含窒素複素環化合物の研究(第49報)N-Acylphenanthrolinium Salt及びN-Acylacridinium SaltとTrimethyl PhosphiteとのReissert Typeの反応その3

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The reaction of 1,7-phenanthroline (1) with various acyl chlorides and trimethyl phosphite in the presence of sodium iodide gave the corresponding α (8)-phosphonates (2) and γ (10)-phosphonates (3) as observed in the reaction of benzo [f] quinoline, while in Reissert reaction γ-type's compound was not obtained. In the similar reaction to 4,7-phenanthroline (4), the corresponding α, α'-diphosphonates (5) and α, γ'-diphosphonates (6) were obtained. Furthermore cis-(5b_2 and 5c_2) and trans-(5b_1 and 5c_1) isomers were separated by silicagel column chromatography from α, α'-diphosphonates (5b and 5c). α-Phosphonates (2,5) and γ-phosphonates (3,6) were identified by comparison of ^<13>C-nuclear magnetic resonance and ultraviolet spectra with those of phosphonates obtained from quinoline and benzo [f] quinoline. 1,10-Phenanthroline (7) was recovered in the similar reaction. The reaction of acridine (8) with trimethyl phosphite gave 9-phosphonates (9).
公益社団法人日本薬学会の論文
1987-12-25