Synthesis

A convenient one-step synthesis of ethyl 2-[N-(diethoxycarbonyl)(ethoxy)-methyl] amino-4-nitrobenzoate and analogues by rearrangement of 2, 4- …

S Kinastowski, S Wnuk

Index: Kinastowski, Stefan; Wnuk, Stanislaw Synthesis, 1983 , # 8 p. 654 - 659

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Citation Number: 2

Abstract

It was noted that 3a behaves abnormally under Michael reaction conditions. On reaction with piperidine in ethanol in-stead of addition of piperidine to the polarized double bond,: 1 compound with a completely changed carbon skeleton, not containing a piperidine fragment, ie ethyl 2-[N-(diethoxycan bonyl)(ethoxy)-methyl] amino-4-nitrobenzoate (5a) is formed. Use of pyrrolidine, diethylamine, or diisobutylamine also gave rise to 5a.