Abstract
A straightforward reaction sequence consisting of a Sonogashira coupling of protected
propargylic amines, a cobalt-catalysed neutral Diels-Alder reaction, DDQ oxidation
of the dihydroaromatic intermediate, a sodium borohydride reduction and an acid induced
Friedel-Crafts-type cyclisation approach incorporating four simple starting materials
leads to polyfunctionalised polycyclic products. Based on the electronic, steric and
structural preconditions either seven-membered dibenzoazepine derivatives or alternatively
six- or eight-membered isoindoline derivatives are formed.
Key words
cobalt - Diels-Alder - cyclisation - Friedel-Crafts - heterocycles
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