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

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

• 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

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

• 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

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

• 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

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

• ], 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

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

• .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

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

• 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

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

• 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

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

• 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

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

• 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

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

• 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

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• methine C-3 protons displayed in a 1H,1H-NOESY spectrum of 4 (Figure S10 in Supporting Information File 1). Compound 4 was then submitted to Cu(I)-catalyzed 1,3-dipolar cycloaddition with selected halogen-substituted and non-substituted aromatic azides to yield target N-heterocyclic hybrids 5–8 containing

Mechanochemical synthesis of small organic molecules

• Tapas Kumar Achar,
• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

• -Triazoles have important applications in pharmaceutical chemistry [150] and traditionally they are prepared by 1,3-dipolar cycloaddition reactions at high temperature, long reaction times and produce low yield with multiple products [151]. In 2013, Ranu and co-workers reported mechanochemical synthesis of

Synthesis of oligonucleotides on a soluble support

• Harri Lönnberg

Beilstein J. Org. Chem. 2017, 13, 1368–1387, doi:10.3762/bjoc.13.134

• support (Scheme 3) [42]. Owing to the symmetrical structure of the support, NMR and mass spectroscopic characterization is possible at any stage of the chain assembly. The 3´-terminal nucleoside was immobilized to this support as a 3´-O-(4-pentynoyl) derivative by Cu(I)-catalyzed 1,3-dipolar cycloaddition

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

• Ludmila Škorpilová,
• Silvie Rimpelová,
• Michal Jurášek,
• Miloš Buděšínský,
• Jana Lokajová,
• Roman Effenberg,
• Petr Slepička,
• Tomáš Ruml,
• Eva Kmoníčková,
• Pavel B. Drašar and
• Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

• compound is shown in Scheme 1, part B. Propargyl-ChL [35] was introduced into Huisgen copper-catalyzed 1,3-dipolar cycloaddition [36] (CuAAC) with BODIPY 3. This microwave-assisted reaction catalyzed by CuSO4·5H2O, sodium ascorbate and a catalytic amount of TBTA (tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl

An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks

• Sushil K. Maurya and
• Rohit Rana

Beilstein J. Org. Chem. 2017, 13, 1106–1118, doi:10.3762/bjoc.13.110

• blocks were coupled via 1,3-dipolar cycloaddition (click reaction) iteratively through the development of a greener base-free Cu(I)-catalyzed azide–alkyne cycloaddition reaction. The cycloadducts were then converted to macrocycles by Ru-catalyzed cyclization reaction using greener and non-hazards

New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines

• Aleksey Yu. Vorob’ev,
• Vyacheslav I. Supranovich,
• Gennady I. Borodkin and
• Vyacheslav G. Shubin

Beilstein J. Org. Chem. 2017, 13, 800–805, doi:10.3762/bjoc.13.80

• and a high degree of deuterium incorporation were achieved. The procedure was applied for several 4-R-1-aminopyridinium cations (R = H, Me, OMe). Keywords: deuteration; 1,3-dipolar cycloaddition; pyrazolo[1,5-a]pyridine; 1,2,4-triazolo[1,5-a]pyridine; Introduction Isotopically labeled compounds find

Synthesis of ribavirin 2’-Me-C-nucleoside analogues

• Fanny Cosson,
• Aline Faroux,
• Jean-Pierre Baltaze,
• Jonathan Farjon,
• Régis Guillot,
• Jacques Uziel and
• Nadège Lubin-Germain

Beilstein J. Org. Chem. 2017, 13, 755–761, doi:10.3762/bjoc.13.74

• as for the non-methylated derivative [21]. Then, the 1,3-dipolar cycloaddition reaction of 6 with benzyl azide in toluene at 70 °C led to a mixture of regioisomeric triazoles 7 in a 42:58 ratio. The removal of all protecting groups was achieved by treatment of compounds 7 with ammonia followed by

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

• most attractive way for their preparation is the thermal 1,3-dipolar cycloaddition of alkynes and azides, introduced by Huisgen which usually gives rise to a mixture of 1,4 and 1,5-isomers [16][17][18][19]. More recently, transition metal catalysts based on copper, ruthenium, silver and iridium salts

Isoxazole derivatives as new nitric oxide elicitors in plants

• Anca Oancea,
• Emilian Georgescu,
• Florentina Georgescu,
• Alina Nicolescu,
• Elena Iulia Oprita,
• Catalina Tudora,
• Lucian Vladulescu,
• Marius-Constantin Vladulescu,
• Florin Oancea and
• Calin Deleanu

Beilstein J. Org. Chem. 2017, 13, 659–664, doi:10.3762/bjoc.13.65

• were obtained in good yields by regiospecific 1,3-dipolar cycloaddition reactions between aromatic nitrile oxides, generated in situ from the corresponding hydroxyimidoyl chlorides, with non-symmetrical activated alkynes in the presence of catalytic amounts of copper(I) iodide. Effects of 3,5

• -disubstituted isoxazoles on nitric oxide and reactive oxygen species generation in Arabidopsis tissues was studied using specific diaminofluoresceine dyes as fluorescence indicators. Keywords: chemical elicitor; 1,3-dipolar cycloaddition; isoxazole; nitric oxide; nitrile oxide; reactive oxygen species

• synthetic approaches towards the isoxazole core include the reactions of hydroxylamine with aryl-β-diketones [20], α,β-unsaturated carbonyl compounds [21], or α,β-unsaturated nitriles [22], and 1,3-dipolar cycloaddition reactions between alkenes or alkynes and nitrile oxides [23][24][25]. Nitrile oxides are

A postsynthetically 2’-“clickable” uridine with arabino configuration and its application for fluorescent labeling and imaging of DNA

• Heidi-Kristin Walter,
• Bettina Olshausen,
• Ute Schepers and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2017, 13, 127–137, doi:10.3762/bjoc.13.16

• cells. Keywords: dyes; fluorescence; nucleic acid; oligonucleotide; Introduction The “click”-type reactions [1], in particular the 1,3-dipolar cycloaddition between alkynes and azides (CuAAC) is a broadly applied strategy for postsynthetic oligonucleotide modification since both reactive groups are

Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction

• Manjunatha Narayanarao,
• Lokesh Koodlur,
• Vijayakumar G. Revanasiddappa,
• Subramanya Gopal and
• Susmita Kamila

Beilstein J. Org. Chem. 2016, 12, 2893–2897, doi:10.3762/bjoc.12.288

• -pot multicomponent synthesis. The method uses the 1,3-dipolar cycloaddition reaction between N-alkylvinylindole/indazole and azomethine ylides, prepared in situ from cyclic/acyclic amino acids. The 1,3-dipolar cycloaddition proceeds efficiently under thermal conditions to afford the regio- and

• of biological importance [1][2]. The regio- and stereoselective construction of spiro compounds by utilizing the 1,3-dipolar cycloaddition reaction of azomethine ylides has been reported [3][4][5][6]. However, unlike the previous reports, the present method is concise and facilitates the one-pot

• synthesis of multifunctionalized spiranes. The earlier works reveal the use of different reaction conditions to prepare functionalized spiroindane, spiropyrolidine, spiropyrrolizidine and spirooxindole derivatives. Among them, the 1,3-dipolar cycloaddition based route is preferred due to multiple advantages

Synthesis of spiro[isoindole-1,5’-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction

• Salvatore V. Giofrè,
• Santa Cirmi,
• Raffaella Mancuso,
• Francesco Nicolò,
• Giuseppe Lanza,
• Laura Legnani,
• Agata Campisi,
• Maria A. Chiacchio,
• Michele Navarra,
• Bartolo Gabriele and
• Roberto Romeo

Beilstein J. Org. Chem. 2016, 12, 2793–2807, doi:10.3762/bjoc.12.278

• Farmaco, Università di Catania, Viale A. Doria, 95100 Catania, Italy Dipartimento di Chimica, Università di Pavia, Via Taramelli 12, 27100 Pavia, Italy 10.3762/bjoc.12.278 Abstract A series of spiro[isoindole-1,5-isoxazolidin]-3(2H)-ones has been synthesized by 1,3-dipolar cycloaddition of N

• be linked to the inhibition of the protein–protein p53-MDM2 interaction. Docking measurements support the biological data. Keywords: antitumor agents; DFT studies; 1,3-dipolar cycloaddition; docking studies; spiro-compounds; Introduction The p53 tumor suppressor protein is a transcriptional factor

• construction of the spiro[isoxazolidin-isoindolinone] system. The synthetic scheme (Figure 2) exploits the strategy of the 1,3-dipolar cycloaddition of nitrones on the substrate isoindolin-3-methylene-1-one 2, obtained by a recent methodology of a PdI2 catalyzed aminocarbonylation-N-heterocyclization of 2

A versatile route to polythiophenes with functional pendant groups using alkyne chemistry

• Xiao Huang,
• Li Yang,
• Rikard Emanuelsson,
• Jonas Bergquist,
• Maria Strømme,
• Martin Sjödin and
• Adolf Gogoll

Beilstein J. Org. Chem. 2016, 12, 2682–2688, doi:10.3762/bjoc.12.265

• Huisgen 1,3-dipolar cycloaddition between N-(2-azidoethyl)phthalimide and the alkyne terminal of pyEDOT under ultrasound conditions in 73% yield. Detailed synthetic routes are presented in Supporting Information File 1. Figure 1a shows the cyclic voltammograms (CVs) for electrochemical polymerization of

Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

• Florin Albota,
• Mino R. Caira,
• Constantin Draghici,
• Florea Dumitrascu and
• Denisa E. Dumitrescu

Beilstein J. Org. Chem. 2016, 12, 2503–2510, doi:10.3762/bjoc.12.245

• other metals and represent a versatile tool for obtaining hybrid heterocycles with properties that are useful for the development of new advanced materials and for medicinal purposes [1][2][3][4]. Recently, we obtained, by 1,3-dipolar cycloaddition reactions of sydnone-ylides as bis(1,3-dipoles) with

• interesting chemical reactions of sydnones are their electrophilic substitution at C-4 and their participation in 1,3-dipolar cycloaddition reactions with olefinic and acetylenic dipolarophiles to form pyrazoles and functional transformation at C-4 [20][21][22][23][24][25][26]. Herein we present the synthesis

• of indolizines 4 (Figure 1) with the indolizine directly attached to C-4 of a sydnone ring by the indolizine Chichibabin approach. In addition, the new indolizine structures 5, connected through a keto group to a sydnone ring, were prepared by 1,3-dipolar cycloaddition reaction starting from the same