Synthesis of 3,5-Isoxazolidinediones and 1H‑2,3-Benzoxazine-1,4(3H)‑diones from Aliphatic Oximes and Dicarboxylic Acid Chlorides
The synthesis of the title compounds was carried out by reacting dicarboxylic acid chlorides with oximes in the presence of excess triethylamine. Disubstituted malonyl chlorides gave 2-alkenyl-4,4-dialkyl-3,5-isoxazolidinediones (8a–f) and 2,2′-ethylidene-bis[4,4-dialkyl-3,5-isoxazolidinedione]s (...
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| Veröffentlicht in: | Journal of organic chemistry 2014-04, Vol.79 (7), p.2874-2882 |
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| container_title | Journal of organic chemistry |
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| creator | Izydore, Robert A Jones, Joseph T Mogesa, Benjamin Swain, Ira N Davis-Ward, Ronda G Daniels, Dwayne L Kpakima, Felicia Frazier Spaulding-Phifer, Sharnelle T |
| description | The synthesis of the title compounds was carried out by reacting dicarboxylic acid chlorides with oximes in the presence of excess triethylamine. Disubstituted malonyl chlorides gave 2-alkenyl-4,4-dialkyl-3,5-isoxazolidinediones (8a–f) and 2,2′-ethylidene-bis[4,4-dialkyl-3,5-isoxazolidinedione]s (9a–f). Compounds 9 were formed from 8 and its N-unsubstituted 3,5-isoxazolidinedione decomposition product. Phthaloyl chlorides reacted with acetone oxime to yield 3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-diones (16a–e). Products 16 spontaneously decomposed to give N-unsubstituted 1H-2,3-benzoxazine-1,4(3H)-diones (17a–e) at rates that were dependent on temperature and solvent. Kinetic studies showed that two of the compounds decomposed by zero-order kinetics under neutral conditions. Butanedioyl chloride did not produce a cyclic product. |
| doi_str_mv | 10.1021/jo402708j |
| format | Article |
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Disubstituted malonyl chlorides gave 2-alkenyl-4,4-dialkyl-3,5-isoxazolidinediones (8a–f) and 2,2′-ethylidene-bis[4,4-dialkyl-3,5-isoxazolidinedione]s (9a–f). Compounds 9 were formed from 8 and its N-unsubstituted 3,5-isoxazolidinedione decomposition product. Phthaloyl chlorides reacted with acetone oxime to yield 3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-diones (16a–e). Products 16 spontaneously decomposed to give N-unsubstituted 1H-2,3-benzoxazine-1,4(3H)-diones (17a–e) at rates that were dependent on temperature and solvent. Kinetic studies showed that two of the compounds decomposed by zero-order kinetics under neutral conditions. Butanedioyl chloride did not produce a cyclic product.</description><identifier>ISSN: 0022-3263</identifier><identifier>ISSN: 1520-6904</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo402708j</identifier><identifier>PMID: 24620711</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>acetone ; Benzoxazines - chemical synthesis ; Benzoxazines - chemistry ; chemical reactions ; chemical structure ; chlorides ; Chlorides - chemistry ; Dicarboxylic Acids - chemistry ; Molecular Structure ; organic chemistry ; Oxazolidinones - chemical synthesis ; Oxazolidinones - chemistry ; oximes ; Oximes - chemistry ; Quinazolines - chemical synthesis ; Quinazolines - chemistry ; solvents ; temperature ; triethylamine</subject><ispartof>Journal of organic chemistry, 2014-04, Vol.79 (7), p.2874-2882</ispartof><rights>Copyright © 2014 American Chemical Society</rights><rights>Copyright © 2014 American Chemical Society 2014 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo402708j$$EPDF$$P50$$Gacs$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo402708j$$EHTML$$P50$$Gacs$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24620711$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Izydore, Robert A</creatorcontrib><creatorcontrib>Jones, Joseph T</creatorcontrib><creatorcontrib>Mogesa, Benjamin</creatorcontrib><creatorcontrib>Swain, Ira N</creatorcontrib><creatorcontrib>Davis-Ward, Ronda G</creatorcontrib><creatorcontrib>Daniels, Dwayne L</creatorcontrib><creatorcontrib>Kpakima, Felicia Frazier</creatorcontrib><creatorcontrib>Spaulding-Phifer, Sharnelle T</creatorcontrib><title>Synthesis of 3,5-Isoxazolidinediones and 1H‑2,3-Benzoxazine-1,4(3H)‑diones from Aliphatic Oximes and Dicarboxylic Acid Chlorides</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The synthesis of the title compounds was carried out by reacting dicarboxylic acid chlorides with oximes in the presence of excess triethylamine. Disubstituted malonyl chlorides gave 2-alkenyl-4,4-dialkyl-3,5-isoxazolidinediones (8a–f) and 2,2′-ethylidene-bis[4,4-dialkyl-3,5-isoxazolidinedione]s (9a–f). Compounds 9 were formed from 8 and its N-unsubstituted 3,5-isoxazolidinedione decomposition product. Phthaloyl chlorides reacted with acetone oxime to yield 3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-diones (16a–e). Products 16 spontaneously decomposed to give N-unsubstituted 1H-2,3-benzoxazine-1,4(3H)-diones (17a–e) at rates that were dependent on temperature and solvent. Kinetic studies showed that two of the compounds decomposed by zero-order kinetics under neutral conditions. Butanedioyl chloride did not produce a cyclic product.</description><subject>acetone</subject><subject>Benzoxazines - chemical synthesis</subject><subject>Benzoxazines - chemistry</subject><subject>chemical reactions</subject><subject>chemical structure</subject><subject>chlorides</subject><subject>Chlorides - chemistry</subject><subject>Dicarboxylic Acids - chemistry</subject><subject>Molecular Structure</subject><subject>organic chemistry</subject><subject>Oxazolidinones - chemical synthesis</subject><subject>Oxazolidinones - chemistry</subject><subject>oximes</subject><subject>Oximes - chemistry</subject><subject>Quinazolines - chemical synthesis</subject><subject>Quinazolines - chemistry</subject><subject>solvents</subject><subject>temperature</subject><subject>triethylamine</subject><issn>0022-3263</issn><issn>1520-6904</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>N~.</sourceid><sourceid>EIF</sourceid><recordid>eNqFkctOGzEYhS3UCsJlwQug2VQKUgZ898ymUghtg4TEAlhbvg1xNGOH8aRKWLHgBfqKfZJORIpgxb-x9J_Px0c-ABwjeIYgRufzSCEWsJjvgAFiGOa8hPQLGECIcU4wJ3tgP6U57Icxtgv2MOUYCoQG4OV2HbqZSz5lscrIiOVXKa7UU6y99cFZH4NLmQo2Q9O_z3_wiOQXLjxtkF7O0YgOyfS0V7Zk1cYmG9d-MVOdN9nNyjfb-5feqFbH1bru92PjbTaZ1bH11qVD8LVSdXJH2_MA3P_8cTeZ5tc3v64m4-tc4ZJ2ucbICics1SWtdMkYL0VluEZQcCoIZa7SmpbOFphjUSqMkFEFU5WCVJhCkwPw_dV3sdSNs8aFrlW1XLS-Ue1aRuXlRyX4mXyIvyUpC1YQ3hsMtwZtfFy61MnGJ-PqWgUXl0liuOmDC8Y-RRFDBDKMCOnRk_ex3vL8b6kHvr0CyiQ5j8s29L8kEZSb1-Rb--Qf8uCg-g</recordid><startdate>20140404</startdate><enddate>20140404</enddate><creator>Izydore, Robert A</creator><creator>Jones, Joseph T</creator><creator>Mogesa, Benjamin</creator><creator>Swain, Ira N</creator><creator>Davis-Ward, Ronda G</creator><creator>Daniels, Dwayne L</creator><creator>Kpakima, Felicia Frazier</creator><creator>Spaulding-Phifer, Sharnelle T</creator><general>American Chemical Society</general><scope>N~.</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20140404</creationdate><title>Synthesis of 3,5-Isoxazolidinediones and 1H‑2,3-Benzoxazine-1,4(3H)‑diones from Aliphatic Oximes and Dicarboxylic Acid Chlorides</title><author>Izydore, Robert A ; Jones, Joseph T ; Mogesa, Benjamin ; Swain, Ira N ; Davis-Ward, Ronda G ; Daniels, Dwayne L ; Kpakima, Felicia Frazier ; Spaulding-Phifer, Sharnelle T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a294t-b21d7e7d4b94fb955697fc6b107647345efbb49ed826279a211ca85afa047c8b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>acetone</topic><topic>Benzoxazines - chemical synthesis</topic><topic>Benzoxazines - chemistry</topic><topic>chemical reactions</topic><topic>chemical structure</topic><topic>chlorides</topic><topic>Chlorides - chemistry</topic><topic>Dicarboxylic Acids - chemistry</topic><topic>Molecular Structure</topic><topic>organic chemistry</topic><topic>Oxazolidinones - chemical synthesis</topic><topic>Oxazolidinones - chemistry</topic><topic>oximes</topic><topic>Oximes - chemistry</topic><topic>Quinazolines - chemical synthesis</topic><topic>Quinazolines - chemistry</topic><topic>solvents</topic><topic>temperature</topic><topic>triethylamine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Izydore, Robert A</creatorcontrib><creatorcontrib>Jones, Joseph T</creatorcontrib><creatorcontrib>Mogesa, Benjamin</creatorcontrib><creatorcontrib>Swain, Ira N</creatorcontrib><creatorcontrib>Davis-Ward, Ronda G</creatorcontrib><creatorcontrib>Daniels, Dwayne L</creatorcontrib><creatorcontrib>Kpakima, Felicia Frazier</creatorcontrib><creatorcontrib>Spaulding-Phifer, Sharnelle T</creatorcontrib><collection>American Chemical Society (ACS) Open Access</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Izydore, Robert A</au><au>Jones, Joseph T</au><au>Mogesa, Benjamin</au><au>Swain, Ira N</au><au>Davis-Ward, Ronda G</au><au>Daniels, Dwayne L</au><au>Kpakima, Felicia Frazier</au><au>Spaulding-Phifer, Sharnelle T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 3,5-Isoxazolidinediones and 1H‑2,3-Benzoxazine-1,4(3H)‑diones from Aliphatic Oximes and Dicarboxylic Acid Chlorides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2014-04-04</date><risdate>2014</risdate><volume>79</volume><issue>7</issue><spage>2874</spage><epage>2882</epage><pages>2874-2882</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>The synthesis of the title compounds was carried out by reacting dicarboxylic acid chlorides with oximes in the presence of excess triethylamine. Disubstituted malonyl chlorides gave 2-alkenyl-4,4-dialkyl-3,5-isoxazolidinediones (8a–f) and 2,2′-ethylidene-bis[4,4-dialkyl-3,5-isoxazolidinedione]s (9a–f). Compounds 9 were formed from 8 and its N-unsubstituted 3,5-isoxazolidinedione decomposition product. Phthaloyl chlorides reacted with acetone oxime to yield 3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-diones (16a–e). Products 16 spontaneously decomposed to give N-unsubstituted 1H-2,3-benzoxazine-1,4(3H)-diones (17a–e) at rates that were dependent on temperature and solvent. Kinetic studies showed that two of the compounds decomposed by zero-order kinetics under neutral conditions. Butanedioyl chloride did not produce a cyclic product.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24620711</pmid><doi>10.1021/jo402708j</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of organic chemistry, 2014-04, Vol.79 (7), p.2874-2882 |
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| subjects | acetone Benzoxazines - chemical synthesis Benzoxazines - chemistry chemical reactions chemical structure chlorides Chlorides - chemistry Dicarboxylic Acids - chemistry Molecular Structure organic chemistry Oxazolidinones - chemical synthesis Oxazolidinones - chemistry oximes Oximes - chemistry Quinazolines - chemical synthesis Quinazolines - chemistry solvents temperature triethylamine |
| title | Synthesis of 3,5-Isoxazolidinediones and 1H‑2,3-Benzoxazine-1,4(3H)‑diones from Aliphatic Oximes and Dicarboxylic Acid Chlorides |
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