The Journal of Organic Chemistry

An unusual ring contraction of 7-methyl-1, 7-naphthyridinium and 6-methyl-1, 6-naphthyridinium salts in reaction with liquid ammonia/potassium permanganate

M Wozniak, HC Van der Plas

Index: Wozniak, M.; Plas, H. C. van der; Harkema, S. Journal of Organic Chemistry, 1985 , vol. 50, # 19 p. 3435 - 3437

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Citation Number: 10

Abstract

Results Treatment of a solution of 1 in liquid ammonia with potassium permanganate for 20 min gave a tarry reaction mixture from which we were able to isolate three compounds with TLC:(i) 7, 8-dihydro-8-imino-7-methyl-1, 7-naphthyridine (3, 15%) as proved by microanalysis of its pictrate and lH NMR spectroscopy; its structure was confirmed by converting 3 into 7-methyl-1, 7-naphthyridone-8 (4) 4 by base treatment.(ii) 3-Amino-1, 3- ...