SHKLYAEV et al.
116
3′-H), 6.90 s (1H, 6′-H), 6.97 d (1H, 5′-H), 7.14–
7.28 m (5H, C6H5). 13C NMR spectrum, δC, ppm: 13.1
(9-CH3), 18.6 (COCH3), 26.2 (3-CH3), 29.2 (C9), 36.4
(C10), 43.6 (C4), 53.5 (OCH3), 63.1 (C3), 70.0 (C5),
85.7 (1-CH), 109.1 (C3′), 124.8 (C7), 125.0 (C1′), 126.1
(C3″, C5″), 126.2 (C4″), 128.0 (C6′), 128.2 (C5′), 128.8
(C2″, C6″), 128.8 (C4′), 134.2 (C1″), 153.6 (C2′), 157.4
(C1), 162.6 (C8), 190.2 (C6), 207.7 (COCH3). Found,
%: C 78.73; H 7.75; N 3.32. C29H33NO3. Calculated,
%: C 78.52; H 7.50; N 3.16.
mp 208–212°C. 1H NMR spectrum, δ, ppm: 1.47 s and
1.74 s (3H each, 6-CH3), 1.74–1.84 m (2H, 3′-H),
2.14 d.d (2H, 3-H, J = 13.8 Hz), 2.16 s (3H, 1-CH3),
2.37–2.63 m (5H, 4′-H, 5-H, 5′-H), 2.89–2.99 m (3H,
2′-H, 5-H), 3.51 s (1H, 12b-H), 5.80 m (1H, 2-H),
13
7.06–7.28 m (4H, Harom), 16.26 s (1H, HCl). C NMR
spectrum, δC, ppm: 23.4 (1-CH3), 24.9 (6-CH3), 25.0
(C3′), 27.4 (C4′), 35.1 (C3), 40.6 (C2′), 42.6 (C5′), 46.3
(C5), 47.7 (C12b), 50.2 (C6), 64.9 (C8), 69.1 (C4a), 119.1
(C2), 124.1 (C12), 124.5 (C9), 125.8 (C11), 126.8 (C10),
130.2 (C12a), 133.8 (C8a), 140.0 (C1), 195.9 (C7a), 202.2
(C=O). Found, %: C 78.87; H 7.85; Cl 9.50; N 3.52.
C23H27NO·HCl. Calculated, %: C 74.68; H 7.63;
Cl 9.58; N 3.79.
8-Acetyl-1,6,6-trimethyl-3,4,5,6,7,12b-hexahy-
drodibenzo[d,f]indol-4-one (IV). After separation of
compound III, the mother liquor was evaporated, and
the residue was recrystallized from alcohol. Yield
0.64 g (2%), mp 205–206°C. IR spectrum, ν, cm–1:
This study was performed under financial support
by the Council for Grants at the President of the
Russian Federation (project no. MK-3014.2007.3), by
the Russian Foundation for Basic Research (project no.
07-03-00001), by the Collaboration Program of the
Ural and Siberian Divisions of the Russian Academy
of Sciences “Target-Oriented Synthesis and Optimiza-
tion of Properties of Biologically Active Compounds,”
and by the program of the Presidium of the Russian
Academy of Sciences “Development of Methods for
the Preparation of Chemical Substances and Design of
New Materials.”
1
3220, 1660, 1630, 1600. H NMR spectrum, δ, ppm:
1.21 s and 1.34 s (3H each, 6-CH3), 1.99 d.d (2H,
5-H), 2.05 s (3H, 1-CH3), 2.29 s (3H, COCH3),
2.70 d.d (2H, 3-H, J = 23.1 Hz), 3.56 s (1H, 12b-H),
5.68 m (1H, 2-H), 6.90–7.20 m (4H, Harom), 10.01 br.s
13
(1H, NH). C NMR spectrum, δC, ppm: 22.7 (1-CH3),
26.6 (6-CH3), 29.2 (COCH3), 35.8 (C3), 44.2 (C5), 49.5
(C6), 60.4 (C12b), 60.8 (C4a), 100.6 (C8), 118.4 (C2);
122.0, 123.1, 124.6, 125.1 (Carom); 129.9 (C12a), 133.5
(C8a), 134.5 (C1), 161.5 (C9), 192.3 (COCH3), 205.6
(C4). Found, %: C 78.73; H 7.75; N 3.32. C21H23NO2.
Calculated, %: C 78.47; H 7.21; N 4.36.
REFERENCES
1′,6′,6′-Trimethyl-4′,5′,6′,12b′-tetrahydrospiro-
[cyclopentane-1.8′-dibenzo[d,f]indol]-4′(3′H)-one
hydrochloride (V). A mixture of 1.22 g (10 mmol) of
o-methoxytoluene, 0.72 g (10 mmol) of isobutyral-
dehyde, and 1.6 g (10 mmol) of 1-phenylcyclopentane-
1-carbonitrile in 40 ml of methylene chloride was
added dropwise under stirring to 10 ml of concentrated
sulfuric acid cooled with an ace–water mixture. The
reaction mixture was stirred for 15 min, poured onto
150 g of crushed ice, and extracted with hexane, the
aqueous phase was neutralized to pH 7–8 with aqueous
ammonia and extracted with methylene chloride (3×
30 ml), the extract was dried over anhydrous magne-
sium sulfate under stirring in an argon atmosphere and
filtered, and dry hydrogen chloride was passed through
the filtrate. When the mixture became transparent, the
precipitate was filtered off and recrystallized from
propan-2-ol. Yield 0.64 g (18%), colorless crystals,
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 1 2010