Synthesis of 2'-arylazabicyclo-3-spiro-4'(5')-imidazolines

Article abstract of DOI:10.1055/s-1994-25584

A method is described for the synthesis of a series of 2'-aryl-3-azabicyclospiro-4'(5')-imidazolines via the reaction of azabicyclic 1,2-diamines with aryl imidate salts. Competing reactions in the synthesis of the diamines such as the reduction of amino nitriles with LiAlH₄ lead to some anomalous products. In the Pinner synthesis, unstable pyridine-type imidates were stabilized as their N-oxide derivatives.