Synthesis of Terminal N‐Vinylazoles from Aromatic Aldehydes, DMSO, and Azoles Based DMSO as Terminal Carbon Synthon
A protocol for the synthesis of terminal N‐vinylazoles from aromatic aldehydes, DMSO, and azoles has been reported. In this strategy, DMSO was involved in the construction of the C=C bond as a terminal carbon synthon. Both aromatic aldehydes and azoles could be well tolerated and give the correspond...
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Veröffentlicht in: | Advanced synthesis & catalysis 2021-10, Vol.363 (19), p.4621-4626 |
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container_title | Advanced synthesis & catalysis |
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creator | Nie, Zhiwen Lv, Huifang Li, Hui Su, Miaodong Yang, Tonglin Luo, Weiping Liu, Qiang Guo, Cancheng |
description | A protocol for the synthesis of terminal N‐vinylazoles from aromatic aldehydes, DMSO, and azoles has been reported. In this strategy, DMSO was involved in the construction of the C=C bond as a terminal carbon synthon. Both aromatic aldehydes and azoles could be well tolerated and give the corresponding terminal N‐vinylazoles in 52–91% yields. Based on preliminary experiments, a plausible mechanism is proposed. |
doi_str_mv | 10.1002/adsc.202100663 |
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In this strategy, DMSO was involved in the construction of the C=C bond as a terminal carbon synthon. Both aromatic aldehydes and azoles could be well tolerated and give the corresponding terminal N‐vinylazoles in 52–91% yields. Based on preliminary experiments, a plausible mechanism is proposed.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202100663</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Aldehydes ; Aromatic Aldehydes ; Azoles ; C=C and C−N bonds Formation ; Carbon ; DMSO ; Heterocyclic compounds ; Synthesis ; Terminal N-vinylazoles</subject><ispartof>Advanced synthesis & catalysis, 2021-10, Vol.363 (19), p.4621-4626</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3173-2f30d9fe36c26b24cf5c49e94d82ff63352d6c5394b414d50c01af03e47c8b053</citedby><cites>FETCH-LOGICAL-c3173-2f30d9fe36c26b24cf5c49e94d82ff63352d6c5394b414d50c01af03e47c8b053</cites><orcidid>0000-0002-8204-9099</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.202100663$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202100663$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Nie, Zhiwen</creatorcontrib><creatorcontrib>Lv, Huifang</creatorcontrib><creatorcontrib>Li, Hui</creatorcontrib><creatorcontrib>Su, Miaodong</creatorcontrib><creatorcontrib>Yang, Tonglin</creatorcontrib><creatorcontrib>Luo, Weiping</creatorcontrib><creatorcontrib>Liu, Qiang</creatorcontrib><creatorcontrib>Guo, Cancheng</creatorcontrib><title>Synthesis of Terminal N‐Vinylazoles from Aromatic Aldehydes, DMSO, and Azoles Based DMSO as Terminal Carbon Synthon</title><title>Advanced synthesis & catalysis</title><description>A protocol for the synthesis of terminal N‐vinylazoles from aromatic aldehydes, DMSO, and azoles has been reported. In this strategy, DMSO was involved in the construction of the C=C bond as a terminal carbon synthon. Both aromatic aldehydes and azoles could be well tolerated and give the corresponding terminal N‐vinylazoles in 52–91% yields. Based on preliminary experiments, a plausible mechanism is proposed.</description><subject>Aldehydes</subject><subject>Aromatic Aldehydes</subject><subject>Azoles</subject><subject>C=C and C−N bonds Formation</subject><subject>Carbon</subject><subject>DMSO</subject><subject>Heterocyclic compounds</subject><subject>Synthesis</subject><subject>Terminal N-vinylazoles</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkMtOwkAUhidGExHdup7ELcW5tsyy1muCsgDdTqZzCSWlxRmIqSsfwWf0SSzUwNLNueX7zzn5AbjEaIgRItfKBD0kiLRNHNMj0MMx5hHDsTje1xydgrMQFgjhZJQkPbCZNtV6bkMRYO3gzPplUakSvvx8fb8VVVOqz7q0ATpfL2HaBrUuNExLY-eNsWEAb5-nkwFUlYFpR96oYM1uDFU4LMyUz-sK7q7V1Tk4caoM9uIv98Hr_d0se4zGk4enLB1HmuKERsRRZISzNNYkzgnTjmsmrGBmRJyLKeXExJpTwXKGmeFII6wcopYlepQjTvvgqtu78vX7xoa1XNQb3_4TJOGJQFgIRFtq2FHa1yF46-TKF0vlG4mR3Fort9bKvbWtQHSCj6K0zT-0TG-n2UH7CwdsfVg</recordid><startdate>20211005</startdate><enddate>20211005</enddate><creator>Nie, Zhiwen</creator><creator>Lv, Huifang</creator><creator>Li, Hui</creator><creator>Su, Miaodong</creator><creator>Yang, Tonglin</creator><creator>Luo, Weiping</creator><creator>Liu, Qiang</creator><creator>Guo, Cancheng</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-8204-9099</orcidid></search><sort><creationdate>20211005</creationdate><title>Synthesis of Terminal N‐Vinylazoles from Aromatic Aldehydes, DMSO, and Azoles Based DMSO as Terminal Carbon Synthon</title><author>Nie, Zhiwen ; Lv, Huifang ; Li, Hui ; Su, Miaodong ; Yang, Tonglin ; Luo, Weiping ; Liu, Qiang ; Guo, Cancheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3173-2f30d9fe36c26b24cf5c49e94d82ff63352d6c5394b414d50c01af03e47c8b053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aldehydes</topic><topic>Aromatic Aldehydes</topic><topic>Azoles</topic><topic>C=C and C−N bonds Formation</topic><topic>Carbon</topic><topic>DMSO</topic><topic>Heterocyclic compounds</topic><topic>Synthesis</topic><topic>Terminal N-vinylazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nie, Zhiwen</creatorcontrib><creatorcontrib>Lv, Huifang</creatorcontrib><creatorcontrib>Li, Hui</creatorcontrib><creatorcontrib>Su, Miaodong</creatorcontrib><creatorcontrib>Yang, Tonglin</creatorcontrib><creatorcontrib>Luo, Weiping</creatorcontrib><creatorcontrib>Liu, Qiang</creatorcontrib><creatorcontrib>Guo, Cancheng</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nie, Zhiwen</au><au>Lv, Huifang</au><au>Li, Hui</au><au>Su, Miaodong</au><au>Yang, Tonglin</au><au>Luo, Weiping</au><au>Liu, Qiang</au><au>Guo, Cancheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Terminal N‐Vinylazoles from Aromatic Aldehydes, DMSO, and Azoles Based DMSO as Terminal Carbon Synthon</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2021-10-05</date><risdate>2021</risdate><volume>363</volume><issue>19</issue><spage>4621</spage><epage>4626</epage><pages>4621-4626</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A protocol for the synthesis of terminal N‐vinylazoles from aromatic aldehydes, DMSO, and azoles has been reported. In this strategy, DMSO was involved in the construction of the C=C bond as a terminal carbon synthon. Both aromatic aldehydes and azoles could be well tolerated and give the corresponding terminal N‐vinylazoles in 52–91% yields. Based on preliminary experiments, a plausible mechanism is proposed.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202100663</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-8204-9099</orcidid></addata></record> |
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subjects | Aldehydes Aromatic Aldehydes Azoles C=C and C−N bonds Formation Carbon DMSO Heterocyclic compounds Synthesis Terminal N-vinylazoles |
title | Synthesis of Terminal N‐Vinylazoles from Aromatic Aldehydes, DMSO, and Azoles Based DMSO as Terminal Carbon Synthon |
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