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

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

  • Bernd Strehmel,
  • Christian Schmitz,
  • Ceren Kütahya,
  • Yulian Pang,
  • Anke Drewitz and
  • Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

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Published 18 Mar 2020

The use of isoxazoline and isoxazole scaffolding in the design of novel thiourea and amide liquid-crystalline compounds

  • Itamar L. Gonçalves,
  • Rafaela R. da Rosa,
  • Vera L. Eifler-Lima and
  • Aloir A. Merlo

Beilstein J. Org. Chem. 2020, 16, 175–184, doi:10.3762/bjoc.16.20

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  • , 8, 9, 12 and 13 were then prepared by [3 + 2]-1,3-dipolar cycloaddition of nitrile oxide (ArCNO) formed in situ from oximes and a number of alkenes as dipolarophiles, to yield the precursors of the cycloadducts isoxazolines 2, 7 and 11 regioselectively. The cycloadducts were subjected to SnCl2
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Published 06 Feb 2020

Unexpected one-pot formation of the 1H-6a,8a-epiminotricyclopenta[a,c,e][8]annulene system from cyclopentanone, ammonia and dimethyl fumarate. Synthesis of highly strained polycyclic nitroxide and EPR study

  • Sergey A. Dobrynin,
  • Igor A. Kirilyuk,
  • Yuri V. Gatilov,
  • Andrey A. Kuzhelev,
  • Olesya A. Krumkacheva,
  • Matvey V. Fedin,
  • Michael K. Bowman and
  • Elena G. Bagryanskaya

Beilstein J. Org. Chem. 2019, 15, 2664–2670, doi:10.3762/bjoc.15.259

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  • observed in a one-pot synthesis from cyclopentanone, dimethyl fumarate and ammonium acetate. This multistep reaction includes 1,3-dipolar cycloaddition of dimethyl fumarate to the cyclic azomethine ylide formed in situ from cyclopentanone and ammonia. The polycyclic amine product was easily converted into
  • nitroxide [4]. Here we report the unexpected formation of a highly strained polycyclic amine from cyclopentanone, dimethyl fumarate and ammonium acetate. This multistep reaction obviously includes the 1,3-dipolar cycloaddition of dimethyl fumarate with cyclic azomethine ylide formed in situ from
  • heterocycle formation [11]. Presumably, a prototropic shift in the enamine-imine intermediate 4 is followed by electrocyclization to the cyclic azomethine ylide, which then reacts with dimethyl fumarate in a 1,3-dipolar cycloaddition. The suggested mechanism accounts for the trans-position of the methyne
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Published 07 Nov 2019

AgNTf2-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives

  • Ziping Cao,
  • Jiekun Zhu,
  • Li Liu,
  • Yuanling Pang,
  • Laijin Tian,
  • Xuejun Sun and
  • Xin Meng

Beilstein J. Org. Chem. 2019, 15, 2623–2630, doi:10.3762/bjoc.15.255

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  • tethered to cyclohexadienones that can be converted into complex polycycles by Ag-carbenoid-initiated cascades [16]. Recently, Zhu’s group developed a tandem 1,3dipolar cycloaddition/cyclopropanation silver-catalyzed reaction of enynals with alkenes [17]. In our previous studies, this silver carbene
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Published 04 Nov 2019

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

  • Gerardo M. Ojeda,
  • Prabhat Ranjan,
  • Pavel Fedoseev,
  • Lisandra Amable,
  • Upendra K. Sharma,
  • Daniel G. Rivera and
  • Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

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  • prospect of the tetrazole hybridization strategy in drug discovery. Among the most versatile methods for obtaining tetrazoles are the Ugi-azide four-component reaction (Ugi-azide-4CR) [14][15][16] and the 1,3-dipolar cycloaddition of azides with (acyl)cyanides [17][18]. The Ugi-azide-4CR enables the
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Published 16 Oct 2019

Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition

  • Yulia V. Khoroshunova,
  • Denis A. Morozov,
  • Andrey I. Taratayko,
  • Polina D. Gladkikh,
  • Yuri I. Glazachev and
  • Igor A. Kirilyuk

Beilstein J. Org. Chem. 2019, 15, 2036–2042, doi:10.3762/bjoc.15.200

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  • synthesis of new pyrrolidine nitroxides from 5,5-dialkyl-1-pyrroline N-oxides via the introduction of a pent-4-enyl group to the nitrone carbon followed by an intramolecular 1,3-dipolar cycloaddition reaction and isoxazolidine ring opening. The kinetics of reduction of the new nitroxides with ascorbate were
  • studied and compared to those of previously published (1S,2R,3′S,4′S,5′S,2″R)-dispiro[(2-hydroxymethyl)cyclopentan-1,2′-(3′,4′-di-tert-butoxy)pyrrolidine-5′,1″-(2″-hydroxymethyl)cyclopentane]-1′-oxyl (1). Keywords: aldonitrone; 1,3-dipolar cycloaddition; pyrrolidine nitroxides; 1-pyrroline-N-oxide
  • -enylmagnesium bromide to the corresponding nitrone, oxidation to alkenylnitrone, intramolecular 1,3-dipolar cycloaddition, and isoxazolidine ring opening. Nitroxide 1 showed both an unexpectedly low reduction rate [6] and long relaxation times t1 and tm at room temperature [4]. Unexpectedly high resistance of
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Published 27 Aug 2019

Attempted synthesis of a meta-metalated calix[4]arene

  • Christopher D. Jurisch and
  • Gareth E. Arnott

Beilstein J. Org. Chem. 2019, 15, 1996–2002, doi:10.3762/bjoc.15.195

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  • Ullmann-type coupling to give aryl azide 2, which readily reacted with phenylacetylene in a copper-catalyzed Huisgen 1,3-dipolar cycloaddition to give 1,2,3-triazole 3 (Scheme 1). The formation of the ruthenacycle was then achieved using Albrecht’s method involving regioselective methylation of triazole 3
  • our case column chromatography was only used once (to purify the monoazidocalix[4]arene 7), whilst the other procedure needed chromatography at each step. Introduction of the triazole moiety onto the upper rim of the calix[4]arene was then achieved with a copper-catalyzed Huisgen 1,3-dipolar
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Published 22 Aug 2019

Application of chiral 2-isoxazoline for the synthesis of syn-1,3-diol analogs

  • Juanjuan Feng,
  • Tianyu Li,
  • Jiaxin Zhang and
  • Peng Jiao

Beilstein J. Org. Chem. 2019, 15, 1840–1847, doi:10.3762/bjoc.15.179

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  • our continuous efforts in asymmetric syntheses and applications of chiral 2-isoxazolines [49][50][51]. Results and Discussion Our synthesis commenced with a chiral 3,5-disubstituted-2-isoxazoline 3 or 4, which were prepared from silyl nitronate through an asymmetric 1,3-dipolar cycloaddition developed
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Published 01 Aug 2019

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

  • Iwona E. Głowacka,
  • Aleksandra Trocha,
  • Andrzej E. Wróblewski and
  • Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

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  • four stereoisomers with low (ca. 3:1) diastereoselectivity and in a non-enantioselective manner (Scheme 46) [21]. Undoubtedly, it was the 1,3-dipolar cycloaddition of the azomethine ylide 180 with an electron-rich alkene. Fortunately, cycloadducts (2R,3R,4S)-, (2S,3S,4R)-, (2R,3S,4R)- and (2S,3R,4S
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Published 23 Jul 2019

Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts

  • Anthony Choi,
  • Rebecca M. Morley and
  • Iain Coldham

Beilstein J. Org. Chem. 2019, 15, 1480–1484, doi:10.3762/bjoc.15.149

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Published 03 Jul 2019

Introduction of an isoxazoline unit to the β-position of porphyrin via regioselective 1,3-dipolar cycloaddition reaction

  • Xiujun Liu,
  • Xiang Ma and
  • Yaqing Feng

Beilstein J. Org. Chem. 2019, 15, 1434–1440, doi:10.3762/bjoc.15.143

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  • Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, China 10.3762/bjoc.15.143 Abstract Isoxazoline-linked porphyrins have been synthesized by a regioselective 1,3-dipolar cycloaddition reaction between vinylporphyrin 2 and nitrile oxides. The steric interaction directed the
  • [15][16][17][18][19][20][21][22][23][24]. Among them, the 1,3-dipolar cycloaddition reaction [25] is an efficient method to fuse five-membered rings on the periphery of the porphyrin framework. Because the periphery double bonds of the porphyrin macrocycle are nice dipolarophiles, and can trap 1,3
  • ], but also have a broad spectrum of interesting bioactivities, e.g., anti-inflammatory [40][41]. In addition, a few porphyrin-based dipoles have been also reported [42]. Recently, a 1,3-dipolar cycloaddition reaction was performed between the vinyl group at methyl pheophorbide A and the in-situ
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Published 28 Jun 2019

Synthesis of non-racemic 4-nitro-2-sulfonylbutan-1-ones via Ni(II)-catalyzed asymmetric Michael reaction of β-ketosulfones

  • Alexander N. Reznikov,
  • Anastasiya E. Sibiryakova,
  • Marat R. Baimuratov,
  • Eugene V. Golovin,
  • Victor B. Rybakov and
  • Yuri N. Klimochkin

Beilstein J. Org. Chem. 2019, 15, 1289–1297, doi:10.3762/bjoc.15.127

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  • cytotoxicity [9]. However, it is of great importance to obtain all stereoisomers for the study of biological activity. Therefore, the development of methods for the asymmetric synthesis of polyfunctional sulfones is valuable. The most notable of them are Ag- and Cu-catalyzed 1,3-dipolar cycloaddition reactions
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Published 12 Jun 2019

Diaminoterephthalate–α-lipoic acid conjugates with fluorinated residues

  • Leon Buschbeck,
  • Aleksandra Markovic,
  • Gunther Wittstock and
  • Jens Christoffers

Beilstein J. Org. Chem. 2019, 15, 981–991, doi:10.3762/bjoc.15.96

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  • example for an application in biochemistry, Figure 1 shows a compound with cyclooctyne and maleimide as functional units. It was used as a "turn-on" fluorescence probe for cross-linking proteins [13]. The highly reactive cyclooctyne residue undergoes 1,3-dipolar cycloadditions with organoazides (copper
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Published 26 Apr 2019

Synthesis and selected transformations of 2-unsubstituted 1-(adamantyloxy)imidazole 3-oxides: straightforward access to non-symmetric 1,3-dialkoxyimidazolium salts

  • Grzegorz Mlostoń,
  • Małgorzata Celeda,
  • Katarzyna Urbaniak,
  • Marcin Jasiński,
  • Vladyslav Bakhonsky,
  • Peter R. Schreiner and
  • Heinz Heimgartner

Beilstein J. Org. Chem. 2019, 15, 497–505, doi:10.3762/bjoc.15.43

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  • -heterocycles, N-oxides 1 cannot be prepared via oxidation of the parent imidazoles by treatment with an oxidizing agent, e.g., with a percarboxylic acid [6]. Imidazole N-oxides are versatile substrates for the preparation of diverse imidazole derivatives and the most characteristic feature is their 1,3-dipolar
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Published 19 Feb 2019

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

  • Andrejs Šišuļins,
  • Jonas Bucevičius,
  • Yu-Ting Tseng,
  • Irina Novosjolova,
  • Kaspars Traskovskis,
  • Ērika Bizdēna,
  • Huan-Tsung Chang,
  • Sigitas Tumkevičius and
  • Māris Turks

Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41

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  • synthesis of a novel library of 9-alkyl-2-amino-6-triazolylpurine derivatives. Thus, copper-catalyzed azide–alkyne 1,3-dipolar cycloaddition reaction of compounds 6a–c with different para-substituted phenylacetylenes produced the expected compounds 7a–f, 8a–f and 9 (Scheme 1). The yields of 1,3-dipolar
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Published 15 Feb 2019

Synthesis of nonracemic hydroxyglutamic acids

  • Dorota G. Piotrowska,
  • Iwona E. Głowacka,
  • Andrzej E. Wróblewski and
  • Liwia Lubowiecka

Beilstein J. Org. Chem. 2019, 15, 236–255, doi:10.3762/bjoc.15.22

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  • diastereoselectivities of 1,3-dipolar cycloadditions which allow to control stereochemistries at C3 and C5 [79][80]. To illustrate this concept the E/Z mixture of nitrone 70 was reacted with acrylamide 71 prepared from (2S)-bornane-10,2-sultam to afford mainly (20:1) the isoxazolidine (3S,5S)-72 easily separable from
  • obtained after cleavage of 84 under basic conditions. From pyroglutamic acid In case of low availability of selected stereoisomers of 4-hydroxyprolines asymmetric syntheses of enantiomeric 4-hydroxypyroglutamates have been elaborated employing 1,3-dipolar cycloadditions of homochiral nitrones and acrylates
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Published 25 Jan 2019

Copper(I)-catalyzed tandem reaction: synthesis of 1,4-disubstituted 1,2,3-triazoles from alkyl diacyl peroxides, azidotrimethylsilane, and alkynes

  • Muhammad Israr,
  • Changqing Ye,
  • Munira Taj Muhammad,
  • Yajun Li and
  • Hongli Bao

Beilstein J. Org. Chem. 2018, 14, 2916–2922, doi:10.3762/bjoc.14.270

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  • ], derived from the Huisgen’s 1,3-dipolar cycloaddition of azides and alkynes [22], has conceivably emerged as the premier example of click chemistry. Generally, organic azides are used as the azido source in most of the CuAAC reactions (Scheme 1a) [23]. However, the organic azides with low molecular weight
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Published 23 Nov 2018

Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis

  • Robby Vroemans,
  • Yenthel Verhaegen,
  • My Tran Thi Dieu and
  • Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 2689–2697, doi:10.3762/bjoc.14.246

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  • .14.246 Abstract A new metal-free one-pot three-component procedure towards fully substituted triazolochromenes has been developed, starting from commercially available materials. Salicylaldehydes and nitroalkenes were reacted under solvent-free conditions, followed by a 1,3-dipolar cycloaddition of the
  • prove the plausibility of the one-pot three-component reaction, we commenced our trials with the synthesis and isolation of 3-nitro-2H-chromene (3) as reported in the literature [15], followed by the 1,3-dipolar cycloaddition of the nitroalkene moiety with organic azides. We based the 1,3-dipolar
  • -nitrochromenes. Because our first step is best performed solvent-free, we opted to try our own optimized solvent-free conditions for the in situ syntheses of 3-nitro-2H-chromenes, followed by the 1,3-dipolar cycloaddition in a reaction vial. Despite being a two-pot procedure, purification of the intermediate 3
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Published 22 Oct 2018

One hundred years of benzotropone chemistry

  • Arif Dastan,
  • Haydar Kilic and
  • Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

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  • tropone unit: In 1975, Franck-Neumann and Martina reported the reaction of dimethyl diazomethane with tropone and benzotropones [83]. This reaction gave benzo-4,5-dimethyl-8,8-cyclooctatrienone (94, 30% isolable yield) as an insertion product via a carbonyl group and pyrazoline 95 as 1,3-dipolar addition
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Published 23 May 2018

An efficient and facile access to highly functionalized pyrrole derivatives

  • Meng Gao,
  • Wenting Zhao,
  • Hongyi Zhao,
  • Ziyun Lin,
  • Dongfeng Zhang and
  • Haihong Huang

Beilstein J. Org. Chem. 2018, 14, 884–890, doi:10.3762/bjoc.14.75

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  • Chinese Academy of Medical Sciences, 1 Xian Nong Tan Street, Beijing 100050, China 10.3762/bjoc.14.75 Abstract A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily
  • substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could deliver more active compounds for medicinal chemistry research. Keywords: azomethine ylides; 1,3-dipolar cycloaddition; one-pot synthesis; polysubstituted pyrroles; pyrrolo[3,4-c]pyrrole-1,3-diones
  • methods have been reported till now to synthesize pyrroles and pyrrole containing analogs [6]. In the past decade, 1,3-dipolar cycloaddition has become a fundamental synthetic method for the construction of nitrogen-containing five-membered heterocycles including pyrroles. It is worth to note that
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Published 20 Apr 2018

Syn-selective silicon Mukaiyama-type aldol reactions of (pentafluoro-λ6-sulfanyl)acetic acid esters with aldehydes

  • Anna-Lena Dreier,
  • Andrej V. Matsnev,
  • Joseph S. Thrasher and
  • Günter Haufe

Beilstein J. Org. Chem. 2018, 14, 373–380, doi:10.3762/bjoc.14.25

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  • [22]. There are not many transformations of aliphatic SF5 compounds described in the literature. Among them are the preparation and derivatization of SF5-aldehydes [23], Diels–Alder reactions [24][25][26], the “click reaction” of SF5-acetylenes with azides to form triazoles [27], and 1,3-dipolar
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Published 08 Feb 2018

Recent applications of click chemistry for the functionalization of gold nanoparticles and their conversion to glyco-gold nanoparticles

  • Vivek Poonthiyil,
  • Thisbe K. Lindhorst,
  • Vladimir B. Golovko and
  • Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 11–24, doi:10.3762/bjoc.14.2

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  • azide–alkyne Huisgen cycloaddition AuNP surface modification using NCAAC The azide–alkyne Huisgen cycloaddition (AAC) is a 1,3-dipolar cycloaddition between an organic azide and an alkyne that gives triazole products [37][38]. The non-catalysed azide–alkyne Huisgen cycloaddition (NCAAC) is very slow
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Published 03 Jan 2018

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

  • Myriam Drouin and
  • Jean-François Paquin

Beilstein J. Org. Chem. 2017, 13, 2637–2658, doi:10.3762/bjoc.13.262

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  • reacted easily in a SN2 reaction to give a more functionalized molecule. For example, treatment of the chlorinated monofluoroalkene with NaN3 provided the corresponding N3-containing monofluoroalkene. The azide group underwent a 1,3-dipolar cycloaddition to give a 1,2,3-triazole, which is also a peptide
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Published 12 Dec 2017

Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters: A new entry for the synthesis of multisubstituted thiophenes

  • Jury J. Medvedev,
  • Ilya V. Efimov,
  • Yuri M. Shafran,
  • Vitaliy V. Suslonov,
  • Vasiliy A. Bakulev and
  • Valerij A. Nikolaev

Beilstein J. Org. Chem. 2017, 13, 2569–2576, doi:10.3762/bjoc.13.253

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  • reaction with N-phenyl maleimide, gives rise to formation of S-containing heterocycles by 1,3-dipolar cycloaddition [35]. However, to the best of our knowledge, there are no literature data on analogous intramolecular reactions of C=S ylides involving thiocarbonyl and any other nucleophilic group within
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Published 30 Nov 2017

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

  • Elisandra Scapin,
  • Paulo R. S. Salbego,
  • Caroline R. Bender,
  • Alexandre R. Meyer,
  • Anderson B. Pagliari,
  • Tainára Orlando,
  • Geórgia C. Zimmer,
  • Clarissa P. Frizzo,
  • Helio G. Bonacorso,
  • Nilo Zanatta and
  • Marcos A. P. Martins

Beilstein J. Org. Chem. 2017, 13, 2396–2407, doi:10.3762/bjoc.13.237

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  • reactions were planned between phenylacetylene and compounds 6a–c. The 1,2,3-triazole synthesis from the 1,3-dipolar cycloaddition reaction between 6a–c and terminal alkynes catalyzed by copper salts (CuAAC) [41][42][43] confirms that the reaction passes through an azide intermediate. In addition to mild
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Published 10 Nov 2017
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