4
-Alkylaminocinnolines (10a-g) (General Method). A solution of compound 9 (0.17 g, 1 mmol) in
alkylamine was kept at 20°C for the time given in Table 3, and then evaporated to dryness. The residue was
treated with water (10 ml), neutralized with NH OH, and evaporated again. The product was recrystallized from
benzene (10e,f from petroleum ether, and 10g was washed out of the mixture with hot methanol until colorless).
Amine 10b was chromatographed on an Al column with CHCl as eluant (for R see Table 3) before
recrystallization. Compounds 10a-g consist of colorless or bright-yellow crystals.
-Aminocinnoline (10h). Compound 10g (0.2 g, 1 mmol) was added to a solution of potassium
4
O
2 3
3
f
4
(
0.156 g, 4 mmol) in liquid ammonia (30 ml) at -60°C. After 10 min KMnO (0.158 g, 1 mmol) was added to the
4
bright-yellow solution. The solution was stirred for 5 h while the temperature was raised stepwise to 20°C. The
ammonia evaporated. The residue was extracted with methanol (20 ml), the extract was concentrated to 5 ml
and chromatographed on an Al
2
O
3
column with CHCl
3
as eluent. The fraction collected had the R shown in
f
Table 3. Compound 10h consists of creamy crystals; mp 210°C (dec.), which corresponds to data from [17].
-(ω-Aminoalklylamino)cinnoline N(2)-Oxides (13a,b). A solution of compound 15 [18] (0.2 g,
mmol) in 2-4 ml of the corresponding diaminoalkane was kept for 7 d at 20°C and then evaporated to dryness.
The residue was dissolved in methanol (5 ml) and chromatographed on an Al column with 1:1 CHCl
CH OH as eluent. The bright-yellow fraction was collected (for R see Table 3). Compounds 13a,b consist of
bright-yellow crystals.
4
1
2
O
3
3
–
3
f
4
-(ω-Aminoalklylamino)cinnoline N(1)-Oxides (14a,b). A solution of compound 16 (0.1 g, 0.5 mmol) in
the corresponding diaminoalkane (2-3 ml) was kept for 1 d at 20°C and then evaporated to dryness. The residue
was washed clean from impurities with boiling methanol until colorless. Compounds 14a,b are colorless crystals.
This work was carried out with a grant from the Russian Fund for Fundamental Research (grant
No. 01-3-32338).
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