Synthetic Utilization of Polynitroaromatic Compounds. 3. Preparation of Substituted Dibenz[b,f][1,4]oxazepine-11(10H)-ones from 2,4,6-Trinitrobenzoic Acid via Nucleophilic Displacement of Nitro Groups
1,3-Dinitrodibenz[b,f][1,4]oxazepin-11(10H)-one, prepared by intramolecular displacement of nitro group in N-(2-hydroxyphenyl)-2,4,6-trinitrobenzamide, reacts with O- and S-nucleophiles to yield the products of mono- or bis-substitution of the nitro groups. The nitro group in position 3 is displaced...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2005-11, Vol.70 (23), p.9371-9376 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 9376 |
|---|---|
| container_issue | 23 |
| container_start_page | 9371 |
| container_title | Journal of organic chemistry |
| container_volume | 70 |
| creator | Samet, Alexander V Marshalkin, Victor N Kislyi, Konstantine A Chernysheva, Natalya B Strelenko, Yuri A Semenov, Victor V |
| description | 1,3-Dinitrodibenz[b,f][1,4]oxazepin-11(10H)-one, prepared by intramolecular displacement of nitro group in N-(2-hydroxyphenyl)-2,4,6-trinitrobenzamide, reacts with O- and S-nucleophiles to yield the products of mono- or bis-substitution of the nitro groups. The nitro group in position 3 is displaced first. This observation is in contrast with earlier results for the nitro-substituted benzoannulated five-membered heterocycles. This difference in reactivity is likely due to the increased steric hindrance for peri-nitro group displacement in the case of the benzoannulated seven-membered heterocycle. N-Alkylation of the nitro-substituted dibenz[b,f][1,4]oxazepin-11(10H)-ones yields analogues of a known antidepressant drug Sintamil. The structure of the products is confirmed by NOE experiments and alternative synthesis. |
| doi_str_mv | 10.1021/jo051425c |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68766954</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>68766954</sourcerecordid><originalsourceid>FETCH-LOGICAL-a351t-4362f31827f91eb34add763d9691d4bb41fd273eac7f1078d069cecb3eb9aaa23</originalsourceid><addsrcrecordid>eNptkU9v0zAYhyMEYmVw4AsgX0BMaor_JE5ynApsiGlUaicO0xQ59hvNI7GD7aC1n5CPhUOrcsEXH_y8v-eVf0nymuAFwZR8eLA4JxnN5ZNkRnKKU17h7Gkyw5jSlFHOTpIX3j_gePI8f56cEE55yQmeJb_XWxPuIWiJboLu9E4EbQ2yLVrZbmt0cFY424sJWNp-sKNRfoHYAq0cDMId8fXY-KDDGEChj7oBs7tt5u3dLZlnd_ZR7GDQBlJC3hN8eZZaAx61MRjReTbn6cbpv65pzkbVudQK_dICXY-yAzvcx9VkzPVDJyT0YMLkvJ5G0IWz4-BfJs9a0Xl4dbhPk5vPnzbLy_Tq28WX5flVKlhOQpoxTltGSlq0FYGGZUKpgjNV8YqorGky0ipaMBCyaAkuSoV5JUE2DJpKCEHZafJunzs4-3MEH-peewldJwzY0de8LDiv8iyCZ3tQOuu9g7YenO6F29YE11Nt9bG2yL45hI5ND-ofeegpAuke0D7A4_FduB81L1iR15vVus7KvPrKvq_qdeTf7nkhffSMzsQ_-Y_4D987sK8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68766954</pqid></control><display><type>article</type><title>Synthetic Utilization of Polynitroaromatic Compounds. 3. Preparation of Substituted Dibenz[b,f][1,4]oxazepine-11(10H)-ones from 2,4,6-Trinitrobenzoic Acid via Nucleophilic Displacement of Nitro Groups</title><source>MEDLINE</source><source>ACS Journals: American Chemical Society Web Editions</source><creator>Samet, Alexander V ; Marshalkin, Victor N ; Kislyi, Konstantine A ; Chernysheva, Natalya B ; Strelenko, Yuri A ; Semenov, Victor V</creator><creatorcontrib>Samet, Alexander V ; Marshalkin, Victor N ; Kislyi, Konstantine A ; Chernysheva, Natalya B ; Strelenko, Yuri A ; Semenov, Victor V</creatorcontrib><description>1,3-Dinitrodibenz[b,f][1,4]oxazepin-11(10H)-one, prepared by intramolecular displacement of nitro group in N-(2-hydroxyphenyl)-2,4,6-trinitrobenzamide, reacts with O- and S-nucleophiles to yield the products of mono- or bis-substitution of the nitro groups. The nitro group in position 3 is displaced first. This observation is in contrast with earlier results for the nitro-substituted benzoannulated five-membered heterocycles. This difference in reactivity is likely due to the increased steric hindrance for peri-nitro group displacement in the case of the benzoannulated seven-membered heterocycle. N-Alkylation of the nitro-substituted dibenz[b,f][1,4]oxazepin-11(10H)-ones yields analogues of a known antidepressant drug Sintamil. The structure of the products is confirmed by NOE experiments and alternative synthesis.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo051425c</identifier><identifier>PMID: 16268610</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Dibenzoxazepines - chemical synthesis ; Dibenzoxazepines - chemistry ; Molecular Structure ; Nitro Compounds - chemistry</subject><ispartof>Journal of organic chemistry, 2005-11, Vol.70 (23), p.9371-9376</ispartof><rights>Copyright © 2005 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a351t-4362f31827f91eb34add763d9691d4bb41fd273eac7f1078d069cecb3eb9aaa23</citedby><cites>FETCH-LOGICAL-a351t-4362f31827f91eb34add763d9691d4bb41fd273eac7f1078d069cecb3eb9aaa23</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/jo051425c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo051425c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16268610$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Samet, Alexander V</creatorcontrib><creatorcontrib>Marshalkin, Victor N</creatorcontrib><creatorcontrib>Kislyi, Konstantine A</creatorcontrib><creatorcontrib>Chernysheva, Natalya B</creatorcontrib><creatorcontrib>Strelenko, Yuri A</creatorcontrib><creatorcontrib>Semenov, Victor V</creatorcontrib><title>Synthetic Utilization of Polynitroaromatic Compounds. 3. Preparation of Substituted Dibenz[b,f][1,4]oxazepine-11(10H)-ones from 2,4,6-Trinitrobenzoic Acid via Nucleophilic Displacement of Nitro Groups</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>1,3-Dinitrodibenz[b,f][1,4]oxazepin-11(10H)-one, prepared by intramolecular displacement of nitro group in N-(2-hydroxyphenyl)-2,4,6-trinitrobenzamide, reacts with O- and S-nucleophiles to yield the products of mono- or bis-substitution of the nitro groups. The nitro group in position 3 is displaced first. This observation is in contrast with earlier results for the nitro-substituted benzoannulated five-membered heterocycles. This difference in reactivity is likely due to the increased steric hindrance for peri-nitro group displacement in the case of the benzoannulated seven-membered heterocycle. N-Alkylation of the nitro-substituted dibenz[b,f][1,4]oxazepin-11(10H)-ones yields analogues of a known antidepressant drug Sintamil. The structure of the products is confirmed by NOE experiments and alternative synthesis.</description><subject>Dibenzoxazepines - chemical synthesis</subject><subject>Dibenzoxazepines - chemistry</subject><subject>Molecular Structure</subject><subject>Nitro Compounds - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkU9v0zAYhyMEYmVw4AsgX0BMaor_JE5ynApsiGlUaicO0xQ59hvNI7GD7aC1n5CPhUOrcsEXH_y8v-eVf0nymuAFwZR8eLA4JxnN5ZNkRnKKU17h7Gkyw5jSlFHOTpIX3j_gePI8f56cEE55yQmeJb_XWxPuIWiJboLu9E4EbQ2yLVrZbmt0cFY424sJWNp-sKNRfoHYAq0cDMId8fXY-KDDGEChj7oBs7tt5u3dLZlnd_ZR7GDQBlJC3hN8eZZaAx61MRjReTbn6cbpv65pzkbVudQK_dICXY-yAzvcx9VkzPVDJyT0YMLkvJ5G0IWz4-BfJs9a0Xl4dbhPk5vPnzbLy_Tq28WX5flVKlhOQpoxTltGSlq0FYGGZUKpgjNV8YqorGky0ipaMBCyaAkuSoV5JUE2DJpKCEHZafJunzs4-3MEH-peewldJwzY0de8LDiv8iyCZ3tQOuu9g7YenO6F29YE11Nt9bG2yL45hI5ND-ofeegpAuke0D7A4_FduB81L1iR15vVus7KvPrKvq_qdeTf7nkhffSMzsQ_-Y_4D987sK8</recordid><startdate>20051111</startdate><enddate>20051111</enddate><creator>Samet, Alexander V</creator><creator>Marshalkin, Victor N</creator><creator>Kislyi, Konstantine A</creator><creator>Chernysheva, Natalya B</creator><creator>Strelenko, Yuri A</creator><creator>Semenov, Victor V</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20051111</creationdate><title>Synthetic Utilization of Polynitroaromatic Compounds. 3. Preparation of Substituted Dibenz[b,f][1,4]oxazepine-11(10H)-ones from 2,4,6-Trinitrobenzoic Acid via Nucleophilic Displacement of Nitro Groups</title><author>Samet, Alexander V ; Marshalkin, Victor N ; Kislyi, Konstantine A ; Chernysheva, Natalya B ; Strelenko, Yuri A ; Semenov, Victor V</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a351t-4362f31827f91eb34add763d9691d4bb41fd273eac7f1078d069cecb3eb9aaa23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Dibenzoxazepines - chemical synthesis</topic><topic>Dibenzoxazepines - chemistry</topic><topic>Molecular Structure</topic><topic>Nitro Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Samet, Alexander V</creatorcontrib><creatorcontrib>Marshalkin, Victor N</creatorcontrib><creatorcontrib>Kislyi, Konstantine A</creatorcontrib><creatorcontrib>Chernysheva, Natalya B</creatorcontrib><creatorcontrib>Strelenko, Yuri A</creatorcontrib><creatorcontrib>Semenov, Victor V</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</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>Samet, Alexander V</au><au>Marshalkin, Victor N</au><au>Kislyi, Konstantine A</au><au>Chernysheva, Natalya B</au><au>Strelenko, Yuri A</au><au>Semenov, Victor V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthetic Utilization of Polynitroaromatic Compounds. 3. Preparation of Substituted Dibenz[b,f][1,4]oxazepine-11(10H)-ones from 2,4,6-Trinitrobenzoic Acid via Nucleophilic Displacement of Nitro Groups</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-11-11</date><risdate>2005</risdate><volume>70</volume><issue>23</issue><spage>9371</spage><epage>9376</epage><pages>9371-9376</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>1,3-Dinitrodibenz[b,f][1,4]oxazepin-11(10H)-one, prepared by intramolecular displacement of nitro group in N-(2-hydroxyphenyl)-2,4,6-trinitrobenzamide, reacts with O- and S-nucleophiles to yield the products of mono- or bis-substitution of the nitro groups. The nitro group in position 3 is displaced first. This observation is in contrast with earlier results for the nitro-substituted benzoannulated five-membered heterocycles. This difference in reactivity is likely due to the increased steric hindrance for peri-nitro group displacement in the case of the benzoannulated seven-membered heterocycle. N-Alkylation of the nitro-substituted dibenz[b,f][1,4]oxazepin-11(10H)-ones yields analogues of a known antidepressant drug Sintamil. The structure of the products is confirmed by NOE experiments and alternative synthesis.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>16268610</pmid><doi>10.1021/jo051425c</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2005-11, Vol.70 (23), p.9371-9376 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68766954 |
| source | MEDLINE; ACS Journals: American Chemical Society Web Editions |
| subjects | Dibenzoxazepines - chemical synthesis Dibenzoxazepines - chemistry Molecular Structure Nitro Compounds - chemistry |
| title | Synthetic Utilization of Polynitroaromatic Compounds. 3. Preparation of Substituted Dibenz[b,f][1,4]oxazepine-11(10H)-ones from 2,4,6-Trinitrobenzoic Acid via Nucleophilic Displacement of Nitro Groups |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T19%3A46%3A58IST&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.%203.%20Preparation%20of%20Substituted%20Dibenz%5Bb,f%5D%5B1,4%5Doxazepine-11(10H)-ones%20from%202,4,6-Trinitrobenzoic%20Acid%20via%20Nucleophilic%20Displacement%20of%20Nitro%20Groups&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Samet,%20Alexander%20V&rft.date=2005-11-11&rft.volume=70&rft.issue=23&rft.spage=9371&rft.epage=9376&rft.pages=9371-9376&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/jo051425c&rft_dat=%3Cproquest_cross%3E68766954%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=68766954&rft_id=info:pmid/16268610&rfr_iscdi=true |