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A novel route to fused indoles via two consecutive palladium catalyzed reactions, an intramolecular Heck reaction followed by a reductive N-heteroannulation, has been developed. For example, reaction of 2-bromo-3-nitro-1-(3-butenyloxy)benzene with palladium diacetate, and tri(o-tolyl)phosphine in the presence of triethylamine gave a readily separable mixture (18:4:1) of dihydro-4-methylene-5-nitro-2H-1-benzopyran,...
The present study reports the development of a palladium-catalyzed oxidative annulation/nucleophilic substitution sequence affording a library of alkenylated benzopyrans using 2-aryl-1,3-dicarbonyl compounds and allylic acetate. The process is compatible to a wide range of substrates with good functional group tolerance producing the desired heterocycles in moderate to good yields.
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