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Access to a diverse array of bridged benzo[1,5]oxazocine and benzo[1,4]diazepine structures
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dc.contributor.author | Sherborne, Grant J. | |
dc.contributor.author | Diène, Coura | |
dc.contributor.author | Kemmitt, Paul | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2023-11-29T12:30:02Z | |
dc.date.available | 2023-11-29T12:30:02Z | |
dc.date.issued | 2023-11-23 | |
dc.identifier | 296910847 | |
dc.identifier | 4b59827f-4697-481e-bee8-92b31a08e28a | |
dc.identifier | 85179607759 | |
dc.identifier.citation | Sherborne , G J , Diène , C , Kemmitt , P & Smith , A D 2023 , ' Access to a diverse array of bridged benzo[1,5]oxazocine and benzo[1,4]diazepine structures ' , Organic Letters , vol. Articles ASAP . https://doi.org/10.1021/acs.orglett.3c03392 | en |
dc.identifier.issn | 1523-7060 | |
dc.identifier.other | RIS: urn:097156B8CBCE3CB837EE92C6ED1F242E | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/147967335 | |
dc.identifier.uri | https://hdl.handle.net/10023/28790 | |
dc.description.abstract | The preparation of bridged benzo[1,5]oxazocines and benzo[1,4]diazepines is demonstrated from simple aniline and aldehyde starting materials. A one-pot condensation/6π electrocyclization is followed by an intramolecular trapping of the 2,3-dihydroquinoline intermediate by nitrogen or oxygen nucleophiles to give bridged seven- and eight-membered products. Using 3-hydroxypyridinecarboxaldehydes results in a stable zwitterionic structure that can undergo a diastereoselective reduction under hydrogenative conditions. A similar cyclization/hydrogenation pathway with excellent diastereoselectivity is also demonstrated from 2-pyridyl-substituted 1,2,3,4-tetrahydroquinolines. | |
dc.format.extent | 1103886 | |
dc.language.iso | eng | |
dc.relation.ispartof | Organic Letters | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Access to a diverse array of bridged benzo[1,5]oxazocine and benzo[1,4]diazepine structures | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | 10.1021/acs.orglett.3c03392 | |
dc.description.status | Peer reviewed | en |
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