,3-dipolar
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Published 11 May 2023

Functionalization of imidazole N-oxide: a recent discovery in organic transformations

  • Koustav Singha,
  • Imran Habib and
  • Mossaraf Hossain

Beilstein J. Org. Chem. 2022, 18, 1575–1588, doi:10.3762/bjoc.18.168

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  • of ethyl 2-cyano-2-(1,3-dihydro-2H-imidazole-2-ylidene)acetate derivatives via [3 + 2] cycloaddition reactions. C–H/C–Li coupling reaction of 2H-imidazole 1-oxides with pentafluorophenyllithium. Transition-metal-free coupling reaction of 2H-imidazole 1-oxides with polyphenols. Reaction conditions: 1
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Published 22 Nov 2022

Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides

  • Md Imran Hossain,
  • Md Imdadul H. Khan,
  • Seong Jong Kim and
  • Hoang V. Le

Beilstein J. Org. Chem. 2022, 18, 446–458, doi:10.3762/bjoc.18.47

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  • polarity on the keto–enol equilibrium of the 1,3-diketones, which influences the results of the [3 + 2] cycloaddition reactions under mild basic conditions, via nuclear magnetic resonance (NMR) spectroscopy. The 1H NMR spectra of 1-phenyl-1,3-butanedione (2a) in CDCl3 and in methanol-d4 indicated that the
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Published 22 Apr 2022

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

  • Greta Utecht-Jarzyńska,
  • Karolina Nagła,
  • Grzegorz Mlostoń,
  • Heinz Heimgartner,
  • Marcin Palusiak and
  • Marcin Jasiński

Beilstein J. Org. Chem. 2021, 17, 1509–1517, doi:10.3762/bjoc.17.108

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  • fluorine-containing organic molecules combined with the 1,4-quinone moiety can be considered as a challenging problem of current organic synthesis. Thus, the main goal of the present study was to check the course of [3 + 2]-cycloaddition reactions of electron-deficient CF3-substituted nitrile imines 7 with
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Published 28 Jun 2021

All-carbon [3 + 2] cycloaddition in natural product synthesis

  • Zhuo Wang and
  • Junyang Liu

Beilstein J. Org. Chem. 2020, 16, 3015–3031, doi:10.3762/bjoc.16.251

Graphical Abstract
  • ] cycloaddition through diyl trapping with an olefin [14][15] and Trost’s palladium-catalyzed trimethylenemethane cycloaddition [16], which allows the preparation of five-membered carbocycles, have been emerged since the 1970s. Thereafter, many novel and important all-carbon [3 + 2] cycloaddition reactions, such
  • complex natural products. Besides the all-carbon [3 + 2] cycloaddition reactions and the corresponding applications described above, the all-carbon [3 + 2] annulation, which undergoes other possible mechanistic pathways other than cycloaddition, proved its usefulness in forging highly-substituted five
  • undoubtedly an efficient synthetic transformation that creates two C–C bonds in a single reaction. However, the prior protection of the reactive functional groups, such as the hydroxy and amino groups, are still necessary for most of the all-carbon [3 + 2] cycloaddition reactions. We predict that further
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Published 09 Dec 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 a [3 + 2] cycloaddition reactions under UV irradiation with azobis(isobutyronitrile) (AIBN) as the free radical initiator and phenyl disulfide as the catalyst, in which the three-membered rings containing double bonds and substituted olefins were transformed into five-membered-ring structures with
  • used similar disulfide-catalyzed [3 + 2] cycloaddition reactions for the synthesis of polycyclic frameworks. The irradiation of vinylcyclopropanes with alkenes or alkynes in the presence of dibutyl disulfide afford the desired bi- or tricyclic products with 54–88% yield (Scheme 2) [6]. In 2014, Maruoka
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Published 23 Jun 2020

Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes

  • Grzegorz Mlostoń,
  • Mateusz Kowalczyk,
  • André U. Augustin,
  • Peter G. Jones and
  • Daniel B. Werz

Beilstein J. Org. Chem. 2020, 16, 1288–1295, doi:10.3762/bjoc.16.109

Graphical Abstract
  • thioketones reacted with donor–acceptor cyclopropanes in dichloromethane at room temperature in the presence of catalytic amounts of Sc(OTf)3 yielding tetrahydrothiophene derivatives, products of formal [3 + 2]-cycloaddition reactions, in moderate to high yields. In all studied cases, dimethyl 2
  • thioketones to form nearly equal amounts of both diastereoisomeric tetrahydrothiophenes. A low selectivity was also observed in the reaction of a 2-phthalimide-derived cyclopropane with ferrocenyl phenyl thioketone. Keywords: [3 + 2]-cycloaddition reactions; donor–acceptor cyclopropanes; ferrocenyl
  • materials chemistry, and electrochemical studies [19]. In continuation of our studies on organic sulfur compounds and the mechanisms of their reactions, the main goal of the present work was the examination of the formal [3 + 2]-cycloaddition reactions of ferrocenyl-substituted thioketones 8 with D–A
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Published 10 Jun 2020

Synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines via three-component [3 + 2] cycloaddition followed by one-pot N-allylation and intramolecular Heck reactions

  • Xiaoming Ma,
  • Suzhi Meng,
  • Xiaofeng Zhang,
  • Qiang Zhang,
  • Shenghu Yan,
  • Yue Zhang and
  • Wei Zhang

Beilstein J. Org. Chem. 2020, 16, 1225–1233, doi:10.3762/bjoc.16.106

Graphical Abstract
  • reactions to make it a green synthetic method with pot, atom and step economy (PASE) [55][56]. Results and Discussion Following the reported procedures for amino ester- and amino acid-based [3 + 2] cycloaddition reactions, pyrrolidine adducts 5 and 6 were synthesized by a three-component reaction of 1 or 2
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Published 04 Jun 2020

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

  • Pezhman Shiri and
  • Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

Graphical Abstract
  • to be highly active in [3 + 2] cycloaddition reactions of halides, nonactivated terminal alkynes, and sodium azide (Scheme 21). Copper(I) ions were attached to the surface of carbon graphene as outlined in Scheme 21. Therein, GO was generated by Hummer’s method, and ascorbic acid was used to produce
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Published 01 Apr 2020

Synthesis of cis-hydrindan-2,4-diones bearing an all-carbon quaternary center by a Danheiser annulation

  • Gisela V. Saborit,
  • Carlos Cativiela,
  • Ana I. Jiménez,
  • Josep Bonjoch and
  • Ben Bradshaw

Beilstein J. Org. Chem. 2018, 14, 2597–2601, doi:10.3762/bjoc.14.237

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  • Lycopodium alkaloids carinatine A [11][14][15], 8-deoxyserratinine [10], fawcettidine [10], fawcettimine [7][10], lycojaponicumin C [10], lycopladine A [11][13][14][15], lycoposerramine R [13][14], and sieboldine [19][20] (Figure 2). Results and Discussion Despite the potential of [3 + 2] cycloaddition
  • reactions [27] to achieve cis-hydrindan-2,4-diones, their application to rapidly assemble the five-membered ring of the targeted 6,5-bicylic system has not been reported until now. Two examples using cycloaddition processes in this field should be mentioned: Diels–Alder [28] and Pauson–Khand [29] reactions
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Published 09 Oct 2018

Addition of dithi(ol)anylium tetrafluoroborates to α,β-unsaturated ketones

  • Yu-Chieh Huang,
  • An Nguyen,
  • Simone Gräßle,
  • Sylvia Vanderheiden,
  • Nicole Jung and
  • Stefan Bräse

Beilstein J. Org. Chem. 2018, 14, 515–522, doi:10.3762/bjoc.14.37

Graphical Abstract
  • -dithioacetals [4] are of particular interest as attractive nucleophiles for the addition to halonium ions [5][6], acyl chlorides [7] and other electrophiles [8][9][10] and are broadly used as precursors for [2 + 2]-cycloaddition [11][12], (aza)-Diels–Alder reaction [13][14], and [3 + 2]-cycloaddition reactions
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Published 26 Feb 2018

Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

  • Gabriel P. Costa,
  • Natália Seus,
  • Juliano A. Roehrs,
  • Raquel G. Jacob,
  • Ricardo F. Schumacher,
  • Thiago Barcellos,
  • Rafael Luque and
  • Diego Alves

Beilstein J. Org. Chem. 2017, 13, 694–702, doi:10.3762/bjoc.13.68

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Published 11 Apr 2017

Development of chiral metal amides as highly reactive catalysts for asymmetric [3 + 2] cycloadditions

  • Yasuhiro Yamashita,
  • Susumu Yoshimoto,
  • Mark J. Dutton and
  • Shū Kobayashi

Beilstein J. Org. Chem. 2016, 12, 1447–1452, doi:10.3762/bjoc.12.140

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  • amide catalysts in other reactions are ongoing. Experimental A general experimental procedure for conducting catalytic asymmetric [3 + 2] cycloaddition reactions with 0.01 mol % catalyst loading is described. Under an Ar atmosphere, a solution of the preformed chiral CuHMDS catalyst [prepared from KHMDS
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Published 13 Jul 2016

Synergistic chiral iminium and palladium catalysis: Highly regio- and enantioselective [3 + 2] annulation reaction of 2-vinylcyclopropanes with enals

  • Haipan Zhu,
  • Peile Du,
  • Jianjun Li,
  • Ziyang Liao,
  • Guohua Liu,
  • Hao Li and
  • Wei Wang

Beilstein J. Org. Chem. 2016, 12, 1340–1347, doi:10.3762/bjoc.12.127

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  • ; Introduction The power of “donor–acceptor” (D–A) cyclopropanes as versatile 1,3-dipolar components is fuelled by its capacity of serving a complementary approach to a wide array of 5-membered ring structures, which are difficult or impossible to access by classic [3 + 2] cycloaddition reactions [1][2][3][4][5
  • due to the minimization of the A[1][3] interaction. Therefore, it is observed 3a’ produced from corresponding 8a’ as the major diastereomer whereas 3a” as minor one. Conclusion We have developed a cooperative catalytic strategy for highly regio- and enantioselective [3 + 2] cycloaddition reactions of
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Published 29 Jun 2016

Diradical reaction mechanisms in [3 + 2]-cycloadditions of hetaryl thioketones with alkyl- or trimethylsilyl-substituted diazomethanes

  • Grzegorz Mlostoń,
  • Paulina Pipiak and
  • Heinz Heimgartner

Beilstein J. Org. Chem. 2016, 12, 716–724, doi:10.3762/bjoc.12.71

Graphical Abstract
  • -thiadiazolines of type 2 can be obtained at low temperature and subsequently used as precursors of new thiocarbonyl ylides. The latter may be potentially useful for the [3 + 2]-cycloaddition reactions with diverse dipolarophiles leading to five-membered S-heterocycles, such as di- and tetrahydrothiophenes, 1,3
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Published 14 Apr 2016

Synthesis of 2-trifluoromethylpyrazolo[5,1-a]isoquinolines via silver triflate-catalyzed or electrophile-mediated one-pot tandem reaction

  • Xiaoli Zhou,
  • Meiling Liu,
  • Puying Luo,
  • Yingjun Lai,
  • Tangtao Yang and
  • Qiuping Ding

Beilstein J. Org. Chem. 2014, 10, 2286–2292, doi:10.3762/bjoc.10.238

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  • 13C NMR, HRMS, as well as X-ray diffraction analysis (Figure 1, for details, see Supporting Information File 1). Based on this one-pot tandem electrophilic cyclization/[3 + 2] cycloaddition reactions, highly functionalized pyrazolo[5,1-a]isoquinolines can be obtained via palladium-catalyzed cross
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Published 30 Sep 2014

Silver and gold-catalyzed multicomponent reactions

  • Giorgio Abbiati and
  • Elisabetta Rossi

Beilstein J. Org. Chem. 2014, 10, 481–513, doi:10.3762/bjoc.10.46

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  • reaction involving nitriles 52 as pro-nucleophiles (Scheme 28) [71]. Wu and co-workers successfully employed the isoquinolinium-2-ylamides 43 as an ylidic species in two-component tandem [3 + 2]-cycloaddition reactions with a series of substrates including dimethyl acetylenedicarboxylate [72
  • isoquinolinium-2-ylamide 43 undergoes a [3 + 2]-cycloaddition reaction with carbodiimide 54. Further intramolecular rearrangement yields the desired 1-(isoquinolin-1-yl)guanidine 55. Moreover, isoquinolinium-2-ylamides 43 can participate as 1,3-dipoles in [3 + 2]-cycloaddition reactions with in situ generated
  • keteneimines 57 [77] or in [3 + 3] processes with dimethyl cyclopropane-1,1-dicarboxylates 59 [78]. Both these reactions are co-catalyzed, the former by silver triflate and copper bromide and the latter by silver triflate and nickel(II) perchlorate (Scheme 30 and Scheme 31). In [3 + 2]-cycloaddition reactions
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Published 26 Feb 2014

Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives

  • Zhi-Cong Geng,
  • Jian Chen,
  • Ning Li,
  • Xiao-Fei Huang,
  • Yong Zhang,
  • Ya-Wen Zhang and
  • Xing-Wang Wang

Beilstein J. Org. Chem. 2012, 8, 1710–1720, doi:10.3762/bjoc.8.195

Graphical Abstract
  • ], and moreover, pyrazolidines can also be oxidized to afford pyrazolines [8][9][10][11][12] and pyrazoles [13][14][15]. The pyrazolidine structural unit is commonly constructed by [3 + 2] cycloaddition reactions using hydrazones [16][17][18][19][20][21][22][23] or azomethine amines [24][25][26][27] as
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Published 09 Oct 2012

Intramolecular carbenoid ylide forming reactions of 2-diazo-3-keto-4-phthalimidocarboxylic esters derived from methionine and cysteine

  • Marc Enßle,
  • Stefan Buck,
  • Roland Werz and
  • Gerhard Maas

Beilstein J. Org. Chem. 2012, 8, 433–440, doi:10.3762/bjoc.8.49

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  • NOESY NMR experiment indicated the correlation shown in Scheme 6. Intramolecular [3 + 2]-cycloaddition reactions of a carbonyl ylide with a nonactivated but suitably positioned olefinic bond have been known for some time [3][27][28][29][30][31][32][33][34][35] and can be used for the construction of
  • substructure. Trapping of carbonyl ylides with dipolarophiles In situ generated carbonyl ylides can be intercepted not only in intramolecular (as discussed above) but also in intermolecular [3 + 2] cycloaddition reactions (see, for example, [3][18][19][20][41][42]). By analogy with other 2-diazo-3-oxo-4
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Published 22 Mar 2012

Photochemical and thermal intramolecular 1,3-dipolar cycloaddition reactions of new o-stilbene-methylene-3-sydnones and their synthesis

  • Kristina Butković,
  • Željko Marinić,
  • Krešimir Molčanov,
  • Biserka Kojić-Prodić and
  • Marija Šindler-Kulyk

Beilstein J. Org. Chem. 2011, 7, 1663–1670, doi:10.3762/bjoc.7.196

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  • , giving polycyclic compound 14, while the sydnone moiety in the cis isomer 3b gives polycyclic compound 15. Stilbene-methylene-sydnones are useful substrates for photochemical and thermal intramolecular [3 + 2] cycloaddition reactions to heteropolycyclic compounds. Resonance structures of the sydnone ring
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Published 13 Dec 2011
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