关键词: 二氮杂冠醚, 三氮杂冠醚, 糖精

Abstract: In this paper a new method for the synthesis of di- and tri-aza crown ethers starting from saccharin is reported. Saccharin is first alkylated with di-or tri-ethylene glycol dichloride and N,N-(β-chloroethyl) butyl amine in DMF solution in the presence of small amount of potassium iodide. The N-alkylated saccharin is treated with ammonia and transformed into the N-alkylated o-carbamoyl benzene sulfonamide, which is then alkylated once again with ditosylates of di- and tri-ethylene glycol to form the crown ethers on the imino groups protected with o-carbamoyl benzene sulfonyl group. Di- and triaza crown ethers are obtained by removing the protective group on the nitrogen with 20% hydrochloric acid. By this method, are prepared 10 new intermediates, which can be used to synthesize di- and tri-aza crown ethers bridged by like or different chains. The total yield of 1,10-diaza-18-crown-6 amounts to 36% close to that by the high dilution method starting from 1, 8-diaza-3,7-dioxaoctane. Compared with the methods reported in the literature, the features of the new method are. (1) using cheap starting materials (2) the o-carbamoyl benzene sulfonyl protective groups can be removed more easily than tosyl group.