Copper-mediated [3 + 2] oxidative cyclization of oxime acetate and its utility in the formal synthesis of fentiazac
A new protocol for the direct synthesis of 2-aminothiazole has been developed from oxime acetate and readily available sodium thiocyanate using a copper catalyst. The present transformation has good functional group tolerance. Various thiazoles were smoothly synthesized in good to excellent yields....
Gespeichert in:
| Veröffentlicht in: | Organic & biomolecular chemistry 2024-01, Vol.22 (3), p.521-528 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 528 |
|---|---|
| container_issue | 3 |
| container_start_page | 521 |
| container_title | Organic & biomolecular chemistry |
| container_volume | 22 |
| creator | Jadhao, Nitin L Musale, Harish B Gajbhiye, Jayant M Humne, Vivek T |
| description | A new protocol for the direct synthesis of 2-aminothiazole has been developed from oxime acetate and readily available sodium thiocyanate using a copper catalyst. The present transformation has good functional group tolerance. Various thiazoles were smoothly synthesized in good to excellent yields. The applicability of the present method has been extended to the formal synthesis of the non-steroidal and anti-inflammatory drug, fentiazac
via
the Sandmeyer reaction and Suzuki coupling.
The direct synthesis of 2-aminothiazole has been developed from oxime acetate using a copper catalyst. The applicability of the present method is used in the formal synthesis of fentiazac. |
| doi_str_mv | 10.1039/d3ob01882b |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_D3OB01882B</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2915517032</sourcerecordid><originalsourceid>FETCH-LOGICAL-c296t-f88545646e639a55600611fa71ac5adb649be9cc03bfc7f67bad74de918b80ef3</originalsourceid><addsrcrecordid>eNpd0c9v0zAUB3ALMdGu48IdZIkLYgrzj8SOj7RjgFRpl-2EUOQ4z8JVEhfbmcj-elw6isTJz3ofP1nvi9ArSj5QwtVVx31LaF2z9hla0lLKglRcPT_VjCzQeYw7QqiSonyBFrwmtVScL1Hc-P0eQjFA53SCDn_j-BKz79j_cp1O7gGwmU3vHnPtR-ztoTEA1gZS9liPHXYp4im53qUZuxGnH4CtD4PucZzHfIsuHh5aGJPTj9pcoDOr-wgvn84Vur_5dLf5UmxvP3_dfNwWhimRClvXVVmJUoDgSleVIERQarWk2lS6a0WpWlDGEN5aI62Qre5k2YGidVsTsHyF3h3n7oP_OUFMzeCigb7XI_gpNkwRpkomlcr07X9056cw5t9lRauKSsJZVu-PygQfYwDb7IMbdJgbSppDFM01v13_iWKd8ZunkVObt3uif3efwesjCNGcuv-y5L8BhJKN2w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2915517032</pqid></control><display><type>article</type><title>Copper-mediated [3 + 2] oxidative cyclization of oxime acetate and its utility in the formal synthesis of fentiazac</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Jadhao, Nitin L ; Musale, Harish B ; Gajbhiye, Jayant M ; Humne, Vivek T</creator><creatorcontrib>Jadhao, Nitin L ; Musale, Harish B ; Gajbhiye, Jayant M ; Humne, Vivek T</creatorcontrib><description>A new protocol for the direct synthesis of 2-aminothiazole has been developed from oxime acetate and readily available sodium thiocyanate using a copper catalyst. The present transformation has good functional group tolerance. Various thiazoles were smoothly synthesized in good to excellent yields. The applicability of the present method has been extended to the formal synthesis of the non-steroidal and anti-inflammatory drug, fentiazac
via
the Sandmeyer reaction and Suzuki coupling.
The direct synthesis of 2-aminothiazole has been developed from oxime acetate using a copper catalyst. The applicability of the present method is used in the formal synthesis of fentiazac.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d3ob01882b</identifier><identifier>PMID: 38087933</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Acetic acid ; Anti-inflammatory agents ; Catalysts ; Copper ; Functional groups ; Inflammation ; Sodium thiocyanate ; Synthesis ; Thiazoles</subject><ispartof>Organic & biomolecular chemistry, 2024-01, Vol.22 (3), p.521-528</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c296t-f88545646e639a55600611fa71ac5adb649be9cc03bfc7f67bad74de918b80ef3</cites><orcidid>0000-0002-3412-5149</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38087933$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jadhao, Nitin L</creatorcontrib><creatorcontrib>Musale, Harish B</creatorcontrib><creatorcontrib>Gajbhiye, Jayant M</creatorcontrib><creatorcontrib>Humne, Vivek T</creatorcontrib><title>Copper-mediated [3 + 2] oxidative cyclization of oxime acetate and its utility in the formal synthesis of fentiazac</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A new protocol for the direct synthesis of 2-aminothiazole has been developed from oxime acetate and readily available sodium thiocyanate using a copper catalyst. The present transformation has good functional group tolerance. Various thiazoles were smoothly synthesized in good to excellent yields. The applicability of the present method has been extended to the formal synthesis of the non-steroidal and anti-inflammatory drug, fentiazac
via
the Sandmeyer reaction and Suzuki coupling.
The direct synthesis of 2-aminothiazole has been developed from oxime acetate using a copper catalyst. The applicability of the present method is used in the formal synthesis of fentiazac.</description><subject>Acetic acid</subject><subject>Anti-inflammatory agents</subject><subject>Catalysts</subject><subject>Copper</subject><subject>Functional groups</subject><subject>Inflammation</subject><subject>Sodium thiocyanate</subject><subject>Synthesis</subject><subject>Thiazoles</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpd0c9v0zAUB3ALMdGu48IdZIkLYgrzj8SOj7RjgFRpl-2EUOQ4z8JVEhfbmcj-elw6isTJz3ofP1nvi9ArSj5QwtVVx31LaF2z9hla0lLKglRcPT_VjCzQeYw7QqiSonyBFrwmtVScL1Hc-P0eQjFA53SCDn_j-BKz79j_cp1O7gGwmU3vHnPtR-ztoTEA1gZS9liPHXYp4im53qUZuxGnH4CtD4PucZzHfIsuHh5aGJPTj9pcoDOr-wgvn84Vur_5dLf5UmxvP3_dfNwWhimRClvXVVmJUoDgSleVIERQarWk2lS6a0WpWlDGEN5aI62Qre5k2YGidVsTsHyF3h3n7oP_OUFMzeCigb7XI_gpNkwRpkomlcr07X9056cw5t9lRauKSsJZVu-PygQfYwDb7IMbdJgbSppDFM01v13_iWKd8ZunkVObt3uif3efwesjCNGcuv-y5L8BhJKN2w</recordid><startdate>20240117</startdate><enddate>20240117</enddate><creator>Jadhao, Nitin L</creator><creator>Musale, Harish B</creator><creator>Gajbhiye, Jayant M</creator><creator>Humne, Vivek T</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3412-5149</orcidid></search><sort><creationdate>20240117</creationdate><title>Copper-mediated [3 + 2] oxidative cyclization of oxime acetate and its utility in the formal synthesis of fentiazac</title><author>Jadhao, Nitin L ; Musale, Harish B ; Gajbhiye, Jayant M ; Humne, Vivek T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-f88545646e639a55600611fa71ac5adb649be9cc03bfc7f67bad74de918b80ef3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Acetic acid</topic><topic>Anti-inflammatory agents</topic><topic>Catalysts</topic><topic>Copper</topic><topic>Functional groups</topic><topic>Inflammation</topic><topic>Sodium thiocyanate</topic><topic>Synthesis</topic><topic>Thiazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jadhao, Nitin L</creatorcontrib><creatorcontrib>Musale, Harish B</creatorcontrib><creatorcontrib>Gajbhiye, Jayant M</creatorcontrib><creatorcontrib>Humne, Vivek T</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jadhao, Nitin L</au><au>Musale, Harish B</au><au>Gajbhiye, Jayant M</au><au>Humne, Vivek T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-mediated [3 + 2] oxidative cyclization of oxime acetate and its utility in the formal synthesis of fentiazac</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2024-01-17</date><risdate>2024</risdate><volume>22</volume><issue>3</issue><spage>521</spage><epage>528</epage><pages>521-528</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A new protocol for the direct synthesis of 2-aminothiazole has been developed from oxime acetate and readily available sodium thiocyanate using a copper catalyst. The present transformation has good functional group tolerance. Various thiazoles were smoothly synthesized in good to excellent yields. The applicability of the present method has been extended to the formal synthesis of the non-steroidal and anti-inflammatory drug, fentiazac
via
the Sandmeyer reaction and Suzuki coupling.
The direct synthesis of 2-aminothiazole has been developed from oxime acetate using a copper catalyst. The applicability of the present method is used in the formal synthesis of fentiazac.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38087933</pmid><doi>10.1039/d3ob01882b</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-3412-5149</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2024-01, Vol.22 (3), p.521-528 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_D3OB01882B |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acetic acid Anti-inflammatory agents Catalysts Copper Functional groups Inflammation Sodium thiocyanate Synthesis Thiazoles |
| title | Copper-mediated [3 + 2] oxidative cyclization of oxime acetate and its utility in the formal synthesis of fentiazac |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T00%3A19%3A26IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Copper-mediated%20%5B3%20+%202%5D%20oxidative%20cyclization%20of%20oxime%20acetate%20and%20its%20utility%20in%20the%20formal%20synthesis%20of%20fentiazac&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Jadhao,%20Nitin%20L&rft.date=2024-01-17&rft.volume=22&rft.issue=3&rft.spage=521&rft.epage=528&rft.pages=521-528&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/d3ob01882b&rft_dat=%3Cproquest_cross%3E2915517032%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2915517032&rft_id=info:pmid/38087933&rfr_iscdi=true |