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General Procedure. According
to the classical experiment,
[7a]
a
mixture of 0.1 mmol of each of the compounds: isoquinoline and two
unsaturated starting materials were stirred in 0.13 mL of Et2O
for 48 h at 20 °C. After evaporation of solutions to dryness
the residua were analyzed by HPLC. In the case of the products 12, the crude mixtures were purified by
crystallisation or flash-chromatography.
9
HPLC Analysis of
the Reaction Products. The final mixtures were analyzed by
reversed-phase HPLC with detection at 230 nm. The chromatography
was performed on a Hewlett-Packard HP 1090 apparatus equipped with
a diode-array detector. A reverse-phase column was used (Hypersil® BDS
C18, 3µ, 50 × 4.6 mm) under an optimized binary
gradient acetonitrile/water, flow 1 mL/min. To validate
the analytical method, some products and starting materials were
characterized separately. The peaks were assigned to the corresponding
products by comparison to the retention time and UV profiles.
10
Spectral Data
for Compound 12a: 1H NMR (400 MHz, DMSO-d
6): δ = 7.47
(s, 5 H, Ph), 7.36 (d, J = 8.9
Hz, 1 H, CH-9), 7.33-7.28 (m, 2 H, CH-7 and CH-8), 7.20
(d, J = 8.8 Hz,
1 H, CH-6), 7.15 (d, J = 7.8
Hz, 1 H, CH-5), 5.90 (d, J = 7.8
Hz, 1 H, CH-4), 5.68 (s, 1 H, CH-3), 5.54 (s, 1 H, CH-10), 1.89
(br s, 3 H, CH-adamantane), 1.58 (br s, 6 H, CH2-adamantane),
1.47 (br s, 6 H, CH2-adamantane). 13C NMR
(100 MHz, DMSO-d
6): δ = 146.30,
132.49, 132.38, 129.35, 129.26, 129.06, 128.24, 127.30, 125.54,
125.52, 123.54, 123.05, 113.79, 112.74, 106.20, 59.74, 54.10, 52.77, 44.05,
43.50, 35.61, 28.97. MS (70 eV): m/z (%) = 444 (28) [M]+,
417 (14) [M - HCN]+,
282 (28), 265 (51), 135 (100), [C10H15]+.
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Shaabani A.
Teimouri MB.
Bijanzadeh HR.
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