Regioselective Synthesis of 1,2-Dihydroquinolines by a Solvent-Free MgBr2‑Catalyzed Multicomponent Reaction
A highly efficient and regioselective synthesis of 1,2-dihydroquinolines via a multicomponent reaction between an aniline and two ketones is described. This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substitut...
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| Veröffentlicht in: | Journal of organic chemistry 2013-10, Vol.78 (19), p.9614-9626 |
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| container_issue | 19 |
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| container_title | Journal of organic chemistry |
| container_volume | 78 |
| creator | Gutiérrez, Rsuini U Correa, Hans C Bautista, Rafael Vargas, José Luis Jerezano, Alberto V Delgado, Francisco Tamariz, Joaquín |
| description | A highly efficient and regioselective synthesis of 1,2-dihydroquinolines via a multicomponent reaction between an aniline and two ketones is described. This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substituted anilines and nonsymmetrically substituted ketones, principally a single product was found among the four expected regioisomers. A variety of anilines and ketones, including cyclic ketones, were evaluated providing a series of 1,2-dihydroquinolines with diverse substitution patterns. A study of the mechanism is discussed. There is evidence of the in situ formation of the imine as a result of the reaction between the aniline and one of the ketones, before annulation to the heterocyclic ring. |
| doi_str_mv | 10.1021/jo400973g |
| format | Article |
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This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substituted anilines and nonsymmetrically substituted ketones, principally a single product was found among the four expected regioisomers. A variety of anilines and ketones, including cyclic ketones, were evaluated providing a series of 1,2-dihydroquinolines with diverse substitution patterns. A study of the mechanism is discussed. There is evidence of the in situ formation of the imine as a result of the reaction between the aniline and one of the ketones, before annulation to the heterocyclic ring.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo400973g</identifier><identifier>PMID: 24044723</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Bromides - chemistry ; Catalysis ; Magnesium Compounds - chemistry ; Molecular Structure ; Quinolines - chemical synthesis ; Quinolines - chemistry ; Solvents - chemistry ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2013-10, Vol.78 (19), p.9614-9626</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo400973g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo400973g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24044723$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gutiérrez, Rsuini U</creatorcontrib><creatorcontrib>Correa, Hans C</creatorcontrib><creatorcontrib>Bautista, Rafael</creatorcontrib><creatorcontrib>Vargas, José Luis</creatorcontrib><creatorcontrib>Jerezano, Alberto V</creatorcontrib><creatorcontrib>Delgado, Francisco</creatorcontrib><creatorcontrib>Tamariz, Joaquín</creatorcontrib><title>Regioselective Synthesis of 1,2-Dihydroquinolines by a Solvent-Free MgBr2‑Catalyzed Multicomponent Reaction</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A highly efficient and regioselective synthesis of 1,2-dihydroquinolines via a multicomponent reaction between an aniline and two ketones is described. This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substituted anilines and nonsymmetrically substituted ketones, principally a single product was found among the four expected regioisomers. A variety of anilines and ketones, including cyclic ketones, were evaluated providing a series of 1,2-dihydroquinolines with diverse substitution patterns. A study of the mechanism is discussed. There is evidence of the in situ formation of the imine as a result of the reaction between the aniline and one of the ketones, before annulation to the heterocyclic ring.</description><subject>Bromides - chemistry</subject><subject>Catalysis</subject><subject>Magnesium Compounds - chemistry</subject><subject>Molecular Structure</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - chemistry</subject><subject>Solvents - chemistry</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kM1Kw0AUhQdRbP1Z-AIyG8GF0fntOEutVoUWodV1mGRu2ilJpmaSQlz5Cr6iT2JKq3dzFvfjcPgQOqPkmhJGb5ZeEKIVn--hPpWMRANNxD7qE8JYxNmA99BRCEvSnZTyEPWYIEIoxvuomMLc-QA5pLVbA561Zb2A4AL2GaZXLHpwi9ZW_qNxpc9dCQEnLTZ45vM1lHU0qgDwZH5fsZ-v76GpTd5-gsWTJq9d6ouVLzsKT8F09b48QQeZyQOc7vIYvY8e34bP0fj16WV4N44ME7SO0ltqlVQgRGIMETaRRlKtu58yQG3KLScE9CDJstRQkjHFdcattlIoKzLLj9Hltne1WQ6hjgsXUshzU4JvQkyF4FwrLVWHnu_QJinAxqvKFaZq4z9FHXCxBUwa4qVvqrJbHlMSb9TH_-r5L91ndW0</recordid><startdate>20131004</startdate><enddate>20131004</enddate><creator>Gutiérrez, Rsuini U</creator><creator>Correa, Hans C</creator><creator>Bautista, Rafael</creator><creator>Vargas, José Luis</creator><creator>Jerezano, Alberto V</creator><creator>Delgado, Francisco</creator><creator>Tamariz, Joaquín</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20131004</creationdate><title>Regioselective Synthesis of 1,2-Dihydroquinolines by a Solvent-Free MgBr2‑Catalyzed Multicomponent Reaction</title><author>Gutiérrez, Rsuini U ; Correa, Hans C ; Bautista, Rafael ; Vargas, José Luis ; Jerezano, Alberto V ; Delgado, Francisco ; Tamariz, Joaquín</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a241t-c81d757e44baa04db5a51992417ae1dc3d300e96bffca10f2739f3d9d547d4fd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Bromides - chemistry</topic><topic>Catalysis</topic><topic>Magnesium Compounds - chemistry</topic><topic>Molecular Structure</topic><topic>Quinolines - chemical synthesis</topic><topic>Quinolines - chemistry</topic><topic>Solvents - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gutiérrez, Rsuini U</creatorcontrib><creatorcontrib>Correa, Hans C</creatorcontrib><creatorcontrib>Bautista, Rafael</creatorcontrib><creatorcontrib>Vargas, José Luis</creatorcontrib><creatorcontrib>Jerezano, Alberto V</creatorcontrib><creatorcontrib>Delgado, Francisco</creatorcontrib><creatorcontrib>Tamariz, Joaquín</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gutiérrez, Rsuini U</au><au>Correa, Hans C</au><au>Bautista, Rafael</au><au>Vargas, José Luis</au><au>Jerezano, Alberto V</au><au>Delgado, Francisco</au><au>Tamariz, Joaquín</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective Synthesis of 1,2-Dihydroquinolines by a Solvent-Free MgBr2‑Catalyzed Multicomponent Reaction</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2013-10-04</date><risdate>2013</risdate><volume>78</volume><issue>19</issue><spage>9614</spage><epage>9626</epage><pages>9614-9626</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A highly efficient and regioselective synthesis of 1,2-dihydroquinolines via a multicomponent reaction between an aniline and two ketones is described. This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substituted anilines and nonsymmetrically substituted ketones, principally a single product was found among the four expected regioisomers. A variety of anilines and ketones, including cyclic ketones, were evaluated providing a series of 1,2-dihydroquinolines with diverse substitution patterns. A study of the mechanism is discussed. There is evidence of the in situ formation of the imine as a result of the reaction between the aniline and one of the ketones, before annulation to the heterocyclic ring.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24044723</pmid><doi>10.1021/jo400973g</doi><tpages>13</tpages></addata></record> |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Bromides - chemistry Catalysis Magnesium Compounds - chemistry Molecular Structure Quinolines - chemical synthesis Quinolines - chemistry Solvents - chemistry Stereoisomerism |
| title | Regioselective Synthesis of 1,2-Dihydroquinolines by a Solvent-Free MgBr2‑Catalyzed Multicomponent Reaction |
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