Synthesis of 6H-Thieno[3,2-b]pyridin-7-ones from N-(2-X-Carbonyl)-3-thienyl Ketenimines (X = RS, ArO, R₂N) via Consecutive [1,5]-X Sigmatropic Rearrangement and 6π-Electrocyclization

Abstract

N-(2-X-Carbonyl)-3-thienyl ketenimines (X = RS, ArO, R₂N) undergo cyclization under thermal conditions, through a [1,5]-X sigmatropic rearrangement followed by a 6π-electrocyclic ring closure of the resulting intermediate ketene, to provide 6H-thieno[3,2-b]pyridin-7-ones, bearing alkylthio, arylthio, aryloxy or amino groups at their 5-position.

azides - ketenimines - rearrangements - ketenes - thienopyridines

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