Add time:09/02/2019         Source:sciencedirect.com

5-Aminopenta-2,4-dienals, and specially their N,N-disubstituted derivatives (Zincke aldehydes), are known for more than a century but their chemistry has not been highly exploited until recently. They are the most frequently prepared via the ring opening of 1-(2,4-dinitrophenyl)pyridinium salts (Zincke salts) with amines.As these compounds are bisvinylogous formamides, and therefore push–pull dienes, they can behave either as nucleophilic or electrophilic species, and can be used for the construction of nitrogen heterocycles. Vanderwal discovered conditions for intramolecular cycloadditions involving Zincke aldehydes and indoles, allowing the synthesis of natural heterocyclic products. A thermic rearrangement of Zincke aldehydes into (Z) dienamides has also been developed and applied to achieve the synthesis of polycyclic lactams.5-Alkylaminopenta-2,4-dienals have been postulated by Marazano as possible biosynthetic intermediates in the formation of marine alkaloids of the manzamine family, and biomimetic approaches toward the skeleton of some of these compounds were developed, based on this proposal.

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