Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H -pyrroles: Synthesis of Benzo/Furo/Thieno[ e ]-Fused 1 H -Indol-7-oles and Their Transformations
The Co(III)-catalyzed reaction of 1,3-dicarbonyl compounds with 2-(diazoacetyl)-2 -azirines, prepared by a simplified procedure from 2 -azirin-2-carbonyl chlorides, led in high yields to the formation of 2-(diazoacetyl)pyrroles, while leaving the diazoacetyl function intact. The intramolecular aroma...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2019-08, Vol.84 (16), p.10388-10401 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 10401 |
|---|---|
| container_issue | 16 |
| container_start_page | 10388 |
| container_title | Journal of organic chemistry |
| container_volume | 84 |
| creator | Bodunov, Vladimir A Galenko, Ekaterina E Sakharov, Pavel A Novikov, Mikhail S Khlebnikov, Alexander F |
| description | The Co(III)-catalyzed reaction of 1,3-dicarbonyl compounds with 2-(diazoacetyl)-2
-azirines, prepared by a simplified procedure from 2
-azirin-2-carbonyl chlorides, led in high yields to the formation of 2-(diazoacetyl)pyrroles, while leaving the diazoacetyl function intact. The intramolecular aromatic substitution reaction of 2-(diazoacetyl)pyrroles, catalyzed by Cu(OTf)
, provided selectively previously unknown benzo[
]- and hetero[
]-fused indol-7-oles in good yields. Formylation of benzo[
]indol-4-ol led selectively to the 5-formyl derivative, which is a good precursor for an unusual salen ligand and its Ni-complex. Triflates prepared from benzo[
]indol-4-oles gave various 4-substituted benzo[
]indoles carrying aryl, 2-thienyl, 2-pyridyl, and alkynyl groups, in excellent yields using cross-coupling reactions. 4-(2-Pyridyl)benzo[
]indoles, upon treatment with BF
·Et
O/Et
N, afforded a new type of fluorescent boron complexes with large Stokes shifts. |
| doi_str_mv | 10.1021/acs.joc.9b01573 |
| format | Article |
| fullrecord | <record><control><sourceid>pubmed_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_acs_joc_9b01573</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>31309836</sourcerecordid><originalsourceid>FETCH-LOGICAL-c179t-1b77482d965cd741a294e4e9ad2adfb7b5b0070be49805d3562ffaf04962d50b3</originalsourceid><addsrcrecordid>eNo9kT1PwzAQhi0EgvIxsyGPMLjxR5zUbKWitBISA2VCKHLiixqU2pWdIKV_jL-Hy5eXd_A9d6d7ELpkdMwoZ4muwvjdVWNVUiZzcYBGTHJKMkXTQzSilHMieCZO0GkI7zQ-KeUxOhFMUDUR2Qh9PkMLVdd8AJ71ZKY73Q47MHhpO683Lv71rfZ4am3MrnEWuxoLMvVDmyygg5iEk2vT6J3TFXRDe0MYXmCyHbyPeLjFz4Pt1hCasEfvwO5cMu-9S1brBqx7xYDfyLwPceg3uLTGtSQnexhra_BqDY3HK69tqJ3ffG8RztFRrdsAF795hl7m96vZgjw-PSxn00dSsVx1hJV5nk64UZmsTJ4yzVUKKShtuDZ1mZeypDSnJaRqQqURMuN1rWuaqowbSUtxhpKfvpV3IXioi61vNtoPBaPFXkERFRRRQfGrIBJXP8S2Lzdg_uv_bi6-AFOUhPA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H -pyrroles: Synthesis of Benzo/Furo/Thieno[ e ]-Fused 1 H -Indol-7-oles and Their Transformations</title><source>ACS Publications</source><creator>Bodunov, Vladimir A ; Galenko, Ekaterina E ; Sakharov, Pavel A ; Novikov, Mikhail S ; Khlebnikov, Alexander F</creator><creatorcontrib>Bodunov, Vladimir A ; Galenko, Ekaterina E ; Sakharov, Pavel A ; Novikov, Mikhail S ; Khlebnikov, Alexander F</creatorcontrib><description>The Co(III)-catalyzed reaction of 1,3-dicarbonyl compounds with 2-(diazoacetyl)-2
-azirines, prepared by a simplified procedure from 2
-azirin-2-carbonyl chlorides, led in high yields to the formation of 2-(diazoacetyl)pyrroles, while leaving the diazoacetyl function intact. The intramolecular aromatic substitution reaction of 2-(diazoacetyl)pyrroles, catalyzed by Cu(OTf)
, provided selectively previously unknown benzo[
]- and hetero[
]-fused indol-7-oles in good yields. Formylation of benzo[
]indol-4-ol led selectively to the 5-formyl derivative, which is a good precursor for an unusual salen ligand and its Ni-complex. Triflates prepared from benzo[
]indol-4-oles gave various 4-substituted benzo[
]indoles carrying aryl, 2-thienyl, 2-pyridyl, and alkynyl groups, in excellent yields using cross-coupling reactions. 4-(2-Pyridyl)benzo[
]indoles, upon treatment with BF
·Et
O/Et
N, afforded a new type of fluorescent boron complexes with large Stokes shifts.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.9b01573</identifier><identifier>PMID: 31309836</identifier><language>eng</language><publisher>United States</publisher><ispartof>Journal of organic chemistry, 2019-08, Vol.84 (16), p.10388-10401</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c179t-1b77482d965cd741a294e4e9ad2adfb7b5b0070be49805d3562ffaf04962d50b3</citedby><cites>FETCH-LOGICAL-c179t-1b77482d965cd741a294e4e9ad2adfb7b5b0070be49805d3562ffaf04962d50b3</cites><orcidid>0000-0001-7746-7387 ; 0000-0001-9373-8562 ; 0000-0001-5021-7142 ; 0000-0001-5106-4723 ; 0000-0002-6100-0309</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,2766,27929,27930</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31309836$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bodunov, Vladimir A</creatorcontrib><creatorcontrib>Galenko, Ekaterina E</creatorcontrib><creatorcontrib>Sakharov, Pavel A</creatorcontrib><creatorcontrib>Novikov, Mikhail S</creatorcontrib><creatorcontrib>Khlebnikov, Alexander F</creatorcontrib><title>Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H -pyrroles: Synthesis of Benzo/Furo/Thieno[ e ]-Fused 1 H -Indol-7-oles and Their Transformations</title><title>Journal of organic chemistry</title><addtitle>J Org Chem</addtitle><description>The Co(III)-catalyzed reaction of 1,3-dicarbonyl compounds with 2-(diazoacetyl)-2
-azirines, prepared by a simplified procedure from 2
-azirin-2-carbonyl chlorides, led in high yields to the formation of 2-(diazoacetyl)pyrroles, while leaving the diazoacetyl function intact. The intramolecular aromatic substitution reaction of 2-(diazoacetyl)pyrroles, catalyzed by Cu(OTf)
, provided selectively previously unknown benzo[
]- and hetero[
]-fused indol-7-oles in good yields. Formylation of benzo[
]indol-4-ol led selectively to the 5-formyl derivative, which is a good precursor for an unusual salen ligand and its Ni-complex. Triflates prepared from benzo[
]indol-4-oles gave various 4-substituted benzo[
]indoles carrying aryl, 2-thienyl, 2-pyridyl, and alkynyl groups, in excellent yields using cross-coupling reactions. 4-(2-Pyridyl)benzo[
]indoles, upon treatment with BF
·Et
O/Et
N, afforded a new type of fluorescent boron complexes with large Stokes shifts.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNo9kT1PwzAQhi0EgvIxsyGPMLjxR5zUbKWitBISA2VCKHLiixqU2pWdIKV_jL-Hy5eXd_A9d6d7ELpkdMwoZ4muwvjdVWNVUiZzcYBGTHJKMkXTQzSilHMieCZO0GkI7zQ-KeUxOhFMUDUR2Qh9PkMLVdd8AJ71ZKY73Q47MHhpO683Lv71rfZ4am3MrnEWuxoLMvVDmyygg5iEk2vT6J3TFXRDe0MYXmCyHbyPeLjFz4Pt1hCasEfvwO5cMu-9S1brBqx7xYDfyLwPceg3uLTGtSQnexhra_BqDY3HK69tqJ3ffG8RztFRrdsAF795hl7m96vZgjw-PSxn00dSsVx1hJV5nk64UZmsTJ4yzVUKKShtuDZ1mZeypDSnJaRqQqURMuN1rWuaqowbSUtxhpKfvpV3IXioi61vNtoPBaPFXkERFRRRQfGrIBJXP8S2Lzdg_uv_bi6-AFOUhPA</recordid><startdate>20190816</startdate><enddate>20190816</enddate><creator>Bodunov, Vladimir A</creator><creator>Galenko, Ekaterina E</creator><creator>Sakharov, Pavel A</creator><creator>Novikov, Mikhail S</creator><creator>Khlebnikov, Alexander F</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-7746-7387</orcidid><orcidid>https://orcid.org/0000-0001-9373-8562</orcidid><orcidid>https://orcid.org/0000-0001-5021-7142</orcidid><orcidid>https://orcid.org/0000-0001-5106-4723</orcidid><orcidid>https://orcid.org/0000-0002-6100-0309</orcidid></search><sort><creationdate>20190816</creationdate><title>Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H -pyrroles: Synthesis of Benzo/Furo/Thieno[ e ]-Fused 1 H -Indol-7-oles and Their Transformations</title><author>Bodunov, Vladimir A ; Galenko, Ekaterina E ; Sakharov, Pavel A ; Novikov, Mikhail S ; Khlebnikov, Alexander F</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c179t-1b77482d965cd741a294e4e9ad2adfb7b5b0070be49805d3562ffaf04962d50b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bodunov, Vladimir A</creatorcontrib><creatorcontrib>Galenko, Ekaterina E</creatorcontrib><creatorcontrib>Sakharov, Pavel A</creatorcontrib><creatorcontrib>Novikov, Mikhail S</creatorcontrib><creatorcontrib>Khlebnikov, Alexander F</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bodunov, Vladimir A</au><au>Galenko, Ekaterina E</au><au>Sakharov, Pavel A</au><au>Novikov, Mikhail S</au><au>Khlebnikov, Alexander F</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H -pyrroles: Synthesis of Benzo/Furo/Thieno[ e ]-Fused 1 H -Indol-7-oles and Their Transformations</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J Org Chem</addtitle><date>2019-08-16</date><risdate>2019</risdate><volume>84</volume><issue>16</issue><spage>10388</spage><epage>10401</epage><pages>10388-10401</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The Co(III)-catalyzed reaction of 1,3-dicarbonyl compounds with 2-(diazoacetyl)-2
-azirines, prepared by a simplified procedure from 2
-azirin-2-carbonyl chlorides, led in high yields to the formation of 2-(diazoacetyl)pyrroles, while leaving the diazoacetyl function intact. The intramolecular aromatic substitution reaction of 2-(diazoacetyl)pyrroles, catalyzed by Cu(OTf)
, provided selectively previously unknown benzo[
]- and hetero[
]-fused indol-7-oles in good yields. Formylation of benzo[
]indol-4-ol led selectively to the 5-formyl derivative, which is a good precursor for an unusual salen ligand and its Ni-complex. Triflates prepared from benzo[
]indol-4-oles gave various 4-substituted benzo[
]indoles carrying aryl, 2-thienyl, 2-pyridyl, and alkynyl groups, in excellent yields using cross-coupling reactions. 4-(2-Pyridyl)benzo[
]indoles, upon treatment with BF
·Et
O/Et
N, afforded a new type of fluorescent boron complexes with large Stokes shifts.</abstract><cop>United States</cop><pmid>31309836</pmid><doi>10.1021/acs.joc.9b01573</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0001-7746-7387</orcidid><orcidid>https://orcid.org/0000-0001-9373-8562</orcidid><orcidid>https://orcid.org/0000-0001-5021-7142</orcidid><orcidid>https://orcid.org/0000-0001-5106-4723</orcidid><orcidid>https://orcid.org/0000-0002-6100-0309</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2019-08, Vol.84 (16), p.10388-10401 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_acs_joc_9b01573 |
| source | ACS Publications |
| title | Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H -pyrroles: Synthesis of Benzo/Furo/Thieno[ e ]-Fused 1 H -Indol-7-oles and Their Transformations |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-15T07%3A02%3A19IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pubmed_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Selective%20Cu-Catalyzed%20Intramolecular%20Annulation%20of%203-Aryl/Heteryl-2-(diazoacetyl)-1%20H%20-pyrroles:%20Synthesis%20of%20Benzo/Furo/Thieno%5B%20e%20%5D-Fused%201%20H%20-Indol-7-oles%20and%20Their%20Transformations&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Bodunov,%20Vladimir%20A&rft.date=2019-08-16&rft.volume=84&rft.issue=16&rft.spage=10388&rft.epage=10401&rft.pages=10388-10401&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.9b01573&rft_dat=%3Cpubmed_cross%3E31309836%3C/pubmed_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/31309836&rfr_iscdi=true |