Basische Tetrahydro-dibenzofuran-Derivate mit einem Abstand von drei C-Atomen zwischen dem Stickstoff und dem quartären C-Atom

摘要

Pummerer's ketone (1) is a “pharmacophoric synthon”, which can be used for a great number of synthetic variations. We have investigated the insertion of basic groups into C-1, C-2 and C-3. TheClaisenrearrangement of the allylic alcohols2 aand2 bleads to3 aand3 b, the reduction of which produces4 aand4 b. TheMannichreaction of1unexpectedly gives the 2-aminoalkylcompounds7 c-jand the synthesis of the derivatives2e-jwas performed by aminolysis of the 3-chloro-compound