Abstract
N-Alkylation of IIIa, IIIb, IIId - IIIf and 9-acridanone with 3-bromopropyne in dimethyl sulfoxide in the presence of potassium carbonate yielded N-(2-propynyl) derivatives IVa - IVe and VIa, respectively. Ethyl esters IVa, IVb, and IVe were hydrolyzed to IVf - IVh, respectively. Compounds IVf, IVg, IVctreated with bases yielded N-propadienyl derivatives Va - Vc. On the other hand 2-substituted compounds IVd and IVh did not change under the same conditions. Compound VIa treated with powdered potassium hydroxide in dimethyl sulfoxide at room temperature yielded N-(1-propynyl) derivative VII.
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