One‐pot Synthesis of Isoquinoline‐Fused Isoquinolines via Intramolecular Hydroamination/Aza‐Claisen Type Rearrangement Cascade
A one‐pot, two‐step synthesis of isoquinoline‐fused isoquinolines from α‐amino acid esters and 2‐alkynyl benzaldehydes are reported. The strategy comprises an unconventional Pictet‐Spengler reaction between α‐amino acid esters and 2‐alkynyl benzaldehydes to give isoquinoline intermediates. Subsequen...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2021-06, Vol.363 (11), p.2834-2842 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Chiu, Wei‐Jung Chen, Jin‐Yu Liu, Shih‐I Barve, Indrajeet J. Huang, Wan‐Wen Sun, Chung‐Ming |
| description | A one‐pot, two‐step synthesis of isoquinoline‐fused isoquinolines from α‐amino acid esters and 2‐alkynyl benzaldehydes are reported. The strategy comprises an unconventional Pictet‐Spengler reaction between α‐amino acid esters and 2‐alkynyl benzaldehydes to give isoquinoline intermediates. Subsequent gold‐catalyzed intramolecular hydroamination furnishes isoquinoline‐fused isoquinolines. The scope of this strategy is further extended to prepare multisubstituted isoquinoline‐fused isoquinolines via subjecting the N‐allylated isoquinoline intermediates to gold‐catalyzed intramolecular hydroamination followed by aza‐Claisen type rearrangement. |
| doi_str_mv | 10.1002/adsc.202001576 |
| format | Article |
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The strategy comprises an unconventional Pictet‐Spengler reaction between α‐amino acid esters and 2‐alkynyl benzaldehydes to give isoquinoline intermediates. Subsequent gold‐catalyzed intramolecular hydroamination furnishes isoquinoline‐fused isoquinolines. The scope of this strategy is further extended to prepare multisubstituted isoquinoline‐fused isoquinolines via subjecting the N‐allylated isoquinoline intermediates to gold‐catalyzed intramolecular hydroamination followed by aza‐Claisen type rearrangement.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202001576</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Amino acids ; aza claisen-type rearrangement ; Esters ; Gold ; hydroaminati-on ; isoquinoline-fused isoquinolines ; Synthesis</subject><ispartof>Advanced synthesis & catalysis, 2021-06, Vol.363 (11), p.2834-2842</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3546-8e0549a5d47d4e6dfb303960fa83f80a9c3630b9b2992fbceae33a7a80d963d3</citedby><cites>FETCH-LOGICAL-c3546-8e0549a5d47d4e6dfb303960fa83f80a9c3630b9b2992fbceae33a7a80d963d3</cites><orcidid>0000-0002-1804-1578</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.202001576$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202001576$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Chiu, Wei‐Jung</creatorcontrib><creatorcontrib>Chen, Jin‐Yu</creatorcontrib><creatorcontrib>Liu, Shih‐I</creatorcontrib><creatorcontrib>Barve, Indrajeet J.</creatorcontrib><creatorcontrib>Huang, Wan‐Wen</creatorcontrib><creatorcontrib>Sun, Chung‐Ming</creatorcontrib><title>One‐pot Synthesis of Isoquinoline‐Fused Isoquinolines via Intramolecular Hydroamination/Aza‐Claisen Type Rearrangement Cascade</title><title>Advanced synthesis & catalysis</title><description>A one‐pot, two‐step synthesis of isoquinoline‐fused isoquinolines from α‐amino acid esters and 2‐alkynyl benzaldehydes are reported. 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The scope of this strategy is further extended to prepare multisubstituted isoquinoline‐fused isoquinolines via subjecting the N‐allylated isoquinoline intermediates to gold‐catalyzed intramolecular hydroamination followed by aza‐Claisen type rearrangement.</description><subject>Amino acids</subject><subject>aza claisen-type rearrangement</subject><subject>Esters</subject><subject>Gold</subject><subject>hydroaminati-on</subject><subject>isoquinoline-fused isoquinolines</subject><subject>Synthesis</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAQhiMEEqWwMltiTuvE-fJYhY9WqlSJdo8u8QVcJXawE1CYGPgB_EZ-CSlFRUxMPvme5073Os6lRycepf4UhC0mPvUp9cI4OnJGXuSFbuBF_PhQh_TUObN2OzBxEscj532l8PPto9EtWfeqfUQrLdElWVj91EmlK_ndv-0sij-fljxLIAvVGqh1hUVXgSHzXhgNtVTQSq2ms1cY3LQCaVGRTd8guUcwBtQD1qhakoItQOC5c1JCZfHi5x07m9ubTTp3l6u7RTpbugULg8hNkIYBh1AEsQgwEmXOKOMRLSFhZUKBFyxiNOe5z7lf5gUCMgYxJFTwiAk2dq72Yxsz3IG2zba6M2rYmPkhS4IgpiwYqMmeKoy21mCZNUbWYPrMo9ku6GwXdHYIehD4XniRFfb_0Nnsep3-ul-kbYf3</recordid><startdate>20210608</startdate><enddate>20210608</enddate><creator>Chiu, Wei‐Jung</creator><creator>Chen, Jin‐Yu</creator><creator>Liu, Shih‐I</creator><creator>Barve, Indrajeet J.</creator><creator>Huang, Wan‐Wen</creator><creator>Sun, Chung‐Ming</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-1804-1578</orcidid></search><sort><creationdate>20210608</creationdate><title>One‐pot Synthesis of Isoquinoline‐Fused Isoquinolines via Intramolecular Hydroamination/Aza‐Claisen Type Rearrangement Cascade</title><author>Chiu, Wei‐Jung ; Chen, Jin‐Yu ; Liu, Shih‐I ; Barve, Indrajeet J. ; Huang, Wan‐Wen ; Sun, Chung‐Ming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3546-8e0549a5d47d4e6dfb303960fa83f80a9c3630b9b2992fbceae33a7a80d963d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Amino acids</topic><topic>aza claisen-type rearrangement</topic><topic>Esters</topic><topic>Gold</topic><topic>hydroaminati-on</topic><topic>isoquinoline-fused isoquinolines</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chiu, Wei‐Jung</creatorcontrib><creatorcontrib>Chen, Jin‐Yu</creatorcontrib><creatorcontrib>Liu, Shih‐I</creatorcontrib><creatorcontrib>Barve, Indrajeet J.</creatorcontrib><creatorcontrib>Huang, Wan‐Wen</creatorcontrib><creatorcontrib>Sun, Chung‐Ming</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chiu, Wei‐Jung</au><au>Chen, Jin‐Yu</au><au>Liu, Shih‐I</au><au>Barve, Indrajeet J.</au><au>Huang, Wan‐Wen</au><au>Sun, Chung‐Ming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One‐pot Synthesis of Isoquinoline‐Fused Isoquinolines via Intramolecular Hydroamination/Aza‐Claisen Type Rearrangement Cascade</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2021-06-08</date><risdate>2021</risdate><volume>363</volume><issue>11</issue><spage>2834</spage><epage>2842</epage><pages>2834-2842</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A one‐pot, two‐step synthesis of isoquinoline‐fused isoquinolines from α‐amino acid esters and 2‐alkynyl benzaldehydes are reported. The strategy comprises an unconventional Pictet‐Spengler reaction between α‐amino acid esters and 2‐alkynyl benzaldehydes to give isoquinoline intermediates. Subsequent gold‐catalyzed intramolecular hydroamination furnishes isoquinoline‐fused isoquinolines. The scope of this strategy is further extended to prepare multisubstituted isoquinoline‐fused isoquinolines via subjecting the N‐allylated isoquinoline intermediates to gold‐catalyzed intramolecular hydroamination followed by aza‐Claisen type rearrangement.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202001576</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-1804-1578</orcidid></addata></record> |
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| subjects | Amino acids aza claisen-type rearrangement Esters Gold hydroaminati-on isoquinoline-fused isoquinolines Synthesis |
| title | One‐pot Synthesis of Isoquinoline‐Fused Isoquinolines via Intramolecular Hydroamination/Aza‐Claisen Type Rearrangement Cascade |
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