Abstract
Reissert Henze reactions of phenanthroline N-oxides (1-2) with methanesulfonyl chloride gave the corresponding α-(5, 7) and, β-methylsulfonylphenanthroline (6, 8), respectively.
In a similar manner, 8-methylsulfonylated 1-oxide (10) was obtained from 1, 7-phenanthroline 1, 7-dioxide (3), but the reaction of 4, 7-phenanthroline 4, 7-dioxide (4) resulted in the recovery of dioxide (4). The reactions of 1 4 with benzenesulfonyl chloride used instead of methanesulfonyl chloride did not give any reaction products, except tor the reaction of 2 giving 4, 7-phenanthroline-3-carbonitrile.
Meisenheimer reactions of 1-3 with phosphorous oxychloride gave the corresponding α-(11, 14, 17), β-(12, 15, 18), and r-chlorophenanthrolines (13, 16, 19), respectively, while in a similar reaction, the a-chlorophenanthroline (20) as a sole product was obtained from 4 in a high yield.
As for 11 18, 20, minimum inhibitory concentrations (MIC) were 12.5μg/ml for Pseudomonas aeruginosa.
