Ring opening of dihydro-2-pyridones and intramolecular Diels–Alder reactions
A new ring-opening reaction of 5,6-dihydro-2-pyridones was discovered. Compounds 1 and 7 were converted to the dienoic amides 2 and 8 by reaction with sodium hydride at room temperature. N-Allylation of compounds 2 and 8 followed by IMDA reaction provided the cis-fused hexahydro-1-indolones 5 and 10...
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| Veröffentlicht in: | Tetrahedron 2012-01, Vol.68 (4), p.1185-1191 |
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| creator | Chou, Shang-Shing P. Wu, Chien-Jung J. |
| description | A new ring-opening reaction of 5,6-dihydro-2-pyridones was discovered. Compounds
1 and
7 were converted to the dienoic amides
2 and
8 by reaction with sodium hydride at room temperature. N-Allylation of compounds
2 and
8 followed by IMDA reaction provided the
cis-fused hexahydro-1-indolones
5 and
10, respectively. Treatment of compounds
5 and
10 with DBU in refluxing ethyl acetate gave the conjugated products
6 and
11, which were further transformed to the amides
12–
15. The phenylthio group of compound
11 was substituted by a methyl group to give product
16.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2011.11.060 |
| format | Article |
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1 and
7 were converted to the dienoic amides
2 and
8 by reaction with sodium hydride at room temperature. N-Allylation of compounds
2 and
8 followed by IMDA reaction provided the
cis-fused hexahydro-1-indolones
5 and
10, respectively. Treatment of compounds
5 and
10 with DBU in refluxing ethyl acetate gave the conjugated products
6 and
11, which were further transformed to the amides
12–
15. The phenylthio group of compound
11 was substituted by a methyl group to give product
16.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2011.11.060</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Amides ; Aza-Diels–Alder reaction ; Chemistry ; Diels-Alder reactions ; Dihydro-2-pyridones ; Ethyl acetate ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Intramolecular Diels–Alder reactions ; Isoindolones ; Organic chemistry ; Preparations and properties ; Refluxing ; Ring opening ; Sodium hydrides ; Tetrahedrons</subject><ispartof>Tetrahedron, 2012-01, Vol.68 (4), p.1185-1191</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c360t-4b7e4ad97743c59e1977efcb691612eb07856f863224cfdbf9759b0c3d8eae23</citedby><cites>FETCH-LOGICAL-c360t-4b7e4ad97743c59e1977efcb691612eb07856f863224cfdbf9759b0c3d8eae23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tet.2011.11.060$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27907,27908,45978</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25406534$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Chou, Shang-Shing P.</creatorcontrib><creatorcontrib>Wu, Chien-Jung J.</creatorcontrib><title>Ring opening of dihydro-2-pyridones and intramolecular Diels–Alder reactions</title><title>Tetrahedron</title><description>A new ring-opening reaction of 5,6-dihydro-2-pyridones was discovered. Compounds
1 and
7 were converted to the dienoic amides
2 and
8 by reaction with sodium hydride at room temperature. N-Allylation of compounds
2 and
8 followed by IMDA reaction provided the
cis-fused hexahydro-1-indolones
5 and
10, respectively. Treatment of compounds
5 and
10 with DBU in refluxing ethyl acetate gave the conjugated products
6 and
11, which were further transformed to the amides
12–
15. The phenylthio group of compound
11 was substituted by a methyl group to give product
16.
[Display omitted]</description><subject>Amides</subject><subject>Aza-Diels–Alder reaction</subject><subject>Chemistry</subject><subject>Diels-Alder reactions</subject><subject>Dihydro-2-pyridones</subject><subject>Ethyl acetate</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Intramolecular Diels–Alder reactions</subject><subject>Isoindolones</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Refluxing</subject><subject>Ring opening</subject><subject>Sodium hydrides</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9kMtKAzEUhoMoWC8P4G42gpupJ5fJdHBVvIMoSPchk5zRlGlSk6nQne_gG_okplZcCj-cs_jOf-Aj5ITCmAKV5_PxgMOYAaXjHJCwQ0ZUSFFWgspdMgIQUApgsE8OUpoDZJLxEXl8dv6lCEv0P7MrrHtd2xhKVi7X0dngMRXa28L5IepF6NGseh2LK4d9-vr4nPYWYxFRm8EFn47IXqf7hMe_85DMbq5nl3flw9Pt_eX0oTRcwlCKtkahbVPXgpuqQZo37EwrGyopwxbqSSW7ieSMCdPZtmvqqmnBcDtBjYwfkrNt7TKGtxWmQS1cMtj32mNYJUVrIWTdAOcZpVvUxJBSxE4to1vouFYU1EadmqusTm3UqZysLt-c_tbrZHTfRe2NS3-HrBIgKy4yd7Hlsgt8dxhVMg69QesimkHZ4P758g3uq4S2</recordid><startdate>20120128</startdate><enddate>20120128</enddate><creator>Chou, Shang-Shing P.</creator><creator>Wu, Chien-Jung J.</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>20120128</creationdate><title>Ring opening of dihydro-2-pyridones and intramolecular Diels–Alder reactions</title><author>Chou, Shang-Shing P. ; Wu, Chien-Jung J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c360t-4b7e4ad97743c59e1977efcb691612eb07856f863224cfdbf9759b0c3d8eae23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Amides</topic><topic>Aza-Diels–Alder reaction</topic><topic>Chemistry</topic><topic>Diels-Alder reactions</topic><topic>Dihydro-2-pyridones</topic><topic>Ethyl acetate</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Intramolecular Diels–Alder reactions</topic><topic>Isoindolones</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Refluxing</topic><topic>Ring opening</topic><topic>Sodium hydrides</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chou, Shang-Shing P.</creatorcontrib><creatorcontrib>Wu, Chien-Jung J.</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>Chou, Shang-Shing P.</au><au>Wu, Chien-Jung J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ring opening of dihydro-2-pyridones and intramolecular Diels–Alder reactions</atitle><jtitle>Tetrahedron</jtitle><date>2012-01-28</date><risdate>2012</risdate><volume>68</volume><issue>4</issue><spage>1185</spage><epage>1191</epage><pages>1185-1191</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>A new ring-opening reaction of 5,6-dihydro-2-pyridones was discovered. Compounds
1 and
7 were converted to the dienoic amides
2 and
8 by reaction with sodium hydride at room temperature. N-Allylation of compounds
2 and
8 followed by IMDA reaction provided the
cis-fused hexahydro-1-indolones
5 and
10, respectively. Treatment of compounds
5 and
10 with DBU in refluxing ethyl acetate gave the conjugated products
6 and
11, which were further transformed to the amides
12–
15. The phenylthio group of compound
11 was substituted by a methyl group to give product
16.
[Display omitted]</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2011.11.060</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2012-01, Vol.68 (4), p.1185-1191 |
| issn | 0040-4020 1464-5416 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1744679033 |
| source | Elsevier ScienceDirect Journals Complete - AutoHoldings |
| subjects | Amides Aza-Diels–Alder reaction Chemistry Diels-Alder reactions Dihydro-2-pyridones Ethyl acetate Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Intramolecular Diels–Alder reactions Isoindolones Organic chemistry Preparations and properties Refluxing Ring opening Sodium hydrides Tetrahedrons |
| title | Ring opening of dihydro-2-pyridones and intramolecular Diels–Alder reactions |
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