(S)RN(1) REACTIONS IN IMIDAZO[1,2-A][1,8]NAPHTHYRIDINE SERIES

4-dimethyl-9-nitroimidazo[1,2-a][1,8]naphthyridine was synthesized as reductive alkylating agent and its reactivity with 2-nitropropane anio n was investigated. The S(RN)1 mechanism of the C-alkyation was confir med by the inhibitory effects of p-dinitrobenzene, molecular oxygen an d TEMPO. Extension of this S(RN)1 reaction to various nitronate anions leads after nitrous acid elimination to a new class of imidazo[1,2-a] [1,8]naphthyridine derivatives bearing a trisubstituted double bond at the 8-position.