Relevant bibliographies by topics / Propargylic amine

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  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters
  4. Conference papers

Academic literature on the topic 'Propargylic amine'

Author: Grafiati
Published: 4 June 2021
Last updated: 16 February 2022

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Journal articles on the topic "Propargylic amine"

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Huang, Jian, Han-Han Kong, Si-Jia Li, Rui-Jin Zhang, Hao-Dong Qian, Dan-Ran Li, Jin-Yu He, Yi-Nuo Zheng, and Hao Xu. "Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts." Chemical Communications 57, no. 38 (2021): 4674–77. http://dx.doi.org/10.1039/d1cc00663k.

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Fu, Rugang, and Zheng Li. "N-Propargylation of secondary amines directly using calcium carbide as an acetylene source." Journal of Chemical Research 41, no. 6 (June 2017): 341–45. http://dx.doi.org/10.3184/174751917x14949427622099.

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A one-pot N-propargylation of secondary amines has been achieved by heating the amine with formaldehyde and calcium carbide in DMSO in the presence of CuCl as a catalyst. Fifteen examples of propargylic tertiary amines, 12 of which are novel, were efficiently prepared in yields of 65–84%. The advantages of the method are broad substrate scope and a simple work-up procedure.
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He, Shiyu, Xufei Yan, Yanxi Lei, Haifeng Xiang, and Xiangge Zhou. "Rhodium-catalyzed annulative coupling of N-aryl-2-aminopyridine and propargylic amine via selective C–C and C–H bond activation." Chemical Communications 56, no. 15 (2020): 2284–87. http://dx.doi.org/10.1039/c9cc09777e.

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Yuan, Ruming, Shuhua Xu, and Gang Fu. "Mechanisms of CO2 Incorporation into Propargylic Amine Catalyzed by Ag(I)/Amine Catalysts." Journal of Organic Chemistry 83, no. 19 (September 6, 2018): 11896–904. http://dx.doi.org/10.1021/acs.joc.8b01767.

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Yu, Dingyi, and Yugen Zhang. "Copper-Catalyzed Three-Component Coupling of Terminal Alkyne, Dihalomethane and Amine to Propargylic Amines." Advanced Synthesis & Catalysis 353, no. 1 (January 10, 2011): 163–69. http://dx.doi.org/10.1002/adsc.201000691.

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Takeuchi, Ryo, and Ikuo Ebata. "Cationic Rhodium Complex Catalyzed Highly Selective Hydrosilylation of Propargylic Amine Derivatives." Organometallics 16, no. 16 (August 1997): 3707–10. http://dx.doi.org/10.1021/om970219v.

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Olivi, Nathanaël, Philippe Spruyt, Jean-François Peyrat, Mouâd Alami, and Jean-Daniel Brion. "Tandem amine propargylation-Sonogashira reactions: new three-component coupling leading to functionalized substituted propargylic amines." Tetrahedron Letters 45, no. 12 (March 2004): 2607–10. http://dx.doi.org/10.1016/j.tetlet.2004.01.141.

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Zeng, Suwei, Sen Xu, Yong Wang, Min Yu, Li Zhu, and Xiaoquan Yao. "Copper Nanoparticles Catalyzed Three-Component Coupling of Alkyne, Dihalomethane and Amine for the Synthesis of Propargylic Amine." Chinese Journal of Organic Chemistry 35, no. 4 (2015): 827. http://dx.doi.org/10.6023/cjoc201412045.

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Yu, Dingyi, and Yugen Zhang. "ChemInform Abstract: Copper-Catalyzed Three-Component Coupling of Terminal Alkyne, Dihalomethane and Amine to Propargylic Amines." ChemInform 42, no. 18 (April 7, 2011): no. http://dx.doi.org/10.1002/chin.201118051.

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Majumdar, Krishna C., and Gour H. Jana. "Competitive study of Meisenheimer rearrangement in a substrate tertiary amine with allylic and propargylic moieties." Canadian Journal of Chemistry 76, no. 3 (1998): 297–300. http://dx.doi.org/10.1139/cjc-76-3-297.

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Dissertations / Theses on the topic "Propargylic amine"

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Grimshaw, M. D. "Reactions of propargyl alcohols and propargyl amines at a diruthenium centre." Thesis, University of Bristol, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.274617.

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Blanchet, Jérôme. "Synthèse diastéréosélective d'amines propargyliques α-substituées : application en synthèse asymétrique." Paris 5, 2001. http://www.theses.fr/2001PA05P612.

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Cette thèse développe quelques aspects de la préparation stéréocontrôlée des amines propargyliques α-substituées ainsi que leur application dans le domaine de la synthèse asymétrique. La fonction amine propargylique est relativement peu répandue dans les produits d'origine naturelle mais présente un intérêt majeur pour des cibles synthétiques. Elle combine en effet les multiples réactivités d'une triple liaison avec l'activation que confère un atome d'azote aux carbones voisins. Nous avons voulu développer de nouvelles voies d'accès diastéréosélectives à des molécules incluant ce type d'enchaînement, soit pour l'aspect méthodologique lié à son exploitation fonctionnelle, soit pour aboutir à des séries pharmacologiques originales [. . . ]
The subject of this thesis is the synthesis of chiral α-substituted propargylamines and the evaluation of their utility in asymmetric synthesis. The process consists of the diastereoselective addition of mixed alkynylaluminum reagents to oxazolidines derived from R-(-)-phenylglycinol. This method is a new efficient and scalable route to these molecules. Reaction conditions were determined to afford the primary amines. In the second part of this work the nature of the transfer of chirality in the Meisenheimer and Stevens sigmatropic rearrangements has been investigated [. . . ]
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Richter, Frank. "Development of the Solution-Spray Flash-Vacuum-Pyrolysis Technique in the Synthesis of Allenyl Isothiocyanates and Synthesis of Complex 2-Amino-1,3-thiazole Derivatives." Doctoral thesis, Universitätsbibliothek Chemnitz, 2015. http://nbn-resolving.de/urn:nbn:de:bsz:ch1-qucosa-175339.

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Gas-phase thermolysis is a long-known and well established method for the preparation of reactive species. It is, however, limited to relatively volatile substances, which are easily vaporised. In the present work, the solution-spray technique for preparative scale was developed. With this technique, it is possible to subject low-volatile substances, which hardly vaporise even under high-vacuum conditions, to gas-phase thermolysis. By utilising oil nozzles used in heating and burner systems, it was possible to integrate a stable solution-spray into the existing flash-vacuum-pyrolysis system. The influence of several variables, such as flow-rate, pressure, temperature and solvent was determined. The solution-spray technique was applied in [3,3]-sigmatropic rearrangements of certain propargyl thiocyanates to the corresponding allenyl isothiocyanates. Furthermore, the parent compound propa-1,2-dienyl isothiocyanate was reacted with various sterically demanding primary and secondary amines to form 2-amino-1,3-thiazoles in moderate to excellent yields. Based on this, a catalyst-free four-center three-component reaction was developed. 2-Amino-1,3-thiazoles with complex substituents in 5-position at the heterocyclic ring are formed. Reaction mechanisms are discussed to explain the occurance of a highly substituted 1,3-thiazine structure. The influence of reaction temperature, concentrations and solvent were determined and are also discussed. It was shown that 2-amino-5-methyl-1,3-thiazoles are the apparently first aromatic substance class, that readily undergoes Prins-type 1,3-dioxane ring-formation
Die Gasphasenthermolyse ist eine lang bekannte und etablierte Methodik zur Synthese reaktiver Spezies. Sie ist allerdings auf flüchtige Substanzen mit einer guten Verdampfbarkeit beschränkt. Für schwerflüchtige Verbindungen, welche sich selbst im Hochvakuum nur mäßig oder gar nicht in die Gasphase bringen lassen, wurde in der vorliegenden Arbeit die Solution-Spray-Technik für die Anwendung im präparativen Maßstab entwickelt. Unter Verwendung von Ölzerstäuberdüsen, wie sie in der Heizungs- und Brennertechnik Anwendung finden, wurde die Erzeugung eines stabilen Lösungs-Sprays in die vorhandene Blitzvakuumpyrolyse-Technik integriert. Der Einfluss verschiedener Variablen, wie Flussrate, Druck, Temperatur und Lösungsmittel wurde untersucht. Die Solution-Spray-Technik wurde für die [3,3]-sigmatrope Umlagerung bestimmter Propargylthiocyanate zu Allenyl-isothiocyanaten angewendet. Des Weiteren wurde Propa-1,2-dienylisothiocyanat – das einfachste Allenylisothiocyanat – mit diversen sterisch anspruchsvollen primären und sekundären Aminen in mäßigen bis exzellenten Ausbeuten zu 2-Amino-1,3-thiazolen umgesetzt. Darauf aufbauend konnte eine Vier-Zentren-drei-Komponenten-Reaktion entwickelt werden. Es entstehen in hohen Ausbeuten 2-Amino-1,3-thiazole mit komplexen Substituenten an der 5-Position des Heterocyclus. Reaktionsmechanismen werden diskutiert um die alternative Bildung einer hochsubstituierten 1,3-Thiazinstruktur zu erklären. Der Einfluss von Reaktionstemperatur, Konzentration und Lösungsmittel auf das Produktverhältnis wurde ebenfalls untersucht und wird diskutiert. Es konnte gezeigt werden, dass 2-Amino-5-methyl-1,3-thiazole als offenbar erste aromatische Substanzklasse sehr gute Substrate für die Bildung von 1,3-Dioxanen nach Prins darstellen
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Bartholoméüs, Johan. "Réactions d’amination de liens C-H : synthèse d’amines propargyliques à partir de N-mésyloxycarbamates et études mécanistiques." Thèse, 2016. http://hdl.handle.net/1866/18430.

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Les composés aminés représentent une grande part des substances actives en chimie médicinale. Les travaux rapportés dans cette thèse décrivent les efforts consacrés au développement d’une nouvelle méthode d’amination de liens C-H propargyliques. Notre groupe de recherche a développé depuis quelques années un nouveau précurseur de nitrène métallique, les N-mésyloxycarbamates, permettant d’effectuer des réactions d’amination de liaisons C-H diversement activées. Au cours du développement de notre méthodologie, la synthèse du N-mésyloxycarbamate a fait l’objet de nombreuses optimisations, notamment en améliorant l’échelle globale de la synthèse ainsi que son efficacité. De même, des efforts ont été consacrés pour diminuer le nombre d’étapes nécessaires à la synthèse du réactif en développant la synthèse d’un des intermédiaires de manière énantiosélective. Enfin, la synthèse de ce réactif a également été envisagée à l’aide de la chimie en flux continu. Au cours du développement de la méthode de synthèse d’amines propargyliques, nous avons constaté que l’acide acétique jouait un rôle déterminant dans la conservation de bonnes sélectivités et réactivités de la réaction. Ces différentes observations ont permis de mettre au point un procédé diastéréosélectif efficace permettant d’obtenir des amines propargyliques avec des rendements allant de moyens à bons et avec d’excellentes diastéréosélectivités. A la suite de l’étude de l’étendue de notre procédé, nous avons tenté de déterminer les mécanismes réactionnels qui régissaient la réactivité et la sélectivité de celui-ci. Nous avons ainsi montré que l’espèce réactive du système catalytique était bel et bien un nitrène métallique, et que l’étape cinétiquement déterminante était celle d’insertion. Des expériences faites en oxydant l’espèce catalytique de rhodium ont suggéré que plusieurs états d’oxydation de cette espèce peuvent être présents et actifs dans le système catalytique.
The nitrogen containing compounds represent a large portion of the active substances in medicinal chemistry. The work reported in this manuscript describe the efforts devoted to the development of a new method of amination of propargylic C-H bonds. Our research group has developed recently a new metal nitrene precursor, N-mesyloxycarbamates, to perform amination reactions on various C-H bonds. During the development of our methodology, the synthesis of N-mesyloxycarbamate has undergone many improvements, including improved global scale synthesis and effectiveness. Similarly, efforts were devoted to reduce the number of steps required for the synthesis of the reagent by developing the synthesis of an intermediate enantioselectively. Finally, the synthesis of this reagent was also considered using continuous flow chemistry. During development of the method of synthesis of propargylic amines, we have found that acetic acid plays a key role in the conservation of good selectivity and reactivity of the reaction. These observations allowed to develop an efficient diastereoselective process in order to obtain propargylic amines with moderate to good yields and with excellent diastereoselectivities. Following the study of the scope of our process, we tried to determine the reaction mechanisms governing the reactivity and selectivity. We have shown that the reactive species of the catalyst system was indeed a metal nitrene, and that the rate-determining step was the insertion. Experiments made by oxidizing the rhodium catalytic species suggested that several oxidation states of this species may be present and active in the catalytic system.
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Bhat, Ramakrishna G. "Development Of Novel Methods For The Synthesis Of Amines, Amino Acids And Peptides." Thesis, 2004. http://etd.iisc.ernet.in/handle/2005/1316.

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Cheng, Yuan-Chung, and 鄭原忠. "(Mechanistic Investigation of nucleophilic Addition of Amine and Water to Platinum(II) η^3-Propargyl/Allenyl Complex - A Density Functional Study." Thesis, 1997. http://ndltd.ncl.edu.tw/handle/99991586259283696309.

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Book chapters on the topic "Propargylic amine"

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Speiser, Z., R. Levy, and S. Cohen. "Effects of N-propargyl-1-(R)aminoindan (rasagiline) in models of motor and cognition disorders." In MAO — The Mother of all Amine Oxidases, 287–300. Vienna: Springer Vienna, 1998. http://dx.doi.org/10.1007/978-3-7091-6499-0_29.

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Sterling, J., A. Veinberg, D. Lerner, W. Goldenberg, R. Levy, M. Youdim, and J. Finberg. "(R)(+)-N-Propargyl-1-aminoindan (rasagiline) and derivatives: highly selective and potent inhibitors of monoamine oxidase B." In MAO — The Mother of all Amine Oxidases, 301–5. Vienna: Springer Vienna, 1998. http://dx.doi.org/10.1007/978-3-7091-6499-0_30.

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Finberg, J. P. M., J. Wang, K. Bankiewicz, J. Harvey-White, I. J. Kopin, and D. S. Goldstein. "Increased striatal dopamine production from L-DOPA following selective inhibition of monoamine oxidase B by R(+)-N-propargyl-1-aminoindan (rasagiline) in the monkey." In MAO — The Mother of all Amine Oxidases, 279–85. Vienna: Springer Vienna, 1998. http://dx.doi.org/10.1007/978-3-7091-6499-0_28.

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Bavetsias, Vassilios, Ann L. Jackman, Tim J. Thornton, Krzysztof Pawelczak, F. Thomas Boyle, and Graham M. F. Bisset. "Quinazoline Antifolates Inhibiting Thymidylate Synthase: Synthesis of γ-Linked Peptide and Amide Analogues of 2-Desamino-2-Methyl-N10-Propargyl-5,8-Dideazafolic Acid (ICI 198583)10-Propargyl-5,8-Dideazafolic Acid (ICI 198583)." In Advances in Experimental Medicine and Biology, 593–96. Boston, MA: Springer US, 1993. http://dx.doi.org/10.1007/978-1-4615-2960-6_121.

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Ohno, H., and K. Tomioka. "Reactions of Propargylic Amine Derivatives." In Cumulenes and Allenes, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-044-00122.

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Margaretha, P. "Synthesis from Propargylic Alcohols and 1-Chloro-,,2-trimethylprop-1-en-1-amine." In Chlorine, Bromine, and Iodine, 1. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-035-00145.

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Taber, Douglass F. "Enantioselective Synthesis of Alcohols and Amines: The Fujii/Ohno Synthesis of (+)-Lysergic Acid." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0035.

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Ramón Gómez Arrayás and Juan C. Carretero of the Universidad Autónoma de Madrid effected (Chem. Commun. 2011, 47, 6701) enantioselective conjugate borylation of an unsaturated sulfone 1, leading to the alcohol 2. Robert E. Gawley of the University of Arkansas found (J. Am. Chem. Soc. 2011, 133, 19680) conditions for enantioselective ketone reduction that were selective enough to distinguish between the ethyl and propyl groups of 3 to give 4. Vicente Gotor of the Universidad de Oviedo used (Angew. Chem. Int. Ed. 2011, 50, 8387) an overexpressed Baeyer-Villiger monoxygenase to prepare 6 by dynamic kinetic resolution of 5. Li Deng of Brandeis University prepared (J. Am. Chem. Soc. 2011, 133, 12458) 8 in high ee by kinetic enantioselective migration of the alkene of racemic 7. Bernhard Breit of the Freiburg Institute for Advanced Studies established (J. Am. Chem. Soc. 2011, 133, 20746) the oxygenated quaternary center of 10 by the addition of benzoic acid to the allene 9. Keith R. Fandrick of Boehringer Ingelheim constructed (J. Am. Chem. Soc. 2011, 133, 10332) the oxygenated quaternary center of 13 by enantioselective addition of the propargylic nucleophile 12 to 11. Yian Shi of Colorado State University devised (J. Am. Chem. Soc. 2011, 133, 12914) conditions for the enantioselective transamination of the α-keto ester 14 to the amine 15. Professor Deng added (Adv. Synth. Catal. 2011, 353, 3123) 18 to an enone 17 to give the protected amine 19. Song Ye of the Institute of Chemistry, Beijing effected (J. Am. Chem. Soc. 2011, 133, 15894) elimination/addition of an unsaturated acid chloride 20 to give the γ-amino acid derivative 22. Frank Glorius of the Universität Münster added (Angew. Chem. Int. Ed. 2011, 50, 1410) an aldehyde 23 to 24 to give the amide 25. Sentaro Okamoto of Kanagawa University designed (J. Org. Chem. 2011, 76, 6678) an organocatalyst for the enantioselective Steglich rearrangement of 26, creating the aminated quaternary center of 27. Most impressive of all was the report (Org. Lett. 2011, 13, 5460) by Hélène Lebel of the Université de Montréal of the direct enantioselective C–H amination of 28 to give 29.
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Taber, Douglass. "C-H Functionalization to Form C-O, C-N, and C-C Bonds." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0015.

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A classic example of C-H functionalization is the familiar NBS bromination of a benzylic site. Recent updates of this approach allow for direct alkoxylation (J. Am. Chem. Soc. 2008, 130, 7824) and net amination (Organic Lett. 2008, 10, 1863). For the amination of simple aliphatic H’s, Holger F. Bettinger of Ruhr-Universität Bochum developed (Angew. Chem. Int. Ed. 2008, 47, 4744) the boryl azide 2. The insertion with 1 proceeded to give a statistical mixture of the nitrene insertion products 3 and 4. The tethered C-H functionalization devised (J. Am. Chem. Soc. 2008, 130, 7247) by Phil S. Baran of Scripps-La Jolla is selective, as in the conversion to 5 to 6, but appears to be limited to tertiary and benzylic C-H sites. Michael P. Doyle of the University of Maryland established (J. Org. Chem. 2008, 73, 4317) an elegant protocol for the oxidation of an alkyne such as 7 to the ynone 8. Note that the oxidation did not move the alkyne. Marta Catellani of the Università di Parma reported (Adv. Synth. Cat. 2008, 350, 565) the intriguing Pd-catalyzed conversion of 9 to 10. Under mild conditions, it might likely be possible to hydrolyze the vinyl ether to reveal the phenol 11. Another way of looking at this overall transformation would be to consider the ether 10 to be a protected form of the aldehyde 12. C-H activation can also lead to C-C bond formation. Irena S. Akhrem of the Nesmeyanov Institute, Moscow, described (Tetrahedron Lett. 2008, 49, 1399) a hydride-abstraction protocol for three-component coupling of a hydrocarbon 13 , an amine 14 , and CO, leading to the homologated amide 15. Hua Fu of Tsinghua University, Beijing, showed (J. Org. Chem. 2008 , 73, 3961) that oxidation of an amine 16 led to an intermediate that could be coupled with an alkyne 17 to give the propargylic amine 18. Products 15 and 18 are the result of sp2 and sp coupling, respectively. C-H functionalization leading to sp3 -sp3 coupling is less common. Jin-Quan Yu of Scripps/La Jolla found (J. Am. Chem. Soc. 2008, 130, 7190) that activation of the N-methoxy amide 19 in the presence of the alkyl boronic acid 20 gave smooth coupling, to 21.
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Miles, J. A. L., and J. M. Percy. "Nucleophilic Substitution of Propargylic Alcohols with 1-Fluoro-,-diisopropyl-2-methylprop-1-en-1-amine." In Fluorine, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-034-00187.

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Fiera, L. "Propargylic Primary Amines." In Heteroatom Analogues of Aldehydes and Ketones, 1. Georg Thieme Verlag KG, 2004. http://dx.doi.org/10.1055/sos-sd-027-00364.

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Conference papers on the topic "Propargylic amine"

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Palomo Nicolau, Claudio, Enrique Gomez-Bengoa, Jesus Garcia, Jacqueline Jiménez, Irati Lapuerta, Antonia Mielgo, Miguel Maestro, et al. "Propargylic-Amines and Alcohols Through anti-Selective Mannich and Aldol Reactions." In MOL2NET 2016, International Conference on Multidisciplinary Sciences, 2nd edition. Basel, Switzerland: MDPI, 2016. http://dx.doi.org/10.3390/mol2net-02-08015.

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Dinh Thanh, Nguyen, Do Son Hai, Vu Thi Tuyet Thuy, Do Tien Tung, Cao Thi Le, and Hoang Thi Kim Van. "CATALYSIS INVESTIGATION FOR SYNTHESIS OF 2-AMINO-4H-PYRAN-3-CARBONITRILES CONTAINING PROPARGYL GROUP." In The 21st International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2017. http://dx.doi.org/10.3390/ecsoc-21-04769.

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