15-Oxo-15H-benzo[6,7][1,8]naphthyridino[2,1-b]quinazoline-6-carbonitrile (4a). A. A solution of
the propenenitrile 3e (5 mmol) in DMF (30 ml) was refluxed for 5-6 h or for 1-2 h in the presence of
triethylamine (5 mmol). The precipitate was filtered off, washed with water, alcohol (water in the case of the use
of triethylamine), and dried. A small amount of the product 4a can be separated from the mother liquor by the
addition of water (15 ml).
15-Oxo-15H-benzo[6,7][1,8]naphthyridino[2,1-b]quinazoline-6-carbonitriles
(4b-f)
(General
Method). B. A mixture of the acetonitrile 1 (5 mmol), aldehyde 2 (5 mmol) and triethylamine (5 mmol) in DMF
(30 ml) was refluxed for 4-5 h monitoring the completion of the reaction chromatographically. The precipitate
was filtered off, washed with water and then alcohol, and dried. A small amount of product 4 was separated by
the addition of water (15 ml) to the mother liquor.
3-(1-Aryl-5-chloro-3-methyl-1H-4-pyrazolyl)-2-(1H-benzo[d]imidazol-2-yl)-2-propenenitriles
(8a-d) (General Method). The corresponding 1-aryl-5-chloro-1H-4-pyrazolecarbaldehyde 5 (6 mmol) was
added to a solution of the acetonitrile 6 (6 mmol) in dioxane (15 ml) and refluxed for 1.5-2 h until the starting
acetonitrile had disappeared (TLC). The reaction mixture was cooled and the precipitate was filtered off, washed
with alcohol, and dried. A small amount of additional product can be separated after evaporation of the filtrate.
The compounds obtained are suitable for further reaction without initial purification.
1-Aryl-3-methyl-H-benzo[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyridine-5-carbonitriles
(7a,b,d,e)
(General Method). A. Triethylamine (0.7 ml, 5 mmol) was added to a solution of the propenenitrile 8 (5 mmol)
in DMF (20 ml) and refluxed for 2 h until the starting compound had disappeared (TLC). Water (10-15 ml) was
added to the reaction mixture and the precipitate formed was filtered off, washed with alcohol, and dried.
1-Aryl-3-methyl-1H-benzo[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyridine-5-carbonitriles (7c,f) (General
Method). B. The corresponding aldehyde 5 (5 mmol) and triethylamine (0.7 ml, 5 mmol) were added to a
solution of the acetonitrile 6 (5 mmol) in DMF (15 ml). The mixture was refluxed for 4 h until the starting
acetonitrile had disappeared (TLC). The reaction mixture was cooled, the precipitate was filtered off (if no
precipitate, water (10 ml) was added for its formation), washed with alcohol, and dried. In the first case an
additional amount of product can be separated by the addition of water (10 ml) to the filtrate of the reaction
mixture.
3-(1-Aryl-5-chloro-3-methyl-1H-4-pyrazolyl)-2-(4-oxo-3,4-dihydro-2-quinazolinyl)-2-propene-
nitriles (9a-k) (General Method). A mixture of the acetonitrile 1 (10 mmol) and the aldehyde 5 (10 mmol) in
dioxane (30 ml) was refluxed for 7-10 h, monitoring the completion of the reaction chromatographically. The
reaction mixture was cooled and the precipitate was filtered off, washed with water, and dried.
1-Aryl-3-methyl-11-oxo-1,11-dihydropyrazolo[4',3':5,6]pyrido[2,1-b]quinazoline-5-carbonitriles
(10a-f) (General Method). A solution of 2-propenenitrile 9 (3 mmol) in DMF (30 ml) was treated with
triethylamine (3 mmol) and refluxed for 2-3 h, monitoring the completion of the reaction chromatographically.
The precipitated product 10 was filtered from the cooled reaction mixture, washed with alcohol and water, and
dried. Part of the product was obtained from the mother liquor by the addition of water (15 ml).
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