EXPERIMENTAL
1
The H NMR spectra of 4 were taken on a Varian Mercury-300 spectrometer (300 MHz), while the
spectra of the other compounds were taken on a Tesla BS 567 spectrometer (100 MHz) in DMSO-d6 (amides
2a,b) or CCl4 (4, 6a-d) with HMDS as the internal standard (δ 0.05 ppm). The IR spectra were taken on a
Specord-80 spectrometer in vaseline mull. The electron-impact mass spectra were taken on a MAT-311
spectrometer at 70 eV. The purity of the products were checked by thin-layer chromatography on Silufol
UV-254 plates using 1:3:6 acetone–ethanol–chloroform as the eluent and development by iodine vapor.
Amides 2a,b were recrystallized from acetonitrile, while quinones 6a,d were recrystallized from
petroleum ether (70-100°C fraction). The other products were recrystallized from 2-propanol.
Derivatives 5a,b [9], and 5d [10] were prepared according to reported procedures.
Pyrrolidyl Amide (2a) and Piperidyl Amide of 2-(2',2'-Dimethyl-1',2'-dihydrobenzo[f]isoquinolyl-
4')-2-(2",5"-dihydroxyphenyl)ethanoic Acid and 1-(3',4'-Diethoxyphenyl)-10,11-diethoxy-7,8-dihydro-
indolo[2,1-a]isoquinoline (4) (General Method). A solution of p-benzoquinone (1.08 g, 10 mmol) in dry
methylene chloride (20 ml) was added to a solution of corresponding starting enamine (10 ml) in dry methylene
chloride (50 ml). The solution turns dark-blue. The mixture was heated at reflux for 1 h and the solvent was
distilled off. Treatment of the residue with hexane gave a precipitate, which was filtered off, dried, and
recrystallized.
14-Piperidinocarbonyl- (6a), 14-Morpholinocarbonyl- (6b), and 14-Ethoxycarbonyl-6,6-dimethyl-
5,6-dihydrobenzo[g]naphtho[2,3-b]indolyzine-8,13-dione (6c) (General Method). A sample of 2,3-dichloro-
1,4-naphthoquinone (2.27 g, 10 mmol) was added to a mixture of corresponding enamine 5a-c (10 mmol) with
triethylamine (2.80 ml, 22 mmol) in benzene (100 ml). The resultant dark-blue solution was heated at reflux for
1 h and the triethylamine hydrochloride precipitate was filtered off. The solvent was removed in vacuum and
then treated as in the procedures for 2a,b, and 4.
6,6-Dimethyl-5,6-dihydrobenzo[g]naphtho[2,3-b]indolyzine-8,13-dione (6d).
A
sample of
2,3-dichloro-1,4-naphthoquinone (2.27 g, 10 mmol) was added to a solution of enamine 5d (1.73 g, 10 mmol) in
benzene (10 ml). The resultant dark-blue solution was left stand for 3-4 h at 20°C. A precipitate formed. The
mixture was diluted by adding hexane (50 ml) and then treated as in the procedure for 2a,b, and 4.
REFERENCES
1.
2.
3.
A. G. Mikhailovskii and V. S. Shklyaev, Khim. Geterotsikl. Soedin., 291 (1997) [Chem. Heterocycl.
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K. V. Vatsuro and G. L. Mishchenko, Name Reactions in Organic Chemistry [in Russian], Khimiya,
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(2003).
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5.
A. K. El-Shafei, A. Sultan, and G. Vernin, Heterocycles, 19, 333 (1982).
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7.
N. N. Polygalova, A. G. Mikhailovskii, V. L. Gein, and M. I. Vakhrin, Khim. Geterotsikl. Soedin., 291
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