Diastereoselective construction of cage-like and bridged azaheterocycles through dearomative maximization of the reactive sites of azaarenes
A highly diastereoselective multicomponent dearomative multifunctionalization of N -alkyl activated azaarenes with 1,5-diazapentadienium salts has been developed, which not only represented a significant advance in maximum utilization of the reactive sites of azaarenes, but also provided a convenien...
Gespeichert in:
| Veröffentlicht in: | Organic Chemistry Frontiers 2021-01, Vol.8 (2), p.204-211 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 211 |
|---|---|
| container_issue | 2 |
| container_start_page | 204 |
| container_title | Organic Chemistry Frontiers |
| container_volume | 8 |
| creator | Miao, Hongjie Bai, Xuguan Wang, Lele Yu, Junhui Bu, Zhanwei Wang, Qilin |
| description | A highly diastereoselective multicomponent dearomative multifunctionalization of
N
-alkyl activated azaarenes with 1,5-diazapentadienium salts has been developed, which not only represented a significant advance in maximum utilization of the reactive sites of azaarenes, but also provided a convenient and robust approach to access structurally rigid and synthetically challenging cage-like and bridged azaheterocycles. As an important complement, we also realized the dearomative multi-functionalization of
N
-aryl azaarenes through an
in situ
activation strategy. Moreover, the workup-directed selective tri- and bi-functionalization of isoquinolinium salts have been accomplished. |
| doi_str_mv | 10.1039/D0QO01196G |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2480791951</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2480791951</sourcerecordid><originalsourceid>FETCH-LOGICAL-c281t-610c20bf8d2ada591837cb01ab31b76efbb419b6615c30d6a96a6866001e73a03</originalsourceid><addsrcrecordid>eNpNkN1Kw0AQhRdRsNTe-AQL3gnRnaTZJJfSahUKRdDrMNlMmq1Jtu5uxPYZfGijVfRqfjjnO8wwdg7iCkSUXc_F40oAZHJxxEahiMNgCmF2_K8_ZRPnNkIICGMp4mTEPuYanSdLxlFDyus34sp0ztt-GEzHTcUVrilo9Atx7EpeWF2uqeS4x5oGp1E71ZDjvramX9e8JLSmxW9Si--61Xv8JfmauCU8xDjtB9uwHUhoqSN3xk4qbBxNfuqYPd_dPs3ug-Vq8TC7WQYqTMEHEoQKRVGlZYglxhmkUaIKAVhEUCSSqqKYQlZICbGKRCkxkyhTKYezKYlQRGN2ceBurXntyfl8Y3rbDZF5OE1FkkEWw6C6PKiUNc5ZqvKt1S3aXQ4i_3p4_vfw6BP2E3XP</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2480791951</pqid></control><display><type>article</type><title>Diastereoselective construction of cage-like and bridged azaheterocycles through dearomative maximization of the reactive sites of azaarenes</title><source>Royal Society Of Chemistry Journals 2008-</source><creator>Miao, Hongjie ; Bai, Xuguan ; Wang, Lele ; Yu, Junhui ; Bu, Zhanwei ; Wang, Qilin</creator><creatorcontrib>Miao, Hongjie ; Bai, Xuguan ; Wang, Lele ; Yu, Junhui ; Bu, Zhanwei ; Wang, Qilin</creatorcontrib><description>A highly diastereoselective multicomponent dearomative multifunctionalization of
N
-alkyl activated azaarenes with 1,5-diazapentadienium salts has been developed, which not only represented a significant advance in maximum utilization of the reactive sites of azaarenes, but also provided a convenient and robust approach to access structurally rigid and synthetically challenging cage-like and bridged azaheterocycles. As an important complement, we also realized the dearomative multi-functionalization of
N
-aryl azaarenes through an
in situ
activation strategy. Moreover, the workup-directed selective tri- and bi-functionalization of isoquinolinium salts have been accomplished.</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/D0QO01196G</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Cages ; Crystallography ; NMR ; Nuclear magnetic resonance ; Organic chemistry ; Salts ; Stereoselectivity</subject><ispartof>Organic Chemistry Frontiers, 2021-01, Vol.8 (2), p.204-211</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-610c20bf8d2ada591837cb01ab31b76efbb419b6615c30d6a96a6866001e73a03</citedby><cites>FETCH-LOGICAL-c281t-610c20bf8d2ada591837cb01ab31b76efbb419b6615c30d6a96a6866001e73a03</cites><orcidid>0000-0003-4637-0392</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27911,27912</link.rule.ids></links><search><creatorcontrib>Miao, Hongjie</creatorcontrib><creatorcontrib>Bai, Xuguan</creatorcontrib><creatorcontrib>Wang, Lele</creatorcontrib><creatorcontrib>Yu, Junhui</creatorcontrib><creatorcontrib>Bu, Zhanwei</creatorcontrib><creatorcontrib>Wang, Qilin</creatorcontrib><title>Diastereoselective construction of cage-like and bridged azaheterocycles through dearomative maximization of the reactive sites of azaarenes</title><title>Organic Chemistry Frontiers</title><description>A highly diastereoselective multicomponent dearomative multifunctionalization of
N
-alkyl activated azaarenes with 1,5-diazapentadienium salts has been developed, which not only represented a significant advance in maximum utilization of the reactive sites of azaarenes, but also provided a convenient and robust approach to access structurally rigid and synthetically challenging cage-like and bridged azaheterocycles. As an important complement, we also realized the dearomative multi-functionalization of
N
-aryl azaarenes through an
in situ
activation strategy. Moreover, the workup-directed selective tri- and bi-functionalization of isoquinolinium salts have been accomplished.</description><subject>Aromatic compounds</subject><subject>Cages</subject><subject>Crystallography</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Salts</subject><subject>Stereoselectivity</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>eNpNkN1Kw0AQhRdRsNTe-AQL3gnRnaTZJJfSahUKRdDrMNlMmq1Jtu5uxPYZfGijVfRqfjjnO8wwdg7iCkSUXc_F40oAZHJxxEahiMNgCmF2_K8_ZRPnNkIICGMp4mTEPuYanSdLxlFDyus34sp0ztt-GEzHTcUVrilo9Atx7EpeWF2uqeS4x5oGp1E71ZDjvramX9e8JLSmxW9Si--61Xv8JfmauCU8xDjtB9uwHUhoqSN3xk4qbBxNfuqYPd_dPs3ug-Vq8TC7WQYqTMEHEoQKRVGlZYglxhmkUaIKAVhEUCSSqqKYQlZICbGKRCkxkyhTKYezKYlQRGN2ceBurXntyfl8Y3rbDZF5OE1FkkEWw6C6PKiUNc5ZqvKt1S3aXQ4i_3p4_vfw6BP2E3XP</recordid><startdate>20210126</startdate><enddate>20210126</enddate><creator>Miao, Hongjie</creator><creator>Bai, Xuguan</creator><creator>Wang, Lele</creator><creator>Yu, Junhui</creator><creator>Bu, Zhanwei</creator><creator>Wang, Qilin</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/0000-0003-4637-0392</orcidid></search><sort><creationdate>20210126</creationdate><title>Diastereoselective construction of cage-like and bridged azaheterocycles through dearomative maximization of the reactive sites of azaarenes</title><author>Miao, Hongjie ; Bai, Xuguan ; Wang, Lele ; Yu, Junhui ; Bu, Zhanwei ; Wang, Qilin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-610c20bf8d2ada591837cb01ab31b76efbb419b6615c30d6a96a6866001e73a03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aromatic compounds</topic><topic>Cages</topic><topic>Crystallography</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Salts</topic><topic>Stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miao, Hongjie</creatorcontrib><creatorcontrib>Bai, Xuguan</creatorcontrib><creatorcontrib>Wang, Lele</creatorcontrib><creatorcontrib>Yu, Junhui</creatorcontrib><creatorcontrib>Bu, Zhanwei</creatorcontrib><creatorcontrib>Wang, Qilin</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>Miao, Hongjie</au><au>Bai, Xuguan</au><au>Wang, Lele</au><au>Yu, Junhui</au><au>Bu, Zhanwei</au><au>Wang, Qilin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diastereoselective construction of cage-like and bridged azaheterocycles through dearomative maximization of the reactive sites of azaarenes</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2021-01-26</date><risdate>2021</risdate><volume>8</volume><issue>2</issue><spage>204</spage><epage>211</epage><pages>204-211</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>A highly diastereoselective multicomponent dearomative multifunctionalization of
N
-alkyl activated azaarenes with 1,5-diazapentadienium salts has been developed, which not only represented a significant advance in maximum utilization of the reactive sites of azaarenes, but also provided a convenient and robust approach to access structurally rigid and synthetically challenging cage-like and bridged azaheterocycles. As an important complement, we also realized the dearomative multi-functionalization of
N
-aryl azaarenes through an
in situ
activation strategy. Moreover, the workup-directed selective tri- and bi-functionalization of isoquinolinium salts have been accomplished.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D0QO01196G</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-4637-0392</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2021-01, Vol.8 (2), p.204-211 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
| recordid | cdi_proquest_journals_2480791951 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Aromatic compounds Cages Crystallography NMR Nuclear magnetic resonance Organic chemistry Salts Stereoselectivity |
| title | Diastereoselective construction of cage-like and bridged azaheterocycles through dearomative maximization of the reactive sites of azaarenes |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T14%3A55%3A29IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Diastereoselective%20construction%20of%20cage-like%20and%20bridged%20azaheterocycles%20through%20dearomative%20maximization%20of%20the%20reactive%20sites%20of%20azaarenes&rft.jtitle=Organic%20Chemistry%20Frontiers&rft.au=Miao,%20Hongjie&rft.date=2021-01-26&rft.volume=8&rft.issue=2&rft.spage=204&rft.epage=211&rft.pages=204-211&rft.issn=2052-4129&rft.eissn=2052-4129&rft_id=info:doi/10.1039/D0QO01196G&rft_dat=%3Cproquest_cross%3E2480791951%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2480791951&rft_id=info:pmid/&rfr_iscdi=true |