Antimalarial Studies in the Quinoline Series

The Search for Superior Drugs for Tropical Diseases. Ii. Synthetic Studies in the Quinoline and Phenan-Throline Series. Skraup and Conrad-Limpach-Knorr Reactions

“…But when the Skraup reaction was applied to this amine, the yield of the desired 5-methoxy-l, 10-phenanthroline (XXV) was so small that this product could not be satisfactorily purified and identified. This was disappointing in view of the excellent yields of 1,10-phenanthrolines obtained by Smith and his co-workers (15, 16) from 6methyl-, 6-chloro-, and 6-bromo-8-aminoquinolines; and the success of Burger et al (34) in the preparation of the 1,10-phenanthrolines from 2-chloroand 2-hydroxy-4-methyl-8-aminoquinolines.…”

“…On the other hand, a Skraup applied to 8-aminoquinolines (22,15,16,34) for the preparation of 1,10-phenanthrolines, has been found useful in a number of cases, although our own experience with it has been unsatisfactory.…”

“…Some phenanthroline derivatives have been claimed (3,4,5) to possess analgesic properties, others (5) to exhibit bactericidal activity. Some have been prepared (6,7,34) for pharmacological testing in other directions. The 1,10-phenanthroline (XXXI) is best known from the work of Walden, Hammett, and Chapman (8), who called attention to its ferrous cation complex as a remarkably sensitive oxidation-reduction indicator.The 1,8-phenanthrolines (XXXIII) have been studied but little.…”

Infrared spectra of substituted 1,10-phenanthrolines

“…publications in chronological oxand iiic Lypes of derivatives synthesized in each are listed in Table 1. (4,23,34,36,39,40,43,63,64), but these will not be listed here as they do not represent any major group of 1,10-phenanthrolines.…”

The spectrophotometric determination of dissolved oxygen and other uses of 4,7-dihydroxy-1, 10- phenanthroline

“…The spectrophotometric determination of dissolved oxygen and other uses of 4,7-dihydroxy-l, 10 The organic compound 1,10-phenanthroline has been used since 1934 as a reagent for the spectrophotometric determination of small amounts of iron. In the seventy-six years since the first synthesis of 1,10-phenanthroline, several hundred substituted 1,10-phenanthrolines have been synthesized.…”