Three-membered heterocycles in the synthesis of crown compounds and cryptands (review)

Abstract

The cyclo-oligomerization of oxirane and aziridine and their derivatives in the presence of BF3 leads to the corresponding macroheterocydic compounds. Crown compounds with exocyclic alkyl, aryl, or functional substituents are formed in the reaction of alkyl-, aryl-, and functionally substituted oxiranes or aziridines with dinucleophilic reagents with subsequent intramolecular cyclocondensation of the reaction products. Methods for the synthesis of cryptands that are based on the reaction of diazacrown compounds with diglycidyl ethers of oligoethyleneglycols are described. The reaction of tosylaziridine with α,Ω-alkylenediamines leads to tetrakis(p-toluenesulfamidoethyl)alkylenediamines, the cyclocondensation of which in the presence of 1,2-dibromomethane under interphase-catalysis conditions gives the corresponding cryptands.