Synthesis and Rearrangement of Quinone-Embedded Epoxycyclopentenones: A New Avenue to Pyranonaphthoquinones and Indenopyranones
The epoxyquinones (e.g., 24), readily assembled in one step from the quinols (e.g., 27) by a simplified version of the Dowd oxidation, are shown to undergo rearrangement to pyranonaphthoquinones (e.g., 28) and their ring contracted homologues (e.g., 29) on flash vacuum pyrolysis at 450 °C and 0.01 T...
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| Veröffentlicht in: | Journal of organic chemistry 2009-02, Vol.74 (4), p.1598-1604 |
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| container_title | Journal of organic chemistry |
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| creator | De, Saroj R Ghorai, Sujit K Mal, Dipakranjan |
| description | The epoxyquinones (e.g., 24), readily assembled in one step from the quinols (e.g., 27) by a simplified version of the Dowd oxidation, are shown to undergo rearrangement to pyranonaphthoquinones (e.g., 28) and their ring contracted homologues (e.g., 29) on flash vacuum pyrolysis at 450 °C and 0.01 Torr. The rearrangement has been demonstrated to be useful for a regiospecific synthesis of lambertellin (3). Similarly, the masked aziridinocyclopentanone 9 rearranges to 2-pyridone (37). |
| doi_str_mv | 10.1021/jo801961w |
| format | Article |
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The rearrangement has been demonstrated to be useful for a regiospecific synthesis of lambertellin (3). Similarly, the masked aziridinocyclopentanone 9 rearranges to 2-pyridone (37).</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo801961w</identifier><identifier>PMID: 19199663</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; 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 ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2009-02, Vol.74 (4), p.1598-1604</ispartof><rights>Copyright © 2009 American Chemical Society</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a343t-343144f618a9654a016a93ffc1318cc9b292c925b2366a93d9a9182e4615ab133</citedby><cites>FETCH-LOGICAL-a343t-343144f618a9654a016a93ffc1318cc9b292c925b2366a93d9a9182e4615ab133</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo801961w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo801961w$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21177572$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19199663$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>De, Saroj R</creatorcontrib><creatorcontrib>Ghorai, Sujit K</creatorcontrib><creatorcontrib>Mal, Dipakranjan</creatorcontrib><title>Synthesis and Rearrangement of Quinone-Embedded Epoxycyclopentenones: A New Avenue to Pyranonaphthoquinones and Indenopyranones</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The epoxyquinones (e.g., 24), readily assembled in one step from the quinols (e.g., 27) by a simplified version of the Dowd oxidation, are shown to undergo rearrangement to pyranonaphthoquinones (e.g., 28) and their ring contracted homologues (e.g., 29) on flash vacuum pyrolysis at 450 °C and 0.01 Torr. The rearrangement has been demonstrated to be useful for a regiospecific synthesis of lambertellin (3). Similarly, the masked aziridinocyclopentanone 9 rearranges to 2-pyridone (37).</description><subject>Chemistry</subject><subject>Exact sciences and technology</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>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNptkEFP2zAYhq0JNDrYYX8A-bJJOwT82bFb71ahbiAhGBucI8f5QoMSO8TJIKf9dVylai_4YB_ex89nv4R8AXYGjMP5k18w0ApePpAZSM4SpVl6QGaMcZ4IrsQR-RTCE4tLSvmRHIEGrZUSM_L_7-j6NYYqUOMK-gdN1xn3iA26nvqS3g2V8w6TVZNjUWBBV61_He1oa99GBDdh-EGX9AZf6PIfugFp7-nvMVq8M-26X_vnyTFNuHJFvNROOYYTcliaOuDn7XlMHn6u7i8uk-vbX1cXy-vEiFT0SdwgTUsFC6OVTA0DZbQoSwsCFtbqnGtuNZc5F2qTFNpoWHBMFUiTgxDH5Nvkbbv4Hgx91lTBYl0bh34ImVKai7mSEfw-gbbzIXRYZm1XNaYbM2DZpu1s13ZkT7fSIW-w2JPbeiPwdQuYYE1dxk_bKuw4DjCfyznfc8aG6B86F7t4Z-AbNzaU7Q</recordid><startdate>20090220</startdate><enddate>20090220</enddate><creator>De, Saroj R</creator><creator>Ghorai, Sujit K</creator><creator>Mal, Dipakranjan</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20090220</creationdate><title>Synthesis and Rearrangement of Quinone-Embedded Epoxycyclopentenones: A New Avenue to Pyranonaphthoquinones and Indenopyranones</title><author>De, Saroj R ; Ghorai, Sujit K ; Mal, Dipakranjan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a343t-343144f618a9654a016a93ffc1318cc9b292c925b2366a93d9a9182e4615ab133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</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>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>De, Saroj R</creatorcontrib><creatorcontrib>Ghorai, Sujit K</creatorcontrib><creatorcontrib>Mal, Dipakranjan</creatorcontrib><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>De, Saroj R</au><au>Ghorai, Sujit K</au><au>Mal, Dipakranjan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Rearrangement of Quinone-Embedded Epoxycyclopentenones: A New Avenue to Pyranonaphthoquinones and Indenopyranones</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2009-02-20</date><risdate>2009</risdate><volume>74</volume><issue>4</issue><spage>1598</spage><epage>1604</epage><pages>1598-1604</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The epoxyquinones (e.g., 24), readily assembled in one step from the quinols (e.g., 27) by a simplified version of the Dowd oxidation, are shown to undergo rearrangement to pyranonaphthoquinones (e.g., 28) and their ring contracted homologues (e.g., 29) on flash vacuum pyrolysis at 450 °C and 0.01 Torr. The rearrangement has been demonstrated to be useful for a regiospecific synthesis of lambertellin (3). Similarly, the masked aziridinocyclopentanone 9 rearranges to 2-pyridone (37).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>19199663</pmid><doi>10.1021/jo801961w</doi><tpages>7</tpages></addata></record> |
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| subjects | Chemistry Exact sciences and technology 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 Organic chemistry Preparations and properties |
| title | Synthesis and Rearrangement of Quinone-Embedded Epoxycyclopentenones: A New Avenue to Pyranonaphthoquinones and Indenopyranones |
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