Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous media via tandem addition–cyclization
An electrochemical synthesis of 2-aminobenzoxazoles from 2-aminophenols and isothiocyanates was successfully developed in a one-pot fashion. Using inexpensive and widely available NaI and NaCl co-operatively in catalytic amounts, our electrosynthesis approach provided various 2-aminobenzoxazole prod...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2021-07, Vol.23 (14), p.5189-5194 |
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| container_issue | 14 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
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| creator | Huynh, Thao Nguyen Thanh Tankam, Theeranon Koguchi, Shinichi Rerkrachaneekorn, Tanawat Sukwattanasinitt, Mongkol Wacharasindhu, Sumrit |
| description | An electrochemical synthesis of 2-aminobenzoxazoles from 2-aminophenols and isothiocyanates was successfully developed in a one-pot fashion. Using inexpensive and widely available NaI and NaCl co-operatively in catalytic amounts, our electrosynthesis approach provided various 2-aminobenzoxazole products in moderate to high yields in an open-flask type undivided cell without using any external supporting electrolyte and base. The protocol can be applied to the synthesis of 2-aminobenzothiazoles from the corresponding 2-thiophenols in moderate yields. This protocol has many benefits. It is metal-free and highly scalable and uses inexpensive mediators and EtOH/water as an environmentally friendly solvent under mild conditions. |
| doi_str_mv | 10.1039/D1GC01131F |
| format | Article |
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Using inexpensive and widely available NaI and NaCl co-operatively in catalytic amounts, our electrosynthesis approach provided various 2-aminobenzoxazole products in moderate to high yields in an open-flask type undivided cell without using any external supporting electrolyte and base. The protocol can be applied to the synthesis of 2-aminobenzothiazoles from the corresponding 2-thiophenols in moderate yields. This protocol has many benefits. It is metal-free and highly scalable and uses inexpensive mediators and EtOH/water as an environmentally friendly solvent under mild conditions.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/D1GC01131F</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Aminobenzothiazoles ; Aminophenol ; Aqueous solutions ; Chemical synthesis ; Electrochemistry ; Green chemistry ; Sodium chloride</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2021-07, Vol.23 (14), p.5189-5194</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c189t-17258effff3239ea80f68d63e96c1a79782709ab26e7a5b8bffb166762e662db3</citedby><cites>FETCH-LOGICAL-c189t-17258effff3239ea80f68d63e96c1a79782709ab26e7a5b8bffb166762e662db3</cites><orcidid>0000-0001-6940-1329</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Huynh, Thao Nguyen Thanh</creatorcontrib><creatorcontrib>Tankam, Theeranon</creatorcontrib><creatorcontrib>Koguchi, Shinichi</creatorcontrib><creatorcontrib>Rerkrachaneekorn, Tanawat</creatorcontrib><creatorcontrib>Sukwattanasinitt, Mongkol</creatorcontrib><creatorcontrib>Wacharasindhu, Sumrit</creatorcontrib><title>Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous media via tandem addition–cyclization</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>An electrochemical synthesis of 2-aminobenzoxazoles from 2-aminophenols and isothiocyanates was successfully developed in a one-pot fashion. 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It is metal-free and highly scalable and uses inexpensive mediators and EtOH/water as an environmentally friendly solvent under mild conditions.</description><subject>Aminobenzothiazoles</subject><subject>Aminophenol</subject><subject>Aqueous solutions</subject><subject>Chemical synthesis</subject><subject>Electrochemistry</subject><subject>Green chemistry</subject><subject>Sodium chloride</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpFkM1Kw0AQxxdRsFYvPsGCNyF2P5JNcpTa1oLUi57DZDOhW5Ldmt2KLQi-g2_ok5ha0YFhZuA3X39CLjm74Uzmozs-GzPOJZ8ekQGPlYxykbLjv1yJU3Lm_Yr1UKriAXmfNKhD5_QSW6OhoQuYjxYwbqIWKwMBK-osRmsXqN_asERvPHU1FRG0xroS7c69wc416KmxFF426Dae_jTT194D2ApbClVlgnH26-NTb3VjdrCvzslJDY3Hi984JM_TydP4Pnp4nM3Htw-R5lkeIp6KJMO6NylkjpCxWmWVkpgrzSHN06x_ModSKEwhKbOyrkuuVKoEKiWqUg7J1WHuunP9hT4UK7fpbL-yEEki44zFPO6p6wOlO-d9h3Wx7kwL3bbgrNjLW_zLK78Bs-hvlA</recordid><startdate>20210721</startdate><enddate>20210721</enddate><creator>Huynh, Thao Nguyen Thanh</creator><creator>Tankam, Theeranon</creator><creator>Koguchi, Shinichi</creator><creator>Rerkrachaneekorn, Tanawat</creator><creator>Sukwattanasinitt, Mongkol</creator><creator>Wacharasindhu, Sumrit</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0001-6940-1329</orcidid></search><sort><creationdate>20210721</creationdate><title>Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous media via tandem addition–cyclization</title><author>Huynh, Thao Nguyen Thanh ; Tankam, Theeranon ; Koguchi, Shinichi ; Rerkrachaneekorn, Tanawat ; Sukwattanasinitt, Mongkol ; Wacharasindhu, Sumrit</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c189t-17258effff3239ea80f68d63e96c1a79782709ab26e7a5b8bffb166762e662db3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aminobenzothiazoles</topic><topic>Aminophenol</topic><topic>Aqueous solutions</topic><topic>Chemical synthesis</topic><topic>Electrochemistry</topic><topic>Green chemistry</topic><topic>Sodium chloride</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huynh, Thao Nguyen Thanh</creatorcontrib><creatorcontrib>Tankam, Theeranon</creatorcontrib><creatorcontrib>Koguchi, Shinichi</creatorcontrib><creatorcontrib>Rerkrachaneekorn, Tanawat</creatorcontrib><creatorcontrib>Sukwattanasinitt, Mongkol</creatorcontrib><creatorcontrib>Wacharasindhu, Sumrit</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huynh, Thao Nguyen Thanh</au><au>Tankam, Theeranon</au><au>Koguchi, Shinichi</au><au>Rerkrachaneekorn, Tanawat</au><au>Sukwattanasinitt, Mongkol</au><au>Wacharasindhu, Sumrit</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous media via tandem addition–cyclization</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2021-07-21</date><risdate>2021</risdate><volume>23</volume><issue>14</issue><spage>5189</spage><epage>5194</epage><pages>5189-5194</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>An electrochemical synthesis of 2-aminobenzoxazoles from 2-aminophenols and isothiocyanates was successfully developed in a one-pot fashion. Using inexpensive and widely available NaI and NaCl co-operatively in catalytic amounts, our electrosynthesis approach provided various 2-aminobenzoxazole products in moderate to high yields in an open-flask type undivided cell without using any external supporting electrolyte and base. The protocol can be applied to the synthesis of 2-aminobenzothiazoles from the corresponding 2-thiophenols in moderate yields. This protocol has many benefits. It is metal-free and highly scalable and uses inexpensive mediators and EtOH/water as an environmentally friendly solvent under mild conditions.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D1GC01131F</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-6940-1329</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2021-07, Vol.23 (14), p.5189-5194 |
| issn | 1463-9262 1463-9270 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aminobenzothiazoles Aminophenol Aqueous solutions Chemical synthesis Electrochemistry Green chemistry Sodium chloride |
| title | Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous media via tandem addition–cyclization |
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