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Bu4NHSO4 (TBAHS) is an effective catalyst for the hydrolysis of aziridines and epoxides under mild and non-metal conditions to give the corresponding beta-amino alcohols and 1,2-diols in high yields. The catalyst can be recycled.
During the aziridination of styrene using copper bis(oxazoline) complexes the ee increases with conversion due to further reactions of the product.
Environmentally benign HPA is found to be an efficient catalyst for aziridination of olefins in the presence of inexpensive Chloramine-T as a nitrogen source: instantaneous at room temperature, requires only stoichiometric amount of olefin and no allyl amine side product.
Highly enantioselective aziridination of chalcones catalyzed by a novel backbone 1,8-bisoxazolidinylanthracene (AnBOX) and CuOTf with up to >99% ee and the opposite enantioselectivity compared with the ligands of Evans are described.
A non-heme iron complex catalyses the aziridination of various olefins and the amidation of thioanisole in good yields at the expense of an aryl iodinane.
After the study of different phenylselanyl group activators, halogenation by N-bromosuccinimide (NBS) has been shown to be the most suitable manner for cyclizing beta-phenylselanyl amines into aziridines and also enabled production of oxazolidin-2-ones from N-Boc beta-phenylselanyl amines in excellent yield.
A new robust fluorinated (OC)Ru(salen) complex was designed on the basis of an X-ray structure of its parent complex to show improved turnover numbers (up to 878) and enantioselectivities (up to 99%) in aziridination reactions using p-toluenesulfonyl (Ts) or p-nitrobenzenesulfonyl (Ns) azide as the nitrene precursor; the latter is synthetically advantageous since the Ns group is N-protecting and can be removed under mild conditions.
Organolithium-induced ring-opening of aziridines of 2,5-dihydrofuran (5 and 8) and 1,4-dimethoxybut-2-ene (16, 17 and 23) gives 3-substituted 2-aminobut-3-en-1-ols 9-15 and amino ethers 18-20 and 24-26.
The direct conversion of dihydrofuran and dihydropyrrole N-triisopropylbenzenesulfonyl aziridines into alkynyl amino alcohols and diamines respectively can be achieved using 3 equiv. sec-butyllithium-PMDETA in THF; use of n-butyllithium and (-)-sparteine in Et2O gave an alkynyl amino alcohol in 60% ee.
Aziridine N-carbonyl radicals, generated by irradiating the corresponding S-oxalyl xanthates, undergo ring opening to give 2-isocyanato radicals, which can be trapped by an external olefin.
The work described was undertaken after the observation that the diuresis induced by several derivatives of ethyleneimine could be correlated with their content of ethyleneimine. The preparation of (35)S-labelled di(aziridin-1-yl) sulphoxide (diethyleneiminosulphoxide) is described together with its metabolism in rat, mouse, rabbit and dog. The drug was completely metabolized in all species and, with the exception of the dog, most of the activity was excreted in the urine within 3 days. The main radioactive metabolite in all species was sulphate. In vitro studies demonstrated that the compound was slowly broken down to sulphite and free ethyleneimine; this hydrolysis was greatly accelerated in the presence of phosphate.
Three chemical derivatives of mitomycin C cause loss of viability, inhibition of deoxyribonucleic acid synthesis, and inhibition of cell division in bacteria. Each of these drugs lacks the C(1)-C(2) aziridine ring previously postulated to be essential for the bactericidal effect of mitomycin C.
Two analogs of the antiestrogen tamoxifen, which bear a chemically reactive aziridine function in place of the dimethylamino group, bind to the estrogen receptor from rat uterus and from MCF-7 human breast cancer cells and appear to react irreversibly with the receptor at the estrogen binding site, in a time-and concentration-dependent fashion. BEcause these compounds are effective receptor inactivators in uterus and breast cancer cells, they should prove to be useful probes for investigating the role of receptor in regulating cellular responses to estrogen and in studying the dynamics of estrogen receptor synthesis and turnover.
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