Copper-catalyzed domino synthesis of ynamines
The hitherto unexplored N -alkynylation of electron-withdrawing or protecting group free N-heteroarenes such as indole, carbazole and pyrrole was developed using gem -dibromoalkenes to synthesize ynamines under ligand-free copper-catalyzed domino conditions. The development methodology of ynamines w...
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Veröffentlicht in: | Organic & biomolecular chemistry 2021-09, Vol.19 (36), p.7855-786 |
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creator | Rao, Maddali L. N Islam, Sk Shamim Dasgupta, Priyabrata |
description | The hitherto unexplored
N
-alkynylation of electron-withdrawing or protecting group free N-heteroarenes such as indole, carbazole and pyrrole was developed using
gem
-dibromoalkenes to synthesize ynamines under ligand-free copper-catalyzed domino conditions. The development methodology of ynamines was also applied in the synthesis of enynamines, multi-coupled bis-ynamines, tris-ynamines, and the natural product peyonine, demonstrating its broad synthetic scope and applications.
A Cu-catalyzed domino protocol using
gem
-dibromoalkenes and N-heteroarenes is developed for the synthesis of ynamines and it is applied in the synthesis of enynamines, bis/tris-ynamines and peyonine natural product. |
doi_str_mv | 10.1039/d1ob01383a |
format | Article |
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N
-alkynylation of electron-withdrawing or protecting group free N-heteroarenes such as indole, carbazole and pyrrole was developed using
gem
-dibromoalkenes to synthesize ynamines under ligand-free copper-catalyzed domino conditions. The development methodology of ynamines was also applied in the synthesis of enynamines, multi-coupled bis-ynamines, tris-ynamines, and the natural product peyonine, demonstrating its broad synthetic scope and applications.
A Cu-catalyzed domino protocol using
gem
-dibromoalkenes and N-heteroarenes is developed for the synthesis of ynamines and it is applied in the synthesis of enynamines, bis/tris-ynamines and peyonine natural product.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d1ob01383a</identifier><identifier>PMID: 34549214</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Carbazole ; Carbazoles ; Chemical synthesis ; Copper ; Crystallography ; Indoles ; Natural products</subject><ispartof>Organic & biomolecular chemistry, 2021-09, Vol.19 (36), p.7855-786</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-29696b6c40a8d92d1736663a7d627848012412538a42ce3ef93249e38f45741f3</citedby><cites>FETCH-LOGICAL-c337t-29696b6c40a8d92d1736663a7d627848012412538a42ce3ef93249e38f45741f3</cites><orcidid>0000-0003-3410-3617 ; 0000-0002-8889-9545</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34549214$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rao, Maddali L. N</creatorcontrib><creatorcontrib>Islam, Sk Shamim</creatorcontrib><creatorcontrib>Dasgupta, Priyabrata</creatorcontrib><title>Copper-catalyzed domino synthesis of ynamines</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>The hitherto unexplored
N
-alkynylation of electron-withdrawing or protecting group free N-heteroarenes such as indole, carbazole and pyrrole was developed using
gem
-dibromoalkenes to synthesize ynamines under ligand-free copper-catalyzed domino conditions. The development methodology of ynamines was also applied in the synthesis of enynamines, multi-coupled bis-ynamines, tris-ynamines, and the natural product peyonine, demonstrating its broad synthetic scope and applications.
A Cu-catalyzed domino protocol using
gem
-dibromoalkenes and N-heteroarenes is developed for the synthesis of ynamines and it is applied in the synthesis of enynamines, bis/tris-ynamines and peyonine natural product.</description><subject>Carbazole</subject><subject>Carbazoles</subject><subject>Chemical synthesis</subject><subject>Copper</subject><subject>Crystallography</subject><subject>Indoles</subject><subject>Natural products</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpd0c9LwzAUB_AgipvTi3el4EWEapKX5sdxzp8w2EXPJUtT7GibmrSH-tfb2TnBUx7J5z0e3yB0TvAtwaDuMuLWmIAEfYCmhAkR4wTU4b6meIJOQthgTJTg7BhNgCVMUcKmKF64prE-NrrVZf9lsyhzVVG7KPR1-2FDESKXR32th0sbTtFRrstgz3bnDL0_Pb4tXuLl6vl1MV_GBkC0MVVc8TU3DGuZKZoRAZxz0CLjVEgmMaGM0ASkZtRYsLkCypQFmbNEMJLDDF2PcxvvPjsb2rQqgrFlqWvrupDSRAzdBAAP9Oof3bjO18N2W8WUkonig7oZlfEuBG_ztPFFpX2fEpxuQ0wfyOr-J8T5gC93I7t1ZbM9_U1tABcj8MHsX_9-Ab4BlUByyw</recordid><startdate>20210922</startdate><enddate>20210922</enddate><creator>Rao, Maddali L. N</creator><creator>Islam, Sk Shamim</creator><creator>Dasgupta, Priyabrata</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-3410-3617</orcidid><orcidid>https://orcid.org/0000-0002-8889-9545</orcidid></search><sort><creationdate>20210922</creationdate><title>Copper-catalyzed domino synthesis of ynamines</title><author>Rao, Maddali L. N ; Islam, Sk Shamim ; Dasgupta, Priyabrata</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-29696b6c40a8d92d1736663a7d627848012412538a42ce3ef93249e38f45741f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Carbazole</topic><topic>Carbazoles</topic><topic>Chemical synthesis</topic><topic>Copper</topic><topic>Crystallography</topic><topic>Indoles</topic><topic>Natural products</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rao, Maddali L. N</creatorcontrib><creatorcontrib>Islam, Sk Shamim</creatorcontrib><creatorcontrib>Dasgupta, Priyabrata</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rao, Maddali L. N</au><au>Islam, Sk Shamim</au><au>Dasgupta, Priyabrata</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-catalyzed domino synthesis of ynamines</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2021-09-22</date><risdate>2021</risdate><volume>19</volume><issue>36</issue><spage>7855</spage><epage>786</epage><pages>7855-786</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>The hitherto unexplored
N
-alkynylation of electron-withdrawing or protecting group free N-heteroarenes such as indole, carbazole and pyrrole was developed using
gem
-dibromoalkenes to synthesize ynamines under ligand-free copper-catalyzed domino conditions. The development methodology of ynamines was also applied in the synthesis of enynamines, multi-coupled bis-ynamines, tris-ynamines, and the natural product peyonine, demonstrating its broad synthetic scope and applications.
A Cu-catalyzed domino protocol using
gem
-dibromoalkenes and N-heteroarenes is developed for the synthesis of ynamines and it is applied in the synthesis of enynamines, bis/tris-ynamines and peyonine natural product.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>34549214</pmid><doi>10.1039/d1ob01383a</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-3410-3617</orcidid><orcidid>https://orcid.org/0000-0002-8889-9545</orcidid></addata></record> |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Carbazole Carbazoles Chemical synthesis Copper Crystallography Indoles Natural products |
title | Copper-catalyzed domino synthesis of ynamines |
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