3-Nitro-coumarin synthesis via nitrative cyclization of aryl alkynoates using tert-butyl nitrite

Abstract

We report a one-pot metal-free synthesis of 3-nitro-coumarins from aryl alkynoates using TBN (tert-butyl nitrite) as the sole reagent. The radical triggered cyclization and nitration of the aryl alkynoates proceeded in a cascaded manner via nitro radical addition to alkynoates, then 5-exo-trig spirocyclization and ester migration.