A comparative study using conventional methods, ionic liquids, microwave irradiation and combinations thereof for the synthesis of 5-trifluoroacety1-1,2,3,4-tetrahydropyridines
This study reports a comparison between conventional methods, ionic liquids, microwave (MW) irradiation, and combinations thereof for the synthesis of a series of fourteen 1-aryl-2-arylamino-5-trifluoroacety1-1,2,3,4-tetrahydropyridines. In all of the reactions tested, the products were obtained at...
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| Published in | Tetrahedron letters Vol. 59; no. 10; pp. 891 - 894 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier
07.03.2018
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| Abstract | This study reports a comparison between conventional methods, ionic liquids, microwave (MW) irradiation, and combinations thereof for the synthesis of a series of fourteen 1-aryl-2-arylamino-5-trifluoroacety1-1,2,3,4-tetrahydropyridines. In all of the reactions tested, the products were obtained at very good yields (87-97%), but the reaction times were very different, depending on the method used. Comparing to other methods, the time decreased to 1 min when [BMIM]BF4 under MW irradiation was used, thus evidencing a synergic effect. (C) 2018 Elsevier Ltd. All rights reserved. |
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| AbstractList | This study reports a comparison between conventional methods, ionic liquids, microwave (MW) irradiation, and combinations thereof for the synthesis of a series of fourteen 1-aryl-2-arylamino-5-trifluoroacety1-1,2,3,4-tetrahydropyridines. In all of the reactions tested, the products were obtained at very good yields (87-97%), but the reaction times were very different, depending on the method used. Comparing to other methods, the time decreased to 1 min when [BMIM]BF4 under MW irradiation was used, thus evidencing a synergic effect. (C) 2018 Elsevier Ltd. All rights reserved. |
| Author | Lobo, Marti M. Zanatta, Nilo Mittersteiner, Mateus Bonacorso, Helio G. Martins, Marcos A. P. Andrade, Valquiria P. Frizzo, Clarissa P. |
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| Cites_doi | 10.1021/co100055x 10.1016/j.bmcl.2017.03.043 10.1021/ol5020637 10.1016/j.ijantimicag.2016.11.024 10.1007/s11030-009-9159-3 10.1021/ja2119833 10.1002/poc.863 10.1021/ja028937i 10.1021/jo016297g 10.1016/j.bmcl.2007.03.010 10.1002/jhet.2271 10.1021/acscombsci.5b00154 10.1002/chem.200900044 10.1002/ejoc.200801119 10.1021/cr078399y 10.1016/j.ejmech.2015.10.026 10.1021/acs.orglett.5b01937 10.1016/j.tetlet.2010.11.131 10.1021/co200188g 10.1055/s-0029-1218779 |
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| Keywords | Heterocycles Tetrahydropyridin-2-arylamines TETRAHYDROPYRIDINES Ionic liquids Microwave irradiation SELECTIVE INHIBITORS CASCADE |
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| References | Duttwyler, S (WOS:000301550800035) 2012; 134 Martinez-Palou, R (WOS:000274437200002) 2010; 14 Sun, SH (WOS:000341344600044) 2014; 16 Zanatta, N (WOS:000363901300027) 2015; 52 Silva, L (WOS:000397148100007) 2017; 49 Prola, LDT (WOS:000310015100012) 2012; 23 Chiappe, C (WOS:000227926800001) 2005; 18 Leadbeater, NE (WOS:000175323600062) 2002; 67 GESSNER, W (WOS:A1985ACM1700009) 1985; 28 Dhinakaran, I (WOS:000375886800005) 2016; 18 da Nascimento, M da G (000426411000008.6) 2015; 112 Das, P (WOS:000360102900024) 2015; 17 Wu, W (WOS:000401492500027) 2017; 27 Huang, HB (WOS:000180468900008) 2003; 125 Aeluri, R (WOS:000366232100003) 2015; 106 Sridharan, V (WOS:000265955200010) 2009; 15 Martins, MAP (WOS:000256738100007) 2008; 108 Zanatta, N (WOS:000264683800022) 2009; 2009 Chanda, K (WOS:000300116000007) 2012; 14 Wang, HJ (WOS:000288183000013) 2011; 13 Zanatta, N (WOS:000280710200003) 2010 Chang, MY (WOS:000286997100008) 2011; 52 Blilmel, M (000426411000008.2) 2014; 16 Leon, LG (WOS:000246675700001) 2007; 17 Mali, KS (000426411000008.14) 2005; 123 |
| References_xml | – volume: 13 start-page: 181 year: 2011 ident: WOS:000288183000013 article-title: Cerium Ammonium Nitrate-Catalyzed Multicomponent Reaction for Efficient Synthesis of Functionalized Tetrahydropyridines publication-title: ACS COMBINATORIAL SCIENCE doi: 10.1021/co100055x contributor: fullname: Wang, HJ – volume: 27 start-page: 2210 year: 2017 ident: WOS:000401492500027 article-title: The discovery of tetrahydropyridine analogs as hNav1.7 selective inhibitors for analgesia publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS doi: 10.1016/j.bmcl.2017.03.043 contributor: fullname: Wu, W – volume: 16 start-page: 4520 year: 2014 ident: WOS:000341344600044 article-title: Synthesis of Tetrahydropyridine Derivatives through a Modular Assembly Reaction Using 3,4-Dihydropyran as Dual Substrate and Template publication-title: ORGANIC LETTERS doi: 10.1021/ol5020637 contributor: fullname: Sun, SH – volume: 49 start-page: 308 year: 2017 ident: WOS:000397148100007 article-title: In vitro and in silico analysis of the efficiency of tetrahydropyridines as drug efflux inhibitors in Escherichia coli publication-title: INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS doi: 10.1016/j.ijantimicag.2016.11.024 contributor: fullname: Silva, L – volume: 123 year: 2005 ident: 000426411000008.14 publication-title: J Chem Phys. contributor: fullname: Mali, KS – volume: 112 start-page: 1 year: 2015 ident: 000426411000008.6 publication-title: J Mot Catal B Enzym. contributor: fullname: da Nascimento, M da G – volume: 14 start-page: 3 year: 2010 ident: WOS:000274437200002 article-title: Microwave-assisted synthesis using ionic liquids publication-title: MOLECULAR DIVERSITY doi: 10.1007/s11030-009-9159-3 contributor: fullname: Martinez-Palou, R – volume: 134 start-page: 4064 year: 2012 ident: WOS:000301550800035 article-title: Highly Diastereoselective Synthesis of Tetrahydropyridines by a C-H Activation-Cyclization-Reduction Cascade publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja2119833 contributor: fullname: Duttwyler, S – volume: 18 start-page: 275 year: 2005 ident: WOS:000227926800001 article-title: Ionic liquids: solvent properties and organic reactivity publication-title: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY doi: 10.1002/poc.863 contributor: fullname: Chiappe, C – volume: 125 start-page: 626 year: 2003 ident: WOS:000180468900008 article-title: Highly enantioenriched tetrahydropyridines from chiral organosilanes: Application to the synthesis of quinolizidine alkaloid (-)-217A publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja028937i contributor: fullname: Huang, HB – volume: 67 start-page: 3145 year: 2002 ident: WOS:000175323600062 article-title: A study of the ionic liquid mediated microwave heating of organic solvents publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo016297g contributor: fullname: Leadbeater, NE – volume: 17 start-page: 2681 year: 2007 ident: WOS:000246675700001 article-title: Antiproliferative activity of 2-alkyl-4-halopiperidines and 2-alkyl-4-halo-1,2,5,6-tetrahydropyridines in solid tumor cell lines publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS doi: 10.1016/j.bmcl.2007.03.010 contributor: fullname: Leon, LG – volume: 52 start-page: 1776 year: 2015 ident: WOS:000363901300027 article-title: Synthesis of 1-Arylethyl-2-arylethylamino-5-trifluoroacetyl-1,2,3,4-tetrahydropyridines and Related Compounds with Potential Cell Efflux Pump Inhibition publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY doi: 10.1002/jhet.2271 contributor: fullname: Zanatta, N – volume: 23 start-page: 1663 year: 2012 ident: WOS:000310015100012 article-title: Synthesis of Novel Quinolines using TsOH/Ionic Liquid under Microwave publication-title: JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY contributor: fullname: Prola, LDT – volume: 18 start-page: 236 year: 2016 ident: WOS:000375886800005 article-title: Chemodivergent, One-Pot, Multi-Component Synthesis of Pyrroles and Tetrahydropyridines under Solvent- and Catalyst-Free Conditions Using the Grinding Method publication-title: ACS COMBINATORIAL SCIENCE doi: 10.1021/acscombsci.5b00154 contributor: fullname: Dhinakaran, I – volume: 15 start-page: 4565 year: 2009 ident: WOS:000265955200010 article-title: A Very Efficient Cerium(IV) Ammonium Nitrate Catalyzed, Four-Component Synthesis of Tetrahydropyridines and Its Application in the Concise Generation of Functionalized Homoquinolizine Frameworks publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200900044 contributor: fullname: Sridharan, V – volume: 16 start-page: 6012 year: 2014 ident: 000426411000008.2 publication-title: Org Lett. contributor: fullname: Blilmel, M – volume: 2009 start-page: 1435 year: 2009 ident: WOS:000264683800022 article-title: Highly Chemoselective Synthesis of 6-Alkoxy-1-alkyl(aryl)-3-trifluoroacetyl-1,4,5,6-tetrahydropyridines and 1-Alkyl(aryl)-6-amino-3-trifluoroacetyl-1,4,5,6-tetrahydropyridines publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.200801119 contributor: fullname: Zanatta, N – volume: 108 start-page: 2015 year: 2008 ident: WOS:000256738100007 article-title: Ionic liquids in heterocyclic synthesis publication-title: CHEMICAL REVIEWS doi: 10.1021/cr078399y contributor: fullname: Martins, MAP – volume: 106 start-page: 26 year: 2015 ident: WOS:000366232100003 article-title: Highly functionalized tetrahydropyridines are cytotoxic and selective inhibitors of human puromycin sensitive aminopeptidase publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1016/j.ejmech.2015.10.026 contributor: fullname: Aeluri, R – volume: 17 start-page: 4030 year: 2015 ident: WOS:000360102900024 article-title: Synthesis of 1,2,3,6-Tetrahydropyridines via Aminophosphate Enabled Anionic Cascade and Acid Catalyzed Cyclization Approaches publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b01937 contributor: fullname: Das, P – volume: 28 start-page: 311 year: 1985 ident: WOS:A1985ACM1700009 article-title: SYNTHESIS AND DIHYDROPTERIDINE REDUCTASE INHIBITORY EFFECTS OF POTENTIAL METABOLITES OF THE NEUROTOXIN 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: GESSNER, W – volume: 52 start-page: 588 year: 2011 ident: WOS:000286997100008 article-title: Synthesis of 1,2,4-trisubstituted-1,2,5,6-tetrahydropyridines publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2010.11.131 contributor: fullname: Chang, MY – volume: 14 start-page: 115 year: 2012 ident: WOS:000300116000007 article-title: Microwave-Assisted Linear Approach Toward Highly Substituted Benzo[d]oxazol-5-yl-1H-benzo[d]imidazole on Ionic Liquid Support publication-title: ACS COMBINATORIAL SCIENCE doi: 10.1021/co200188g contributor: fullname: Chanda, K – start-page: 2348 year: 2010 ident: WOS:000280710200003 article-title: An Efficient Synthesis of Oxa- and Aza-Condensed Tetrahydropyridines from Cyclic Enones publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-0029-1218779 contributor: fullname: Zanatta, N |
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| Title | A comparative study using conventional methods, ionic liquids, microwave irradiation and combinations thereof for the synthesis of 5-trifluoroacety1-1,2,3,4-tetrahydropyridines |
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