Science of Synthesis

Ayaz, M.; De Moliner, F.; Morales, G. A.; Hulme, C., Science of Synthesis: Multicomponent Reactions, (2014) 1, 119.

The addition of a cyanide ion to azaheterocycles (e.g., quinolines, isoquinolines, and pyridines) in the presence of an acyl chloride is commonly known as the Reissert reaction.[‌95‌] Under these conditions, the ring is activated by covalent bonding between the nitrogen and the acylating agent, which allows the nucleophilic attack of a cyanide ion in an analogous fashion to the Strecker mechanism. However, almost all publications about this transformation describe a limited number of examples and the overall scope of the reaction is thus difficult to outline. Nevertheless, good examples of this methodology, forming tetrahydroisoquinolines ‌24‌ and dihydroisoquinolines ‌25‌, are shown in ‌Scheme 23‌.[‌104‌]

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References