The synthesis of 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones from 6-oxo-6H-1,2-oxazine-3-carboxylates
A simple procedure was developed for the synthesis of 2 H -pyrido[3,4- c ][1,2]benzoxazine-2,4(3 H )-diones by the treatment of o -fluorophenyl-substituted 6-oxo-6 H -1,2-oxazine-3-carboxylates with primary amines. The reaction proceeded according to the mechanism previously described for the format...
Gespeichert in:
| Veröffentlicht in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2023-02, Vol.59 (1-2), p.101-104 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 104 |
|---|---|
| container_issue | 1-2 |
| container_start_page | 101 |
| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
| container_volume | 59 |
| creator | Ivanov, Dmitry S. Zaitseva, Elvira R. Smirnov, Alexander Yu Nizovtsev, Alexey V. Baleeva, Nadezhda S. Baranov, Mikhail S. |
| description | A simple procedure was developed for the synthesis of 2
H
-pyrido[3,4-
c
][1,2]benzoxazine-2,4(3
H
)-diones by the treatment of
o
-fluorophenyl-substituted 6-oxo-6
H
-1,2-oxazine-3-carboxylates with primary amines. The reaction proceeded according to the mechanism previously described for the formation of 3-(hydroxyimino)pyridine-2,6-diones followed by intramolecular nucleophilic substitution involving the hydroxyimino group to form the 1,2-oxazine ring. |
| doi_str_mv | 10.1007/s10593-023-03168-0 |
| format | Article |
| fullrecord | <record><control><sourceid>gale_proqu</sourceid><recordid>TN_cdi_proquest_journals_2803474932</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><galeid>A746327374</galeid><sourcerecordid>A746327374</sourcerecordid><originalsourceid>FETCH-LOGICAL-c358t-c2bb94e9016304b562f8f7a90b572aa4c6aaa88319d8bcd8e97be17eb00e585a3</originalsourceid><addsrcrecordid>eNp9kcFqGzEQhkVpoK6TF8hpoZcWLEfSaFfaYzBNHQj0kpyMEZJ2NlGwV660ATtPX6XbklsRIzHD92tm-Am55GzJGVNXmbO6BcpECeCNpuwDmfFaAdVQw0cyY4y1FLgQn8jnnJ9LqriWMxLun7DKp2F8whxyFftKrOnhlEIXN7CQ1G83fCG2DofXeLSvYUAqFvIrrL_RLsQBc9WnuK8aGo-RNmtaYPoPBOptcvF42tkR8zk56-0u48Xfd04ebr7fr9b07ueP29X1HfVQ65F64VwrsWW8ASZd3Yhe98q2zNVKWCt9Y63VGnjbaec7ja1yyBU6xrDWtYU5-TL9e0jx1wvm0TzHlzSUlkZoBlLJFkShlhP1aHdowtDHMVlfTof74MtifSj1ayUbEAqULAIxCXyKOSfszSGFvU0nw5l588BMHpjigfnjQbnnBCZRLvDwiOl9lv-ofgNGmIaO</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2803474932</pqid></control><display><type>article</type><title>The synthesis of 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones from 6-oxo-6H-1,2-oxazine-3-carboxylates</title><source>Springer Online Journals Complete</source><creator>Ivanov, Dmitry S. ; Zaitseva, Elvira R. ; Smirnov, Alexander Yu ; Nizovtsev, Alexey V. ; Baleeva, Nadezhda S. ; Baranov, Mikhail S.</creator><creatorcontrib>Ivanov, Dmitry S. ; Zaitseva, Elvira R. ; Smirnov, Alexander Yu ; Nizovtsev, Alexey V. ; Baleeva, Nadezhda S. ; Baranov, Mikhail S.</creatorcontrib><description>A simple procedure was developed for the synthesis of 2
H
-pyrido[3,4-
c
][1,2]benzoxazine-2,4(3
H
)-diones by the treatment of
o
-fluorophenyl-substituted 6-oxo-6
H
-1,2-oxazine-3-carboxylates with primary amines. The reaction proceeded according to the mechanism previously described for the formation of 3-(hydroxyimino)pyridine-2,6-diones followed by intramolecular nucleophilic substitution involving the hydroxyimino group to form the 1,2-oxazine ring.</description><identifier>ISSN: 0009-3122</identifier><identifier>EISSN: 1573-8353</identifier><identifier>DOI: 10.1007/s10593-023-03168-0</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Amines ; Benzoxazines ; Carboxylates ; Chemistry ; Chemistry and Materials Science ; Organic Chemistry ; Pharmacy ; Resveratrol ; Substitution reactions ; Synthesis</subject><ispartof>Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2023-02, Vol.59 (1-2), p.101-104</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><rights>COPYRIGHT 2023 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c358t-c2bb94e9016304b562f8f7a90b572aa4c6aaa88319d8bcd8e97be17eb00e585a3</citedby><cites>FETCH-LOGICAL-c358t-c2bb94e9016304b562f8f7a90b572aa4c6aaa88319d8bcd8e97be17eb00e585a3</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/s10593-023-03168-0$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10593-023-03168-0$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>315,782,786,27931,27932,41495,42564,51326</link.rule.ids></links><search><creatorcontrib>Ivanov, Dmitry S.</creatorcontrib><creatorcontrib>Zaitseva, Elvira R.</creatorcontrib><creatorcontrib>Smirnov, Alexander Yu</creatorcontrib><creatorcontrib>Nizovtsev, Alexey V.</creatorcontrib><creatorcontrib>Baleeva, Nadezhda S.</creatorcontrib><creatorcontrib>Baranov, Mikhail S.</creatorcontrib><title>The synthesis of 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones from 6-oxo-6H-1,2-oxazine-3-carboxylates</title><title>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</title><addtitle>Chem Heterocycl Comp</addtitle><description>A simple procedure was developed for the synthesis of 2
H
-pyrido[3,4-
c
][1,2]benzoxazine-2,4(3
H
)-diones by the treatment of
o
-fluorophenyl-substituted 6-oxo-6
H
-1,2-oxazine-3-carboxylates with primary amines. The reaction proceeded according to the mechanism previously described for the formation of 3-(hydroxyimino)pyridine-2,6-diones followed by intramolecular nucleophilic substitution involving the hydroxyimino group to form the 1,2-oxazine ring.</description><subject>Amines</subject><subject>Benzoxazines</subject><subject>Carboxylates</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>Resveratrol</subject><subject>Substitution reactions</subject><subject>Synthesis</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kcFqGzEQhkVpoK6TF8hpoZcWLEfSaFfaYzBNHQj0kpyMEZJ2NlGwV660ATtPX6XbklsRIzHD92tm-Am55GzJGVNXmbO6BcpECeCNpuwDmfFaAdVQw0cyY4y1FLgQn8jnnJ9LqriWMxLun7DKp2F8whxyFftKrOnhlEIXN7CQ1G83fCG2DofXeLSvYUAqFvIrrL_RLsQBc9WnuK8aGo-RNmtaYPoPBOptcvF42tkR8zk56-0u48Xfd04ebr7fr9b07ueP29X1HfVQ65F64VwrsWW8ASZd3Yhe98q2zNVKWCt9Y63VGnjbaec7ja1yyBU6xrDWtYU5-TL9e0jx1wvm0TzHlzSUlkZoBlLJFkShlhP1aHdowtDHMVlfTof74MtifSj1ayUbEAqULAIxCXyKOSfszSGFvU0nw5l588BMHpjigfnjQbnnBCZRLvDwiOl9lv-ofgNGmIaO</recordid><startdate>20230201</startdate><enddate>20230201</enddate><creator>Ivanov, Dmitry S.</creator><creator>Zaitseva, Elvira R.</creator><creator>Smirnov, Alexander Yu</creator><creator>Nizovtsev, Alexey V.</creator><creator>Baleeva, Nadezhda S.</creator><creator>Baranov, Mikhail S.</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20230201</creationdate><title>The synthesis of 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones from 6-oxo-6H-1,2-oxazine-3-carboxylates</title><author>Ivanov, Dmitry S. ; Zaitseva, Elvira R. ; Smirnov, Alexander Yu ; Nizovtsev, Alexey V. ; Baleeva, Nadezhda S. ; Baranov, Mikhail S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c358t-c2bb94e9016304b562f8f7a90b572aa4c6aaa88319d8bcd8e97be17eb00e585a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Amines</topic><topic>Benzoxazines</topic><topic>Carboxylates</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><topic>Resveratrol</topic><topic>Substitution reactions</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ivanov, Dmitry S.</creatorcontrib><creatorcontrib>Zaitseva, Elvira R.</creatorcontrib><creatorcontrib>Smirnov, Alexander Yu</creatorcontrib><creatorcontrib>Nizovtsev, Alexey V.</creatorcontrib><creatorcontrib>Baleeva, Nadezhda S.</creatorcontrib><creatorcontrib>Baranov, Mikhail S.</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>Ivanov, Dmitry S.</au><au>Zaitseva, Elvira R.</au><au>Smirnov, Alexander Yu</au><au>Nizovtsev, Alexey V.</au><au>Baleeva, Nadezhda S.</au><au>Baranov, Mikhail S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The synthesis of 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones from 6-oxo-6H-1,2-oxazine-3-carboxylates</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2023-02-01</date><risdate>2023</risdate><volume>59</volume><issue>1-2</issue><spage>101</spage><epage>104</epage><pages>101-104</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>A simple procedure was developed for the synthesis of 2
H
-pyrido[3,4-
c
][1,2]benzoxazine-2,4(3
H
)-diones by the treatment of
o
-fluorophenyl-substituted 6-oxo-6
H
-1,2-oxazine-3-carboxylates with primary amines. The reaction proceeded according to the mechanism previously described for the formation of 3-(hydroxyimino)pyridine-2,6-diones followed by intramolecular nucleophilic substitution involving the hydroxyimino group to form the 1,2-oxazine ring.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10593-023-03168-0</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-3122 |
| ispartof | Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2023-02, Vol.59 (1-2), p.101-104 |
| issn | 0009-3122 1573-8353 |
| language | eng |
| recordid | cdi_proquest_journals_2803474932 |
| source | Springer Online Journals Complete |
| subjects | Amines Benzoxazines Carboxylates Chemistry Chemistry and Materials Science Organic Chemistry Pharmacy Resveratrol Substitution reactions Synthesis |
| title | The synthesis of 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones from 6-oxo-6H-1,2-oxazine-3-carboxylates |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-04T23%3A06%3A46IST&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=The%20synthesis%20of%202H-pyrido%5B3,4-c%5D%5B1,2%5Dbenzoxazine-2,4(3H)-diones%20from%206-oxo-6H-1,2-oxazine-3-carboxylates&rft.jtitle=Chemistry%20of%20heterocyclic%20compounds%20(New%20York,%20N.Y.%201965)&rft.au=Ivanov,%20Dmitry%20S.&rft.date=2023-02-01&rft.volume=59&rft.issue=1-2&rft.spage=101&rft.epage=104&rft.pages=101-104&rft.issn=0009-3122&rft.eissn=1573-8353&rft_id=info:doi/10.1007/s10593-023-03168-0&rft_dat=%3Cgale_proqu%3EA746327374%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=2803474932&rft_id=info:pmid/&rft_galeid=A746327374&rfr_iscdi=true |