Inverse Electron Demand Diels Alder Reaction of Aza‑o‑Quinone Methides and Enaminones: Accessing 3‑Aroyl Quinolines and Indeno[1,2‑b]quinolinones
We have developed a Diels Alder cycloaddition route toward 3-aroyl quinolines from enaminones and in situ generated aza-o-quinone methides. The reaction was found to be general with a range of substituted enaminones and aza-o-quinone methides, and we could validate the applicability of the methodolo...
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| Veröffentlicht in: | Journal of organic chemistry 2022-11, Vol.87 (21), p.13708-13714 |
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| container_end_page | 13714 |
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| container_issue | 21 |
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| container_title | Journal of organic chemistry |
| container_volume | 87 |
| creator | P, Rahul S, Veena John, Jubi |
| description | We have developed a Diels Alder cycloaddition route toward 3-aroyl quinolines from enaminones and in situ generated aza-o-quinone methides. The reaction was found to be general with a range of substituted enaminones and aza-o-quinone methides, and we could validate the applicability of the methodology in gram scale. We also demonstrated a one-pot strategy toward 3-acyl quinolines starting from the corresponding aliphatic ketones. Finally, we utilized the 3-aroyl quinolines for synthesizing indeno[1,2-b]quinolinones via a Pd-catalyzed dual C–H activation approach. |
| doi_str_mv | 10.1021/acs.joc.2c01361 |
| format | Article |
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The reaction was found to be general with a range of substituted enaminones and aza-o-quinone methides, and we could validate the applicability of the methodology in gram scale. We also demonstrated a one-pot strategy toward 3-acyl quinolines starting from the corresponding aliphatic ketones. Finally, we utilized the 3-aroyl quinolines for synthesizing indeno[1,2-b]quinolinones via a Pd-catalyzed dual C–H activation approach.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.2c01361</identifier><identifier>PMID: 36177973</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Cycloaddition Reaction ; Electrons ; Indolequinones ; Quinolones</subject><ispartof>Journal of organic chemistry, 2022-11, Vol.87 (21), p.13708-13714</ispartof><rights>2022 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-fed4f0bd82a391e63e7aa86441c137d897b9b75034e21d3100a5db1729ed9bde3</citedby><cites>FETCH-LOGICAL-a333t-fed4f0bd82a391e63e7aa86441c137d897b9b75034e21d3100a5db1729ed9bde3</cites><orcidid>0000-0003-0483-2026</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.2c01361$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.2c01361$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36177973$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>P, Rahul</creatorcontrib><creatorcontrib>S, Veena</creatorcontrib><creatorcontrib>John, Jubi</creatorcontrib><title>Inverse Electron Demand Diels Alder Reaction of Aza‑o‑Quinone Methides and Enaminones: Accessing 3‑Aroyl Quinolines and Indeno[1,2‑b]quinolinones</title><title>Journal of organic chemistry</title><addtitle>J. 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Finally, we utilized the 3-aroyl quinolines for synthesizing indeno[1,2-b]quinolinones via a Pd-catalyzed dual C–H activation approach.</description><subject>Cycloaddition Reaction</subject><subject>Electrons</subject><subject>Indolequinones</subject><subject>Quinolones</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kc1K9DAUhoMoOv6s3UmWwmfH_LTN1F3RUQcUUXQlUtLkVCttokn7ga68BZfenldixqnuDIRAzvO8cHgR2qZkTAmj-1L58aNVY6YI5SldQiOaMBKlGYmX0YgQxiLOUr6G1r1_JOEkSbKK1gIqRCb4CH3MzH9wHvC0AdU5a_ARtNJofFRD43HeaHD4CqTq6jCzFc5f5efbuw33sq-NNYDPoXuoNXg816ZGtt_f_gDnSoH3tbnHPOC5sy8N_paa2gz4zGgw9pbusUCUd8_DdO5vopVKNh62hncD3RxPrw9Po7OLk9lhfhZJznkXVaDjipR6wiTPKKQchJSTNI6polzoSSbKrBQJ4TEwqjklRCa6pIJloLNSA99Au4vcJ2efe_Bd0dZeQdNIA7b3BROMxJxNSBbQ_QWqnPXeQVU8ubqV7qWgpJj3UYQ-itBHMfQRjJ0hvC9b0L_8TwEB-LcAFmbvTNj1z7gvEkGbTA</recordid><startdate>20221104</startdate><enddate>20221104</enddate><creator>P, Rahul</creator><creator>S, Veena</creator><creator>John, Jubi</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>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-0483-2026</orcidid></search><sort><creationdate>20221104</creationdate><title>Inverse Electron Demand Diels Alder Reaction of Aza‑o‑Quinone Methides and Enaminones: Accessing 3‑Aroyl Quinolines and Indeno[1,2‑b]quinolinones</title><author>P, Rahul ; S, Veena ; John, Jubi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-fed4f0bd82a391e63e7aa86441c137d897b9b75034e21d3100a5db1729ed9bde3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Cycloaddition Reaction</topic><topic>Electrons</topic><topic>Indolequinones</topic><topic>Quinolones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>P, Rahul</creatorcontrib><creatorcontrib>S, Veena</creatorcontrib><creatorcontrib>John, Jubi</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>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>P, Rahul</au><au>S, Veena</au><au>John, Jubi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inverse Electron Demand Diels Alder Reaction of Aza‑o‑Quinone Methides and Enaminones: Accessing 3‑Aroyl Quinolines and Indeno[1,2‑b]quinolinones</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2022-11-04</date><risdate>2022</risdate><volume>87</volume><issue>21</issue><spage>13708</spage><epage>13714</epage><pages>13708-13714</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>We have developed a Diels Alder cycloaddition route toward 3-aroyl quinolines from enaminones and in situ generated aza-o-quinone methides. The reaction was found to be general with a range of substituted enaminones and aza-o-quinone methides, and we could validate the applicability of the methodology in gram scale. We also demonstrated a one-pot strategy toward 3-acyl quinolines starting from the corresponding aliphatic ketones. 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| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2022-11, Vol.87 (21), p.13708-13714 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Cycloaddition Reaction Electrons Indolequinones Quinolones |
| title | Inverse Electron Demand Diels Alder Reaction of Aza‑o‑Quinone Methides and Enaminones: Accessing 3‑Aroyl Quinolines and Indeno[1,2‑b]quinolinones |
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