Access to a diverse array of bridged benzo[1,5]oxazocine and benzo[1,4]diazepine structures

Grant J. Sherborne*, Coura Diène, Paul Kemmitt, Andrew D. Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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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.
Original languageEnglish
JournalOrganic Letters
VolumeArticles ASAP
Early online date23 Nov 2023
DOIs
Publication statusE-pub ahead of print - 23 Nov 2023

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