Thiazolidine-2,4-dione in benzoylation reaction
The direction of the benzoylation reaction of thiazolidine-2,4-dione under the conditions of basic and general acid catalysis was studied. It was shown that the direction of benzoylation of thiazolidine-2,4-dione at the cyclic nitrogen atom or oxygen atoms depends on two major factors: the solvent a...
Gespeichert in:
| Veröffentlicht in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2019-02, Vol.55 (2), p.178-183 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 183 |
|---|---|
| container_issue | 2 |
| container_start_page | 178 |
| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
| container_volume | 55 |
| creator | Levshin, Igor B. Rastorgueva, Nina A. Kiselev, Alexey V. Vedenkin, Alexandr S. Stovbun, Sergey V. Churakov, Andrei V. Saveliev, Oleg Yu Polshakov, Vladimir I. |
| description | The direction of the benzoylation reaction of thiazolidine-2,4-dione under the conditions of basic and general acid catalysis was studied. It was shown that the direction of benzoylation of thiazolidine-2,4-dione at the cyclic nitrogen atom or oxygen atoms depends on two major factors: the solvent and the presence of cations. A nonpolar solvent and triethylamine direct the reaction toward the formation of the dibenzoyl product, which was isolated and characterized for the first time. The structure of this compound has been unambiguously identified using NMR and X-ray diffraction analysis. A hydrogen bond between the nitrogen atom of the dibenzoyl product and the proton of the chloroform molecule was found in crystal structure. |
| doi_str_mv | 10.1007/s10593-019-02436-2 |
| format | Article |
| fullrecord | <record><control><sourceid>gale_proqu</sourceid><recordid>TN_cdi_proquest_journals_2203232869</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><galeid>A581343928</galeid><sourcerecordid>A581343928</sourcerecordid><originalsourceid>FETCH-LOGICAL-c358t-ca1a1ea60488f6c84d86df6177882d6c1d91786769422251177ecb264656d1513</originalsourceid><addsrcrecordid>eNp9kE1PAjEQhhujiYj-AU8kXi10ph_bPRLiV0LiBc9NabtYsuxidznAr7e4Jt7MHGY6fZ_p9CXkHtgUGCtmHTBZcsqgpAwFVxQvyAhkwanmkl-SEWOspBwQr8lN123zsQAtRmS2-oz21NbRxyZQfBTUx7YJk9hM1qE5tcfa9rkxScG6c3FLripbd-HuN4_Jx_PTavFKl-8vb4v5kjoudU-dBQvBKia0rpTTwmvlKwVFoTV65cCXUGhVqFIgooR8EdwalVBSeZDAx-RhmLtP7dchdL3ZtofU5CcNIuPIUasyq6aDamPrYGJTtX2yLocPu-jyP6qY-3OpgQteos4ADoBLbdelUJl9ijubjgaYOTtpBidNdtL8OGkwQ3yAuixuNiH97fIP9Q1u_HLo</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2203232869</pqid></control><display><type>article</type><title>Thiazolidine-2,4-dione in benzoylation reaction</title><source>SpringerNature Complete Journals</source><creator>Levshin, Igor B. ; Rastorgueva, Nina A. ; Kiselev, Alexey V. ; Vedenkin, Alexandr S. ; Stovbun, Sergey V. ; Churakov, Andrei V. ; Saveliev, Oleg Yu ; Polshakov, Vladimir I.</creator><creatorcontrib>Levshin, Igor B. ; Rastorgueva, Nina A. ; Kiselev, Alexey V. ; Vedenkin, Alexandr S. ; Stovbun, Sergey V. ; Churakov, Andrei V. ; Saveliev, Oleg Yu ; Polshakov, Vladimir I.</creatorcontrib><description>The direction of the benzoylation reaction of thiazolidine-2,4-dione under the conditions of basic and general acid catalysis was studied. It was shown that the direction of benzoylation of thiazolidine-2,4-dione at the cyclic nitrogen atom or oxygen atoms depends on two major factors: the solvent and the presence of cations. A nonpolar solvent and triethylamine direct the reaction toward the formation of the dibenzoyl product, which was isolated and characterized for the first time. The structure of this compound has been unambiguously identified using NMR and X-ray diffraction analysis. A hydrogen bond between the nitrogen atom of the dibenzoyl product and the proton of the chloroform molecule was found in crystal structure.</description><identifier>ISSN: 0009-3122</identifier><identifier>EISSN: 1573-8353</identifier><identifier>DOI: 10.1007/s10593-019-02436-2</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Benzoylation ; Bonds (Securities) ; Catalysis ; Chemistry ; Chemistry and Materials Science ; Chloroform ; Crystal structure ; Diketones ; Hydrogen ; Hydrogen bonds ; Molecular structure ; Nitrogen (Chemical element) ; NMR ; Nuclear magnetic resonance ; Organic Chemistry ; Oxygen atoms ; Pharmacy ; Solvents ; Triethylamine ; X-ray diffraction</subject><ispartof>Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2019-02, Vol.55 (2), p.178-183</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2019</rights><rights>COPYRIGHT 2019 Springer</rights><rights>Copyright Springer Nature B.V. 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c358t-ca1a1ea60488f6c84d86df6177882d6c1d91786769422251177ecb264656d1513</citedby><cites>FETCH-LOGICAL-c358t-ca1a1ea60488f6c84d86df6177882d6c1d91786769422251177ecb264656d1513</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10593-019-02436-2$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10593-019-02436-2$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Levshin, Igor B.</creatorcontrib><creatorcontrib>Rastorgueva, Nina A.</creatorcontrib><creatorcontrib>Kiselev, Alexey V.</creatorcontrib><creatorcontrib>Vedenkin, Alexandr S.</creatorcontrib><creatorcontrib>Stovbun, Sergey V.</creatorcontrib><creatorcontrib>Churakov, Andrei V.</creatorcontrib><creatorcontrib>Saveliev, Oleg Yu</creatorcontrib><creatorcontrib>Polshakov, Vladimir I.</creatorcontrib><title>Thiazolidine-2,4-dione in benzoylation reaction</title><title>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</title><addtitle>Chem Heterocycl Comp</addtitle><description>The direction of the benzoylation reaction of thiazolidine-2,4-dione under the conditions of basic and general acid catalysis was studied. It was shown that the direction of benzoylation of thiazolidine-2,4-dione at the cyclic nitrogen atom or oxygen atoms depends on two major factors: the solvent and the presence of cations. A nonpolar solvent and triethylamine direct the reaction toward the formation of the dibenzoyl product, which was isolated and characterized for the first time. The structure of this compound has been unambiguously identified using NMR and X-ray diffraction analysis. A hydrogen bond between the nitrogen atom of the dibenzoyl product and the proton of the chloroform molecule was found in crystal structure.</description><subject>Benzoylation</subject><subject>Bonds (Securities)</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chloroform</subject><subject>Crystal structure</subject><subject>Diketones</subject><subject>Hydrogen</subject><subject>Hydrogen bonds</subject><subject>Molecular structure</subject><subject>Nitrogen (Chemical element)</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><subject>Oxygen atoms</subject><subject>Pharmacy</subject><subject>Solvents</subject><subject>Triethylamine</subject><subject>X-ray diffraction</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kE1PAjEQhhujiYj-AU8kXi10ph_bPRLiV0LiBc9NabtYsuxidznAr7e4Jt7MHGY6fZ_p9CXkHtgUGCtmHTBZcsqgpAwFVxQvyAhkwanmkl-SEWOspBwQr8lN123zsQAtRmS2-oz21NbRxyZQfBTUx7YJk9hM1qE5tcfa9rkxScG6c3FLripbd-HuN4_Jx_PTavFKl-8vb4v5kjoudU-dBQvBKia0rpTTwmvlKwVFoTV65cCXUGhVqFIgooR8EdwalVBSeZDAx-RhmLtP7dchdL3ZtofU5CcNIuPIUasyq6aDamPrYGJTtX2yLocPu-jyP6qY-3OpgQteos4ADoBLbdelUJl9ijubjgaYOTtpBidNdtL8OGkwQ3yAuixuNiH97fIP9Q1u_HLo</recordid><startdate>20190201</startdate><enddate>20190201</enddate><creator>Levshin, Igor B.</creator><creator>Rastorgueva, Nina A.</creator><creator>Kiselev, Alexey V.</creator><creator>Vedenkin, Alexandr S.</creator><creator>Stovbun, Sergey V.</creator><creator>Churakov, Andrei V.</creator><creator>Saveliev, Oleg Yu</creator><creator>Polshakov, Vladimir I.</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20190201</creationdate><title>Thiazolidine-2,4-dione in benzoylation reaction</title><author>Levshin, Igor B. ; Rastorgueva, Nina A. ; Kiselev, Alexey V. ; Vedenkin, Alexandr S. ; Stovbun, Sergey V. ; Churakov, Andrei V. ; Saveliev, Oleg Yu ; Polshakov, Vladimir I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c358t-ca1a1ea60488f6c84d86df6177882d6c1d91786769422251177ecb264656d1513</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Benzoylation</topic><topic>Bonds (Securities)</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chloroform</topic><topic>Crystal structure</topic><topic>Diketones</topic><topic>Hydrogen</topic><topic>Hydrogen bonds</topic><topic>Molecular structure</topic><topic>Nitrogen (Chemical element)</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic Chemistry</topic><topic>Oxygen atoms</topic><topic>Pharmacy</topic><topic>Solvents</topic><topic>Triethylamine</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Levshin, Igor B.</creatorcontrib><creatorcontrib>Rastorgueva, Nina A.</creatorcontrib><creatorcontrib>Kiselev, Alexey V.</creatorcontrib><creatorcontrib>Vedenkin, Alexandr S.</creatorcontrib><creatorcontrib>Stovbun, Sergey V.</creatorcontrib><creatorcontrib>Churakov, Andrei V.</creatorcontrib><creatorcontrib>Saveliev, Oleg Yu</creatorcontrib><creatorcontrib>Polshakov, Vladimir I.</creatorcontrib><collection>CrossRef</collection><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Levshin, Igor B.</au><au>Rastorgueva, Nina A.</au><au>Kiselev, Alexey V.</au><au>Vedenkin, Alexandr S.</au><au>Stovbun, Sergey V.</au><au>Churakov, Andrei V.</au><au>Saveliev, Oleg Yu</au><au>Polshakov, Vladimir I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thiazolidine-2,4-dione in benzoylation reaction</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2019-02-01</date><risdate>2019</risdate><volume>55</volume><issue>2</issue><spage>178</spage><epage>183</epage><pages>178-183</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>The direction of the benzoylation reaction of thiazolidine-2,4-dione under the conditions of basic and general acid catalysis was studied. It was shown that the direction of benzoylation of thiazolidine-2,4-dione at the cyclic nitrogen atom or oxygen atoms depends on two major factors: the solvent and the presence of cations. A nonpolar solvent and triethylamine direct the reaction toward the formation of the dibenzoyl product, which was isolated and characterized for the first time. The structure of this compound has been unambiguously identified using NMR and X-ray diffraction analysis. A hydrogen bond between the nitrogen atom of the dibenzoyl product and the proton of the chloroform molecule was found in crystal structure.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10593-019-02436-2</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-3122 |
| ispartof | Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2019-02, Vol.55 (2), p.178-183 |
| issn | 0009-3122 1573-8353 |
| language | eng |
| recordid | cdi_proquest_journals_2203232869 |
| source | SpringerNature Complete Journals |
| subjects | Benzoylation Bonds (Securities) Catalysis Chemistry Chemistry and Materials Science Chloroform Crystal structure Diketones Hydrogen Hydrogen bonds Molecular structure Nitrogen (Chemical element) NMR Nuclear magnetic resonance Organic Chemistry Oxygen atoms Pharmacy Solvents Triethylamine X-ray diffraction |
| title | Thiazolidine-2,4-dione in benzoylation reaction |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-29T00%3A59%3A37IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-gale_proqu&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Thiazolidine-2,4-dione%20in%20benzoylation%20reaction&rft.jtitle=Chemistry%20of%20heterocyclic%20compounds%20(New%20York,%20N.Y.%201965)&rft.au=Levshin,%20Igor%20B.&rft.date=2019-02-01&rft.volume=55&rft.issue=2&rft.spage=178&rft.epage=183&rft.pages=178-183&rft.issn=0009-3122&rft.eissn=1573-8353&rft_id=info:doi/10.1007/s10593-019-02436-2&rft_dat=%3Cgale_proqu%3EA581343928%3C/gale_proqu%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2203232869&rft_id=info:pmid/&rft_galeid=A581343928&rfr_iscdi=true |