42. Attempts to find new antimalarials. Part XXIII. Derivatives of 3 : 4 : 2′ : 3′-pyridoacridine and 1 : 2 : 2′ : 3′-pyridoacridine

Substituted 1,10-Phenanthrolines, XII. Benzo and Pyrido Derivatives1

“…With the object of preparing quino [8, [1,10]phenanthroline (XII), 4,5-diaminoacridine10•11 was subjected to a double Skraup reaction. As this was at first unsuccessful, a similar reaction was successfully run on the corresponding diaminoacri-done10•11 yielding the quinophenanthrolinone.…”

“…Caled, for C2oHi6F02: C, 78.4; H, 4.9; F, 6.2. Found: C, 78.2; H, 4.8; F, 6. The synthesis of the following fused ring compounds is described-benzo [6 ]and [t] [1,10 Iphenanthrolines and the 5,6,-7,8-tetrahydro derivative of the latter; pyrido [3,2-/][l,7]phenanthroline; quino [8,[1,10] phenanthroline. The synthesis of 5,6,7,8 -tetrahydrobenzo-…”

“…We have also prepared the 6-isomer (IX) by hydrogenation IX; R = H X; R = C1 R of 7-chlorobenzo [6][l,10]phenanthroline (X), previously obtained from o-chloroanthranilic acid and 8-aminoquinoline. 8 We have prepared X by reduction of 4-nitroacridone9 to the amino derivative followed by a Skraup reaction forming benzo [6]-[1,10 ]phenanthrolin-7 [12H ]-one (XI) and treatment of this with a phosphorus pentachloridephosphoryl chloride mixture. By reduction of the above aminoacridone to the aminoacridine, followed by a Skraup reaction, IX was also obtained.…”

DERIVATIVES OF THE PYRIDOQUINOLINES1

“…There is good evidence that an electron withdrawing group in the 2-position of the Atabrine nucleus can replace the usual 3-chloro group without marked diminution in activity. Thus, the 2-nitro and the pyrido(3,2-a) derivatives of 7-methoxy-9-substituted-aminoacridines are reported active (1,2).…”