A facile protocol for the preparation of 2-carboxylated thieno [2,3- b ] indoles: a de novo access to alkaloid thienodolin
A metal-free strategy, alternative to the known complex cycloaddition reactions, towards 2-carboxylated thieno [2,3- ] indole derivatives has been successfully developed. The novel approach involves as starting materials easy accessible 1,2-diaza-1,3-dienes and indoline 2-thione and requires mild re...
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Veröffentlicht in: | Organic & biomolecular chemistry 2022-05, Vol.20 (20), p.4167-4175 |
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creator | Mari, Giacomo De Crescentini, Lucia Favi, Gianfranco Santeusanio, Stefania Mantellini, Fabio |
description | A metal-free strategy, alternative to the known complex cycloaddition reactions, towards 2-carboxylated thieno [2,3-
] indole derivatives has been successfully developed. The novel approach involves as starting materials easy accessible 1,2-diaza-1,3-dienes and indoline 2-thione and requires mild reaction conditions. Furthermore, the easy work-up required makes this method amenable for a one-pot approach as demonstrated in the preparation of thienodolin, a natural product isolated from
that exhibits valuable biological properties. |
doi_str_mv | 10.1039/d2ob00440b |
format | Article |
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that exhibits valuable biological properties.</description><subject>Alkaloids</subject><subject>Antineoplastic Agents</subject><subject>Biological properties</subject><subject>Carboxylic Acids</subject><subject>Cycloaddition</subject><subject>Cycloaddition Reaction</subject><subject>Dienes</subject><subject>Indoles</subject><subject>Natural products</subject><subject>Thiophenes</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0UtLAzEQB_AgitXqxQ8gAS8iruaxSXa9tfUJhV70JLLkiavppiZbsX56t7b14ClD-M0wwx-AI4wuMKLlpSFBIZTnSG2BPZwLkSFGy-2_mqAe2E_pDSFcCp7vgh5ljOKCoz3wPYBO6tpbOIuhDTp46EKE7evyw85klG0dGhgcJJmWUYWvhZetNZ2obRPgMzmnGVTwBdaNCd6mKyihsbAJnwFKrW1KsO0q_y59qDdtnaybA7DjpE_2cP32wdPtzePoPhtP7h5Gg3GmSYHbjDkhpVFClAQzxDDJiVAOO0OdwloTh3ghjEY2R9xwIhl1mHFODXYql07SPjhdze0u_Jjb1FbTOmnrvWxsmKeKcI7zgjDBO3ryj76FeWy67ZaqpIIXBenU2UrpGFKK1lWzWE9lXFQYVctEqmsyGf4mMuzw8XrkXE2t-aObCOgPDxKFLQ</recordid><startdate>20220526</startdate><enddate>20220526</enddate><creator>Mari, Giacomo</creator><creator>De Crescentini, Lucia</creator><creator>Favi, Gianfranco</creator><creator>Santeusanio, Stefania</creator><creator>Mantellini, Fabio</creator><general>Royal Society of Chemistry</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><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/0000-0001-7987-5309</orcidid><orcidid>https://orcid.org/0000-0002-5076-942X</orcidid><orcidid>https://orcid.org/0000-0002-8239-3340</orcidid><orcidid>https://orcid.org/0000-0003-3112-819X</orcidid><orcidid>https://orcid.org/0000-0002-1140-5404</orcidid></search><sort><creationdate>20220526</creationdate><title>A facile protocol for the preparation of 2-carboxylated thieno [2,3- b ] indoles: a de novo access to alkaloid thienodolin</title><author>Mari, Giacomo ; De Crescentini, Lucia ; Favi, Gianfranco ; Santeusanio, Stefania ; Mantellini, Fabio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-5f7aadb7792150512427bf1fd3fb1cc2f0687dc0e406d62a53f15663d1fb4afa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkaloids</topic><topic>Antineoplastic Agents</topic><topic>Biological properties</topic><topic>Carboxylic Acids</topic><topic>Cycloaddition</topic><topic>Cycloaddition Reaction</topic><topic>Dienes</topic><topic>Indoles</topic><topic>Natural products</topic><topic>Thiophenes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mari, Giacomo</creatorcontrib><creatorcontrib>De Crescentini, Lucia</creatorcontrib><creatorcontrib>Favi, Gianfranco</creatorcontrib><creatorcontrib>Santeusanio, Stefania</creatorcontrib><creatorcontrib>Mantellini, Fabio</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><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>Mari, Giacomo</au><au>De Crescentini, Lucia</au><au>Favi, Gianfranco</au><au>Santeusanio, Stefania</au><au>Mantellini, Fabio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A facile protocol for the preparation of 2-carboxylated thieno [2,3- b ] indoles: a de novo access to alkaloid thienodolin</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2022-05-26</date><risdate>2022</risdate><volume>20</volume><issue>20</issue><spage>4167</spage><epage>4175</epage><pages>4167-4175</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A metal-free strategy, alternative to the known complex cycloaddition reactions, towards 2-carboxylated thieno [2,3-
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source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Alkaloids Antineoplastic Agents Biological properties Carboxylic Acids Cycloaddition Cycloaddition Reaction Dienes Indoles Natural products Thiophenes |
title | A facile protocol for the preparation of 2-carboxylated thieno [2,3- b ] indoles: a de novo access to alkaloid thienodolin |
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