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The intermediary, covalent σ adducts formed in the reaction of nitroquinolines with the ylide generated from 1,1,1-trimethylhydrazinium iodide (TMHI) were detected by H NMR spectroscopy. Quantum-chemical calculations of the transition state (TS) energy and heats of formation of the σ adducts were done. The results of the calculations agree with high regioselectivity observed for the amination of 3-, 5-, 6-, 7and 8-nitroquinolines with (TMHI) via a vicarious nucleophilic substitution (VNS) reaction. High yields of the products substituted with amino substituent, mainly in the ortho position relation to the nitro group, are obtained.

Study of the regioselectivity of vicarious nucleophilic amination of mononitroquinolines with 1,1,1-trimethylhydrazinium iodide (TMHI)