[<i>m</i>+<i>n</i>]-Dipolar cycloaddition is a powerful and widely used strategy for synthesizing heterocyclic compounds in a single operation without giving rise to byproducts. Among the known dipoles, azomethine ylide, consisting of an iminium ion adjacent to a carbanion, is an allyl anionic type 1,3-dipole that can be applied to construct N-heterocyclic compounds. However, most studies have mainly focused on [3+2]-dipolar cycloaddition using well-known 1,3-dipoles and 2p-dipolarophiles, while scarce attention has been focused on the development of new types of dipoles, such as 1,2-dipole, 1,4-dipole, and 1,5-dipole, for the formation of non-five-membered heterocycles. In this presentation, regio-, stereo-, siteselective dipolar cycloadditions of the isolable pyridinium zwitterion, which are extraordinary tools for formation of N-heterocyclic compounds, will be present.

Pyridinium zwitterion as a new dipole for the construction of heterocycles

253rd National Meeting (2017)

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