Metal-free and Selectfluor-mediated diverse transformations of 2-alkylthiobenzamides to access 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles
Diverse transformations of 2-alkylthiobenzamides have been established to synthesize 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles in the presence of Selectfluor. Both NaI–HI and TFA–Ac 2 O systems control the selective C–S bond cleavage and C–H bond functionali...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2022-07, Vol.9 (15), p.4016-4022 |
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| container_issue | 15 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Dai, Shengfei Yang, Ke Luo, Yanqi Xu, Ziyuan Li, Zhi Li, Zhengyi Li, Bijin Sun, Xiaoqiang |
| description | Diverse transformations of 2-alkylthiobenzamides have been established to synthesize 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles in the presence of Selectfluor. Both NaI–HI and TFA–Ac
2
O systems control the selective C–S bond cleavage and C–H bond functionalization to access 2,3-dihydrobenzothiazin-4-ones and 2-substituted 2,3-dihydrobenzothiazin-4-ones, respectively. Notably, this is the first example of using Selectfluor as a methylene source to construct important 2,3-dihydrobenzothiazin-4-ones. In the presence of HCl, benzoisothiazol-3-ones were obtained in good yields. Furthermore, 2-alkylthiobenzonitriles could also be prepared using the same NaI–HI system
via
a thioether-directed and Selectfluor-mediated dehydration of 2-alkylthiobenzamides. |
| doi_str_mv | 10.1039/D2QO00663D |
| format | Article |
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2
O systems control the selective C–S bond cleavage and C–H bond functionalization to access 2,3-dihydrobenzothiazin-4-ones and 2-substituted 2,3-dihydrobenzothiazin-4-ones, respectively. Notably, this is the first example of using Selectfluor as a methylene source to construct important 2,3-dihydrobenzothiazin-4-ones. In the presence of HCl, benzoisothiazol-3-ones were obtained in good yields. Furthermore, 2-alkylthiobenzonitriles could also be prepared using the same NaI–HI system
via
a thioether-directed and Selectfluor-mediated dehydration of 2-alkylthiobenzamides.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D2QO00663D</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Dehydration ; Hydrogen bonds ; Organic chemistry</subject><ispartof>Organic Chemistry Frontiers, 2022-07, Vol.9 (15), p.4016-4022</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c211t-bbdc66004cf4588bd38f7353732c9283169bbbfc3857407db8712a1a27ea06023</citedby><cites>FETCH-LOGICAL-c211t-bbdc66004cf4588bd38f7353732c9283169bbbfc3857407db8712a1a27ea06023</cites><orcidid>0000-0001-9653-0687 ; 0000-0001-9506-4338</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27929,27930</link.rule.ids></links><search><creatorcontrib>Dai, Shengfei</creatorcontrib><creatorcontrib>Yang, Ke</creatorcontrib><creatorcontrib>Luo, Yanqi</creatorcontrib><creatorcontrib>Xu, Ziyuan</creatorcontrib><creatorcontrib>Li, Zhi</creatorcontrib><creatorcontrib>Li, Zhengyi</creatorcontrib><creatorcontrib>Li, Bijin</creatorcontrib><creatorcontrib>Sun, Xiaoqiang</creatorcontrib><title>Metal-free and Selectfluor-mediated diverse transformations of 2-alkylthiobenzamides to access 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles</title><title>Organic Chemistry Frontiers</title><description>Diverse transformations of 2-alkylthiobenzamides have been established to synthesize 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles in the presence of Selectfluor. Both NaI–HI and TFA–Ac
2
O systems control the selective C–S bond cleavage and C–H bond functionalization to access 2,3-dihydrobenzothiazin-4-ones and 2-substituted 2,3-dihydrobenzothiazin-4-ones, respectively. Notably, this is the first example of using Selectfluor as a methylene source to construct important 2,3-dihydrobenzothiazin-4-ones. In the presence of HCl, benzoisothiazol-3-ones were obtained in good yields. Furthermore, 2-alkylthiobenzonitriles could also be prepared using the same NaI–HI system
via
a thioether-directed and Selectfluor-mediated dehydration of 2-alkylthiobenzamides.</description><subject>Dehydration</subject><subject>Hydrogen bonds</subject><subject>Organic chemistry</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdkd1KAzEQhRdRsNTe-AQB76TR_Oxmdy-l9Q-UIur1kk0mNHV3U5NUaB_LJ3TdCopXM3xzODPMSZJTSi4o4eXlnD0tCBGCzw-SESMZwyll5eGf_jiZhLAihFCWCZLlo-TzEaJssPEASHYaPUMDKppm4zxuQVsZQSNtP8AHQNHLLhjnWxmt6wJyBjEsm7dtE5fW1dDtZGs1BBQdkkpBCIhNOdZ2udV-mLteKHe2wyl2HYQpGqANe-4azAc-nPLP2nU2ettAOEmOjGwCTH7qOHm9uX6Z3eGHxe397OoBK0ZpxHWtlRCEpMqkWVHUmhcm5xnPOVMlKzgVZV3XRvEiy1OS67rIKZNUshwkEYTxcXK29117976BEKuV2_iuX1kxUaZp1r9a9KrzvUp5F4IHU629baXfVpRU37FUv7HwL-VUgu8</recordid><startdate>20220726</startdate><enddate>20220726</enddate><creator>Dai, Shengfei</creator><creator>Yang, Ke</creator><creator>Luo, Yanqi</creator><creator>Xu, Ziyuan</creator><creator>Li, Zhi</creator><creator>Li, Zhengyi</creator><creator>Li, Bijin</creator><creator>Sun, Xiaoqiang</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0001-9653-0687</orcidid><orcidid>https://orcid.org/0000-0001-9506-4338</orcidid></search><sort><creationdate>20220726</creationdate><title>Metal-free and Selectfluor-mediated diverse transformations of 2-alkylthiobenzamides to access 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles</title><author>Dai, Shengfei ; Yang, Ke ; Luo, Yanqi ; Xu, Ziyuan ; Li, Zhi ; Li, Zhengyi ; Li, Bijin ; Sun, Xiaoqiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c211t-bbdc66004cf4588bd38f7353732c9283169bbbfc3857407db8712a1a27ea06023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Dehydration</topic><topic>Hydrogen bonds</topic><topic>Organic chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dai, Shengfei</creatorcontrib><creatorcontrib>Yang, Ke</creatorcontrib><creatorcontrib>Luo, Yanqi</creatorcontrib><creatorcontrib>Xu, Ziyuan</creatorcontrib><creatorcontrib>Li, Zhi</creatorcontrib><creatorcontrib>Li, Zhengyi</creatorcontrib><creatorcontrib>Li, Bijin</creatorcontrib><creatorcontrib>Sun, Xiaoqiang</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dai, Shengfei</au><au>Yang, Ke</au><au>Luo, Yanqi</au><au>Xu, Ziyuan</au><au>Li, Zhi</au><au>Li, Zhengyi</au><au>Li, Bijin</au><au>Sun, Xiaoqiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal-free and Selectfluor-mediated diverse transformations of 2-alkylthiobenzamides to access 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2022-07-26</date><risdate>2022</risdate><volume>9</volume><issue>15</issue><spage>4016</spage><epage>4022</epage><pages>4016-4022</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>Diverse transformations of 2-alkylthiobenzamides have been established to synthesize 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles in the presence of Selectfluor. Both NaI–HI and TFA–Ac
2
O systems control the selective C–S bond cleavage and C–H bond functionalization to access 2,3-dihydrobenzothiazin-4-ones and 2-substituted 2,3-dihydrobenzothiazin-4-ones, respectively. Notably, this is the first example of using Selectfluor as a methylene source to construct important 2,3-dihydrobenzothiazin-4-ones. In the presence of HCl, benzoisothiazol-3-ones were obtained in good yields. Furthermore, 2-alkylthiobenzonitriles could also be prepared using the same NaI–HI system
via
a thioether-directed and Selectfluor-mediated dehydration of 2-alkylthiobenzamides.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D2QO00663D</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-9653-0687</orcidid><orcidid>https://orcid.org/0000-0001-9506-4338</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2022-07, Vol.9 (15), p.4016-4022 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Dehydration Hydrogen bonds Organic chemistry |
| title | Metal-free and Selectfluor-mediated diverse transformations of 2-alkylthiobenzamides to access 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles |
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