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Abstract
AbstractHeating a range of suitably substituted diazoacetoacetates produced a family of 2‐(1,3‐dioxolan‐2‐yl)phenyl ketenes that, under thermal conditions, smoothly underwent a [1,5]‐H shift/6π‐electrocyclic ring‐closure sequence to give 1H‐2‐benzopyrans. The application of such processes to ketenes, produced by replacing the phenyl scaffolding with a thiophene ring, afforded thienopyrans. The aza‐Wittig reaction of these 2‐(1,3‐dioxolan‐2‐yl)phenyl and thienyl ketenes with N‐aryliminophosphoranes provided analogous ketenimines that transform into the respective 1(2H)isoquinolinones and thienopyridinones under similar thermal conditions, following the same type of cascade sequence.
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