Chemistry of Reissert Compounds

The chemistry of Reissert compounds has been the subject of numerous general reviews (3-10). In 1973 Popp gave a summary on the use of Reissert compounds in the synthesis of isoquinoline alkaloids and related compounds (7). We now wish to summarize new results that have appeared from 1973 to the end of 1985 for the application of Reissert compounds in the synthesis of isoquinoline as well as indole alkaloids. 

The Chemistry of Reissert Compounds F. D. Popp, Bull. Soc. Chim. Belg., 1981, 90, 609-613. 

Popp, F. D., Developments in the Chemistry of Reissert Compounds, 1968-1978, 24, 187 Reissert Compounds,... 

The chemistry of Reissert compounds, for example, N-acyldihydroquin-aldonitriles (1) and Af-acyldihydroisoquinaldonitriles (2), was the subject of a review in an earlier volume of this series. The application of Reissert compounds to the synthesis of isoquinoline alkaloids and related compounds... 

The anion of the Reissert compound (62.1) reacts at or below room temperature with an aldimine or an isothiocyanate by cycloaddition, and then displacement of the nitrile to form a tricyclic isoquinoline. The chemistry of Reissert compounds has been reviewed [2488, 2959a], as have the synthetic uses of isothiocyanates [3990]. 

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