The synthesis of emetine and related compounds. VII. The utility of Bi-functional catalysts in amine-ester interactions.

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Bi-functional catalysts such as 2-hydroxypyridine are shown to be valuable in promoting the reaction between a variety of aliphatic amines and non-activated esters to give substituted amides; they are less effective with aniline. This method has been applied to the synthesis of the emetine intermediate, an N-substituted benzo[a] quinolizineacetamide (II), and analogues.