Synthesis of Isobenzofuran Derivatives as Heterocyclic Analogues of the Herbicide Sindone B

Article abstract of DOI:10.1002/prac.19943360411

The target compounds 21-27 were synthesized via bromination of the N,N,1,1-tetramethylisobenzofuranamines 13, 15 and 16, subsequent bromine-lithium exchange and reaction with propanal or propanoyl chloride, respectively.In the course of some model reactions undertaken to test a synthetic strategy based on directed ortho-lithiation governed by the dimethylamino-group a useful synthesis of the ketone 3 was developed.