One-pot synthesis of highly diversified tetrahydropyridines by tandem condensation of aldehydes, amines, and β-ketoesters
Silica-supported boron trifluoride (BF3·SiO2) was used as an efficient and reusable catalyst for the synthesis of highly diversified tetrahydropyridines by one-pot multicomponent reactions of amines and aldehydes with β-ketoester. This method proceeds through the intermolecular Mannich reaction foll...
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| Veröffentlicht in: | Tetrahedron 2012-01, Vol.68 (1), p.363-369 |
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| creator | Ramachandran, Rajamanickam Jayanthi, Sampathkumar Jeong, Yeon Tae |
| description | Silica-supported boron trifluoride (BF3·SiO2) was used as an efficient and reusable catalyst for the synthesis of highly diversified tetrahydropyridines by one-pot multicomponent reactions of amines and aldehydes with β-ketoester. This method proceeds through the intermolecular Mannich reaction followed by intramolecular Mannich reaction. The observed hydrogen bonding interaction was studied in detail with single crystal X-ray diffraction analysis and Etter’s graph. Finally, this method has the advantage of easy work-up, convenient, relatively short reaction times and the products were isolated with high yields.
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| doi_str_mv | 10.1016/j.tet.2011.09.105 |
| format | Article |
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[Display omitted]</description><subject>Aldehydes</subject><subject>Amines</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Diffraction</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Graphs</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Hydrogen bonding</subject><subject>One-pot synthesis</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Silica-supported boron trifluoride</subject><subject>Synthesis (chemistry)</subject><subject>Tandem reaction</subject><subject>Tetrahedrons</subject><subject>Tetrahydropyridines</subject><subject>Theory of reactions, general kinetics. Catalysis. 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Nomenclature, chemical documentation, computer chemistry</topic><topic>X-rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ramachandran, Rajamanickam</creatorcontrib><creatorcontrib>Jayanthi, Sampathkumar</creatorcontrib><creatorcontrib>Jeong, Yeon Tae</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ramachandran, Rajamanickam</au><au>Jayanthi, Sampathkumar</au><au>Jeong, Yeon Tae</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-pot synthesis of highly diversified tetrahydropyridines by tandem condensation of aldehydes, amines, and β-ketoesters</atitle><jtitle>Tetrahedron</jtitle><date>2012-01-07</date><risdate>2012</risdate><volume>68</volume><issue>1</issue><spage>363</spage><epage>369</epage><pages>363-369</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>Silica-supported boron trifluoride (BF3·SiO2) was used as an efficient and reusable catalyst for the synthesis of highly diversified tetrahydropyridines by one-pot multicomponent reactions of amines and aldehydes with β-ketoester. 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| ispartof | Tetrahedron, 2012-01, Vol.68 (1), p.363-369 |
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| language | eng |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Aldehydes Amines Catalysis Catalysts: preparations and properties Chemistry Diffraction Exact sciences and technology General and physical chemistry Graphs Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Hydrogen bonding One-pot synthesis Organic chemistry Preparations and properties Silica-supported boron trifluoride Synthesis (chemistry) Tandem reaction Tetrahedrons Tetrahydropyridines Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry X-rays |
| title | One-pot synthesis of highly diversified tetrahydropyridines by tandem condensation of aldehydes, amines, and β-ketoesters |
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