Synthesis of Novel Thiazolidin‐4‐ones and Thiazinan‐4‐ones Analogous to Rosiglitazone
This work reports the synthesis of thiazolidin‐4‐ones and thiazinan‐4‐ones analogous to rosiglitazone, a potent antidiabetic drug. The desired compounds were synthesized with moderate to good yields by one‐pot reactions between different primary amines, mercaptoacetic or mercaptopropionic acids, and...
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| Veröffentlicht in: | Journal of heterocyclic chemistry 2019-01, Vol.56 (1), p.251-259 |
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| container_title | Journal of heterocyclic chemistry |
| container_volume | 56 |
| creator | Neves, Adriana M. Campos, José C. Gouvêa, Daniela P. Berwaldt, Gabriele A. Goulart, Taís B. Avila, Cinara T. Machado, Pablo Zimmer, Geórgia C. Cunico, Wilson |
| description | This work reports the synthesis of thiazolidin‐4‐ones and thiazinan‐4‐ones analogous to rosiglitazone, a potent antidiabetic drug. The desired compounds were synthesized with moderate to good yields by one‐pot reactions between different primary amines, mercaptoacetic or mercaptopropionic acids, and the 4‐(2‐(methyl(pyridin‐2‐yl)amino)ethoxy)benzaldehyde. The cyclocondensation reactions were carried out for 20 h, and all the products were characterized by 1H and 13C nuclear magnetic resonance spectroscopy, mass spectrometry, and one example by X‐ray diffraction. |
| doi_str_mv | 10.1002/jhet.3402 |
| format | Article |
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The desired compounds were synthesized with moderate to good yields by one‐pot reactions between different primary amines, mercaptoacetic or mercaptopropionic acids, and the 4‐(2‐(methyl(pyridin‐2‐yl)amino)ethoxy)benzaldehyde. The cyclocondensation reactions were carried out for 20 h, and all the products were characterized by 1H and 13C nuclear magnetic resonance spectroscopy, mass spectrometry, and one example by X‐ray diffraction.</description><identifier>ISSN: 0022-152X</identifier><identifier>EISSN: 1943-5193</identifier><identifier>DOI: 10.1002/jhet.3402</identifier><language>eng</language><publisher>Hoboken: Wiley Subscription Services, Inc</publisher><subject>Amines ; Benzaldehyde ; Chemical synthesis ; Mass spectrometry ; NMR ; Nuclear magnetic resonance ; Nuclear reactions ; X-ray diffraction</subject><ispartof>Journal of heterocyclic chemistry, 2019-01, Vol.56 (1), p.251-259</ispartof><rights>2018 Wiley Periodicals, Inc.</rights><rights>2019 Wiley Periodicals, Inc.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3322-518c17100d37213e07f7038c94babe8d6b62ae38d462620bf4dba1c0ffe698353</citedby><cites>FETCH-LOGICAL-c3322-518c17100d37213e07f7038c94babe8d6b62ae38d462620bf4dba1c0ffe698353</cites><orcidid>0000-0003-2577-5323 ; 0000-0002-3084-3020</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%2Fjhet.3402$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjhet.3402$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Neves, Adriana M.</creatorcontrib><creatorcontrib>Campos, José C.</creatorcontrib><creatorcontrib>Gouvêa, Daniela P.</creatorcontrib><creatorcontrib>Berwaldt, Gabriele A.</creatorcontrib><creatorcontrib>Goulart, Taís B.</creatorcontrib><creatorcontrib>Avila, Cinara T.</creatorcontrib><creatorcontrib>Machado, Pablo</creatorcontrib><creatorcontrib>Zimmer, Geórgia C.</creatorcontrib><creatorcontrib>Cunico, Wilson</creatorcontrib><title>Synthesis of Novel Thiazolidin‐4‐ones and Thiazinan‐4‐ones Analogous to Rosiglitazone</title><title>Journal of heterocyclic chemistry</title><description>This work reports the synthesis of thiazolidin‐4‐ones and thiazinan‐4‐ones analogous to rosiglitazone, a potent antidiabetic drug. The desired compounds were synthesized with moderate to good yields by one‐pot reactions between different primary amines, mercaptoacetic or mercaptopropionic acids, and the 4‐(2‐(methyl(pyridin‐2‐yl)amino)ethoxy)benzaldehyde. The cyclocondensation reactions were carried out for 20 h, and all the products were characterized by 1H and 13C nuclear magnetic resonance spectroscopy, mass spectrometry, and one example by X‐ray diffraction.</description><subject>Amines</subject><subject>Benzaldehyde</subject><subject>Chemical synthesis</subject><subject>Mass spectrometry</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Nuclear reactions</subject><subject>X-ray diffraction</subject><issn>0022-152X</issn><issn>1943-5193</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kM1Kw0AUhQdRMFYXvkHAlYu085e_ZSnVKkVBK7iRYZLcaabEmZpJlbryEXxGn8SpcePCxeVyOd89HA5CpwQPCcZ0tKqhGzKO6R4KSM5ZFJOc7aPAazQiMX08REfOrfxJWJoG6Ol-a7oanHahVeGNfYUmXNRavttGV9p8fXxyP9aAC6Wpekkb-UcYG9nYpd24sLPhnXV62ejOOxg4RgdKNg5OfvcAPVxMF5NZNL-9vJqM51HJmM8Vk6wkqc9fsdTnApyqFLOszHkhC8iqpEioBJZVPKEJxYXiVSFJiZWCJM9YzAborPddt_ZlA64TK7tpfSwnKElinOU8p54676mytc61oMS61c-y3QqCxa49sWtP7Nrz7Khn33QD2_9BcT2bLn4-vgFJ-nVr</recordid><startdate>201901</startdate><enddate>201901</enddate><creator>Neves, Adriana M.</creator><creator>Campos, José C.</creator><creator>Gouvêa, Daniela P.</creator><creator>Berwaldt, Gabriele A.</creator><creator>Goulart, Taís B.</creator><creator>Avila, Cinara T.</creator><creator>Machado, Pablo</creator><creator>Zimmer, Geórgia C.</creator><creator>Cunico, Wilson</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-2577-5323</orcidid><orcidid>https://orcid.org/0000-0002-3084-3020</orcidid></search><sort><creationdate>201901</creationdate><title>Synthesis of Novel Thiazolidin‐4‐ones and Thiazinan‐4‐ones Analogous to Rosiglitazone</title><author>Neves, Adriana M. ; Campos, José C. ; Gouvêa, Daniela P. ; Berwaldt, Gabriele A. ; Goulart, Taís B. ; Avila, Cinara T. ; Machado, Pablo ; Zimmer, Geórgia C. ; Cunico, Wilson</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3322-518c17100d37213e07f7038c94babe8d6b62ae38d462620bf4dba1c0ffe698353</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Amines</topic><topic>Benzaldehyde</topic><topic>Chemical synthesis</topic><topic>Mass spectrometry</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Nuclear reactions</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Neves, Adriana M.</creatorcontrib><creatorcontrib>Campos, José C.</creatorcontrib><creatorcontrib>Gouvêa, Daniela P.</creatorcontrib><creatorcontrib>Berwaldt, Gabriele A.</creatorcontrib><creatorcontrib>Goulart, Taís B.</creatorcontrib><creatorcontrib>Avila, Cinara T.</creatorcontrib><creatorcontrib>Machado, Pablo</creatorcontrib><creatorcontrib>Zimmer, Geórgia C.</creatorcontrib><creatorcontrib>Cunico, Wilson</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of heterocyclic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Neves, Adriana M.</au><au>Campos, José C.</au><au>Gouvêa, Daniela P.</au><au>Berwaldt, Gabriele A.</au><au>Goulart, Taís B.</au><au>Avila, Cinara T.</au><au>Machado, Pablo</au><au>Zimmer, Geórgia C.</au><au>Cunico, Wilson</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Novel Thiazolidin‐4‐ones and Thiazinan‐4‐ones Analogous to Rosiglitazone</atitle><jtitle>Journal of heterocyclic chemistry</jtitle><date>2019-01</date><risdate>2019</risdate><volume>56</volume><issue>1</issue><spage>251</spage><epage>259</epage><pages>251-259</pages><issn>0022-152X</issn><eissn>1943-5193</eissn><abstract>This work reports the synthesis of thiazolidin‐4‐ones and thiazinan‐4‐ones analogous to rosiglitazone, a potent antidiabetic drug. 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| identifier | ISSN: 0022-152X |
| ispartof | Journal of heterocyclic chemistry, 2019-01, Vol.56 (1), p.251-259 |
| issn | 0022-152X 1943-5193 |
| language | eng |
| recordid | cdi_proquest_journals_2165089492 |
| source | Wiley Journals |
| subjects | Amines Benzaldehyde Chemical synthesis Mass spectrometry NMR Nuclear magnetic resonance Nuclear reactions X-ray diffraction |
| title | Synthesis of Novel Thiazolidin‐4‐ones and Thiazinan‐4‐ones Analogous to Rosiglitazone |
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