The Reaction of Thio Acids with Azides: A New Mechanism and New Synthetic Applications
A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are sug...
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| Veröffentlicht in: | Journal of the American Chemical Society 2003-07, Vol.125 (26), p.7754-7755 |
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| container_end_page | 7755 |
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| container_issue | 26 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 125 |
| creator | Shangguan, Ning Katukojvala, Sreenivas Greenberg, Rachel Williams, Lawrence J |
| description | A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water. |
| doi_str_mv | 10.1021/ja0294919 |
| format | Article |
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The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja0294919</identifier><identifier>PMID: 12822965</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Amides - chemical synthesis ; Azides - chemistry ; Chemistry ; Exact sciences and technology ; Kinetics and mechanisms ; Organic chemistry ; Reactivity and mechanisms ; Sulfhydryl Compounds - chemistry</subject><ispartof>Journal of the American Chemical Society, 2003-07, Vol.125 (26), p.7754-7755</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-3499b6885507ef131f7d7e426824d98021c08d9ffb300142907c879dbacabb9f3</citedby><cites>FETCH-LOGICAL-a379t-3499b6885507ef131f7d7e426824d98021c08d9ffb300142907c879dbacabb9f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja0294919$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja0294919$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14949682$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12822965$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shangguan, Ning</creatorcontrib><creatorcontrib>Katukojvala, Sreenivas</creatorcontrib><creatorcontrib>Greenberg, Rachel</creatorcontrib><creatorcontrib>Williams, Lawrence J</creatorcontrib><title>The Reaction of Thio Acids with Azides: A New Mechanism and New Synthetic Applications</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water.</description><subject>Amides - chemical synthesis</subject><subject>Azides - chemistry</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Kinetics and mechanisms</subject><subject>Organic chemistry</subject><subject>Reactivity and mechanisms</subject><subject>Sulfhydryl Compounds - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkLtOwzAUhi0EgnIZeAHkBSSGgO1cbLOFCiioXAQFwWQ5jq24pEmJU3GZWHlNngSXVnRhOvLx50_-fwC2MTrAiODDoUSERxzzJdDBMUFBjEmyDDoIIRJQloRrYN25oT9GhOFVsIYJI4QncQc8DQoNb7VUra0rWBs4KGwNU2VzB19tW8D0w-baHX1_fsEUXulXeKlVISvrRlBW-e_m7r1qC91aBdPxuLRKTl1uE6wYWTq9NZ8b4P70ZNDtBf3rs_Nu2g9kSHkbhBHnWcJYHCOqDQ6xoTnVEUkYiXLOfDyFWM6NyUKEcEQ4oopRnmdSySzjJtwAezPvuKlfJtq1YmSd0mUpK11PnKBhhLh_6cH9Gaia2rlGGzFu7Eg27wIjMe1R_PXo2Z25dJKNdL4g58V5YHcOSKdkaRpZKesWXOQ9PoLnghlnXavf_u5l8ywSGtJYDG7uxCPuXTz0jxNxsfBK5cSwnjSV7-6fD_4AZhiT2A</recordid><startdate>20030702</startdate><enddate>20030702</enddate><creator>Shangguan, Ning</creator><creator>Katukojvala, Sreenivas</creator><creator>Greenberg, Rachel</creator><creator>Williams, Lawrence J</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><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>7X8</scope></search><sort><creationdate>20030702</creationdate><title>The Reaction of Thio Acids with Azides: A New Mechanism and New Synthetic Applications</title><author>Shangguan, Ning ; Katukojvala, Sreenivas ; Greenberg, Rachel ; Williams, Lawrence J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-3499b6885507ef131f7d7e426824d98021c08d9ffb300142907c879dbacabb9f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Amides - chemical synthesis</topic><topic>Azides - chemistry</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Kinetics and mechanisms</topic><topic>Organic chemistry</topic><topic>Reactivity and mechanisms</topic><topic>Sulfhydryl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shangguan, Ning</creatorcontrib><creatorcontrib>Katukojvala, Sreenivas</creatorcontrib><creatorcontrib>Greenberg, Rachel</creatorcontrib><creatorcontrib>Williams, Lawrence J</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shangguan, Ning</au><au>Katukojvala, Sreenivas</au><au>Greenberg, Rachel</au><au>Williams, Lawrence J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Reaction of Thio Acids with Azides: A New Mechanism and New Synthetic Applications</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2003-07-02</date><risdate>2003</risdate><volume>125</volume><issue>26</issue><spage>7754</spage><epage>7755</epage><pages>7754-7755</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12822965</pmid><doi>10.1021/ja0294919</doi><tpages>2</tpages></addata></record> |
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| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2003-07, Vol.125 (26), p.7754-7755 |
| issn | 0002-7863 1520-5126 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Amides - chemical synthesis Azides - chemistry Chemistry Exact sciences and technology Kinetics and mechanisms Organic chemistry Reactivity and mechanisms Sulfhydryl Compounds - chemistry |
| title | The Reaction of Thio Acids with Azides: A New Mechanism and New Synthetic Applications |
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