Thia-Michael Addition Reactions Using 2-[Bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides as Odorless and Efficient Thiol Equivalents
ABSTRACT A series of 2-[bis(alkylthio)methylene]-3-oxo-N-O-tolylbutanamides 1 have been investigated as nonthiolic and odorless thiol equivalents in thia-Michael addition reactions. The cleavage of compounds 1 is initiated by NaOH in EtOH; the in situ generated thiolate anions undergo facile conjuga...
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| Veröffentlicht in: | Synlett 2006-02, Vol.2006 (2), p.283-287 |
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| container_end_page | 287 |
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| container_issue | 2 |
| container_start_page | 283 |
| container_title | Synlett |
| container_volume | 2006 |
| creator | Dong, Dewen Yu, Haifeng Ouyang, Yan Liu, Qun Bi, Xihe Lu, Yumei |
| description | ABSTRACT
A series of 2-[bis(alkylthio)methylene]-3-oxo-N-O-tolylbutanamides 1 have been investigated as nonthiolic and odorless thiol equivalents in thia-Michael addition reactions. The cleavage of compounds 1 is initiated by NaOH in EtOH; the in situ generated thiolate anions undergo facile conjugate addition to α,β-unsaturated carbonyl compounds 2 affording the corresponding β-keto sulfides 3 in very high yields. Meanwhile, 3-oxo-N-O-tolylbutanamide 4, the precursor of compounds 1, can be recovered from the novel thia-Michael addition reactions as a byproduct in good yield. |
| doi_str_mv | 10.1055/s-2005-923602 |
| format | Article |
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A series of 2-[bis(alkylthio)methylene]-3-oxo-N-O-tolylbutanamides 1 have been investigated as nonthiolic and odorless thiol equivalents in thia-Michael addition reactions. The cleavage of compounds 1 is initiated by NaOH in EtOH; the in situ generated thiolate anions undergo facile conjugate addition to α,β-unsaturated carbonyl compounds 2 affording the corresponding β-keto sulfides 3 in very high yields. Meanwhile, 3-oxo-N-O-tolylbutanamide 4, the precursor of compounds 1, can be recovered from the novel thia-Michael addition reactions as a byproduct in good yield.</description><identifier>ISSN: 0936-5214</identifier><identifier>EISSN: 1437-2096</identifier><identifier>DOI: 10.1055/s-2005-923602</identifier><language>eng</language><subject>letter</subject><ispartof>Synlett, 2006-02, Vol.2006 (2), p.283-287</ispartof><rights>Georg Thieme Verlag Stuttgart · New York</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c274t-738cacf4e2d96c0a265ef96181815bec59b8f5951c356e0f746a61fa39a737823</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2005-923602.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2005-923602$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Dong, Dewen</creatorcontrib><creatorcontrib>Yu, Haifeng</creatorcontrib><creatorcontrib>Ouyang, Yan</creatorcontrib><creatorcontrib>Liu, Qun</creatorcontrib><creatorcontrib>Bi, Xihe</creatorcontrib><creatorcontrib>Lu, Yumei</creatorcontrib><title>Thia-Michael Addition Reactions Using 2-[Bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides as Odorless and Efficient Thiol Equivalents</title><title>Synlett</title><addtitle>Synlett</addtitle><description>ABSTRACT
A series of 2-[bis(alkylthio)methylene]-3-oxo-N-O-tolylbutanamides 1 have been investigated as nonthiolic and odorless thiol equivalents in thia-Michael addition reactions. The cleavage of compounds 1 is initiated by NaOH in EtOH; the in situ generated thiolate anions undergo facile conjugate addition to α,β-unsaturated carbonyl compounds 2 affording the corresponding β-keto sulfides 3 in very high yields. Meanwhile, 3-oxo-N-O-tolylbutanamide 4, the precursor of compounds 1, can be recovered from the novel thia-Michael addition reactions as a byproduct in good yield.</description><subject>letter</subject><issn>0936-5214</issn><issn>1437-2096</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNp1kE1LAzEQhoMoWKtH7zkqGM3HJrs5VqkfUC1IexJZ0mzipmY3uknF_Qf-bLfUq8xhXoaHd2ZeAE4JviSY86uIKMYcScoEpntgRDKWDyMp9sEISyYQpyQ7BEcxrjEmWSHxCPwsaqfQo9O1Mh5OqsolF1r4bJTeigiX0bVvkKKXaxfPlH_vfapdOG9MqntvWvOKGArfAT2hgFLwvV9tkmpV4yoToYpwXoXOmzjotoJTa512pk1wWBs8nH5u3JcabFI8BgdW-WhO_voYLG-ni5t7NJvfPdxMZkjTPEsoZ4VW2maGVlJorKjgxkpBiqH4ymguV4XlkhPNuDDY5plQgljFpMpZXlA2Bmjnq7sQY2ds-dG5RnV9SXC5jbGM5TbGchfjwF_s-OFt05hyHTZdOxz4D_4Lk8l03A</recordid><startdate>20060201</startdate><enddate>20060201</enddate><creator>Dong, Dewen</creator><creator>Yu, Haifeng</creator><creator>Ouyang, Yan</creator><creator>Liu, Qun</creator><creator>Bi, Xihe</creator><creator>Lu, Yumei</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20060201</creationdate><title>Thia-Michael Addition Reactions Using 2-[Bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides as Odorless and Efficient Thiol Equivalents</title><author>Dong, Dewen ; Yu, Haifeng ; Ouyang, Yan ; Liu, Qun ; Bi, Xihe ; Lu, Yumei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c274t-738cacf4e2d96c0a265ef96181815bec59b8f5951c356e0f746a61fa39a737823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>letter</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dong, Dewen</creatorcontrib><creatorcontrib>Yu, Haifeng</creatorcontrib><creatorcontrib>Ouyang, Yan</creatorcontrib><creatorcontrib>Liu, Qun</creatorcontrib><creatorcontrib>Bi, Xihe</creatorcontrib><creatorcontrib>Lu, Yumei</creatorcontrib><collection>CrossRef</collection><jtitle>Synlett</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dong, Dewen</au><au>Yu, Haifeng</au><au>Ouyang, Yan</au><au>Liu, Qun</au><au>Bi, Xihe</au><au>Lu, Yumei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thia-Michael Addition Reactions Using 2-[Bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides as Odorless and Efficient Thiol Equivalents</atitle><jtitle>Synlett</jtitle><addtitle>Synlett</addtitle><date>2006-02-01</date><risdate>2006</risdate><volume>2006</volume><issue>2</issue><spage>283</spage><epage>287</epage><pages>283-287</pages><issn>0936-5214</issn><eissn>1437-2096</eissn><abstract>ABSTRACT
A series of 2-[bis(alkylthio)methylene]-3-oxo-N-O-tolylbutanamides 1 have been investigated as nonthiolic and odorless thiol equivalents in thia-Michael addition reactions. The cleavage of compounds 1 is initiated by NaOH in EtOH; the in situ generated thiolate anions undergo facile conjugate addition to α,β-unsaturated carbonyl compounds 2 affording the corresponding β-keto sulfides 3 in very high yields. Meanwhile, 3-oxo-N-O-tolylbutanamide 4, the precursor of compounds 1, can be recovered from the novel thia-Michael addition reactions as a byproduct in good yield.</abstract><doi>10.1055/s-2005-923602</doi><tpages>5</tpages></addata></record> |
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| ispartof | Synlett, 2006-02, Vol.2006 (2), p.283-287 |
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| language | eng |
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| source | Thieme Connect Journals |
| subjects | letter |
| title | Thia-Michael Addition Reactions Using 2-[Bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides as Odorless and Efficient Thiol Equivalents |
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