87338-07-6Relevant academic research and scientific papers
An Alternative Synthesis of Cyclic Aza Compounds
Boerjesson, L.,Welch, C. J.
, p. 621 - 626 (2007/10/02)
A series of cyclic mono-, di- and poly-aza compounds has been synthesised in moderate to good yields by reaction of p-toluenesulfonamide and either α,ω-ditosylates or α,ω-dichlorides.
MACROHETEROCYCES. XXXVI. A CONVENIENT METHOD FOR SYNTHESIS OF DI- AND POLYAZACROWN ETHERS
Luk'yanenko, N.G.,Basok, S.S.,Filonova, L.K.
, p. 1562 - 1571 (2007/10/02)
A method is proposed for the production of di- and polyazacrown ethers by the condensation of bissulfonamides with dibromides or ditosyloxy derivatives in a two-phase aqueous alkali-toluene (benzene) system.The optimum concentration range for the substrate and the alkylating agent is 0.017-0.1 M.The catalytic activity of the quaternary ammonium salts decreases in the order (Bu)4NI > (Bu4)NBr > (Bu4)NCl > (Bu4)NHSO4 > (C2H5)3C6H5CH2NCl >> (Et)4NI > (Et)4NBr.The highest yields of te 12-membered azacrown ethers are obtained in the presence of lithium hyroxide, and the largest yields of the crown ethers with larger ring sizes are obtained in the presence of sodium or potassium hydroxide, and this is probably due to the matrix effects of the cation.
MACROHETEROCYCLES. PART 44. FACILE SYNTHESIS OF AZACROWN ETHERS AND CRYPTANDS IN A TWO-PHASE SYSTEM
Lukyanenko, Nikolai G.,Basok, Stepan S.,Filonova, Lyubov K.
, p. 3141 - 3148 (2007/10/02)
A facile procedure is proposed for the preparation of azacrown ethers and cryptands by condensation of dibromides or ethylene glycol bis(toluene-p-sulphonate)s with acyclic bis(sulphonamide)s or with bisdiazacrown ethers, respectively.The reaction was carried out in a two-phase system of aqueous alkali-toluene (benzene)in the presence of quaternary ammonium salts as phase transfer catalysts.The catalytic activity decreased in the sequence: Bu4NI ca.Bu4NBr > Bu4NCl > Bu4NHSO4 > Et3NCH2C6H5NCl.Maximum yields of twelve-membered azacrown ethers are obtained when lithium hydroxide is used, while crown ethers of larger size are observed in the presence of sodium or potassium hydroxides; this may be due to a template effect.
Synthesis of Aza Macrocycles by Nucleophilic Ring Closure with Cesium Tosylamides
Vriesema, Bindert K.,Buter, Jan,Kellogg, Richard M.
, p. 110 - 113 (2007/10/02)
Long-chain diamines as their bis tosylamide derivatives are deprotonated by Cs2CO3 in dimethylformamide solution to give the dicesium salts.These react smoothly with various dibromides or dimesylates to afford the cyclic diamines as their tosyl derivatives.The yields, depending on the size of the ring, range between 25percent and 95percent of isolated product.The largest ring made, 1,12-diazaoctacosane (as the tosylamide derivative) was isolated in 60percent yield.The tosyl groups are readily removed with sodium amalgam in Na2HPO4-buffered methanolic solution.Chiral macrocyclic amines have also been prepared by using this cesium salt method.
