Search results

Search for "1,3-dipolar" in Full Text gives 192 result(s) in Beilstein Journal of Organic Chemistry.

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

  • Dmitry E. Shybanov,
  • Maxim E. Kukushkin,
  • Eugene V. Babaev,
  • Nikolai V. Zyk and
  • Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

Graphical Abstract
  • method was successfully used to generate highly active nitrile oxides and nitrilimines for 1,3-dipolar cycloaddition reactions [19][20][21]. Based on our previous experience with diffusion mixing, we assumed that formaldehyde vapor diffusion into the reaction would lead to an extremely low concentration
PDF
Album
Supp Info
Full Research Paper
Published 04 Feb 2025

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

  • Lucía Campos-Prieto,
  • Aitor García-Rey,
  • Eddy Sotelo and
  • Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

Graphical Abstract
  • years, the Ugi reaction has emerged as a highly considered reaction due to its mild conditions, broad applications, and product diversity. It enables the selective assembly of precursors, facilitating various post-reaction transformations such as deprotection cyclization, 1,3-dipolar cycloaddition, and
PDF
Album
Review
Published 03 Dec 2024

Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

  • Marzieh Norouzi,
  • Mohammad Taghi Nazeri,
  • Ahmad Shaabani and
  • Behrouz Notash

Beilstein J. Org. Chem. 2024, 20, 2870–2882, doi:10.3762/bjoc.20.241

Graphical Abstract
  • with 1,10-phenanthroline as cyclic imine under solvent-free conditions for the synthesis of pyrrole-fused phenanthroline. This reaction proceeds via in situ formation of zwitterion I through reaction of the aldehyde and malononitrile followed by 1,3-dipolar cycloaddition (Scheme 1a) [41]. Chen and co
PDF
Album
Supp Info
Full Research Paper
Published 11 Nov 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

Graphical Abstract
  • were overcome by the addition–cyclocondensation of α,β-unsaturated ketones. Embedding 1,3-dipolar cycloadditions into a one-pot process has additionally been developed for concise syntheses of pyrazoles. The MCR strategy also allows for concatenating classical condensation-based methodology with modern
  • with electrophiles, such as deuteration or electrophilic chlorination using N-chlorosuccinimide, in this consecutive three-component synthesis to give persubstituted pyrazoles 165 (Scheme 55) [162]. (3 + 2)-Cycloaddition – C2 building blocks as substrates 1,3-Dipolar cycloadditions are important
  • formed in situ from aromatic aldehydes and tosylhydrazine. After basic treatment of these tosylhydrazones followed by 1,3-dipolar cycloaddition with terminal alkynes, the corresponding pyrazoles 168 are obtained. The regioselectivity of this synthesis can be explained by steric causes and the favored
PDF
Album
Review
Published 16 Aug 2024

Syntheses and medicinal chemistry of spiro heterocyclic steroids

  • Laura L. Romero-Hernández,
  • Ana Isabel Ahuja-Casarín,
  • Penélope Merino-Montiel,
  • Sara Montiel-Smith,
  • José Luis Vega-Báez and
  • Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

Graphical Abstract
  • synthesis of 2H-furan-3-ones from mestranol [23]. Initially, a 1,3-dipolar regioselective cycloaddition occurred between the alkyne group of mestranol and an alkanonitrile oxide generated in situ from the corresponding oxime, yielding isoxazoles 31. Later, a reductive ring cleavage of the isoxazole ring was
  • ninhydrin. Estrone-derived dispiropyrrolidines 43, 44, and 45 were obtained in a regio- and stereoselective manner (ylide attacks by the α-steroidal face) in yields ranging from 66% to 72%. 1,3-Dipolar cyclization of azomethine ylides can also be achieved using (E)-steroidal arylidenes at C-16. In 2014, Liu
  • , such as a one-pot four-component synthesis and the use of ionic liquids as solvents [30]. Kanchithalaivan et al. [31] reported a library of 16-spiro pyrrolo[1,2-c][1,3]thiazoles of trans-androsterone and DHEA (49a and 49b, respectively). The syntheses were achieved through the 1,3-dipolar cycloaddition
PDF
Album
Review
Published 24 Jul 2024

Tetrabutylammonium iodide-catalyzed oxidative α-azidation of β-ketocarbonyl compounds using sodium azide

  • Christopher Mairhofer,
  • David Naderer and
  • Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1510–1517, doi:10.3762/bjoc.20.135

Graphical Abstract
  • ][10][11][12][13][14]. For example, such molecules can be utilized to access free amines [3][13] and undergo Staudinger-type ligations [14]. Furthermore, they can be very efficiently employed for triazole-forming 1,3-dipolar cycloadditions with alkynes (“click-chemistry”) [9][10][11][12]. As a
PDF
Album
Supp Info
Full Research Paper
Published 05 Jul 2024

Enhanced reactivity of Li+@C60 toward thermal [2 + 2] cycloaddition by encapsulated Li+ Lewis acid

  • Hiroshi Ueno,
  • Yu Yamazaki,
  • Hiroshi Okada,
  • Fuminori Misaizu,
  • Ken Kokubo and
  • Hidehiro Sakurai

Beilstein J. Org. Chem. 2024, 20, 653–660, doi:10.3762/bjoc.20.58

Graphical Abstract
  • accelerated 1,3-dipolar and Diels–Alder reactions [12][13], it is noteworthy that the anticipated diverse properties resulting from the derivatization of Li+@C60 have not yet been fully realized. To further leverage the unique properties of the novel ion-endohedral fullerene, achieving diverse property tuning
PDF
Album
Supp Info
Full Research Paper
Published 25 Mar 2024

Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production

  • Cristina Castanyer,
  • Anna Pla-Quintana,
  • Anna Roglans,
  • Albert Artigas and
  • Miquel Solà

Beilstein J. Org. Chem. 2024, 20, 272–279, doi:10.3762/bjoc.20.28

Graphical Abstract
  • medical applications) and improving their stability, among other desirable properties. The most common reactions used to functionalize fullerenes are Diels–Alder and 1,3-dipolar cycloadditions and Bingel–Hirsch cyclopropanations [19][20]. In most cases, functionalization occurs while preserving the carbon
PDF
Album
Supp Info
Full Research Paper
Published 13 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

Graphical Abstract
  • other derivatives in good yields [37] (Scheme 1). Later, Wu et al. described a diastereoselective 1,3-dipolar cycloaddition of trifluoroacetaldehyde hydrazones with α,β-ethenyl ketones to obtain polysubstituted pyrazolidines and pyrazolines. These reactions were carried out under two different sets of
  • under basic conditions, and expanded the synthetic method to N-substituted acylhydrazones [106][107] (Scheme 18). In the early development of 1,3-dipolar cycloadditions of azomethine imines, the acyclic azomethine imines were unstable and their in situ preparation required Brønsted acid or thermal
  • trifluoromethyl acylhydrazones as 1,3-dipolar agents to react with β-nitrostyrenes [114], maleates [115], cyclopentadiene [116] and maleimides [117] for the synthesis of CF3-substituted pyrazolidine derivatives. These reactions were conducted under basic conditions and in the presence of Cu(OTf)2 (Scheme 19a). As
PDF
Album
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

Graphical Abstract
  • -type AMYs in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse heterocycles related to some bioactive compounds and natural products. Keywords: [3 + 2] cycloaddition; decarboxylation; 1,3-dipolar; double cycloaddition; one-pot synthesis; multicomponent reaction; semi
  • -stabilized azomethine ylide; Introduction The 1,3-dipolar cycloaddition of azomethine ylides (AMYs) [1][2][3][4][5][6] is a powerful method for the synthesis of bioactive pyrrolidine-containing compounds and natural product analogs [7][8][9][10][11][12][13][14][15]. AMYs generated from the reaction of
  • products 3c and 3d can be used for a second cycloaddition to form products 4a and 4b. The non-stabilized AMYs C1 and C2 have neither an EWG nor an Ar group to localize the negative charge. The 1,3-dipolar cycloadditions of C-type AMYs lead to the formation of [3 + 2] adducts 5 or 6 with low regio- and
PDF
Album
Perspective
Published 06 Nov 2023

Lewis acid-promoted direct synthesis of isoxazole derivatives

  • Dengxu Qiu,
  • Chenhui Jiang,
  • Pan Gao and
  • Yu Yuan

Beilstein J. Org. Chem. 2023, 19, 1562–1567, doi:10.3762/bjoc.19.113

Graphical Abstract
  • oxide E [23], which can be converted to the desired isoxazole with 1a through a 1,3-dipolar cycloaddition. Conclusion In conclusion, we have developed an efficient and concise synthesis of isoxazole nitrogen heterocycles by direct C–H-bond activation of methyl heteroaromatics. The method avoids using
PDF
Album
Supp Info
Full Research Paper
Published 16 Oct 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

Graphical Abstract
  • -difluoroalkenes that subsequently undergoes a cycloaddition reaction. Results and Discussion While investigating 1,3-dipolar cycloaddition reactions between organic azides and gem-difluoroalkenes to obtain the 4-fluoro-1,4-disubstituted 1,2,3-triazole regioisomers, we observed an interesting reactivity while
PDF
Album
Supp Info
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

Graphical Abstract
  • 1,3-dipolar cycloaddition and belongs to the general category of [π4s + π2s] cycloadditions. It is an important method to construct a five-membered heterocyclic ring [66]. As discussed earlier, the Cu atom in NHC–Cu(I) complexes has nucleophilic character, which allows binding to the positive end of
PDF
Album
Review
Published 20 Sep 2023

One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives

  • Hans-Ulrich Reissig and
  • Fei Yu

Beilstein J. Org. Chem. 2023, 19, 1399–1407, doi:10.3762/bjoc.19.101

Graphical Abstract
  • ]). Mechanistic aspects of the CuAAC have been studied in detail [16][17]. Whereas the traditional 1,3-dipolar cycloaddition (Huisgen reaction) [18][19][20] of azides and alkynes requires often – but not always – relatively harsh conditions and proceeds with moderate regioselectivity only [21], the copper
PDF
Album
Supp Info
Full Research Paper
Published 18 Sep 2023

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

  • Xiu-Yu Chen,
  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

Graphical Abstract
  • ; isoquinolino[1,2-f][1,6]naphthyridine; Introduction Among various well-known cycloaddition reactions such as the 1,3-dipolar cycloaddition reaction, Diels–Alder reaction, and the Povarov reaction, the cycloaddition reaction of Huisgen 1,4-dipoles with activated alkenes received increasing attention [1][2][3
PDF
Album
Supp Info
Full Research Paper
Published 29 Jun 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

Graphical Abstract
  • -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
PDF
Album
Supp Info
Full Research Paper
Published 11 May 2023

Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones

  • Manuel Pedrón,
  • Jana Sendra,
  • Irene Ginés,
  • Tomás Tejero,
  • Jose L. Vicario and
  • Pedro Merino

Beilstein J. Org. Chem. 2023, 19, 477–486, doi:10.3762/bjoc.19.37

Graphical Abstract
  • common reaction conditions. The reaction has been defined by Houk and Rueping as a (3+ + 2) monopolar cycloaddition [33] pointing out the protonated state of the imino nitrogen of the hydrazone in contrast to the well-known 1,3-dipolar cycloaddition of azomethine imines in which the terminal nitrogen has
PDF
Album
Supp Info
Full Research Paper
Published 20 Apr 2023

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

  • Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

Graphical Abstract
  • of the synthesis and properties of various porphyrin-triazole hybrids, this review will discuss some of the key reactions involved in the preparation of triazole-linked porphyrin conjugates. Keywords: azide–alkyne; click chemistry; CuAAC; 1,3-dipolar cycloaddition; porphyrin; 1,2,3-triazole
  • connect a porphyrin with a chromophoric group. Among these, the copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction [1][2] of azides with terminal alkynes is a popular and well established process to link a porphyrin with other moieties via 1,2,3-triazole group [3] (Figure 1). The term “click
  • ] exploited the concept of “click chemistry” for the construction of β-substituted-triazoloporphyrins 3a–c in 65–95% yield by the reaction of β-azidotetraphenylporphyrins 1 with various arylalkynes 2a–c via copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction in DMF at 50 °C in the presence of CuSO4
PDF
Album
Review
Published 22 Mar 2023

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

  • Bram Ryckaert,
  • Ellen Demeyere,
  • Frederick Degroote,
  • Hilde Janssens and
  • Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

Graphical Abstract
  • group) are especially favored here [92][93], and these allyl cations can also be seen as 1,3-dipoles, cross-conjugated by a carbonyl (Scheme 13b). As can be expected from this 1,3-dipolar nature, such amphiphilic allyl cations can also be used in (3 + 2) cycloadditions, though this has so far been
PDF
Album
Review
Published 02 Feb 2023

One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles

  • Juan Lu,
  • Bin Yao,
  • Desheng Zhan,
  • Zhuo Sun,
  • Yun Ji and
  • Xiaofeng Zhang

Beilstein J. Org. Chem. 2022, 18, 1607–1616, doi:10.3762/bjoc.18.171

Graphical Abstract
  • introduced in this study. Subsequently one equivalent of aldehyde and olefinic oxindole in situ were followed by decarboxylative 1,3-dipolar cycloaddition for diastereoselective synthesis of spirooxindolepyrrolothiazoles with generating 5 new bonds, 5 stereocenters and two heterocycles (Scheme 1C and Scheme
  •  2C). Results and Discussion The optimized reaction conditions of stepwise, one-pot and cascade (two-step with one operational step) processes for N,S-acetalation and decarboxylative 1,3-dipolar cycloaddition were developed by using two equivalents of 4-bromobenzaldehyde (1a), ʟ-cysteine (2) and
  • . Subsequent decarboxylation of thiazolooxazol-1-one I affords non-stabilized azomethine ylide (AY) for 1,3-dipolar cycloaddition with olefinic oxindole 4a to give spirooxindolepyrrolothiazoles 5 and 7. The endo-TS is more favorable than exo-TS for the 1,3-dipolar cycloaddition to afford the major and minor
PDF
Album
Supp Info
Full Research Paper
Published 28 Nov 2022

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

Graphical Abstract
  • reaction of Meldrum’s acid (26) and aldehyde 27 resulting in the formation of the electron-deficient enone 30, which then participated in a Michael-type addition reaction with 1,3-dipolar 2-unsubstituted imidazole N-oxide 28 to provide the intermediate 31. In the last step, the final product 29 was
PDF
Album
Review
Published 22 Nov 2022

Synthesis of N-phenyl- and N-thiazolyl-1H-indazoles by copper-catalyzed intramolecular N-arylation of ortho-chlorinated arylhydrazones

  • Yara Cristina Marchioro Barbosa,
  • Guilherme Caneppele Paveglio,
  • Claudio Martin Pereira de Pereira,
  • Sidnei Moura,
  • Cristiane Storck Schwalm,
  • Gleison Antonio Casagrande and
  • Lucas Pizzuti

Beilstein J. Org. Chem. 2022, 18, 1079–1087, doi:10.3762/bjoc.18.110

Graphical Abstract
  • bendazac [10], the anti-inflammatory agent benzydamine [11], and the antiemetic agent granisetron [12] are commercially available examples. In view of the abovementioned interest, an increasing number of approaches for the synthesis of 1H-indazoles has been recently reported, including 1,3-dipolar
PDF
Album
Supp Info
Full Research Paper
Published 23 Aug 2022

Synthesis of novel alkynyl imidazopyridinyl selenides: copper-catalyzed tandem selenation of selenium with 2-arylimidazo[1,2-a]pyridines and terminal alkynes

  • Mio Matsumura,
  • Kaho Tsukada,
  • Kiwa Sugimoto,
  • Yuki Murata and
  • Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 863–871, doi:10.3762/bjoc.18.87

Graphical Abstract
  • reagents and 1,3-dipolar azide–alkyne cycloaddition based on the alkyne moiety. Keywords: alkynyl imidazopyridinyl selenide; copper catalyst; imidazo[1,2-a]pyridine; selenium; tandem reaction; terminal alkyne; Introduction Imidazo[1,2-a]pyridines are important heterocycles that serve as key functional
  • –Prakash reagent (TMSCF3) in the presence of Cs2CO3 as base in MeCN at 0 °C gave product 7 with a trifluoromethyl group. Stefani et al. reported the 1,3-dipolar azide–alkyne cycloaddition (AAC) of organotellanyl alkynes with organic azides in the presence of a copper reagent to form 5-organotellanyl-1,2,3
  • regioselective 1,3-dipolar azide–alkyne cycloaddition to form 5-selanyl-1,2,3-triazole. The investigation of the biological activity of the compounds obtained in this study and the application of this synthesis route using other heterocycles, instead of imidazopyridine, are currently underway in our laboratory
PDF
Album
Supp Info
Full Research Paper
Published 19 Jul 2022

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

Graphical Abstract
  • 1,3-dipolar cycloaddition (1,3-DC) reactions of cyclopropenes to the stable azomethine ylide – protonated form of Ruhemann's purple (PRP) has been developed. Both 3-substituted and 3,3-disubstituted cyclopropenes reacted with PRP, affording the corresponding bis-spirocyclic 3-azabicyclo[3.1.0]hexane
  • [15]. In our recent studies, great attention was paid to developing methods for the synthesis of spiro[3-azabicyclo[3.1.0]hexanes] based on 1,3-dipolar cycloaddition reactions involving azomethine ylides and cyclopropene dipolarophiles, and also the in vitro activity of some synthesized compounds has
  • been explored [19][20][21][22][23][24]. To generate azomethine ylides, we used a classical method based on the reaction of cyclic carbonyl compounds with α-amino acids. Μono-, bi-, and tetracyclic carbonyl compounds were utilized in these studies. 1,3-Dipolar cycloaddition of cyclopropenes to
PDF
Album
Supp Info
Full Research Paper
Published 29 Jun 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

Graphical Abstract
  • , β-ketoesters or β-ketoamides are a commonly used 2-step route to 3,4,5-trisubstituted isoxazoles [24][25]. Xiao Zhou et al. recently reported a direct access to 3,4,5-trisubstituted isoxazoles via an enolate-mediated 1,3-dipolar cycloaddition of β-functionalized ketones with nitrile oxides using
PDF
Album
Supp Info
Full Research Paper
Published 22 Apr 2022
Other Beilstein-Institut Open Science Activities