Synthetic route for the novel pyrimidine-substituted alkanoate, acetohydrazide, and imines: Synthon for β-lactams

Abstract

ABSTRACTA simple and efficient synthesis of novel pyrimidine-substituted alkanoate, acetohydrazide, and imines is described. The synthesis of novel ethyl 2-(2,6-dimethylpyrimidin-4-yloxy)acetate (EDMPyA) 2 was performed through SN2 O-alkylation of 2,6-dimethyl-4-hydroxypyrimidine 1 with ethyl haloacetate. The compound EDMPyA 2 was subjected to nucleophilic substitution reaction with hydrazine hydrate to afford novel 2-(2,6-dimethylpyrimidin-4-yloxy)acetohydrazide (DMPyAH) 3. This DMPyAH 3 upon condensation with differently substituted carbonyl compounds (aldehydes/ketones) furnished DMPyAH imines (DMPyAH-I) 4a–d. These imines can be used for the preparation of unique β-lactams. The structure elucidation of all the newly synthesized compounds was performed using spectroscopy (FT-IR, 1H and 13C NMR) and elemental analysis (C, H, N).