Copper and manganese co-mediated cascade aza-Michael addition/cyclization and azidation of 1,3-enynes: regioselective synthesis of fully substituted azido pyrroles
An efficient Cu and Mn co-mediated aerobic oxidative cyclization and azidation reaction of 1,3-enynes with amines and trimethylsilyl azide (TMSN 3 ) for the synthesis of fully substituted azido pyrroles has been developed. The three-component reaction has the characteristics of high regioselectivity...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2020-11, Vol.18 (43), p.898-8915 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Ge, Junying Ding, Qiuping Yang, Man He, Tian Peng, Yiyuan |
| description | An efficient Cu and Mn co-mediated aerobic oxidative cyclization and azidation reaction of 1,3-enynes with amines and trimethylsilyl azide (TMSN
3
) for the synthesis of fully substituted azido pyrroles has been developed. The three-component reaction has the characteristics of high regioselectivity, wide substrate scope, and mild reaction conditions. A preliminary mechanism for this transformation is proposed.
A Cu and Mn co-mediated aerobic oxidative cyclization and azidation reaction of 1,3-enynes with amines and trimethylsilyl azide has been developed to synthesize fully substituted azido pyrroles. |
| doi_str_mv | 10.1039/d0ob01927e |
| format | Article |
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3
) for the synthesis of fully substituted azido pyrroles has been developed. The three-component reaction has the characteristics of high regioselectivity, wide substrate scope, and mild reaction conditions. A preliminary mechanism for this transformation is proposed.
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) for the synthesis of fully substituted azido pyrroles has been developed. The three-component reaction has the characteristics of high regioselectivity, wide substrate scope, and mild reaction conditions. A preliminary mechanism for this transformation is proposed.
A Cu and Mn co-mediated aerobic oxidative cyclization and azidation reaction of 1,3-enynes with amines and trimethylsilyl azide has been developed to synthesize fully substituted azido pyrroles.</description><subject>Amines</subject><subject>Copper</subject><subject>Crystallography</subject><subject>Manganese</subject><subject>Pyrroles</subject><subject>Regioselectivity</subject><subject>Substitutes</subject><subject>Substrates</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpdkUtv1DAURi0EomVgwx5kiQ1ChPoR2wk7GMpDKuoG1pEfN60rT5zaCVLm7_BHcTplkFj5Wvfo2Po-hJ5T8o4S3p45Eg2hLVPwAJ3SWqmKCN4-PM6MnKAnOd-QAilZP0YnnFPKOBen6Pc2jiMkrAeHd3q40gNkwDZWO3BeT-Cw1dlqB1jvdfXd22sNAWvn_OTjcGYXG_xer_OdQu-9O9xij-lbXsGwFON7nODKxwwB7OR_Ac7LMF1D9nnl-jmEBefZ5MlP8_rmqol4XFKKAfJT9KjXIcOz-3ODfn4-_7H9Wl1cfvm2_XBRWc7VVDFrTdNQIfsamOWydsRJ1khiaN_XyjVGKGGEkbSlZd1aZlsjGisVcVTXjG_Q64N3TPF2hjx1O58thFBCiXPuWC0EVaxhtKCv_kNv4pyG8ruVaiWpZcl3g94cKJtizgn6bkx-p9PSUdKt1XWfyOXHu-rOC_zyXjmbEv4R_dtVAV4cgJTtcfuve_4HUiygAA</recordid><startdate>20201112</startdate><enddate>20201112</enddate><creator>Ge, Junying</creator><creator>Ding, Qiuping</creator><creator>Yang, Man</creator><creator>He, Tian</creator><creator>Peng, Yiyuan</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/0000-0002-2162-5742</orcidid></search><sort><creationdate>20201112</creationdate><title>Copper and manganese co-mediated cascade aza-Michael addition/cyclization and azidation of 1,3-enynes: regioselective synthesis of fully substituted azido pyrroles</title><author>Ge, Junying ; Ding, Qiuping ; Yang, Man ; He, Tian ; Peng, Yiyuan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-2ccb88156f4e2c364d0d62860b1ff47d8b575b5b6191c369c2c9b58c670d1a423</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amines</topic><topic>Copper</topic><topic>Crystallography</topic><topic>Manganese</topic><topic>Pyrroles</topic><topic>Regioselectivity</topic><topic>Substitutes</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ge, Junying</creatorcontrib><creatorcontrib>Ding, Qiuping</creatorcontrib><creatorcontrib>Yang, Man</creatorcontrib><creatorcontrib>He, Tian</creatorcontrib><creatorcontrib>Peng, Yiyuan</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>Ge, Junying</au><au>Ding, Qiuping</au><au>Yang, Man</au><au>He, Tian</au><au>Peng, Yiyuan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper and manganese co-mediated cascade aza-Michael addition/cyclization and azidation of 1,3-enynes: regioselective synthesis of fully substituted azido pyrroles</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2020-11-12</date><risdate>2020</risdate><volume>18</volume><issue>43</issue><spage>898</spage><epage>8915</epage><pages>898-8915</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>An efficient Cu and Mn co-mediated aerobic oxidative cyclization and azidation reaction of 1,3-enynes with amines and trimethylsilyl azide (TMSN
3
) for the synthesis of fully substituted azido pyrroles has been developed. The three-component reaction has the characteristics of high regioselectivity, wide substrate scope, and mild reaction conditions. A preliminary mechanism for this transformation is proposed.
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| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2020-11, Vol.18 (43), p.898-8915 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_journals_2459604623 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amines Copper Crystallography Manganese Pyrroles Regioselectivity Substitutes Substrates |
| title | Copper and manganese co-mediated cascade aza-Michael addition/cyclization and azidation of 1,3-enynes: regioselective synthesis of fully substituted azido pyrroles |
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