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Review | Regular issue | Vol 55, No. 7, 2001, pp.1365-1397
Published online, 1st January, 1970
DOI: 10.3987/REV-01-539
Review on Reactions of Acetylacetaldehyde with Aromatic and Biogenic Amines and Indoles — Synthesis of Heterocycles via Hydroxymethylene Ketones

Ramiro Quintanilla-Licea* and Hans-Joachim Teuber

*Facultad de Ciencias Químicas, Universidad Autónoma de Nuevo León, Cd. Universitaria, 66400 San NicolÁs, d.l.G., N.L., Mexico


In 1960 Teuber et al. started with the study of the reactions of several derivatives of acetylacetaldehyde with aromatic and biogenic amines (dopamine and tryptamine), as well as indole compounds. Teuber’s scientific work resulted in a series of heterocyclic skeletons that are related to alkaloids such as strychnine, yohimbine, ajmalicine and emetine as well as to some analogues of bis-indole alkaloids. We review Teuber’s research results as well as reactions from other authors working in this field obtained within the last 40 years (1960 -2000).