The Reissert reaction with 1, 6-naphthyridine occurs at the nitrogen atom of 6-position. In the same reaction with 1, 6-naphthyridine 1-oxide, 6-oxide, and 1, 6-dioxide, N-oxide group reacts and gives 2-cyano-, 5-cyano-, and 2, 5-dicyano-derivatives as expected. And 1, 6-dioxide reacts with KCN in MeOH to give 2-methoxy-5-cyano-1, 6-naphthyridine, 2-methoxy-1, 6-naphthyridine-5-carboxamide, 2-methoxy-1, 6-naphthyridine 6-oxide. The same recation with 1-oxide gives 1, 6-naphthyridine and 2-methoxy-1, 6-naphthyridine or 2-methoxy-1, 6-naphthyridine-5-carboxamide. The mechanism of these novel reactions was proposed.