Chapter 1 Reissert Synthesis of Isoquinoline and Indole Alkaloids

Abstract

Publisher Summary This chapter describes the preparation and reaction of Reissert compounds, synthesis of isoquinoline alkaloids, and synthesis of indole alkaloid analogs. The most frequently used method for the preparation of isoquinoline Reissert compounds is treatment of an isoquinoline with acyl chloride and potassium cyanide in water or in a dichloromethane–water solvent system. Although, this method can be successfully applied in a great number of syntheses, it has also some disadvantages. Acid-catalyzed hydrolysis of Reissert compounds results in an aldehyde, a formal reduction product of the acyl halide utilized in the Reissert compound formation. The synthetic approach via Reissert compounds proves to be one of the most efficient routes to the alkaloids. More recently, the synthesis of aporphines, phthalideisoquinolines, and ellipticines, all of them possessing different valuable pharmacological properties, have become the target of organic chemists. The Reissert approach has proved to be a good synthetic tool with general applicability to the synthesis of these types of alkaloids.