Vicarious Nucleophilic Substitution of Hydrogen and Formation of Aziridine Rings in Reactions of Benzonaphthyridines and their N-Oxides with Chloromethyl Phenyl Sulfone

Summary.  Treatment of benzonaphthyridines with chloromethyl phenyl sulfone in the presence of base led to the formation of aziridine rings annelated to the benzonaphthyridine skeleton, whereas their N-oxides underwent vicarious nucleophilic substitution of hydrogen (VNS), thus leading to the corresponding phenylsulfonylmethyl derivatives. Received December 11, 2000. Accepted (revised) January 22, 2001