Metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates toward thieno[3,4-]quinolin-4(5)-ones
A new metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates for producing thieno[3,4- c ]quinolin-4(5 H )-ones is presented. This reaction employs benzoylperoxide (BPO) as the oxidant and sodium thiocyanate as the sulfur source to enable the formation of three chemical bonds,...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2019-06, Vol.55 (47), p.6727-673 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Yu, Jiang-Xi Niu, Shijie Hu, Ming Xiang, Jian-Nan Li, Jin-Heng |
| description | A new metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates for producing thieno[3,4-
c
]quinolin-4(5
H
)-ones is presented. This reaction employs benzoylperoxide (BPO) as the oxidant and sodium thiocyanate as the sulfur source to enable the formation of three chemical bonds, two C-S bonds and one C-C bond, in a single reaction, and represents a new, practical access to S-heterocycles with the avoidance of the use of metal catalysts and excess bases.
Transition-metal- and base-free oxidative [2+2+1] heteroannulation of 1,7-enynes with NaSCN as the sulphur source is developed. |
| doi_str_mv | 10.1039/c9cc02242b |
| format | Article |
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c
]quinolin-4(5
H
)-ones is presented. This reaction employs benzoylperoxide (BPO) as the oxidant and sodium thiocyanate as the sulfur source to enable the formation of three chemical bonds, two C-S bonds and one C-C bond, in a single reaction, and represents a new, practical access to S-heterocycles with the avoidance of the use of metal catalysts and excess bases.
Transition-metal- and base-free oxidative [2+2+1] heteroannulation of 1,7-enynes with NaSCN as the sulphur source is developed.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c9cc02242b</identifier><identifier>PMID: 31119230</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Base metal ; Chemical bonds ; Chemical reactions ; Crystallography ; Organic chemistry ; Sodium thiocyanate</subject><ispartof>Chemical communications (Cambridge, England), 2019-06, Vol.55 (47), p.6727-673</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-ed039b64f4d4c662cc5a9afbbf30bcdd2741e7db682ea7f15af7128054532a033</citedby><cites>FETCH-LOGICAL-c337t-ed039b64f4d4c662cc5a9afbbf30bcdd2741e7db682ea7f15af7128054532a033</cites><orcidid>0000-0002-1523-8391 ; 0000-0001-7215-7152</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31119230$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yu, Jiang-Xi</creatorcontrib><creatorcontrib>Niu, Shijie</creatorcontrib><creatorcontrib>Hu, Ming</creatorcontrib><creatorcontrib>Xiang, Jian-Nan</creatorcontrib><creatorcontrib>Li, Jin-Heng</creatorcontrib><title>Metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates toward thieno[3,4-]quinolin-4(5)-ones</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>A new metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates for producing thieno[3,4-
c
]quinolin-4(5
H
)-ones is presented. This reaction employs benzoylperoxide (BPO) as the oxidant and sodium thiocyanate as the sulfur source to enable the formation of three chemical bonds, two C-S bonds and one C-C bond, in a single reaction, and represents a new, practical access to S-heterocycles with the avoidance of the use of metal catalysts and excess bases.
Transition-metal- and base-free oxidative [2+2+1] heteroannulation of 1,7-enynes with NaSCN as the sulphur source is developed.</description><subject>Base metal</subject><subject>Chemical bonds</subject><subject>Chemical reactions</subject><subject>Crystallography</subject><subject>Organic chemistry</subject><subject>Sodium thiocyanate</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpdkd9PGzEMxyM0BAx42fumk_bCaAP5edd73E6DTSray5CQquqUyznqVdcEktyg__1SWjppfrFlf2zZ_iL0gZIrSnh5rUutCWOCNQfohPJcYCkmD-82sSxxwYU8Ru9DWJJkVE6O0DGnlJaMkxMU7iCqHhsPkLmXrlWx-wPZjI3YiM6zBUTwTlk79KngbOZMRscFBru2ELLnLi6yuOicXiurYspE96x8u8mBdTM-Fnj-NHTW9Z3F4kJ-wS71naFDo_oA5zt_iu5vvv-ufuDpr9uf1dcp1pwXEUObjmtyYUQrdJ4zraUqlWkaw0mj25YVgkLRNvmEgSoMlcoUlE2IFJIzRTg_RRfbuY_ePQ0QYr3qgoa-VxbcEGrGOKOsYDlJ6Of_0KUbvE3bbaiclJxwmqjLLaW9C8GDqR99t1J-XVNSb6Soq7KqXqX4luBPu5FDs4J2j779PgEft4APel_9pyX_CwQajDU</recordid><startdate>20190606</startdate><enddate>20190606</enddate><creator>Yu, Jiang-Xi</creator><creator>Niu, Shijie</creator><creator>Hu, Ming</creator><creator>Xiang, Jian-Nan</creator><creator>Li, Jin-Heng</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1523-8391</orcidid><orcidid>https://orcid.org/0000-0001-7215-7152</orcidid></search><sort><creationdate>20190606</creationdate><title>Metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates toward thieno[3,4-]quinolin-4(5)-ones</title><author>Yu, Jiang-Xi ; Niu, Shijie ; Hu, Ming ; Xiang, Jian-Nan ; Li, Jin-Heng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-ed039b64f4d4c662cc5a9afbbf30bcdd2741e7db682ea7f15af7128054532a033</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Base metal</topic><topic>Chemical bonds</topic><topic>Chemical reactions</topic><topic>Crystallography</topic><topic>Organic chemistry</topic><topic>Sodium thiocyanate</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yu, Jiang-Xi</creatorcontrib><creatorcontrib>Niu, Shijie</creatorcontrib><creatorcontrib>Hu, Ming</creatorcontrib><creatorcontrib>Xiang, Jian-Nan</creatorcontrib><creatorcontrib>Li, Jin-Heng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yu, Jiang-Xi</au><au>Niu, Shijie</au><au>Hu, Ming</au><au>Xiang, Jian-Nan</au><au>Li, Jin-Heng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates toward thieno[3,4-]quinolin-4(5)-ones</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2019-06-06</date><risdate>2019</risdate><volume>55</volume><issue>47</issue><spage>6727</spage><epage>673</epage><pages>6727-673</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A new metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates for producing thieno[3,4-
c
]quinolin-4(5
H
)-ones is presented. This reaction employs benzoylperoxide (BPO) as the oxidant and sodium thiocyanate as the sulfur source to enable the formation of three chemical bonds, two C-S bonds and one C-C bond, in a single reaction, and represents a new, practical access to S-heterocycles with the avoidance of the use of metal catalysts and excess bases.
Transition-metal- and base-free oxidative [2+2+1] heteroannulation of 1,7-enynes with NaSCN as the sulphur source is developed.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>31119230</pmid><doi>10.1039/c9cc02242b</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-1523-8391</orcidid><orcidid>https://orcid.org/0000-0001-7215-7152</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2019-06, Vol.55 (47), p.6727-673 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_journals_2236093031 |
| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Base metal Chemical bonds Chemical reactions Crystallography Organic chemistry Sodium thiocyanate |
| title | Metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates toward thieno[3,4-]quinolin-4(5)-ones |
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