Novel polycyclic Diels-Alder adducts from ring distorted 3-aza[5] and 3-aza[6] (1,7) naphthalenophanes

Abstract

Dedicated to Professor Jim Coxon on the occasion of his 65th birthday. AbstractRing distorted 3-aza[5] and 3-aza [6](1,7)naphthalenophanes have been shown to undergo ready Diels-Alder cycloaddition reactions with 4-phenyl-1,2,4-triazoline-3,5-dione, tetracyanoethylene, 1,1-dicyanoethylene and 1,1-diethyl methylenemalonate to form new functionalized polycyclic heterocyclic derivatives. Addition was shown to occur selectively in each case in the less substituted aromatic ring of the naphthalene moiety.