Studies in the chemistry of nitrogen heterocycles

Cyanochlorination and cyanogenation of the hetero-ring of various isoquinolines has been achieved by reaction with sulphuryl chloride, with potassium cyanide at room temperature. Application of the method to the isoquinolines Reissert compound gave a chlorohydrin derivative which was more easily prepared by the action of hypochlorous acid. This chlorohydrin underwent novel rearrangement reactions on base-catalysed elimination of hydrogen chloride: an isochromene ring was first produced which rearranged further to generate a new isoquinoline system. Autoxidation of the anion derived from the isoquinoline Reissert compound was shown to give isoquinaldonitrile. The reaction of Nb-benzyltryptamine with formaldehyde has been studied and an improved preparation of Nb-methyltryptamine developed.