From Diethyl 1,3-Diethoxycarbonylglutaconate and Its Derivatives

Levy prepared monosubstituted aminomethylenemalonates (356) in the reactions of diethoxycarbonylglutaconate (8, R = H) and aminoester hydrochlorides in the presence of sodium ethylate in boiling ethanol (14JCS27). 

The reactions of 2-(3,4-dimethoxyphenyl)ethylamine hydrochlorides with the sodium derivative of diethoxycarbonylglutaconate (8, R = H) in refluxing ethanol afforded the corresponding aminomethylenemalonates (357) in 84-885 yields (56JOC336). 

Diethyl aminomethylenemalonate (13) was prepared in the reaction of the ethoxycarbonyl derivative of diethoxycarbonylglutaconate (8, R = CH2COOEt) and ammonia (02JPR1). 

3-Amino-5-(pyridyl)thiophene-2-carboxylic acids (359) were reacted with diethyl methylenemalonate in DMF at 150°C for 2 hr to give N-[5-(pyridyl)thien-3-yl]aminomethylenemalonates (360) 61-62% yields [82-JAP(K) 116077], 

The rearrangement and subsequent reaction of nitrones (361) with diethyl malonate on the action of sodium ethylate in boiling benzene afforded monoethyl 3-indolylaminomethylenemalonates (362) in 17-72% yields (82ZOR2001 83ZOR1518). 

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