Divergent synthesis of 4,6-diarylated pyridin-2(1H)-ones from chalcones: novel access to 2,4,6-triaryl pyridines
A wide range of 4,6-diarylated/heterylated pyridin-2(1H)-one derivatives were synthesized in good to excellent yields from 1,3-diarylated/heterylated-2-propen-1-ones (chalcones) in one pot under metal and base-free conditions. This domino reaction suggests a novel mechanism comprising of Michael add...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2015-06, Vol.13 (21), p.5944-5954 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Khajuria, Rajni Kannaboina, Prakash Kapoor, Kamal K Gupta, Annah Raina, Gaurav Jassal, Amanpreet Kaur Rana, Love Karan Hundal, Maninder S Das, Parthasarathi |
| description | A wide range of 4,6-diarylated/heterylated pyridin-2(1H)-one derivatives were synthesized in good to excellent yields from 1,3-diarylated/heterylated-2-propen-1-ones (chalcones) in one pot under metal and base-free conditions. This domino reaction suggests a novel mechanism comprising of Michael addition followed by amination, subsequent intramolecular amidation and finally dehydronitrosation. The usefulness of the designed 4,6-diarylated/heterylated pyridin-2(1H)-one derivatives has further been demonstrated by synthesizing medicinally important 2,4,6-triaryl/heteryl pyridines via Pd-catalyzed cross-coupling reaction. |
| doi_str_mv | 10.1039/c5ob00545k |
| format | Article |
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This domino reaction suggests a novel mechanism comprising of Michael addition followed by amination, subsequent intramolecular amidation and finally dehydronitrosation. 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This domino reaction suggests a novel mechanism comprising of Michael addition followed by amination, subsequent intramolecular amidation and finally dehydronitrosation. The usefulness of the designed 4,6-diarylated/heterylated pyridin-2(1H)-one derivatives has further been demonstrated by synthesizing medicinally important 2,4,6-triaryl/heteryl pyridines via Pd-catalyzed cross-coupling reaction.</description><subject>Amination</subject><subject>Catalysis</subject><subject>Chalcones - chemical synthesis</subject><subject>Chalcones - chemistry</subject><subject>Cyclization</subject><subject>Models, Molecular</subject><subject>Palladium - chemistry</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kE1PwkAQQDdGI4he_AFmj2io7me3eFP8wEjCRc_Ndjsr1bZbdwsJ_94CwmlmkpeXyUPokpJbSvj4zkiXESKF_DlCfSqUiojk4-PDzkgPnYXwTQgdq1icoh6TY6a4kH3UPBUr8F9Qtzis63YBoQjYWSxGcZQX2q9L3UKOm7Uv8qKO2JBOryNXQ8DWuwqbhS7N5rzHtVtBibUxEAJuHWajjaP1W8leAOEcnVhdBrj4nwP0-fL8MZlGs_nr2-RhFhkueRtRA4xqwQzhwmYJz6w2caZYTghPLJOZSjIqOKHcKsVskmghEyYolSApBcIHaLjzNt79LiG0aVUEA2Wpa3DLkNK4wxkXserQmx1qvAvBg00bX1Td2ykl6aZwOpHzx23h9w6--vcuswryA7pPyv8AJB90rw</recordid><startdate>20150607</startdate><enddate>20150607</enddate><creator>Khajuria, Rajni</creator><creator>Kannaboina, Prakash</creator><creator>Kapoor, Kamal K</creator><creator>Gupta, Annah</creator><creator>Raina, Gaurav</creator><creator>Jassal, Amanpreet Kaur</creator><creator>Rana, Love Karan</creator><creator>Hundal, Maninder S</creator><creator>Das, Parthasarathi</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20150607</creationdate><title>Divergent synthesis of 4,6-diarylated pyridin-2(1H)-ones from chalcones: novel access to 2,4,6-triaryl pyridines</title><author>Khajuria, Rajni ; Kannaboina, Prakash ; Kapoor, Kamal K ; Gupta, Annah ; Raina, Gaurav ; Jassal, Amanpreet Kaur ; Rana, Love Karan ; Hundal, Maninder S ; Das, Parthasarathi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-1ce21a42c034fb83bfac6b72d0038f25b78b143013f772f88a45824115e511e03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Amination</topic><topic>Catalysis</topic><topic>Chalcones - chemical synthesis</topic><topic>Chalcones - chemistry</topic><topic>Cyclization</topic><topic>Models, Molecular</topic><topic>Palladium - chemistry</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Khajuria, Rajni</creatorcontrib><creatorcontrib>Kannaboina, Prakash</creatorcontrib><creatorcontrib>Kapoor, Kamal K</creatorcontrib><creatorcontrib>Gupta, Annah</creatorcontrib><creatorcontrib>Raina, Gaurav</creatorcontrib><creatorcontrib>Jassal, Amanpreet Kaur</creatorcontrib><creatorcontrib>Rana, Love Karan</creatorcontrib><creatorcontrib>Hundal, Maninder S</creatorcontrib><creatorcontrib>Das, Parthasarathi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Khajuria, Rajni</au><au>Kannaboina, Prakash</au><au>Kapoor, Kamal K</au><au>Gupta, Annah</au><au>Raina, Gaurav</au><au>Jassal, Amanpreet Kaur</au><au>Rana, Love Karan</au><au>Hundal, Maninder S</au><au>Das, Parthasarathi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Divergent synthesis of 4,6-diarylated pyridin-2(1H)-ones from chalcones: novel access to 2,4,6-triaryl pyridines</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2015-06-07</date><risdate>2015</risdate><volume>13</volume><issue>21</issue><spage>5944</spage><epage>5954</epage><pages>5944-5954</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A wide range of 4,6-diarylated/heterylated pyridin-2(1H)-one derivatives were synthesized in good to excellent yields from 1,3-diarylated/heterylated-2-propen-1-ones (chalcones) in one pot under metal and base-free conditions. 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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amination Catalysis Chalcones - chemical synthesis Chalcones - chemistry Cyclization Models, Molecular Palladium - chemistry Pyridines - chemical synthesis Pyridines - chemistry |
| title | Divergent synthesis of 4,6-diarylated pyridin-2(1H)-ones from chalcones: novel access to 2,4,6-triaryl pyridines |
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