Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 20, Pages 5788-5791Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802188
Keywords
benzazepines; heterocycle; ring contraction; tetrahydroisoquinolines; urea
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Funding
- EPSRC
- Bristol Centre for Doctoral Training in Chemical Synthesis
- AstraZeneca through a CASE award
- Deutsche Forschungsgemeinschaft [LE 3853/1-1]
- EPSRC [EP/K03927X/1, EP/L018527/1, EP/L018527/2] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K03927X/1] Funding Source: researchfish
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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.
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