Construction of novel bridged aromatic ring-fused oxazocine frameworks via an N-heterocyclic carbene-catalyzed azabenzoin reaction and radical-initiated cascade cyclization
A novel and efficient method for the construction of 1,5-methanobenzo[ f ][1,3]oxazocin-6-one compounds from o -vinyl benzaldehydes and N -acylarylimines has been developed. The synthesis proceeded through the sequential NHC-catalyzed azabenzoin reaction and radical-initiated regioselective intramol...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2021-08, Vol.8 (15), p.4192-4201 |
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| creator | Niu, Shuang-Shuo Cheng, Ying |
| description | A novel and efficient method for the construction of 1,5-methanobenzo[
f
][1,3]oxazocin-6-one compounds from
o
-vinyl benzaldehydes and
N
-acylarylimines has been developed. The synthesis proceeded through the sequential NHC-catalyzed azabenzoin reaction and radical-initiated regioselective intramolecular cascade cyclizations. This protocol features mild conditions, good functional group tolerance and high yields of products. Novel 6,10-methanopyrido[3,2-
f
][1,3]oxazocin-5-ones could also be synthesized from 2-vinylnicotinaldehyde and
N
-acylarylimines based on this method. Capitalizing on the operational simplicity and use of efficient C–C and C–X bond-forming reactions, this protocol combining NHC-catalyzed and radical-initiated reactions enables the assembly of bridged aromatic ring-fused oxazocine derivatives with versatile functional and structural diversities. |
| doi_str_mv | 10.1039/D1QO00483B |
| format | Article |
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f
][1,3]oxazocin-6-one compounds from
o
-vinyl benzaldehydes and
N
-acylarylimines has been developed. The synthesis proceeded through the sequential NHC-catalyzed azabenzoin reaction and radical-initiated regioselective intramolecular cascade cyclizations. This protocol features mild conditions, good functional group tolerance and high yields of products. Novel 6,10-methanopyrido[3,2-
f
][1,3]oxazocin-5-ones could also be synthesized from 2-vinylnicotinaldehyde and
N
-acylarylimines based on this method. Capitalizing on the operational simplicity and use of efficient C–C and C–X bond-forming reactions, this protocol combining NHC-catalyzed and radical-initiated reactions enables the assembly of bridged aromatic ring-fused oxazocine derivatives with versatile functional and structural diversities.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D1QO00483B</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Chemical reactions ; Chemical synthesis ; Construction ; Crystallography ; Functional groups ; NMR ; Nuclear magnetic resonance ; Organic chemistry ; Structure-function relationships</subject><ispartof>Organic Chemistry Frontiers, 2021-08, Vol.8 (15), p.4192-4201</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-4dd020d2f2899b2025622368fba503c0a44213821f364fc35b811cf0713539a83</citedby><cites>FETCH-LOGICAL-c259t-4dd020d2f2899b2025622368fba503c0a44213821f364fc35b811cf0713539a83</cites><orcidid>0000-0002-2598-2974</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Niu, Shuang-Shuo</creatorcontrib><creatorcontrib>Cheng, Ying</creatorcontrib><title>Construction of novel bridged aromatic ring-fused oxazocine frameworks via an N-heterocyclic carbene-catalyzed azabenzoin reaction and radical-initiated cascade cyclization</title><title>Organic Chemistry Frontiers</title><description>A novel and efficient method for the construction of 1,5-methanobenzo[
f
][1,3]oxazocin-6-one compounds from
o
-vinyl benzaldehydes and
N
-acylarylimines has been developed. The synthesis proceeded through the sequential NHC-catalyzed azabenzoin reaction and radical-initiated regioselective intramolecular cascade cyclizations. This protocol features mild conditions, good functional group tolerance and high yields of products. Novel 6,10-methanopyrido[3,2-
f
][1,3]oxazocin-5-ones could also be synthesized from 2-vinylnicotinaldehyde and
N
-acylarylimines based on this method. Capitalizing on the operational simplicity and use of efficient C–C and C–X bond-forming reactions, this protocol combining NHC-catalyzed and radical-initiated reactions enables the assembly of bridged aromatic ring-fused oxazocine derivatives with versatile functional and structural diversities.</description><subject>Aromatic compounds</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Construction</subject><subject>Crystallography</subject><subject>Functional groups</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Structure-function relationships</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpNkV9LwzAUxYsoOOZe_AQB34TqTdJs7aPOvzAUQZ_LbZrMzC6ZSTpdP5Mf0s4J-nQvh989h8tJkmMKZxR4cX5Fnx4Bspxf7iUDBoKlGWXF_r_9MBmFsAAAysQYxGSQfE2dDdG3MhpnidPEurVqSOVNPVc1Qe-WGI0k3th5qtvQa-4TOyeNVUR7XKoP598CWRskaMlD-qqi8k5uZNNfSfSVsiqVGLHZdFvDDnulc8YSr3CXirYmHmsjsUmNNdFg7EmJQWKtyI9Vh1vyKDnQ2AQ1-p3D5OXm-nl6l84eb--nF7NUMlHENKtrYFAzzfKiqBj0vzLGx7muUACXgFnGKM8Z1XycaclFlVMqNUwoF7zAnA-Tk53vyrv3VoVYLlzrbR9ZMiEEh5yyrKdOd5T0LgSvdLnyZol-U1Iot4WUf4Xwb8GPgHU</recordid><startdate>20210807</startdate><enddate>20210807</enddate><creator>Niu, Shuang-Shuo</creator><creator>Cheng, Ying</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-2598-2974</orcidid></search><sort><creationdate>20210807</creationdate><title>Construction of novel bridged aromatic ring-fused oxazocine frameworks via an N-heterocyclic carbene-catalyzed azabenzoin reaction and radical-initiated cascade cyclization</title><author>Niu, Shuang-Shuo ; Cheng, Ying</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-4dd020d2f2899b2025622368fba503c0a44213821f364fc35b811cf0713539a83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aromatic compounds</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Construction</topic><topic>Crystallography</topic><topic>Functional groups</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Structure-function relationships</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Niu, Shuang-Shuo</creatorcontrib><creatorcontrib>Cheng, Ying</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Niu, Shuang-Shuo</au><au>Cheng, Ying</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Construction of novel bridged aromatic ring-fused oxazocine frameworks via an N-heterocyclic carbene-catalyzed azabenzoin reaction and radical-initiated cascade cyclization</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2021-08-07</date><risdate>2021</risdate><volume>8</volume><issue>15</issue><spage>4192</spage><epage>4201</epage><pages>4192-4201</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>A novel and efficient method for the construction of 1,5-methanobenzo[
f
][1,3]oxazocin-6-one compounds from
o
-vinyl benzaldehydes and
N
-acylarylimines has been developed. The synthesis proceeded through the sequential NHC-catalyzed azabenzoin reaction and radical-initiated regioselective intramolecular cascade cyclizations. This protocol features mild conditions, good functional group tolerance and high yields of products. Novel 6,10-methanopyrido[3,2-
f
][1,3]oxazocin-5-ones could also be synthesized from 2-vinylnicotinaldehyde and
N
-acylarylimines based on this method. Capitalizing on the operational simplicity and use of efficient C–C and C–X bond-forming reactions, this protocol combining NHC-catalyzed and radical-initiated reactions enables the assembly of bridged aromatic ring-fused oxazocine derivatives with versatile functional and structural diversities.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D1QO00483B</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-2598-2974</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2021-08, Vol.8 (15), p.4192-4201 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
| recordid | cdi_proquest_journals_2555308124 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Aromatic compounds Chemical reactions Chemical synthesis Construction Crystallography Functional groups NMR Nuclear magnetic resonance Organic chemistry Structure-function relationships |
| title | Construction of novel bridged aromatic ring-fused oxazocine frameworks via an N-heterocyclic carbene-catalyzed azabenzoin reaction and radical-initiated cascade cyclization |
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