Thiol–Yne Coupling of Propargylamine under Solvent‐Free Conditions by Bond Anion Relay Chemistry: An Efficient Synthesis of Thiazolidin‐2‐ylideneamine
Thiol–yne coupling of propargylamine with isothiocyanate has been developed under metal‐ and solvent‐free conditions. The addition of propargylamine to isothiocyanate gives propargylthiourea. This intermediate in situ undergoes intramolecular 5‐exo‐dig cyclization to give thiazolidin‐2‐ylideneamine....
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| Veröffentlicht in: | European journal of organic chemistry 2017-08, Vol.2017 (28), p.4130-4139 |
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| container_issue | 28 |
| container_start_page | 4130 |
| container_title | European journal of organic chemistry |
| container_volume | 2017 |
| creator | Ranjan, Alok Deore, Abhijit S. Yerande, Swapnil G. Dethe, Dattatraya H. |
| description | Thiol–yne coupling of propargylamine with isothiocyanate has been developed under metal‐ and solvent‐free conditions. The addition of propargylamine to isothiocyanate gives propargylthiourea. This intermediate in situ undergoes intramolecular 5‐exo‐dig cyclization to give thiazolidin‐2‐ylideneamine. A through‐bond anion relay reaction occurs by attack of the sulfur (not the nitrogen) atom on the alkyne in a highly regioselective manner at ambient temperature. Wide varieties of thiazolidin‐2‐ylideneamine derivatives were formed in excellent yields.
Thiol–yne coupling of propargylamine with isothiocyanate has been developed under metal‐ and solvent‐free conditions. The addition of propargylamine to isothiocyanate gives propargylthiourea. This intermediate in situ undergoes intramolecular 5‐exo‐dig cyclization to give thiazolidin‐2‐ylideneamine. Wide varieties of thiazolidin‐2‐ylideneamine derivatives were formed in excellent yields. |
| doi_str_mv | 10.1002/ejoc.201700603 |
| format | Article |
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Thiol–yne coupling of propargylamine with isothiocyanate has been developed under metal‐ and solvent‐free conditions. The addition of propargylamine to isothiocyanate gives propargylthiourea. This intermediate in situ undergoes intramolecular 5‐exo‐dig cyclization to give thiazolidin‐2‐ylideneamine. Wide varieties of thiazolidin‐2‐ylideneamine derivatives were formed in excellent yields.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201700603</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Ambient temperature ; Anion relay chemistry ; Anions ; Chemical synthesis ; Coupling ; Cyclization ; Heterocycles ; Relay ; Solvents ; Sulfur ; Synthetic methods ; Thiazolidin‐2‐ylideneamine ; Thiol‐ynes</subject><ispartof>European journal of organic chemistry, 2017-08, Vol.2017 (28), p.4130-4139</ispartof><rights>2017 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3173-d615da6ca78603fdab64f44499540990210d712465a9b8577b97a01ae2904fa3</citedby><cites>FETCH-LOGICAL-c3173-d615da6ca78603fdab64f44499540990210d712465a9b8577b97a01ae2904fa3</cites><orcidid>0000-0003-2734-210X</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%2Fejoc.201700603$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201700603$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27911,27912,45561,45562</link.rule.ids></links><search><creatorcontrib>Ranjan, Alok</creatorcontrib><creatorcontrib>Deore, Abhijit S.</creatorcontrib><creatorcontrib>Yerande, Swapnil G.</creatorcontrib><creatorcontrib>Dethe, Dattatraya H.</creatorcontrib><title>Thiol–Yne Coupling of Propargylamine under Solvent‐Free Conditions by Bond Anion Relay Chemistry: An Efficient Synthesis of Thiazolidin‐2‐ylideneamine</title><title>European journal of organic chemistry</title><description>Thiol–yne coupling of propargylamine with isothiocyanate has been developed under metal‐ and solvent‐free conditions. The addition of propargylamine to isothiocyanate gives propargylthiourea. This intermediate in situ undergoes intramolecular 5‐exo‐dig cyclization to give thiazolidin‐2‐ylideneamine. A through‐bond anion relay reaction occurs by attack of the sulfur (not the nitrogen) atom on the alkyne in a highly regioselective manner at ambient temperature. Wide varieties of thiazolidin‐2‐ylideneamine derivatives were formed in excellent yields.
Thiol–yne coupling of propargylamine with isothiocyanate has been developed under metal‐ and solvent‐free conditions. The addition of propargylamine to isothiocyanate gives propargylthiourea. This intermediate in situ undergoes intramolecular 5‐exo‐dig cyclization to give thiazolidin‐2‐ylideneamine. Wide varieties of thiazolidin‐2‐ylideneamine derivatives were formed in excellent yields.</description><subject>Alkynes</subject><subject>Ambient temperature</subject><subject>Anion relay chemistry</subject><subject>Anions</subject><subject>Chemical synthesis</subject><subject>Coupling</subject><subject>Cyclization</subject><subject>Heterocycles</subject><subject>Relay</subject><subject>Solvents</subject><subject>Sulfur</subject><subject>Synthetic methods</subject><subject>Thiazolidin‐2‐ylideneamine</subject><subject>Thiol‐ynes</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFUT1PwzAUjBBIlMLKbIk55TlxkpqtRC0fqlQEHWCKnMRpXaV2sBNQmPoTkNj5cf0lOBTByGA93_PdOz2f45xiGGAA75yvVDbwAEcAIfh7Tg8DpS6EFPbtnfjExdR_PHSOjFkBAA1D3HM-50uhyu3m40lyFKumKoVcIFWgO60qphdtydbCPjUy5xo9qPKFy3q7eZ9o3vFlLmqhpEFpiy4tQiNpIbrnJWtRvORrYWrdXtg2GheFyIRVo4dW1ktuhOl8rD97U6XIhbRjPXtaC7jk377HzkHBSsNPfmrfmU_G8_janc6ubuLR1M18HPluHuIgZ2HGoqFdvchZGpKCEEJpQOwngIchj7BHwoDRdBhEUUojBphxjwIpmN93znZjK62eG27qZKUaLa1jgqkXeBj7w8iyBjtWppUxmhdJpcWa6TbBkHQRJF0EyW8EVkB3gldR8vYfdjK-ncV_2i-_npBZ</recordid><startdate>20170802</startdate><enddate>20170802</enddate><creator>Ranjan, Alok</creator><creator>Deore, Abhijit S.</creator><creator>Yerande, Swapnil G.</creator><creator>Dethe, Dattatraya H.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-2734-210X</orcidid></search><sort><creationdate>20170802</creationdate><title>Thiol–Yne Coupling of Propargylamine under Solvent‐Free Conditions by Bond Anion Relay Chemistry: An Efficient Synthesis of Thiazolidin‐2‐ylideneamine</title><author>Ranjan, Alok ; Deore, Abhijit S. ; Yerande, Swapnil G. ; Dethe, Dattatraya H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3173-d615da6ca78603fdab64f44499540990210d712465a9b8577b97a01ae2904fa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkynes</topic><topic>Ambient temperature</topic><topic>Anion relay chemistry</topic><topic>Anions</topic><topic>Chemical synthesis</topic><topic>Coupling</topic><topic>Cyclization</topic><topic>Heterocycles</topic><topic>Relay</topic><topic>Solvents</topic><topic>Sulfur</topic><topic>Synthetic methods</topic><topic>Thiazolidin‐2‐ylideneamine</topic><topic>Thiol‐ynes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ranjan, Alok</creatorcontrib><creatorcontrib>Deore, Abhijit S.</creatorcontrib><creatorcontrib>Yerande, Swapnil G.</creatorcontrib><creatorcontrib>Dethe, Dattatraya H.</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ranjan, Alok</au><au>Deore, Abhijit S.</au><au>Yerande, Swapnil G.</au><au>Dethe, Dattatraya H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thiol–Yne Coupling of Propargylamine under Solvent‐Free Conditions by Bond Anion Relay Chemistry: An Efficient Synthesis of Thiazolidin‐2‐ylideneamine</atitle><jtitle>European journal of organic chemistry</jtitle><date>2017-08-02</date><risdate>2017</risdate><volume>2017</volume><issue>28</issue><spage>4130</spage><epage>4139</epage><pages>4130-4139</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Thiol–yne coupling of propargylamine with isothiocyanate has been developed under metal‐ and solvent‐free conditions. The addition of propargylamine to isothiocyanate gives propargylthiourea. This intermediate in situ undergoes intramolecular 5‐exo‐dig cyclization to give thiazolidin‐2‐ylideneamine. A through‐bond anion relay reaction occurs by attack of the sulfur (not the nitrogen) atom on the alkyne in a highly regioselective manner at ambient temperature. Wide varieties of thiazolidin‐2‐ylideneamine derivatives were formed in excellent yields.
Thiol–yne coupling of propargylamine with isothiocyanate has been developed under metal‐ and solvent‐free conditions. The addition of propargylamine to isothiocyanate gives propargylthiourea. This intermediate in situ undergoes intramolecular 5‐exo‐dig cyclization to give thiazolidin‐2‐ylideneamine. Wide varieties of thiazolidin‐2‐ylideneamine derivatives were formed in excellent yields.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201700603</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-2734-210X</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkynes Ambient temperature Anion relay chemistry Anions Chemical synthesis Coupling Cyclization Heterocycles Relay Solvents Sulfur Synthetic methods Thiazolidin‐2‐ylideneamine Thiol‐ynes |
| title | Thiol–Yne Coupling of Propargylamine under Solvent‐Free Conditions by Bond Anion Relay Chemistry: An Efficient Synthesis of Thiazolidin‐2‐ylideneamine |
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