Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylate
This note describes a sequence converting an oxime-substituted pyrrolidine into a trisubstituted pyrrole structure. The synthetic route is based on a double chlorination of the pyrrolidine substrate followed by the base induced formation of both an imine and a nitrile oxide functionality. The latter...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2017-08-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2017/3/M951 |
| _version_ | 1818266865273667584 |
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| author | Marcus Baumann Ian R. Baxendale |
| author_facet | Marcus Baumann Ian R. Baxendale |
| author_sort | Marcus Baumann |
| collection | DOAJ |
| description | This note describes a sequence converting an oxime-substituted pyrrolidine into a trisubstituted pyrrole structure. The synthetic route is based on a double chlorination of the pyrrolidine substrate followed by the base induced formation of both an imine and a nitrile oxide functionality. The latter reacts with an immobilized thiourea to yield an isothiocyanate which upon elimination generates the final pyrrole in an unprecedented cascade of events. |
| first_indexed | 2024-12-12T20:13:29Z |
| format | Article |
| id | doaj.art-f06e255d83554ffd8dd707d3d7cced9e |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-12-12T20:13:29Z |
| publishDate | 2017-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-f06e255d83554ffd8dd707d3d7cced9e2022-12-22T00:13:27ZengMDPI AGMolbank1422-85992017-08-0120173M95110.3390/M951M951Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylateMarcus Baumann0Ian R. Baxendale1Department of Chemistry, University of Durham, South Road, DH13LE, United KingdomDepartment of Chemistry, University of Durham, South Road, DH13LE, United KingdomThis note describes a sequence converting an oxime-substituted pyrrolidine into a trisubstituted pyrrole structure. The synthetic route is based on a double chlorination of the pyrrolidine substrate followed by the base induced formation of both an imine and a nitrile oxide functionality. The latter reacts with an immobilized thiourea to yield an isothiocyanate which upon elimination generates the final pyrrole in an unprecedented cascade of events.https://www.mdpi.com/1422-8599/2017/3/M951pyrrolepyrrolidineheterocyclerearrangementisothiocyanatechlorination |
| spellingShingle | Marcus Baumann Ian R. Baxendale Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylate Molbank pyrrole pyrrolidine heterocycle rearrangement isothiocyanate chlorination |
| title | Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylate |
| title_full | Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylate |
| title_fullStr | Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylate |
| title_full_unstemmed | Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylate |
| title_short | Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylate |
| title_sort | ethyl 5 4 bromophenyl 4 methyl 1h pyrrole 2 carboxylate |
| topic | pyrrole pyrrolidine heterocycle rearrangement isothiocyanate chlorination |
| url | https://www.mdpi.com/1422-8599/2017/3/M951 |
| work_keys_str_mv | AT marcusbaumann ethyl54bromophenyl4methyl1hpyrrole2carboxylate AT ianrbaxendale ethyl54bromophenyl4methyl1hpyrrole2carboxylate |