Novel route to fused nitrogen heterocycles by olefin metathesis

Abstract

A novel technique for the efficient synthesis of fused nitrogen heterocycles has been developed that features the molybdenum alkylidene-catalyzed metathesis of α,ω-dienes containing a nitrogen atom in the chain linking the two olefinic functional groups. The starting materials may be readily prepared in three steps from succinimide and glutarimide via sequential Mitsunobu alkylation, sodium borohydride reduction, and addition of a vinyl cuprate to an N-acyliminium salt generated in situ.