Synthesis of Nitriles via the Iodine-Mediated Dehydrosulfurization of Thioamides
A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I2) is described herein. The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl gr...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2020/07/01, Vol.68(7), pp.679-681 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | Murata, Yuki Iwasa, Hitomi Matsumura, Mio Yasuike, Shuji |
| description | A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I2) is described herein. The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides. |
| doi_str_mv | 10.1248/cpb.c20-00228 |
| format | Article |
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The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c20-00228</identifier><identifier>PMID: 32612004</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Aerobic conditions ; Aromatic compounds ; cyanamide ; Cyanamides ; dehydrosulfurization ; Iodine ; Iodine - chemistry ; Molecular Structure ; nitrile ; Nitriles ; Nitriles - chemical synthesis ; Nitriles - chemistry ; Room temperature ; Synthesis ; thioamide ; Thioamides - chemistry ; Triethylamine</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2020/07/01, Vol.68(7), pp.679-681</ispartof><rights>2020 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c702t-3447d921f6eeb1b822d7c4af24734a8ab630e857d2eb77570ddaa1827d4060643</citedby><cites>FETCH-LOGICAL-c702t-3447d921f6eeb1b822d7c4af24734a8ab630e857d2eb77570ddaa1827d4060643</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32612004$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Murata, Yuki</creatorcontrib><creatorcontrib>Iwasa, Hitomi</creatorcontrib><creatorcontrib>Matsumura, Mio</creatorcontrib><creatorcontrib>Yasuike, Shuji</creatorcontrib><creatorcontrib>School of Pharmaceutical Sciences</creatorcontrib><creatorcontrib>Aichi Gakuin University</creatorcontrib><title>Synthesis of Nitriles via the Iodine-Mediated Dehydrosulfurization of Thioamides</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I2) is described herein. The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides.</description><subject>Aerobic conditions</subject><subject>Aromatic compounds</subject><subject>cyanamide</subject><subject>Cyanamides</subject><subject>dehydrosulfurization</subject><subject>Iodine</subject><subject>Iodine - chemistry</subject><subject>Molecular Structure</subject><subject>nitrile</subject><subject>Nitriles</subject><subject>Nitriles - chemical synthesis</subject><subject>Nitriles - chemistry</subject><subject>Room temperature</subject><subject>Synthesis</subject><subject>thioamide</subject><subject>Thioamides - chemistry</subject><subject>Triethylamine</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkEtv1DAUhS1ERYfCki2KxKabtNeP2J4lGkqpVB4SZW059g3xKI_BTpCGX48zU6YSm2vJ9_M5x4eQNxSuKBP62u3qK8egBGBMPyMryoUqK8b4c7ICgHXJuOTn5GVK24xUoPgLcs6ZpAxArMi37_thajGFVIxN8SVMMXSYit_BFvm6uBt9GLD8jD7YCX3xAdu9j2Oau2aO4Y-dwjgsDx_aMNo-eEyvyFlju4SvH88L8uPjzcPmU3n_9fZu8_6-dArYVHIhlF8z2kjEmtaaMa-csA0TigurbS05oK6UZ1grVSnw3lqqmfICJEjBL8jlUXcXx18zpsn0ITnsOjvgOCfDBF0rSnklM_ruP3Q7znHI6Q7U4qhUpsoj5fL_UsTG7GLobdwbCmap2uSqTa7aHKrO_NtH1bnu0Z_of91m4PYI5G1wthuHLnf55O2Sci32wTA4iEoNygCtDEi1zkMv4TUTkJU2R6VtmuxPPFnZOAXX4SGY1EYt4xTwadvaaHDgfwEyyacO</recordid><startdate>20200701</startdate><enddate>20200701</enddate><creator>Murata, Yuki</creator><creator>Iwasa, Hitomi</creator><creator>Matsumura, Mio</creator><creator>Yasuike, Shuji</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20200701</creationdate><title>Synthesis of Nitriles via the Iodine-Mediated Dehydrosulfurization of Thioamides</title><author>Murata, Yuki ; Iwasa, Hitomi ; Matsumura, Mio ; Yasuike, Shuji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c702t-3447d921f6eeb1b822d7c4af24734a8ab630e857d2eb77570ddaa1827d4060643</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aerobic conditions</topic><topic>Aromatic compounds</topic><topic>cyanamide</topic><topic>Cyanamides</topic><topic>dehydrosulfurization</topic><topic>Iodine</topic><topic>Iodine - chemistry</topic><topic>Molecular Structure</topic><topic>nitrile</topic><topic>Nitriles</topic><topic>Nitriles - chemical synthesis</topic><topic>Nitriles - chemistry</topic><topic>Room temperature</topic><topic>Synthesis</topic><topic>thioamide</topic><topic>Thioamides - chemistry</topic><topic>Triethylamine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Murata, Yuki</creatorcontrib><creatorcontrib>Iwasa, Hitomi</creatorcontrib><creatorcontrib>Matsumura, Mio</creatorcontrib><creatorcontrib>Yasuike, Shuji</creatorcontrib><creatorcontrib>School of Pharmaceutical Sciences</creatorcontrib><creatorcontrib>Aichi Gakuin University</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Murata, Yuki</au><au>Iwasa, Hitomi</au><au>Matsumura, Mio</au><au>Yasuike, Shuji</au><aucorp>School of Pharmaceutical Sciences</aucorp><aucorp>Aichi Gakuin University</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Nitriles via the Iodine-Mediated Dehydrosulfurization of Thioamides</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2020-07-01</date><risdate>2020</risdate><volume>68</volume><issue>7</issue><spage>679</spage><epage>681</epage><pages>679-681</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I2) is described herein. The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>32612004</pmid><doi>10.1248/cpb.c20-00228</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 2020/07/01, Vol.68(7), pp.679-681 |
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| language | eng |
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| source | MEDLINE; Full-Text Journals in Chemistry (Open access); J-STAGE日本語サイト (Free Access); EZB Electronic Journals Library |
| subjects | Aerobic conditions Aromatic compounds cyanamide Cyanamides dehydrosulfurization Iodine Iodine - chemistry Molecular Structure nitrile Nitriles Nitriles - chemical synthesis Nitriles - chemistry Room temperature Synthesis thioamide Thioamides - chemistry Triethylamine |
| title | Synthesis of Nitriles via the Iodine-Mediated Dehydrosulfurization of Thioamides |
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