Diversification of 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts: Access to the azepino[3,4,5-cd]indoles and spiroindolines
[Display omitted] 4-Bromo-1H-indole-3-carbaldehyde has been explored as a key building block for a post-Ugi assembly of azepino[3,4,5-cd]indoles and spiroindolines. First, the corresponding Ugi adducts were successfully employed in palladium-catalyzed reductive Heck cyclization producing a range of...
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| Veröffentlicht in: | Tetrahedron letters 2023-10, Vol.130, p.154769, Article 154769 |
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| creator | Zaman, Manzoor Hasan, Muhammad Peshkov, Anatoly A. Puzyk, Aleksandra Wang, Yuqing Lim, Chang-Keun Pereshivko, Olga P. Peshkov, Vsevolod A. |
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4-Bromo-1H-indole-3-carbaldehyde has been explored as a key building block for a post-Ugi assembly of azepino[3,4,5-cd]indoles and spiroindolines. First, the corresponding Ugi adducts were successfully employed in palladium-catalyzed reductive Heck cyclization producing a range of azepinoindoles. Then, 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts were subjected to cationic gold catalysis affording tetracyclic spiroindolines. Furthermore, the aryl bromide moiety retained in the resulting spiroindolines was found to be amendable to further functionalization via Suzuki and Sonogashira couplings. |
| doi_str_mv | 10.1016/j.tetlet.2023.154769 |
| format | Article |
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4-Bromo-1H-indole-3-carbaldehyde has been explored as a key building block for a post-Ugi assembly of azepino[3,4,5-cd]indoles and spiroindolines. First, the corresponding Ugi adducts were successfully employed in palladium-catalyzed reductive Heck cyclization producing a range of azepinoindoles. Then, 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts were subjected to cationic gold catalysis affording tetracyclic spiroindolines. Furthermore, the aryl bromide moiety retained in the resulting spiroindolines was found to be amendable to further functionalization via Suzuki and Sonogashira couplings.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2023.154769</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>catalytic activity ; gold ; indoles ; moieties</subject><ispartof>Tetrahedron letters, 2023-10, Vol.130, p.154769, Article 154769</ispartof><rights>2023 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c288t-d6e89147901c039b079c812dface3c0144d1ba3659f225c5fab41e0276dd40cb3</cites><orcidid>0000-0003-4583-196X ; 0000-0002-1036-3230</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040403923004793$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Zaman, Manzoor</creatorcontrib><creatorcontrib>Hasan, Muhammad</creatorcontrib><creatorcontrib>Peshkov, Anatoly A.</creatorcontrib><creatorcontrib>Puzyk, Aleksandra</creatorcontrib><creatorcontrib>Wang, Yuqing</creatorcontrib><creatorcontrib>Lim, Chang-Keun</creatorcontrib><creatorcontrib>Pereshivko, Olga P.</creatorcontrib><creatorcontrib>Peshkov, Vsevolod A.</creatorcontrib><title>Diversification of 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts: Access to the azepino[3,4,5-cd]indoles and spiroindolines</title><title>Tetrahedron letters</title><description>[Display omitted]
4-Bromo-1H-indole-3-carbaldehyde has been explored as a key building block for a post-Ugi assembly of azepino[3,4,5-cd]indoles and spiroindolines. First, the corresponding Ugi adducts were successfully employed in palladium-catalyzed reductive Heck cyclization producing a range of azepinoindoles. Then, 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts were subjected to cationic gold catalysis affording tetracyclic spiroindolines. Furthermore, the aryl bromide moiety retained in the resulting spiroindolines was found to be amendable to further functionalization via Suzuki and Sonogashira couplings.</description><subject>catalytic activity</subject><subject>gold</subject><subject>indoles</subject><subject>moieties</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LAzEQhoMoWKv_wEOOHpqabLJfHgTxGwQvehIJ2cmsTdluapIKevSXu3U9O5eBYZ4X3oeQY8HngovidDlPmDpM84xnci5yVRb1DpmIqpRM5pXYJRPOFWeKy3qfHMS45MMUFZ-Q7yv3gSG61oFJzvfUt1SxJviVZ-KOud76DplkYEJjOouLT4vMYhgoS5_fHDXWbiDFM3oBgDHS5GlaIDVfuHa9f5EzNcsZ2NcxKVLTWxrXLvjfg-sxHpK91nQRj_72lDzfXD9d3rGHx9v7y4sHBllVJWYLrGqhypoLGHo0vKyhEpltDaAELpSyojGyyOs2y3LIW9MogTwrC2sVh0ZOycmYuw7-fYMx6ZWLgF1nevSbqKXIZcbl1tqUqPEVgo8xYKvXwa1M-NSC661yvdSjcr1VrkflA3Y-YjjU-HAYdASHPaB1ASFp693_AT-hQYy6</recordid><startdate>20231025</startdate><enddate>20231025</enddate><creator>Zaman, Manzoor</creator><creator>Hasan, Muhammad</creator><creator>Peshkov, Anatoly A.</creator><creator>Puzyk, Aleksandra</creator><creator>Wang, Yuqing</creator><creator>Lim, Chang-Keun</creator><creator>Pereshivko, Olga P.</creator><creator>Peshkov, Vsevolod A.</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0003-4583-196X</orcidid><orcidid>https://orcid.org/0000-0002-1036-3230</orcidid></search><sort><creationdate>20231025</creationdate><title>Diversification of 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts: Access to the azepino[3,4,5-cd]indoles and spiroindolines</title><author>Zaman, Manzoor ; Hasan, Muhammad ; Peshkov, Anatoly A. ; Puzyk, Aleksandra ; Wang, Yuqing ; Lim, Chang-Keun ; Pereshivko, Olga P. ; Peshkov, Vsevolod A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c288t-d6e89147901c039b079c812dface3c0144d1ba3659f225c5fab41e0276dd40cb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>catalytic activity</topic><topic>gold</topic><topic>indoles</topic><topic>moieties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zaman, Manzoor</creatorcontrib><creatorcontrib>Hasan, Muhammad</creatorcontrib><creatorcontrib>Peshkov, Anatoly A.</creatorcontrib><creatorcontrib>Puzyk, Aleksandra</creatorcontrib><creatorcontrib>Wang, Yuqing</creatorcontrib><creatorcontrib>Lim, Chang-Keun</creatorcontrib><creatorcontrib>Pereshivko, Olga P.</creatorcontrib><creatorcontrib>Peshkov, Vsevolod A.</creatorcontrib><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zaman, Manzoor</au><au>Hasan, Muhammad</au><au>Peshkov, Anatoly A.</au><au>Puzyk, Aleksandra</au><au>Wang, Yuqing</au><au>Lim, Chang-Keun</au><au>Pereshivko, Olga P.</au><au>Peshkov, Vsevolod A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diversification of 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts: Access to the azepino[3,4,5-cd]indoles and spiroindolines</atitle><jtitle>Tetrahedron letters</jtitle><date>2023-10-25</date><risdate>2023</risdate><volume>130</volume><spage>154769</spage><pages>154769-</pages><artnum>154769</artnum><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
4-Bromo-1H-indole-3-carbaldehyde has been explored as a key building block for a post-Ugi assembly of azepino[3,4,5-cd]indoles and spiroindolines. First, the corresponding Ugi adducts were successfully employed in palladium-catalyzed reductive Heck cyclization producing a range of azepinoindoles. Then, 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts were subjected to cationic gold catalysis affording tetracyclic spiroindolines. Furthermore, the aryl bromide moiety retained in the resulting spiroindolines was found to be amendable to further functionalization via Suzuki and Sonogashira couplings.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2023.154769</doi><orcidid>https://orcid.org/0000-0003-4583-196X</orcidid><orcidid>https://orcid.org/0000-0002-1036-3230</orcidid></addata></record> |
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| ispartof | Tetrahedron letters, 2023-10, Vol.130, p.154769, Article 154769 |
| issn | 0040-4039 1873-3581 |
| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | catalytic activity gold indoles moieties |
| title | Diversification of 4-bromo-1H-indole-3-carbaldehyde-derived Ugi adducts: Access to the azepino[3,4,5-cd]indoles and spiroindolines |
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