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We describe herein the ring-opening reaction of chiral 1,1’-sulfonyl bis-aziridines with various neutral and anionic nucleophiles, including benzylamine, piperidine, acetate, allyl thiolate, cyanide anion, and sodium ethoxide. These reactions afforded bis-opened or/and mono-opened compounds via a regioselective attack on the non-substituted methylene of aziridine ring. The structures of the products were confirmed based on spectral analysis (IR, 1H NMR, and 13C NMR). A theoretical study involving density functional theory (DFT) was used to rationalize the region-selective ring-opening of starting bis-aziridines.
Herein, we describe an efficient one-step synthesis of new fused benzothiadiazepine-1,1-dioxides and macrocyclic sulfamides. The synthesis of these compounds was achieved in moderate yields starting from previously described N,N′-disubstituted symmetric sulfamides and N-tert-butoxycarbonyl, N′-alkyl sulfamide. The chemical structures of all the new compounds reported in this work were confirmed by NMR, IR, and mass spectrometry. These compounds are beneficial building blocks that can be used in deriving new chemical entities that exert a wide spectrum of pharmacological activities.
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