A Novel Synthesis of 4H-1, 4-Benzoxazines
The reaction of methyl 2-chloro-5-ethoxycarbonylamino-4-fluorobenzoate (4a) and 1-bromo-3, 3-dimethyl-2-butanone (2) in the presence of 2.2 eq of lithium bis(trimethylsilyl)amide afforded the 4H-1, 4-benzoxazine (6a) in good yield instead of the expected 4-oxazolin-2-one (5a). The generality of the...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1996/09/15, Vol.44(9), pp.1663-1668 |
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| container_end_page | 1668 |
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| container_issue | 9 |
| container_start_page | 1663 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 44 |
| creator | KUDO, Noriaki FURUTA, Satoru SATO, Kazuo |
| description | The reaction of methyl 2-chloro-5-ethoxycarbonylamino-4-fluorobenzoate (4a) and 1-bromo-3, 3-dimethyl-2-butanone (2) in the presence of 2.2 eq of lithium bis(trimethylsilyl)amide afforded the 4H-1, 4-benzoxazine (6a) in good yield instead of the expected 4-oxazolin-2-one (5a). The generality of the reaction and the mechanism are discussed. |
| doi_str_mv | 10.1248/cpb.44.1663 |
| format | Article |
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Pharm. Bull.</addtitle><description>The reaction of methyl 2-chloro-5-ethoxycarbonylamino-4-fluorobenzoate (4a) and 1-bromo-3, 3-dimethyl-2-butanone (2) in the presence of 2.2 eq of lithium bis(trimethylsilyl)amide afforded the 4H-1, 4-benzoxazine (6a) in good yield instead of the expected 4-oxazolin-2-one (5a). The generality of the reaction and the mechanism are discussed.</description><subject>4-oxazolin-2-one</subject><subject>4H-1, 4-benzoxazine</subject><subject>Chemistry</subject><subject>electron-withdrawing group</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>intramolecular cyclization</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>α-bromoketone</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><recordid>eNpFkE1PwzAMhiMEEmNw4g9UgguCDjsfbXoc42NIExyAc5SlCetU2pF0iO3X06rTuNgHP34sv4ScI4yQcnlrVvMR5yNMEnZABsh4GgtK2SEZAEAWU5awY3ISwhKACkjZgFyNo5f6x5bR26ZqFjYUIapdxKcx3kQ8vrPVtv7V26Ky4ZQcOV0Ge7brQ_Lx-PA-mcaz16fnyXgWGyFpE-uc5oyK1IlcUJsKlJnkUuhkDpk1DDCHhEnHHNoEDOYWhWXOiQxSqrmkbEgueu_K199rGxq1rNe-ak8q5AkwbF9JW-q6p4yvQ_DWqZUvvrTfKATVZaHaLBTnqsuipS93Th2MLp3XlSnCfqXFgXNssfseW4ZGf9r9XPumMKXtlJgJ2WmzvnT2__FCe2Ur9geDlnJ3</recordid><startdate>1996</startdate><enddate>1996</enddate><creator>KUDO, Noriaki</creator><creator>FURUTA, Satoru</creator><creator>SATO, Kazuo</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>1996</creationdate><title>A Novel Synthesis of 4H-1, 4-Benzoxazines</title><author>KUDO, Noriaki ; FURUTA, Satoru ; SATO, Kazuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c582t-ad2d3257f5d52e751898485a6b09ec301d0638f3f1e60c1de15e3ff59072a4823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>4-oxazolin-2-one</topic><topic>4H-1, 4-benzoxazine</topic><topic>Chemistry</topic><topic>electron-withdrawing group</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>intramolecular cyclization</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>α-bromoketone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KUDO, Noriaki</creatorcontrib><creatorcontrib>FURUTA, Satoru</creatorcontrib><creatorcontrib>SATO, Kazuo</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KUDO, Noriaki</au><au>FURUTA, Satoru</au><au>SATO, Kazuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Novel Synthesis of 4H-1, 4-Benzoxazines</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. 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| ispartof | Chemical and Pharmaceutical Bulletin, 1996/09/15, Vol.44(9), pp.1663-1668 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | J-STAGE Free; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | 4-oxazolin-2-one 4H-1, 4-benzoxazine Chemistry electron-withdrawing group Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms intramolecular cyclization Organic chemistry Preparations and properties α-bromoketone |
| title | A Novel Synthesis of 4H-1, 4-Benzoxazines |
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