Synthesis of 6,13‐Dihydroxyimino‐5,12‐Dimethyl‐ 7,14‐Dioxo‐1,4,8,11‐Tetraazacyclotetradeca‐4,11‐Diene

Abstract

6,13‐Dihydroxyimino‐5,12‐dimethyl‐7,14‐dioxo‐1,4,8,11‐tetraazacyclotetradeca‐4,11‐diene 2 was prepared by condensation of ethyl α‐oximinoacetoacetate with ethylenediamine in tetrahydrofuran at room temperature. Reduction of 2 gave the corresponding 6,13‐dihydroxyimino‐5,12‐dimethyl‐7,14‐dioxo‐1,4,8,11‐tetraazacyclotetradecane 3. Acylation of 2 afforded 6,13‐bis(O‐acetoxyimino)‐5,12‐dimethyl‐7,14‐dioxo‐1,4,8,1 l‐tetraazacyclotetradeca‐4,11‐diene 4. The structures of 2, 3 and 4 were determined by IR, NMR and mass spectroscopy.