Synthesis of Aryl Amides from Acyl-Bunte Salts and Aryl Azides
In this study, we developed an efficient method for the synthesis of aryl amides from sodium thiosulfate pentahydrate, organic anhydrides, and aryl azides. Sodium thiosulfate may be used as the sulfur source, which reacts with anhydrides to generate acyl-Bunte salt; this salt reacts with aryl azides...
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Veröffentlicht in: | Journal of organic chemistry 2023-08, Vol.88 (15), p.10501-10507 |
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container_title | Journal of organic chemistry |
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creator | Chen, Li-Jia Kuo, Chia-Jou Liang, Chien-Fu |
description | In this study, we developed an efficient method for the synthesis of aryl amides from sodium thiosulfate pentahydrate, organic anhydrides, and aryl azides. Sodium thiosulfate may be used as the sulfur source, which reacts with anhydrides to generate acyl-Bunte salt; this salt reacts with aryl azides via the in situ generation of thiocarboxylate. Using our method, we successfully synthesized a key bioactive compound. The advantages of one-pot two-step reactions include operational simplicity, structurally diverse products with favorable yields, use of less toxic odorless reagents, and easy applicability to large-scale operations. |
doi_str_mv | 10.1021/acs.joc.3c00477 |
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Sodium thiosulfate may be used as the sulfur source, which reacts with anhydrides to generate acyl-Bunte salt; this salt reacts with aryl azides via the in situ generation of thiocarboxylate. Using our method, we successfully synthesized a key bioactive compound. The advantages of one-pot two-step reactions include operational simplicity, structurally diverse products with favorable yields, use of less toxic odorless reagents, and easy applicability to large-scale operations.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.3c00477</identifier><identifier>PMID: 37493962</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2023-08, Vol.88 (15), p.10501-10507</ispartof><rights>2023 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-b5bc6297a481a44a2045866c0f11482c30f89cec25790756fbb02e6c9fb2c7493</citedby><cites>FETCH-LOGICAL-a333t-b5bc6297a481a44a2045866c0f11482c30f89cec25790756fbb02e6c9fb2c7493</cites><orcidid>0000-0001-8438-5873</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.3c00477$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.3c00477$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37493962$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Li-Jia</creatorcontrib><creatorcontrib>Kuo, Chia-Jou</creatorcontrib><creatorcontrib>Liang, Chien-Fu</creatorcontrib><title>Synthesis of Aryl Amides from Acyl-Bunte Salts and Aryl Azides</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>In this study, we developed an efficient method for the synthesis of aryl amides from sodium thiosulfate pentahydrate, organic anhydrides, and aryl azides. Sodium thiosulfate may be used as the sulfur source, which reacts with anhydrides to generate acyl-Bunte salt; this salt reacts with aryl azides via the in situ generation of thiocarboxylate. Using our method, we successfully synthesized a key bioactive compound. 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Org. Chem</addtitle><date>2023-08-04</date><risdate>2023</risdate><volume>88</volume><issue>15</issue><spage>10501</spage><epage>10507</epage><pages>10501-10507</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>In this study, we developed an efficient method for the synthesis of aryl amides from sodium thiosulfate pentahydrate, organic anhydrides, and aryl azides. Sodium thiosulfate may be used as the sulfur source, which reacts with anhydrides to generate acyl-Bunte salt; this salt reacts with aryl azides via the in situ generation of thiocarboxylate. Using our method, we successfully synthesized a key bioactive compound. 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title | Synthesis of Aryl Amides from Acyl-Bunte Salts and Aryl Azides |
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