Abstract
1. From diethylethoxymethylene malonate and
the appropriate aniline, 4-chloroquinoline,
6-methoxy-4-chloroquinoline and L.:6-dichloroquinoline
have been prepared.
2. These chloro compounds have been used in
the synthesis of 2:3-benz-γ-carboline, 15-methoxy-2:3-benz-γ-carboline and 15- chloro -2:3- benz -ycarboline.
The unambiguous synthesis of the
former base has cleared up certain discrepancies
which existed in the literature.
3. The 2:3-benz-γ-carbolines have been treated with
diethylaminoethyl chloride to obtain basic side
chain derivatives. In this way, the following
have been prepared:
1-diethylaminoethyl- 2:3-benz-γ- carboline .
4-diethylaminoethyl-2:3-benz-γ-isocarboline.
5-methoxy-4-diethylaminoethyl-2:3-benz-γ-isocarboline.
15-chloro-l-diethylaminoethyl-2:3-benz-γ-carboline.
15-chloro-4-diethylaminoethyl-2:3-benz-γ-isocarboline.
In addition, 4-methyl-2:3-benz-γ-isocarboline
and 15-chloro-4-methyl-2:3-benz-γ-isocarboline
were also prepared.
4. The constitution of 1-diethylaminoethyl-2:3:4'-3'0benz-γ-carboline (and by analogy, of the
corresponding 15-methoxy- and 15-chloro-compounds)
has been established from a study of its methiodides.
5. The synthesis of 2:3:4':3'-quinoquinolo-4-one,
6'-methoxy-2:3:4':3'-quinoquinolo-4-one,
6'-chloro-2:3:4':3'-quinoquinolo-4-one, and of
4-chloro-2:3:4':3'-quinoquinoline, 6'-methoxy-4-chloro-2:3:4':3'-quinoquinoline and
4:6'-dichloro-2:3:4':3'-quinoquinoline from the
corresponding 4-anilinoquinoline-3-carboxylic
acids, has been described. These compounds are
isomeric with the 5-chloropyridoacridines, which
they resemble markedly in properties.
6. From the above chloroquinoquinolines, bases
have been obtained by condensing them with amines
such as ammonia, diethylaminoethylamine and
2-amino-5-diethylaminopentane. The constitution
of the products obtained is still uncertain.
