Synthetic Utilization of Polynitroaromatic Compounds. 2. Synthesis of 4,6-Dinitro-1,2-benzisothiazol-3-ones and 4,6-Dinitro-1,2-benzisothiazoles from 2-Benzylthio-4,6-dinitrobenzamides
Cyclization of 2-benzylthio-4,6-dinitrobenzamides to 4,6-dinitro-1,2-benzisothiazol-3-ones was achieved using SO2Cl2 in CH2Cl2 at room temperature. Alkylation of these heterocycles proceeded in a nonregioselective manner to yield a mixture of corresponding O- and N-alkylated products. Oxidation of 4...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2000-12, Vol.65 (25), p.8439-8443 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 8443 |
|---|---|
| container_issue | 25 |
| container_start_page | 8439 |
| container_title | Journal of organic chemistry |
| container_volume | 65 |
| creator | Zlotin, S. G Kislitsin, P. G Podgursky, A. I Samet, A. V Semenov, V. V Buchanan, A. C Gakh, Andrei A |
| description | Cyclization of 2-benzylthio-4,6-dinitrobenzamides to 4,6-dinitro-1,2-benzisothiazol-3-ones was achieved using SO2Cl2 in CH2Cl2 at room temperature. Alkylation of these heterocycles proceeded in a nonregioselective manner to yield a mixture of corresponding O- and N-alkylated products. Oxidation of 4,6-dinitro-1,2-benzisothiazoles (50% H2O2 in AcOH) afforded the corresponding S-oxides and S,S-dioxides, depending on oxidation conditions. Unexpectedly, oxidation of a 3-methoxy derivative resulted in ring opening with the formation of the corresponding sulfamide. Chlorination of these 4,6-dinitro-1,2-benzisothiazol-3-ones (PCl5−POCl3) gave the expected 3-chloroisothiazoles. |
| doi_str_mv | 10.1021/jo000480c |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_72468778</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>72468778</sourcerecordid><originalsourceid>FETCH-LOGICAL-a349t-15d18fc991f816ffbefdaa1acba20aaf18bdde7a4c76efac99ab7a94f692fe9e3</originalsourceid><addsrcrecordid>eNqF0UFrFDEUB_AgFrtWD34BmYuC0KxJZiaZOeqqrVKw0O05vJkkNHUmWZMMuPvJ_HhmOku9COYSePm994c8hF5RsqaE0ff3nhBSNaR_gla0ZgTzllRP0YoQxnDJeHmKnsd4nxGp6_oZOqX5sJqTFfp9s3fpTifbF7fJDvYAyXpXeFNc-2HvbAoegh9hBhs_7vzkVFwXbF0sjdHGGVfnHH-yDxzTc4Y77Q42-nRn4eAHXGLvdCzAqf_IjEyOKxj-mOv7IZc9nlvU0jJrGK3S8QU6MTBE_fJ4n6HbL5-3m0t89f3i6-bDFYayahOmtaKN6duWmoZyYzptFACFvgNGAAxtOqW0gKoXXBvIEDoBbWV4y4xudXmG3i5zd8H_nHRMcrSx18MATvspSsEq3gjRZPhugX3wMQZt5C7YEcJeUiLnNcnHNWX7-jh06kat_srjXjLAC7Ax6V-P7xB-SC5KUcvt9U2O3n7bCi4kz_7N4qGPOWcKLv_JP4L_AJg4rBU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>72468778</pqid></control><display><type>article</type><title>Synthetic Utilization of Polynitroaromatic Compounds. 2. Synthesis of 4,6-Dinitro-1,2-benzisothiazol-3-ones and 4,6-Dinitro-1,2-benzisothiazoles from 2-Benzylthio-4,6-dinitrobenzamides</title><source>ACS Publications</source><creator>Zlotin, S. G ; Kislitsin, P. G ; Podgursky, A. I ; Samet, A. V ; Semenov, V. V ; Buchanan, A. C ; Gakh, Andrei A</creator><creatorcontrib>Zlotin, S. G ; Kislitsin, P. G ; Podgursky, A. I ; Samet, A. V ; Semenov, V. V ; Buchanan, A. C ; Gakh, Andrei A</creatorcontrib><description>Cyclization of 2-benzylthio-4,6-dinitrobenzamides to 4,6-dinitro-1,2-benzisothiazol-3-ones was achieved using SO2Cl2 in CH2Cl2 at room temperature. Alkylation of these heterocycles proceeded in a nonregioselective manner to yield a mixture of corresponding O- and N-alkylated products. Oxidation of 4,6-dinitro-1,2-benzisothiazoles (50% H2O2 in AcOH) afforded the corresponding S-oxides and S,S-dioxides, depending on oxidation conditions. Unexpectedly, oxidation of a 3-methoxy derivative resulted in ring opening with the formation of the corresponding sulfamide. Chlorination of these 4,6-dinitro-1,2-benzisothiazol-3-ones (PCl5−POCl3) gave the expected 3-chloroisothiazoles.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo000480c</identifier><identifier>PMID: 11112560</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2000-12, Vol.65 (25), p.8439-8443</ispartof><rights>Copyright © 2000 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a349t-15d18fc991f816ffbefdaa1acba20aaf18bdde7a4c76efac99ab7a94f692fe9e3</citedby><cites>FETCH-LOGICAL-a349t-15d18fc991f816ffbefdaa1acba20aaf18bdde7a4c76efac99ab7a94f692fe9e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo000480c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo000480c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11112560$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zlotin, S. G</creatorcontrib><creatorcontrib>Kislitsin, P. G</creatorcontrib><creatorcontrib>Podgursky, A. I</creatorcontrib><creatorcontrib>Samet, A. V</creatorcontrib><creatorcontrib>Semenov, V. V</creatorcontrib><creatorcontrib>Buchanan, A. C</creatorcontrib><creatorcontrib>Gakh, Andrei A</creatorcontrib><title>Synthetic Utilization of Polynitroaromatic Compounds. 2. Synthesis of 4,6-Dinitro-1,2-benzisothiazol-3-ones and 4,6-Dinitro-1,2-benzisothiazoles from 2-Benzylthio-4,6-dinitrobenzamides</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Cyclization of 2-benzylthio-4,6-dinitrobenzamides to 4,6-dinitro-1,2-benzisothiazol-3-ones was achieved using SO2Cl2 in CH2Cl2 at room temperature. Alkylation of these heterocycles proceeded in a nonregioselective manner to yield a mixture of corresponding O- and N-alkylated products. Oxidation of 4,6-dinitro-1,2-benzisothiazoles (50% H2O2 in AcOH) afforded the corresponding S-oxides and S,S-dioxides, depending on oxidation conditions. Unexpectedly, oxidation of a 3-methoxy derivative resulted in ring opening with the formation of the corresponding sulfamide. Chlorination of these 4,6-dinitro-1,2-benzisothiazol-3-ones (PCl5−POCl3) gave the expected 3-chloroisothiazoles.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNqF0UFrFDEUB_AgFrtWD34BmYuC0KxJZiaZOeqqrVKw0O05vJkkNHUmWZMMuPvJ_HhmOku9COYSePm994c8hF5RsqaE0ff3nhBSNaR_gla0ZgTzllRP0YoQxnDJeHmKnsd4nxGp6_oZOqX5sJqTFfp9s3fpTifbF7fJDvYAyXpXeFNc-2HvbAoegh9hBhs_7vzkVFwXbF0sjdHGGVfnHH-yDxzTc4Y77Q42-nRn4eAHXGLvdCzAqf_IjEyOKxj-mOv7IZc9nlvU0jJrGK3S8QU6MTBE_fJ4n6HbL5-3m0t89f3i6-bDFYayahOmtaKN6duWmoZyYzptFACFvgNGAAxtOqW0gKoXXBvIEDoBbWV4y4xudXmG3i5zd8H_nHRMcrSx18MATvspSsEq3gjRZPhugX3wMQZt5C7YEcJeUiLnNcnHNWX7-jh06kat_srjXjLAC7Ax6V-P7xB-SC5KUcvt9U2O3n7bCi4kz_7N4qGPOWcKLv_JP4L_AJg4rBU</recordid><startdate>20001215</startdate><enddate>20001215</enddate><creator>Zlotin, S. G</creator><creator>Kislitsin, P. G</creator><creator>Podgursky, A. I</creator><creator>Samet, A. V</creator><creator>Semenov, V. V</creator><creator>Buchanan, A. C</creator><creator>Gakh, Andrei A</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20001215</creationdate><title>Synthetic Utilization of Polynitroaromatic Compounds. 2. Synthesis of 4,6-Dinitro-1,2-benzisothiazol-3-ones and 4,6-Dinitro-1,2-benzisothiazoles from 2-Benzylthio-4,6-dinitrobenzamides</title><author>Zlotin, S. G ; Kislitsin, P. G ; Podgursky, A. I ; Samet, A. V ; Semenov, V. V ; Buchanan, A. C ; Gakh, Andrei A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a349t-15d18fc991f816ffbefdaa1acba20aaf18bdde7a4c76efac99ab7a94f692fe9e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zlotin, S. G</creatorcontrib><creatorcontrib>Kislitsin, P. G</creatorcontrib><creatorcontrib>Podgursky, A. I</creatorcontrib><creatorcontrib>Samet, A. V</creatorcontrib><creatorcontrib>Semenov, V. V</creatorcontrib><creatorcontrib>Buchanan, A. C</creatorcontrib><creatorcontrib>Gakh, Andrei A</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zlotin, S. G</au><au>Kislitsin, P. G</au><au>Podgursky, A. I</au><au>Samet, A. V</au><au>Semenov, V. V</au><au>Buchanan, A. C</au><au>Gakh, Andrei A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthetic Utilization of Polynitroaromatic Compounds. 2. Synthesis of 4,6-Dinitro-1,2-benzisothiazol-3-ones and 4,6-Dinitro-1,2-benzisothiazoles from 2-Benzylthio-4,6-dinitrobenzamides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2000-12-15</date><risdate>2000</risdate><volume>65</volume><issue>25</issue><spage>8439</spage><epage>8443</epage><pages>8439-8443</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Cyclization of 2-benzylthio-4,6-dinitrobenzamides to 4,6-dinitro-1,2-benzisothiazol-3-ones was achieved using SO2Cl2 in CH2Cl2 at room temperature. Alkylation of these heterocycles proceeded in a nonregioselective manner to yield a mixture of corresponding O- and N-alkylated products. Oxidation of 4,6-dinitro-1,2-benzisothiazoles (50% H2O2 in AcOH) afforded the corresponding S-oxides and S,S-dioxides, depending on oxidation conditions. Unexpectedly, oxidation of a 3-methoxy derivative resulted in ring opening with the formation of the corresponding sulfamide. Chlorination of these 4,6-dinitro-1,2-benzisothiazol-3-ones (PCl5−POCl3) gave the expected 3-chloroisothiazoles.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11112560</pmid><doi>10.1021/jo000480c</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2000-12, Vol.65 (25), p.8439-8443 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_72468778 |
| source | ACS Publications |
| title | Synthetic Utilization of Polynitroaromatic Compounds. 2. Synthesis of 4,6-Dinitro-1,2-benzisothiazol-3-ones and 4,6-Dinitro-1,2-benzisothiazoles from 2-Benzylthio-4,6-dinitrobenzamides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-19T13%3A35%3A35IST&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=Synthetic%20Utilization%20of%20Polynitroaromatic%20Compounds.%202.%20Synthesis%20of%204,6-Dinitro-1,2-benzisothiazol-3-ones%20and%204,6-Dinitro-1,2-benzisothiazoles%20from%202-Benzylthio-4,6-dinitrobenzamides&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Zlotin,%20S.%20G&rft.date=2000-12-15&rft.volume=65&rft.issue=25&rft.spage=8439&rft.epage=8443&rft.pages=8439-8443&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/jo000480c&rft_dat=%3Cproquest_cross%3E72468778%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=72468778&rft_id=info:pmid/11112560&rfr_iscdi=true |