Y. Kishida, N. Nakamura
Dec 25, 1969
Citations
0
Influential Citations
4
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
The addition reaction of diethyl acetamidomalonate anion to ethyl α, β-dibromoacrylate (I) and base catalyzed reactions of the adduct, diethyl 4-acetamido-2-bromo-4-carbethoxytrans-glutaconate (IIIb), were described. Addition of bromine to ethyl propiolate in carbon tetrachloride or acetic acid gave exclusively ethyl cis-α, β-dibromoacrylate (Ia). The reaction of both Ia and ethyl trans-α, β-dibromoacrylate (Ib) with diethyl acetamidomalonate anion gave the same product IIIb. Treatment of IIIb with sodium amide or potassium t-butoxide gave ethyl 2-bromo-3-(5-ethoxy-2-methyl-4-oxazolyl) acrylate (VIII). The reaction of IIIb with sodium ethoxide afforded diethyl 4-acetamido-4-ethoxy-trans-glutaconate (XVIII). The structures of VIII and XVIII were proved.