Access to a diverse array of bridged benzo[1,5]oxazocine and benzo[1,4]diazepine structures
Date
23/11/2023Metadata
Show full item recordAbstract
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.
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
Publication
Organic Letters
Status
Peer reviewed
ISSN
1523-7060Type
Journal article
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