The Addition Reaction of Diethyl Acetamidomalonate Anion to Ethyl α, β-Dibromoacrylate, and the Base-catalyzed Reactions of the Adduct

Autor:	Norio Nakamura, Yukichi Kishida
Rok vydání:	1969
Předmět:	Addition reaction Sodium ethoxide Bromine chemistry.chemical_element General Chemistry General Medicine Medicinal chemistry Catalysis Adduct Ethyl propiolate chemistry.chemical_compound Acetic acid chemistry Sodium amide Drug Discovery Organic chemistry
Zdroj:	Chemical and Pharmaceutical Bulletin. 17:2424-2435
ISSN:	1347-5223 0009-2363
DOI:	10.1248/cpb.17.2424
Popis:	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.
Databáze:	OpenAIRE
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