Academic literature on the topic '3-dipolar cycloaddition reaction'

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Journal articles on the topic "3-dipolar cycloaddition reaction"

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Zhan, Desheng, Gang Yang, Tieli Zhou, Sashirekha Nallapati, and Xiaofeng Zhang. "Decarboxylation-Driven Double Annulations: Innovative Multi-Component Reaction Pathways." Molecules 30, no. 7 (2025): 1594. https://doi.org/10.3390/molecules30071594.

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A concerted five-component reaction strategy has been developed, featuring double [3+2] cycloadditions utilizing aspartic acid. This approach provides valuable insights into mechanistic pathways, allowing for the distinction between concerted and stepwise processes based on reaction efficiency and diastereoselectivity. Both aspartic and glutamic acids have been employed for a thorough evaluation and exploration of decarboxylation-driven double annulations. This method effectively constructs pyrrolizidine frameworks through a concerted double 1,3-dipolar cycloaddition with aspartic acid, as wel
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Nallamala, Sirisha, Srikumar Mannem, and Raghunathan Raghavachary. "Highly Efficient Construction of Sugar-Fused Spirochromanono Pyrrolidines/Pyrrolizidines/Thiolizidines via 1,3-Dipolar Cycloaddition of Azomethine Ylides." SynOpen 01, no. 01 (2017): 0063–67. http://dx.doi.org/10.1055/s-0036-1588520.

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A variety of sugar-fused chromanono pyrrolidines/pyrrolizidines/thiolizidines have been synthesized by intermolecular 1,3-dipolar cycloaddition reaction of azomethine ylides (generated from glucose aldehyde and different secondary amino acids) with various 3-arylidene chroman-4-ones as dipolarophiles. The solvent effect on the 1,3-dipolar cycloaddition reaction is also studied.
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WANG, JING-FANG, DONG-QING WEI, CHUN-FANG WANG, et al. "A THEORETICAL STUDY ON THE MECHANISM OF 2:1 1, 3 DIPOLAR CYCLOADDITION REACTIONS." Journal of Theoretical and Computational Chemistry 06, no. 04 (2007): 861–67. http://dx.doi.org/10.1142/s0219633607003489.

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The reactions between nitrile oxides and alkenes are of considerable interest in organic synthesis as the resulting heterocycles are versatile intermediates for the synthesis of natural products and biologically active compounds. In this paper, we design a series of reactions of phosphonyl nitrile oxides with acrylonnitrile, which can give 2:1 cycloaddition products with no crystal structure released so far, and present a detailed theoretical study on the mechanism of the 2:1 1, 3-dipolar cycloaddition reaction, which has been explored with density functional theory calculations at B3LYP/6-31G
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Ogurtsov, Vladimir A., and Oleg A. Rakitin. "New Cycloadditon Reaction of 2-Chloroprop-2-enethioamides with Dialkyl Acetylenedicarboxylates: Synthesis of Dialkyl 2-[4,5-Bis(alkoxycarbonyl)-2-(aryl{alkyl}imino)-3(2H)-thienylidene]-1,3-dithiole-4,5-dicarboxylates." Molecules 27, no. 20 (2022): 6887. http://dx.doi.org/10.3390/molecules27206887.

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The 1,3-dipolar cycloaddition of 1,2-dithiole-3-thiones with alkynes to form 1,3-dithioles is one of the most studied reactions in this class of polysulfur-containing heterocycles. Nucleophilic substitution of chlorine atoms in dimethyl 2-(1,2-dichloro-2-thioxoethylidene)-1,3-dithiole-4,5-dicarboxylate, which was obtained by addition one molecules of DMAD to 4,5-dichloro-3H-1,2-dithiole-3-thione, led to a series of 2-chloro-2-(1,3-dithiol-2-ylidene)ethanethioamides. Cycloaddition reaction of 2-chloro-2-(1,3-dithiol-2-ylidene)ethanethioamides with activated alkynes led to the unexpected formati
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Nallamala, Sirisha, and Raghavachary Raghunathan. "Efficient Synthesis of Dispiropyrrolidines Linked to Sugars." International Journal of Carbohydrate Chemistry 2013 (November 10, 2013): 1–7. http://dx.doi.org/10.1155/2013/340546.

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An expedient method for the synthesis of glyco-dispiropyrrolidines is reported through 1,3-dipolar cycloaddition reaction (1,3 DC reaction). The novel glycosyl dipolarophiles derived from D-glucose underwent neat [3+2] cycloaddition reaction with the azomethine ylides generated from 1,2-diketones and sarcosine to give the corresponding glycosidic heterocycles in good yields.
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Antoci, Vasilichia, Costel Moldoveanu, Ramona Danac, Violeta Mangalagiu, and Gheorghita Zbancioc. "Huisgen [3 + 2] Dipolar Cycloadditions of Phthalazinium Ylides to Activated Symmetric and Non-Symmetric Alkynes." Molecules 25, no. 19 (2020): 4416. http://dx.doi.org/10.3390/molecules25194416.

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We present herein a straightforward and efficient pathway for the synthesis of pyrrolophthalazine cycloadducts via Huisgen [3 + 2] dipolar cycloaddition reactions of phthalazinium ylides to methyl propiolate or dimethyl acetylenedicarboxylate (DMAD). A thoroughly comparative study concerning the efficiency of synthesis, conventional thermal heating (TH) versus microwave (MW) and ultrasound (US) irradiation, has been performed. The cycloaddition reactions of phthalazinium ylides to methyl propiolate occur regiospecific, with a single regioisomer being obtained. Under conventional TH, the cycloa
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Nakamura, Masaharu, Motoki Toganoh, Xio Qun Wang, Shigeru Yamago, and Eiichi Nakamura. "Intramolecular [3 + 2]Cycloaddition Reaction of Dipolar Trimethylenemethane." Chemistry Letters 29, no. 6 (2000): 664–65. http://dx.doi.org/10.1246/cl.2000.664.

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Vale, Luís S. H. P., Joana F. B. Barata, Carla I. M. Santos, et al. "Corroles in 1,3-dipolar cycloaddition reactions." Journal of Porphyrins and Phthalocyanines 13, no. 03 (2009): 358–68. http://dx.doi.org/10.1142/s1088424609000371.

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The azomethine ylide generated from the reaction of a corrole-3-carbaldehyde and N-methylglycine was trapped with dimethyl fumarate, dimethyl acetylenedicarboxylate and fullerene C60 in 1,3-dipolar cycloadditions. A similar azomethine ylide generated from a corrole-2-carbaldehyde was trapped with 1,4-naphthoquinone, yielding the expected dehydrogenated 1,3-dipolar cycloadduct and a quinone-fused corrole derivative. A detailed synchrotron single-crystal X-ray diffraction analysis of the gallium(III)(pyridine) complex of 5,10,15-tris(pentafluorophenyl)corrole-3-carbaldehyde is also presented.
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Salem, Mohammed A., Moustafa A. Gouda, and Ghada G. El-Bana. "Chemistry of 2-(Piperazin-1-yl) Quinoline-3-Carbaldehydes." Mini-Reviews in Organic Chemistry 19, no. 4 (2022): 480–95. http://dx.doi.org/10.2174/1570193x18666211001124510.

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Abstract: This review described the preparation of 2- chloroquinoline-3-carbaldehyde derivatives 18 through Vilsmeier-Haack formylation of N-arylacetamides and the use of them as a key intermediate for the preparation of 2-(piperazin-1-yl) quinoline-3-carbaldehydes. The synthesis of the 2- (piperazin-1-yl) quinolines derivatives was explained through the following chemical reactions: acylation, sulfonylation, Claisen-Schmidt condensation, 1, 3-dipolar cycloaddition, one-pot multicomponent reactions (MCRs), reductive amination, Grignard reaction and Kabachnik-Field’s reaction.
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Deng, Yongming, Qing-Qing Cheng, and Michael Doyle. "Asymmetric [3+3] Cycloaddition for Heterocycle Synthesis." Synlett 28, no. 14 (2017): 1695–706. http://dx.doi.org/10.1055/s-0036-1588453.

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Asymmetric syntheses of six-membered ring heterocycles are important research targets not only in synthetic organic chemistry but also in pharmaceuticals. The [3+3]-cycloaddition methodology is a complementary strategy to [4+2] cycloaddition for the synthesis of heterocyclic compounds. Recent progress in [3+3]-cycloaddition processes provide powerful asymmetric methodologies for the construction of six-membered ring heterocycles with one to three heteroatoms in the ring. In this account, synthetic efforts during the past five years toward the synthesis of enantioenriched six-membered ring hete
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Dissertations / Theses on the topic "3-dipolar cycloaddition reaction"

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Kafley, Saurav. "Synthesis and 1, 3 -dipolar cycloaddition reaction of N-phenyl £ chlora nitrone." Thesis, University of North Bengal, 2010. http://hdl.handle.net/123456789/1419.

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Schmitt, Gérard. "Réactions de l'hydrofluoroborate d'un composé de Reissert sur divers alcenes : Compétition entre cycloaddition dipolaire-1,3 et cycloaddition de Diels-Alder." Besançon, 1987. http://www.theses.fr/1987BESA2041.

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Chakraborty, Bhaskar. "Studies of 1, 3 Dipolar cycloaddition reactions with N- cyclohexyl Nitrones." Thesis, University of North Bengal, 1995. http://hdl.handle.net/123456789/768.

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Sultan, Nisrine. "Preparations selectives de derives du 7-oxanorborna-2,5-diene : utilisation comme formes masquées de composés acetyleniques." Thesis, Paris 11, 2011. http://www.theses.fr/2011PA112132.

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En vue d’effectuer des préparations sélectives de composés hétérocycliques, une étude de la synthèse et de la réactivité de 7-oxanorborna-2,5-diènes portant des groupes électroattracteurs différents sur les positions 2 et 3 a été réalisée. Ces composés sont des formes masquées de composés acétyléniques dissymétriques.Dans un premier temps, nous avons optimisé une nouvelle méthode de synthèse sélective d’acétylènedicarboxylates dissymétriques par mono-transestérification d’acétylènedicarboxylates de dialkyle symétriques avec des alcools en présence de la lipase de Candida rugosa. Cette méthode
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Toh, Ophilia Ndi. "Synthesis Towards Fulminic Acid and Its Derivatives in 1, 3-Dipolar Cycloaddition Reactions." Digital Commons @ East Tennessee State University, 2008. https://dc.etsu.edu/etd/1982.

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A new approach to fulminic acid cycloadditions has been developed. At reduced temperatures, fulminic acid is generated in situ and undergoes 1, 3-diploar cycloaddition reactions with dipolarophiles to form isoxazolines and/or its dimers. This procedure represents a novel, safe general method for the one-step generation of fulminic acid, which complements existing potentially explosive protocols.
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Bala, Kason. "1, 3-dipolar cycloaddition reactions in aqueous media and investigations into solid phase ether synthesis." Thesis, University College London (University of London), 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.397163.

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Rai, Neelam. "Greener synthesis and 1, 3-dipolar cycloaddition reactions of a amino nitrones and studies of biological activities of the cycloadducts." Thesis, University of North Bengal, 2017. http://ir.nbu.ac.in/handle/123456789/2663.

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Richter, Sebastian. "Neue binäre CN-Verbindungen sowie Vorläufersubstanzen von monomerem C3N4." Doctoral thesis, Universitätsbibliothek Chemnitz, 2014. http://nbn-resolving.de/urn:nbn:de:bsz:ch1-qucosa-155547.

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Gegenstand dieser Arbeit sind Versuche zur Synthese neuer binärer Kohlenstoffnitride im Allgemeinen und von C3N4-Vorläuferverbindungen im Speziellen. Hierbei werden v. a. die Herstellung und die Eigenschaften organischer Polyazide beschrieben, die aufgrund ihrer Gefährlichkeit durch zahlreiche Folgereaktionen in weniger brisante Moleküle überführt werden mussten. Als Derivatisierungsreaktionen kamen hierbei beispielsweise die 1,3-dipolare Cycloaddition mit Norbornen und Cyclooctin, die STAUDINGER-Reaktion mit verschiedenen Phosphinen sowie die Aza-WITTIG-Reaktion zum Einsatz. Es konnten dabei
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Yalcinkaya, Hatice. "Studies On The Reaction Of Acyl Phosphonates With Aldehydes In The Presence Of Proline." Master's thesis, METU, 2009. http://etd.lib.metu.edu.tr/upload/3/12610359/index.pdf.

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Acyl phosphonates are interesting precursors for the synthesis of biologically active compounds. In the first part, the acyl phosphonates are synthesized starting from the corresponding acyl chloride. The acyl chlorides are converted into acyl phosphonates by using trialkylphosphites. The reaction of acyl phosphonates with aldehydes in the presence of proline furnished not the suggested aldol products via proline catalyzed aldol reaction but bicyclic products via one pot tricomponent 1,3-dipolar cycloaddition reaction. The formation of the bicyclic compound was suggested as followed<br>The
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Berndt, Christian. "Bildungstendenz und Reaktionen von α-Azidoalkoholen". Doctoral thesis, Universitätsbibliothek Chemnitz, 2013. http://nbn-resolving.de/urn:nbn:de:bsz:ch1-qucosa-112553.

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Gegenstand der vorliegenden Arbeit ist die Synthese von α-Azidoalkoholen durch die Reaktion von aliphatischen sowie aromatischen Aldehyden mit Stickstoffwasserstoffsäure. Dabei stellt sich ein Gleichgewicht ein, dessen Lage durch die Ermittlung der Gleichgewichtskonstanten quantitativ bestimmt wird. In jedem Fall besteht die Möglichkeit, den α-Azidoalkohol in der Gleichgewichtsmischung zu charakterisieren und teilweise gelingt die Isolierung der reinen α-Azidoalkohole bei tiefen Temperaturen sowie deren Charakterisierung mittels Tieftemperatur-NMR-Spektroskopie. Die Ausgangsaldehyde für die Sy
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Book chapters on the topic "3-dipolar cycloaddition reaction"

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Hein, Jason E. "[3+2]-Dipolar Cycloadditions in Bioconjugation." In Chemoselective and Bioorthogonal Ligation Reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527683451.ch2.

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Bartnik, Romuald. "Azomethine, carbonyl and thiocarbonyl ylides." In Nitrogen, Oxygen and Sulfur Ylide Chemistry. Oxford University PressOxford, 2002. http://dx.doi.org/10.1093/oso/9780198500179.003.0003.

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Abstract Simple addition of a carbene or carbenoid to a C-N double bond would be expected to result in the formation of an azomethine ylide. This is consistent with electrophilic attack of the carbene at the nitrogen atom lone pair. Formation of ylides in this manner was reviewed by Padwa and Hornbuckle in 1991. The reaction of carbenes with simple imines (Schiff bases) to form azomethine ylides, which then undergo 1,3-dipolar cycloaddition with a second molecule of imine, was first reported in 1972. Bartnik and Mloston subsequently extended this method by using various dipolarophiles. Catalyt
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"Pericyclic Reactions." In Reactivity and Mechanism in Organic Chemistry. The Royal Society of Chemistry, 2022. http://dx.doi.org/10.1039/9781837670970-00101.

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Chapter 3 is dedicated to pericyclic reactions and selected rearrangement reactions, and to reactions involving transient intermediates, such as radicals, diradicals or carbocations. The class of electrocyclic ring-opening reactions is first used to illustrate the application of FMO theory arguments and the classification of reactions as orbital symmetry allowed or forbidden. After a short section on biradical intermediates in cyclization reactions of enediynes and eneyne-allenes, we next analyze cycloaddition reactions with the goal of classifying reactions as concerted or stepwise, as synchr
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Taber, Douglass F. "Alkaloid Synthesis: (+)-Deoxoprosopinine (Krishna), Alkaloid (–)-205B (Micalizio), FR901483 (Huang), (+)-Ibophyllidine (Kwon), (–)-Lycoposerramine-S (Fukuyama), (±)-Crinine (Lautens)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0060.

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Palakodety Radha Krishna of the Indian Institute of Chemical Technology observed (Synlett 2012, 2814) high stereocontrol in the addition of allyltrimethylsilane to the cyclic imine derived from 1. The product piperidine 2 was carried onto (+)-deoxoprosopinine 3. Glenn C. Micalizio of Scripps Florida condensed (J. Am. Chem. Soc. 2012, 134, 15237) the amine 4 with 5. The ensuing intramolecular dipolar cycloaddition led to 6, which was carried onto the Dendrobates alkaloid (–)-205B 7. Pei-Qiang Huang of Xiamen University showed (Org. Lett. 2012, 14, 4834) that the quaternary center of 9 could be
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Taber, Douglass. "Stereocontrolled Carbocyclic Construction: (-)-Mintlactone (Bates), (-)-Gleenol (Kobayashi), (-)-Vibralactone C (Snider)." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0081.

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Nigel S. Simpkins, now at the University of Birmingham, found (Chem. Commun. 2008, 5390) that the prochiral cyclopropane amide 1 could be deprotonated to give, after alkylation, the substituted cyclopropane 3 with high enanantio- and diastereocontrol. In the course of a synthesis of (+)-Lineatin, Ramon Alibés of the Universitat Autònoma de Barcelona optimized (J. Org. Chem. 2008, 73, 5944) the photochemical cycloaddition of 4 and 5 to give, after reductive dechlorination, the cyclobutene 6. In a related reaction, José L. García Ruano and M. Rosario Martín of the Universidad Autónoma de Madrid
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Wolkenberg, S. E., and R. M. Garbaccio. "[3+2]-Dipolar Cycloaddition Reactions." In Three Carbon-Heteroatom Bonds: Acid Halides; Carboxylic Acids and Acid Salts. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-020-00439.

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"3. 1,3-Dipolar cycloaddition reactions." In High Pressure Organic Synthesis. De Gruyter, 2019. http://dx.doi.org/10.1515/9783110556841-003.

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Taber, Douglass F. "C–O Ring Construction: (+)-Varitriol (Liu), (+)-Isatisine A (Panek), (+)-Herboxidiene/GEX1A (Ghosh), (–)-Englerin A (Chain), Platensimycin (Lear/Wright)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0050.

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En route to (+)-varitriol 4, Xue-Wei Liu of Nanyang Technological University coupled (Org. Lett. 2011, 13, 42) the glycosyl fluoride derived from 1 with the alkynyl fluoroborate salt 2 to give 3. James S. Panek of Boston University condensed (Org. Lett. 2011, 13, 502) the enantiomerically pure allyl silane 6 with the aldehyde 5 to give the tetrahydrofuran 7. Further elaboration led to (+)-isatisine A 8, the only alkaloid so far isolated from the roots and leaves of the traditional Asian folk medicine Isatis indigotica. Arun K. Ghosh of Purdue University effected (Org. Lett. 2011, 13, 66) oxida
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Taber, Douglass F. "The Lee Synthesis of (−)-Crinipellin A." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0098.

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The crinipellins are the only tetraquinane natural products. The enone crinipellins, including crinipellin A 3, have anticancer activity. Hee-Yoon Lee of the Korea Advanced Institute of Science and Technology (KAIST) envisioned (J. Am. Chem. Soc. 2014, 136, 10274) the assembly of 2 and thus 3 by the intramolecular dipolar cycloaddition of the diazoalkane derived from the tosylhydrazone 1. The initial cyclopentene was prepared from commercial 4 following the Williams procedure. Conjugate addition of the Grignard reagent 5 in the presence of TMS-Cl led to the silyl enol ether 6. Regeneration of
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Conference papers on the topic "3-dipolar cycloaddition reaction"

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Diaconu, Dumitrela, Violeta Mangalagiu, Dorina Amariucai-Mantu, Vasilichia Antoci, Ramona Danac, and Ionel Mangalagiu. "1,3-dipolar cycloaddition reactions of benzimidazolium-ylides to an activated symmetric alkyne." In Scientific seminar with international participation "New frontiers in natural product chemistry". Institute of Chemistry, Republic of Moldova, 2023. http://dx.doi.org/10.19261/nfnpc.2023.ab27.

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The cycloaddition reactions represent an important way to obtain cyclic structures and take place between two or more reactants containing double or triple bonds in the molecule. After Huisgen, the addition of 1,3-dipole to a dipolarophile, takes place through a concerted mechanism, when two  bonds are formed. [1,2] The purpose of this research is to study the Huisgen [3+2] dipolar cycloaddition reactions carried out in a conventional way (stirring at room temperature) and non-conventional way (ultrasonic irradiation), between benzimidazolium-ylides and an activated symmetric substituted alky
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Zbancioc, Gheorghita, Costel Moldoveanu, and Ionel I. Mangalagiu. "Syntheses of new benzoquinoline derivatives with anticancer activity." In Conferința științifică națională cu participare internațională "Integrare prin cercetare și inovare", dedicată Zilei Internaționale a Științei pentru Pace și Dezvoltare. Moldova State University, 2025. https://doi.org/10.59295/spd2024n.92.

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This work synthesized various novel benzo[c]quinoline compounds, detailed their structural features, and examined their anticancer activity in vitro. First, the nitrogen atom in benzo[c]quinoline is quaternized, and the in situ-formed ylide is then subjected to a [3+2] dipolar cycloaddition reaction. A detailed investigation was conducted to determine how successful traditional thermal heating (TH) synthesis was in comparison to microwave (MW) and ultrasonic (US) irradiation. FTIR, HRMS, and NMR were the three spectral techniques that were used to prove the structure of all the obtained compou
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