Oxidative synthesis of benzo[1,4]oxazines from α-branched primary amines and ortho-benzoquinones
The efficient oxidative construction of benzo[1,4]oxazines from simple α-branched amines and ortho-benzoquinones is reported. The procedure pivots on a triethylamine and iodine mediated oxidative ring closure from the ketimine intermediate formed upon their condensation. This reaction was shown to t...
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
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Elsevier
2019
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| _version_ | 1797056437571026944 |
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| author | Vasu, D Leitch, J Dixon, D |
| author_facet | Vasu, D Leitch, J Dixon, D |
| author_sort | Vasu, D |
| collection | OXFORD |
| description | The efficient oxidative construction of benzo[1,4]oxazines from simple α-branched amines and ortho-benzoquinones is reported. The procedure pivots on a triethylamine and iodine mediated oxidative ring closure from the ketimine intermediate formed upon their condensation. This reaction was shown to tolerate a variety of α-branched benzylamines and downstream derivatization to substituted benzomorpholine structures was also demonstrated. |
| first_indexed | 2024-03-06T19:23:01Z |
| format | Journal article |
| id | oxford-uuid:1ac12d20-06f4-49e5-97d4-cc138bac9c8d |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T19:23:01Z |
| publishDate | 2019 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | oxford-uuid:1ac12d20-06f4-49e5-97d4-cc138bac9c8d2022-03-26T10:56:35ZOxidative synthesis of benzo[1,4]oxazines from α-branched primary amines and ortho-benzoquinonesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:1ac12d20-06f4-49e5-97d4-cc138bac9c8dEnglishSymplectic Elements at OxfordElsevier2019Vasu, DLeitch, JDixon, DThe efficient oxidative construction of benzo[1,4]oxazines from simple α-branched amines and ortho-benzoquinones is reported. The procedure pivots on a triethylamine and iodine mediated oxidative ring closure from the ketimine intermediate formed upon their condensation. This reaction was shown to tolerate a variety of α-branched benzylamines and downstream derivatization to substituted benzomorpholine structures was also demonstrated. |
| spellingShingle | Vasu, D Leitch, J Dixon, D Oxidative synthesis of benzo[1,4]oxazines from α-branched primary amines and ortho-benzoquinones |
| title | Oxidative synthesis of benzo[1,4]oxazines from α-branched primary amines and ortho-benzoquinones |
| title_full | Oxidative synthesis of benzo[1,4]oxazines from α-branched primary amines and ortho-benzoquinones |
| title_fullStr | Oxidative synthesis of benzo[1,4]oxazines from α-branched primary amines and ortho-benzoquinones |
| title_full_unstemmed | Oxidative synthesis of benzo[1,4]oxazines from α-branched primary amines and ortho-benzoquinones |
| title_short | Oxidative synthesis of benzo[1,4]oxazines from α-branched primary amines and ortho-benzoquinones |
| title_sort | oxidative synthesis of benzo 1 4 oxazines from α branched primary amines and ortho benzoquinones |
| work_keys_str_mv | AT vasud oxidativesynthesisofbenzo14oxazinesfromabranchedprimaryaminesandorthobenzoquinones AT leitchj oxidativesynthesisofbenzo14oxazinesfromabranchedprimaryaminesandorthobenzoquinones AT dixond oxidativesynthesisofbenzo14oxazinesfromabranchedprimaryaminesandorthobenzoquinones |