C. S. Cho et al.
Scheme 3. A catalytic cycle
reaction temperature and time. The reaction mixture was filtered
through a short silica gel column (ethyl acetate–hexane mixture)
to eliminate inorganic salts. Removal of the solvent left a crude
mixture, which was separated by thin-layer chromatography (silica
gel, ethyl acetate-hexane mixture) to give 1-aryl-1H-pyrrol-2(5H)-
ones 6. Except for 6a and 6i, which were characterized by
gas–liquid chromatography and spectroscopic comparison with
authentic samples synthesized by our recent report,[38] all products
prepared by the above procedure were characterized spectroscop-
ically as shown below.
Anal. Calcd for C15H17NO: C, 79.63; H, 7.94; N, 5.80. Found: C,
79.56; H, 7.89; N, 5.75.
2-(2-Methylphenyl)-2,3,5,6,7,8-hexahydrocyclohepta[c]pyrrol-1(4H)-one (6e)
Solid; m.p. 113–114ꢀC (from hexane–ethyl acetate). 1H NMR (CDCl3)
d 1.63–1.75 (m, 4H, 2CH2), 1.81–1.87 (m, 2H, CH2), 2.22 (s, 3H, CH3),
2.44–2.49 (m, 4H, 2CH2), 4.08 (s, 2H, CH2-N), 7.12–7.15 (m, 1H, CH),
7.19–7.24 (m, 2H, 2CH), 7.26–7.28 (m, 1H, CH). 13C NMR (CDCl3) d
18.51 (CH3), 25.41 (CH2), 27.42 (CH2), 27.46 (CH2), 30.02 (CH2),
31.31 (CH2), 56.53 (CH2-N), 126.79 (aromatic C), 127.55 (aromatic
C), 127.78 (aromatic C), 131.26 (aromatic C), 134.82 (vinyl C),
136.49 (aromatic C), 137.56 (aromatic C), 153.21 (vinyl C), 177.77
(C-O). Anal. Calcd for C15H17NO: C, 79.63; H, 7.94; N, 5.80. Found:
C, 79.50; H, 7.88; N, 5.70.
2-Phenyl-2,3,5,6,7,8-hexahydrocyclohepta[c]pyrrol-1(4H)-one (6b)
Solid; m.p. 126–127ꢀC (from hexane–ethyl acetate). 1H NMR (CDCl3)
d 1.62–1.74 (m, 4H, 2CH2), 1.80–1.86 (m, 2H, CH2), 2.45–2.48 (m, 4H,
2CH2), 4.19 (s, 2H, CH2-N), 7.07–7.11 (m, 1H, CH), 7.33–7.37
(m, 2H, 2CH), 7.72–7.74 (m, 2H, 2CH). 13C NMR (CDCl3) d 25.11
(CH2), 27.33 (CH2), 27.39 (CH2), 29.92 (CH2), 31.22 (CH2), 54.05
(CH2-N), 118.42 (aromatic C), 123.59 (aromatic C), 129.22 (aromatic
C), 135.92 (vinyl C), 139.84 (aromatic C), 152.16 (vinyl C), 171.51
(C-O). Anal. Calcd for C15H17NO: C, 79.26; H, 7.54; N, 6.16. Found:
C, 79.25; H, 7.47; N, 6.14.
2-(4-Chlorophenyl)-2,3,5,6,7,8-hexahydrocyclohepta[c]pyrrol-1(4H)-one (6f)
Solid; m.p. 165–168ꢀC (from hexane–ethyl acetate). 1H NMR (CDCl3)
d 1.61–1.74 (m, 4H, 2CH2), 1.80–1.86 (m, 2H, CH2), 2.45–2.48 (m, 4H,
2CH2), 4.16 (s, 2H, CH2-N), 7.27–7.32 (m, 2H, 2CH), 7.67–7.70
(m, 2H, 2CH). 13C NMR (CDCl3) d 25.08 (CH2), 27.28 (CH2), 27.34
(CH2), 29.74 (CH2), 31.17 (CH2), 53.97 (CH2-N), 119.44 (aromatic
C), 128.51 (aromatic C), 129.19 (aromatic C), 135.91 (vinyl C),
138.43 (aromatic C), 152.34 (vinyl C), 171.47 (C-O). Anal. Calcd
for C15H16ClNO: C, 68.83; H, 6.16; N, 5.35. Found: C, 68.67; H,
6.10; N, 5.32.
2-(4-Methylphenyl)-2,3,5,6,7,8-hexahydrocyclohepta[c]pyrrol-1(4H)-one (6c)
Solid; m.p. 120–121ꢀC (from hexane–CH2Cl2). 1H NMR (CDCl3) d
1.61–1.73 (m, 4H, 2CH2), 1.79–1.85 (m, 2H, CH2), 2.32 (s, 3H, CH3),
2.44–2.46 (m, 4H, 2CH2), 4.15 (s, 2H, CH2-N), 7.15 (d, JHH = 8.5 Hz,
2H, 2CH), 7.59 (d, JHH = 8.5Hz, 2H, 2CH). 13C NMR (CDCl3) d 20.97
(CH3), 25.11 (CH2), 27.34 (CH2), 27.40 (CH2), 29.89 (CH2), 31.21
(CH2), 54.18 (CH2-N), 118.57 (aromatic C), 129.70 (aromatic C),
133.14 (aromatic C), 135.86 (vinyl C), 137.35 (aromatic C), 151.89
(vinyl C), 171.36 (C-O). Anal. Calcd for C16H19NO: C, 79.63; H,
7.94; N, 5.80. Found: C, 79.54; H, 7.85; N, 5.73.
2-Phenyl-2,3,4,5,6,7,8,9-octahydro-1H-cycloocta[c]pyrrol-1-one (6g)
Solid; m.p. 110–111ꢀC (from hexane–ethyl acetate). 1H NMR (CDCl3)
d 1.54–1.56 (m, 4H, 2CH2), 1.67–1.73 (m, 2H, CH2), 1.76–1.82 (m, 2H,
CH2), 2.50–2.56 (m, 4H, 2CH2), 4.21 (s, 2H, CH2-N), 7.07–7.11 (m, 1H,
CH), 7.33–7.38 (m, 2H, 2CH), 7.74–7.77 (m, 2H, 2CH). 13C NMR (CDCl3)
d 22.22 (CH2), 25.83 (CH2), 26.12 (CH2), 26.90 (CH2), 27.72 (CH2),
27.75 (CH2), 53.36 (CH2-N), 118.23 (aromatic C), 123.54 (aromatic
C), 129.23 (aromatic C), 134.13 (vinyl C), 139.91 (aromatic C),
150.78 (vinyl C), 171.35 (C-O). Anal. Calcd for C16H19NO: C, 79.63;
H, 7.94; N, 5.80. Found: C, 79.59; H, 7.84; N, 5.62.
2-(3-Methylphenyl)-2,3,5,6,7,8-hexahydrocyclohepta[c]pyrrol-1(4H)-one (6d)
Solid; m.p. 81–83ꢀC (from hexane–CH2Cl2). 1H NMR (CDCl3) d
1.61–1.73 (m, 4H, 2CH2), 1.78–1.85 (m, 2H, CH2), 2.36 (s, 3H,
CH3), 2.45–2.47 (m, 4H, 2CH2), 4.17 (s, 2H, CH2-N), 6.91 (d, JHH = 7.8
Hz, 1H, CH), 7.49 (d, JHH = 7.8 Hz, 1H, CH), 7.59 (s, 1H, CH), 7.23
(t, JHH = 7.8 Hz, 1H, CH). 13C NMR (CDCl3) d 21.89 (CH3), 25.11
(CH2), 27.33 (CH2), 27.40 (CH2), 29.91 (CH2), 31.20 (CH2), 54.20
(CH2-N), 115.60 (aromatic C), 119.29 (aromatic C), 124.46
(aromatic C), 129.01 (aromatic C), 135.89 (vinyl C), 139.03
(aromatic C), 139.76 (aromatic C), 152.07 (vinyl C), 171.48 (C-O).
2-Phenyl-2,3,4,5,6,7,8,9,10,11,12,13-dodecahydro-1H-cyclododeca[c]pyrrol-1-
one (6h)
Solid; m.p. 99–101ꢀC (from hexane–CH2Cl2). 1H NMR (CDCl3) d
1.35–1.46 (m, 12H, 6CH2), 1.64–1.77 (m, 4H, 2CH2), 2.87 (t, JHH = 6.7
Hz, 2H, CH2), 2.47 (t, JHH = 7.3 Hz, 2H, CH2), 4.20 (s, 2H, CH2-N),
7.06–7.09 (m, 1H, CH), 7.33–7.37 (m, 2H, 2CH), 7.74–7.76 (m, 2H,
2CH). 13C NMR (CDCl3) d 21.25 (CH2), 21.95 (CH2), 22.86 (CH2),
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Appl. Organometal. Chem. (2012)