Abstract
Conjugated heterocycles fused with strained bicyclic skeletons are of considerable interest owing to their effect of angular strain for the physical and chemical properties. In the case with a fused norbornadiene, possible through-space and through-bond interactions of π electrons and the behavior of a cationic intermediate resulting by an electrophilic reaction of the olefin moiety are also of interest. In this context, we have synthesized five- and six-membered heteroaromatics fused with norbornadiene or 2-azanorbornene, and a 1, 4-dihydropyrazine fused with two bornene skeletons. Unusual spectral and redox properties and peculiar cycloaddition reactions probably due to the angular strain of fused rings, as well as the behavior of norbornenyl cations of fused pyridazines and pyrazines are described.
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