Solvent-free synthesis of functionalized pyridine derivatives using Wells-Dawson heteropolyacid as catalyst
Wells-Dawson heteropolyacids (H6P2W18O62·24H2O) were used as catalysts in the Hantzsch-like multicomponent condensation reaction with 3-formylchromones as aldehyde component, a β-ketoester and ammonium acetate, under solvent-free conditions at 80°C. Although the desired products were obtained, funct...
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| Veröffentlicht in: | Tetrahedron letters 2011-08, Vol.52 (34), p.4412-4416 |
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| creator | Sanchez, Laura M. Sathicq, Ángel G. Jios, Jorge L. Baronetti, Graciela T. Thomas, Horacio J. Romanelli, Gustavo P. |
| description | Wells-Dawson heteropolyacids (H6P2W18O62·24H2O) were used as catalysts in the Hantzsch-like multicomponent condensation reaction with 3-formylchromones as aldehyde component, a β-ketoester and ammonium acetate, under solvent-free conditions at 80°C. Although the desired products were obtained, functionalized pyridines were the main reaction product and became the alternative route to dihydropyridine ring formation. Based on the proposed mechanisms for the formation of each of the obtained products, the multicomponent reaction was modified to afford only the functionalized pyridines (60–99%). Our procedure represents a clean alternative for the synthesis of several highly functionalized pyridines. |
| doi_str_mv | 10.1016/j.tetlet.2011.06.048 |
| format | Article |
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Although the desired products were obtained, functionalized pyridines were the main reaction product and became the alternative route to dihydropyridine ring formation. Based on the proposed mechanisms for the formation of each of the obtained products, the multicomponent reaction was modified to afford only the functionalized pyridines (60–99%). Our procedure represents a clean alternative for the synthesis of several highly functionalized pyridines.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2011.06.048</identifier><identifier>CODEN: TELEAY</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>3-Formylchromones ; Ammonium acetate ; Catalysis ; Catalysts ; Catalysts: preparations and properties ; Chemistry ; Cleaning ; Derivatives ; Exact sciences and technology ; Formations ; Functionalized pyridines ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Kinetics and mechanisms ; Multicomponent reaction ; Organic chemistry ; Preparations and properties ; Pyridines ; Reactivity and mechanisms ; Solvent-free organic synthesis ; Synthesis (chemistry) ; Tetrahedrons ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry ; Wells-Dawson heteropolyacid</subject><ispartof>Tetrahedron letters, 2011-08, Vol.52 (34), p.4412-4416</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-4d669cd4b8083855e78142b339ba2e81fcbb78f214d628592c5e295556bf38c33</citedby><cites>FETCH-LOGICAL-c415t-4d669cd4b8083855e78142b339ba2e81fcbb78f214d628592c5e295556bf38c33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040403911009889$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24396961$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Sanchez, Laura M.</creatorcontrib><creatorcontrib>Sathicq, Ángel G.</creatorcontrib><creatorcontrib>Jios, Jorge L.</creatorcontrib><creatorcontrib>Baronetti, Graciela T.</creatorcontrib><creatorcontrib>Thomas, Horacio J.</creatorcontrib><creatorcontrib>Romanelli, Gustavo P.</creatorcontrib><title>Solvent-free synthesis of functionalized pyridine derivatives using Wells-Dawson heteropolyacid as catalyst</title><title>Tetrahedron letters</title><description>Wells-Dawson heteropolyacids (H6P2W18O62·24H2O) were used as catalysts in the Hantzsch-like multicomponent condensation reaction with 3-formylchromones as aldehyde component, a β-ketoester and ammonium acetate, under solvent-free conditions at 80°C. Although the desired products were obtained, functionalized pyridines were the main reaction product and became the alternative route to dihydropyridine ring formation. Based on the proposed mechanisms for the formation of each of the obtained products, the multicomponent reaction was modified to afford only the functionalized pyridines (60–99%). Our procedure represents a clean alternative for the synthesis of several highly functionalized pyridines.</description><subject>3-Formylchromones</subject><subject>Ammonium acetate</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Cleaning</subject><subject>Derivatives</subject><subject>Exact sciences and technology</subject><subject>Formations</subject><subject>Functionalized pyridines</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Kinetics and mechanisms</subject><subject>Multicomponent reaction</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Pyridines</subject><subject>Reactivity and mechanisms</subject><subject>Solvent-free organic synthesis</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><subject>Wells-Dawson heteropolyacid</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9kDtvFDEURi0EEkvgH1C4QaKZwe_xNEgovCJFogBEaXk818TLxF58vYuGX89EG6XkNrc5330cQl5y1nPGzZt936At0HrBOO-Z6Zmyj8iO20F2Ulv-mOwYU6xTTI5PyTPEPdvKWLYjv76W5QS5dbECUFxzuwFMSEuk8ZhDSyX7Jf2FmR7WmuaUgc5Q08m3dAKkR0z5J_0By4Lde_8HS6Y30KCWQ1lWH9JMPdLgm19WbM_Jk-gXhBf3_YJ8__jh2-Xn7vrLp6vLd9ddUFy3Ts3GjGFWk2VWWq1hsFyJScpx8gIsj2GaBhsF30Bh9SiCBjFqrc0UpQ1SXpDX57mHWn4fAZu7TRi2G32GckTHB6XMYAXXG6rOaKgFsUJ0h5pufV0dZ-7Ordu7s1t359Yx4za3W-zV_QaPwS-x-hwSPmSFkqMZDd-4t2cOtndPCarDkCAHmFOF0Nxc0v8X_QP7KZOb</recordid><startdate>20110824</startdate><enddate>20110824</enddate><creator>Sanchez, Laura M.</creator><creator>Sathicq, Ángel G.</creator><creator>Jios, Jorge L.</creator><creator>Baronetti, Graciela T.</creator><creator>Thomas, Horacio J.</creator><creator>Romanelli, Gustavo P.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20110824</creationdate><title>Solvent-free synthesis of functionalized pyridine derivatives using Wells-Dawson heteropolyacid as catalyst</title><author>Sanchez, Laura M. ; Sathicq, Ángel G. ; Jios, Jorge L. ; Baronetti, Graciela T. ; Thomas, Horacio J. ; Romanelli, Gustavo P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-4d669cd4b8083855e78142b339ba2e81fcbb78f214d628592c5e295556bf38c33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>3-Formylchromones</topic><topic>Ammonium acetate</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Cleaning</topic><topic>Derivatives</topic><topic>Exact sciences and technology</topic><topic>Formations</topic><topic>Functionalized pyridines</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Kinetics and mechanisms</topic><topic>Multicomponent reaction</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Pyridines</topic><topic>Reactivity and mechanisms</topic><topic>Solvent-free organic synthesis</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><topic>Wells-Dawson heteropolyacid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sanchez, Laura M.</creatorcontrib><creatorcontrib>Sathicq, Ángel G.</creatorcontrib><creatorcontrib>Jios, Jorge L.</creatorcontrib><creatorcontrib>Baronetti, Graciela T.</creatorcontrib><creatorcontrib>Thomas, Horacio J.</creatorcontrib><creatorcontrib>Romanelli, Gustavo P.</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 letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sanchez, Laura M.</au><au>Sathicq, Ángel G.</au><au>Jios, Jorge L.</au><au>Baronetti, Graciela T.</au><au>Thomas, Horacio J.</au><au>Romanelli, Gustavo P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solvent-free synthesis of functionalized pyridine derivatives using Wells-Dawson heteropolyacid as catalyst</atitle><jtitle>Tetrahedron letters</jtitle><date>2011-08-24</date><risdate>2011</risdate><volume>52</volume><issue>34</issue><spage>4412</spage><epage>4416</epage><pages>4412-4416</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><coden>TELEAY</coden><abstract>Wells-Dawson heteropolyacids (H6P2W18O62·24H2O) were used as catalysts in the Hantzsch-like multicomponent condensation reaction with 3-formylchromones as aldehyde component, a β-ketoester and ammonium acetate, under solvent-free conditions at 80°C. Although the desired products were obtained, functionalized pyridines were the main reaction product and became the alternative route to dihydropyridine ring formation. Based on the proposed mechanisms for the formation of each of the obtained products, the multicomponent reaction was modified to afford only the functionalized pyridines (60–99%). Our procedure represents a clean alternative for the synthesis of several highly functionalized pyridines.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2011.06.048</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | 3-Formylchromones Ammonium acetate Catalysis Catalysts Catalysts: preparations and properties Chemistry Cleaning Derivatives Exact sciences and technology Formations Functionalized pyridines General and physical chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Heterocyclic compounds with only one n hetero atom and condensed derivatives Kinetics and mechanisms Multicomponent reaction Organic chemistry Preparations and properties Pyridines Reactivity and mechanisms Solvent-free organic synthesis Synthesis (chemistry) Tetrahedrons Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Wells-Dawson heteropolyacid |
| title | Solvent-free synthesis of functionalized pyridine derivatives using Wells-Dawson heteropolyacid as catalyst |
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