Medium- and large-ring heterocyclic systems by intramolecular nitrile imine cycloadditions

Abstract

A series of hydrazonyl chlorides bearing an alkenyl chain have been synthesised and treated with silver carbonate. The propensity of the so-formed nitrite Imine intermediates to undergo intramolecular cycloaddition is markedly dependent on the length and the flexibility of the chain. The latter also affected the regio- and the stereo-chemistry of the Intramolecular process. In certain circumstances, tandem intermolecular–Intramolecular cycloadditions took place, to produce largering heterophanes.