Diacetoxyiodobenzene assisted C-O bond formation via sequential acylation and deacylation process: synthesis of benzoxazole amides and their mechanistic study by DFT
An efficient method for the transformation of N-substituted-N'-benzoylthioureas to substituted N-benzoxazol-2-yl-amides using diacetoxyiodobenzene (DIB) is described in this work. The transformation follows the C-O bond formation leading to the benzoxazole derivative, due to oxidative dehydroge...
Gespeichert in:
| Veröffentlicht in: | Organic & biomolecular chemistry 2016-01, Vol.14 (32), p.7735-7745 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 7745 |
|---|---|
| container_issue | 32 |
| container_start_page | 7735 |
| container_title | Organic & biomolecular chemistry |
| container_volume | 14 |
| creator | Nahakpam, Lokendrajit Chipem, Francis A S Chingakham, Brajakishor S Laitonjam, Warjeet S |
| description | An efficient method for the transformation of N-substituted-N'-benzoylthioureas to substituted N-benzoxazol-2-yl-amides using diacetoxyiodobenzene (DIB) is described in this work. The transformation follows the C-O bond formation leading to the benzoxazole derivative, due to oxidative dehydrogenation by DIB, instead of the expected C-S bond formation of the benzothiazole moiety. The C-O bond formation leading to benzoxazole is due to consecutive acylation and deacylation in conjunction with the reduction of two moles of DIB. A plausible mechanism was proposed for the reaction and density functional calculations were also performed to study the reaction mechanism. |
| doi_str_mv | 10.1039/c6ob00968a |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1815707755</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1815707755</sourcerecordid><originalsourceid>FETCH-LOGICAL-c320t-d29de16f3f28e6ec6ed62caf9f73b4a4d06342ba0973e4344b811f69091150183</originalsourceid><addsrcrecordid>eNqNkcFO3DAQhq2KqsDSSx-g8hFVSmvHjh33BkuhSEh7gXPk2GNhlMTbTBZt9n36njUs0CsnjzXf_P-MfkK-cPadM2F-OJVaxoyq7QdyxKXWBauEOXirS3ZIjhEfGONGK_mJHJZaKl6p8oj8vYjWwZS2c0w-tTDsYABqESNO4OmyWNE2DZ6GNPZ2immgj9FShD8bGKZoO2rd3O0bNmMe_v_XY3KA-JPiPEz3kBVpCvTJIm3tLnXZpo8e8HkwA3GkPbh7O2Tr6ChOGz_TdqYXl7cn5GOwHcLnl3dB7i5_3S5_Fzerq-vl2U3hRMmmwpfGA1dBhLIGBU6BV6WzwQQtWmmlZ0rIsrXMaAFSSNnWnAdlmOG8YrwWC3K618275wtxavqIDrrODpA22PCaV5ppXVXvQVmtdM1NRr_tUTcmxBFCsx5jb8e54ax5SrBZqtX5c4JnGf76ortpe_Bv6Gtk4h-vipmD</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1810867819</pqid></control><display><type>article</type><title>Diacetoxyiodobenzene assisted C-O bond formation via sequential acylation and deacylation process: synthesis of benzoxazole amides and their mechanistic study by DFT</title><source>Royal Society Of Chemistry Journals</source><source>Alma/SFX Local Collection</source><creator>Nahakpam, Lokendrajit ; Chipem, Francis A S ; Chingakham, Brajakishor S ; Laitonjam, Warjeet S</creator><creatorcontrib>Nahakpam, Lokendrajit ; Chipem, Francis A S ; Chingakham, Brajakishor S ; Laitonjam, Warjeet S</creatorcontrib><description>An efficient method for the transformation of N-substituted-N'-benzoylthioureas to substituted N-benzoxazol-2-yl-amides using diacetoxyiodobenzene (DIB) is described in this work. The transformation follows the C-O bond formation leading to the benzoxazole derivative, due to oxidative dehydrogenation by DIB, instead of the expected C-S bond formation of the benzothiazole moiety. The C-O bond formation leading to benzoxazole is due to consecutive acylation and deacylation in conjunction with the reduction of two moles of DIB. A plausible mechanism was proposed for the reaction and density functional calculations were also performed to study the reaction mechanism.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c6ob00968a</identifier><identifier>PMID: 27461562</identifier><language>eng</language><publisher>England</publisher><ispartof>Organic & biomolecular chemistry, 2016-01, Vol.14 (32), p.7735-7745</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c320t-d29de16f3f28e6ec6ed62caf9f73b4a4d06342ba0973e4344b811f69091150183</citedby><cites>FETCH-LOGICAL-c320t-d29de16f3f28e6ec6ed62caf9f73b4a4d06342ba0973e4344b811f69091150183</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27461562$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nahakpam, Lokendrajit</creatorcontrib><creatorcontrib>Chipem, Francis A S</creatorcontrib><creatorcontrib>Chingakham, Brajakishor S</creatorcontrib><creatorcontrib>Laitonjam, Warjeet S</creatorcontrib><title>Diacetoxyiodobenzene assisted C-O bond formation via sequential acylation and deacylation process: synthesis of benzoxazole amides and their mechanistic study by DFT</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>An efficient method for the transformation of N-substituted-N'-benzoylthioureas to substituted N-benzoxazol-2-yl-amides using diacetoxyiodobenzene (DIB) is described in this work. The transformation follows the C-O bond formation leading to the benzoxazole derivative, due to oxidative dehydrogenation by DIB, instead of the expected C-S bond formation of the benzothiazole moiety. The C-O bond formation leading to benzoxazole is due to consecutive acylation and deacylation in conjunction with the reduction of two moles of DIB. A plausible mechanism was proposed for the reaction and density functional calculations were also performed to study the reaction mechanism.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqNkcFO3DAQhq2KqsDSSx-g8hFVSmvHjh33BkuhSEh7gXPk2GNhlMTbTBZt9n36njUs0CsnjzXf_P-MfkK-cPadM2F-OJVaxoyq7QdyxKXWBauEOXirS3ZIjhEfGONGK_mJHJZaKl6p8oj8vYjWwZS2c0w-tTDsYABqESNO4OmyWNE2DZ6GNPZ2immgj9FShD8bGKZoO2rd3O0bNmMe_v_XY3KA-JPiPEz3kBVpCvTJIm3tLnXZpo8e8HkwA3GkPbh7O2Tr6ChOGz_TdqYXl7cn5GOwHcLnl3dB7i5_3S5_Fzerq-vl2U3hRMmmwpfGA1dBhLIGBU6BV6WzwQQtWmmlZ0rIsrXMaAFSSNnWnAdlmOG8YrwWC3K618275wtxavqIDrrODpA22PCaV5ppXVXvQVmtdM1NRr_tUTcmxBFCsx5jb8e54ax5SrBZqtX5c4JnGf76ortpe_Bv6Gtk4h-vipmD</recordid><startdate>20160101</startdate><enddate>20160101</enddate><creator>Nahakpam, Lokendrajit</creator><creator>Chipem, Francis A S</creator><creator>Chingakham, Brajakishor S</creator><creator>Laitonjam, Warjeet S</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20160101</creationdate><title>Diacetoxyiodobenzene assisted C-O bond formation via sequential acylation and deacylation process: synthesis of benzoxazole amides and their mechanistic study by DFT</title><author>Nahakpam, Lokendrajit ; Chipem, Francis A S ; Chingakham, Brajakishor S ; Laitonjam, Warjeet S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c320t-d29de16f3f28e6ec6ed62caf9f73b4a4d06342ba0973e4344b811f69091150183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nahakpam, Lokendrajit</creatorcontrib><creatorcontrib>Chipem, Francis A S</creatorcontrib><creatorcontrib>Chingakham, Brajakishor S</creatorcontrib><creatorcontrib>Laitonjam, Warjeet S</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nahakpam, Lokendrajit</au><au>Chipem, Francis A S</au><au>Chingakham, Brajakishor S</au><au>Laitonjam, Warjeet S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diacetoxyiodobenzene assisted C-O bond formation via sequential acylation and deacylation process: synthesis of benzoxazole amides and their mechanistic study by DFT</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2016-01-01</date><risdate>2016</risdate><volume>14</volume><issue>32</issue><spage>7735</spage><epage>7745</epage><pages>7735-7745</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>An efficient method for the transformation of N-substituted-N'-benzoylthioureas to substituted N-benzoxazol-2-yl-amides using diacetoxyiodobenzene (DIB) is described in this work. The transformation follows the C-O bond formation leading to the benzoxazole derivative, due to oxidative dehydrogenation by DIB, instead of the expected C-S bond formation of the benzothiazole moiety. The C-O bond formation leading to benzoxazole is due to consecutive acylation and deacylation in conjunction with the reduction of two moles of DIB. A plausible mechanism was proposed for the reaction and density functional calculations were also performed to study the reaction mechanism.</abstract><cop>England</cop><pmid>27461562</pmid><doi>10.1039/c6ob00968a</doi><tpages>11</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2016-01, Vol.14 (32), p.7735-7745 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1815707755 |
| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| title | Diacetoxyiodobenzene assisted C-O bond formation via sequential acylation and deacylation process: synthesis of benzoxazole amides and their mechanistic study by DFT |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T18%3A26%3A15IST&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=Diacetoxyiodobenzene%20assisted%20C-O%20bond%20formation%20via%20sequential%20acylation%20and%20deacylation%20process:%20synthesis%20of%20benzoxazole%20amides%20and%20their%20mechanistic%20study%20by%20DFT&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Nahakpam,%20Lokendrajit&rft.date=2016-01-01&rft.volume=14&rft.issue=32&rft.spage=7735&rft.epage=7745&rft.pages=7735-7745&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/c6ob00968a&rft_dat=%3Cproquest_cross%3E1815707755%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=1810867819&rft_id=info:pmid/27461562&rfr_iscdi=true |