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Abstract
Tetrahydroisoquinolines and tetrahydrobenzazepines were prepared by acid-promoted ring contraction of cyclic ureas, which were themselves formed by ring expansion of indolines and tetrahydroquinolines. The consequent overall one-carbon insertion reaction gives these 6- and 7-membered heterocyclic scaffolds in three steps from readily available precursors. Other ring sizes may be formed by an alternative elimination reaction of bicyclic structures. Scalability of the method was demonstrated by operating it in a flow system.
Original language | English |
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Pages (from-to) | 5788-5791 |
Number of pages | 4 |
Journal | Angewandte Chemie - International Edition |
Volume | 57 |
Issue number | 20 |
Early online date | 14 Mar 2018 |
DOIs | |
Publication status | Published - 14 May 2018 |
Research Groups and Themes
- BCS and TECS CDTs
Keywords
- benzazepines
- heterocycle
- ring contraction
- tetrahydroisoquinolines
- urea
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Dive into the research topics of 'Consecutive Ring Expansion and Contraction for the Synthesis of 1-Aryl Tetrahydroisoquinolines and Tetrahydrobenzazepines from Readily Available Heterocyclic Precursors'. Together they form a unique fingerprint.Projects
- 1 Finished
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alpha-Arylation and alpha-Vinylation of Enolates: New Reactivity from the Urea Linkage.
Clayden, J. (Principal Investigator)
1/07/15 → 31/05/18
Project: Research