Pan et al.
FULL PAPER
J=7.5 Hz, 1H), 6.70-6.99 (m, 9H), 2.05 (s, 6H); 13C
NMR (100 MHz, CDCl3) δ: 167.7, 139.0, 136.4, 134.9,
133.9, 133.2, 132.6, 129.6, 128.8, 128.5, 128.4, 127.8,
126.7, 124.2, 120.1, 108.1, 18.6; HRMS calcd for
C23H19NO (M+) 325.1467, found 325.1468.
Chem. Lett. 2002, 12, 3557; (h) Hulin, B.; Parker, J. C.; Piotrowski, D.
W. US 2005234065, 2005; (i) Toyooka, K.; Kanamitsu, N.; Yoshimura,
M.; Kuriyama, H.; Tamura, T. WO 2004048332, 2004.
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H.; Takahashi, Y.; Masuma, R. J. Antibiot. 1977, 30, 275; (b) Omura, S.;
Iwai, Y.; Hirano, A. JP 53073501, 1978 [Chem. Abstr. 1978, 89,
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397; (d) Oka, S.; Kodama, M.; Takeda, H.; Tomizuka, N.; Suzuki, H.
Agric. Biol. Chem. 1986, 50, 2723.
(Z)-3-(4-Ethylbenzylidene)-2-phenylisoindolin-1-
1
one (5o) White solid, m.p. 130-132 ℃; H NMR
(400 MHz, CDCl3) δ: 7.95 (d, J=7.4 Hz, 1H), 7.85 (d,
J=7.6 Hz, 1H), 7.67 (t, J=7.6 Hz, 1H), 7.54 (t, J=7.4
Hz, 1H), 7.07 (s, 5H), 6.82 (s, 1H), 6.72-6.78 (m, 4H),
2.45-2.50 (m, 2H), 1.11 (t, J=7.6 Hz, 3H); 13C NMR
(100 MHz, CDCl3) δ: 168.2, 143.9, 138.1, 136.3, 134.2,
132.9, 131.6, 129.7, 129.3, 128.9, 127.6, 127.3, 126.6,
126.2, 124.1, 119.2, 108.0, 28.8, 16.7; HRMS calcd for
C23H19NO (M+) 325.1467, found 325.1466.
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2004, 13, 2347; (c) Bousquet, T.; Fleury, J. F.; Daïch, A.; Netchitaïlo, P.
Tetrahedron 2006, 62, 706.
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204; (b) Ang, W. S.; Halton, B. B. Aust. J. Chem. 1971, 24, 851.
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1969, 34, 919; (b) Parham, W. E.; Jones, L. D. J. Org. Chem. 1976, 41,
1188; (c) Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron 1997,
53, 10313; (d) Couture, A.; Deniau, E.; Ionescu, D.; Grandclaudon, P.
Tetrahedron Lett. 1998, 39, 2319.
(Z)-3-Benzylidene-6-methyl-2-phenylisoindolin-1-
1
one (5q) White solid, m.p. 179-180 ℃; H NMR
(300 MHz, DMSO-d6) δ: 8.01 (d, J=7.6 Hz, 1H), 7.63
(s, 1H), 7.57 (d, J=7.2 Hz, 1H), 7.08 (s, 5H), 7.00 (s,
1H), 6.77-6.94 (m, 5H), 2.47 (s, 3H); 13C NMR (75
MHz, DMSO-d6) δ: 167.85, 140.15, 136.84, 136.72,
134.50, 134.31, 129.73, 128.63, 127.94, 127.71, 127.20,
127.00, 123.76, 120.79, 107.96, 21.71; HRMS calcd for
C22H17NO (M+) 311.1310, found 311.1215.
[7] Rowe, F. M.; McFadyen, W. T.; Peters, A. T. J. Chem. Soc. 1947, 468.
[8] (a) Pojer, P. M.; Ritchie, E.; Taylor, W. C. Aust. J. Chem. 1968, 21, 1375;
(b) Camilleri, P.; Cassola, A. J. Chem. Soc., Chem. Commun. 1978, 807;
(c) Rowe, R. K.; Shelton, B. R. J. Org. Chem. 1990, 55, 4603; (d) Ta-
keuchi, H.; Eguchi, S. J. Chem. Soc., Perkin Trans. 1989, 2149.
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Tetrahedron Lett. 1997, 38, 521; (b) Gutierrez, A. J.; Shea, K. J.;
Svoboda, J. J. J. Org. Chem. 1989, 54, 4335.
(Z)-3-Benzylidene-5-chloro-2-phenylisoindolin-1-
1
one (5r) Pale green solid, m.p. 177-178 ℃; H
[10] Guillaumel, J.; Boccara, N.; Demersemann, P.; Royer, R. J. Chem. Soc.,
Chem. Commun. 1988, 1604.
NMR (400 MHz, CDCl3) δ: 7.88 (d, J=8.1 Hz, 1H),
7.82 (s, 1H), 7.51 (dd, J=8.1, 1.2 Hz, 1H), 7.14-7.04
(m, 5H), 7.00 (t, J=7.2 Hz, 1H), 6.93 (t, J=7.5 Hz,
2H), 6.85 (d, J=7.5 Hz, 2H), 6.80 (s, 1H); 13C NMR
(101 MHz, CDCl3) δ: 165.42, 138.59, 137.35, 134.03,
131.66, 131.52, 128.04, 127.57, 126.71, 125.74, 125.55,
125.36, 124.55, 123.59, 118.26, 107.30; HRMS calcd
for C21H14ClNO (M+) 331.1764, found 331.1665.
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Weidner-Wells, M. A.; Oda, K.; Mazzocchi, P. H. Tetrahedron 1997, 53,
3475.
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Chem. 1963, 28, 498; (b) Milewska, M. J.; Bytner, T.; Polonski, T. Syn-
thesis 1996, 1485.
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Dominh, T.; Johnson, A. L.; Jones, J. E.; Senise, P. P. Jr. J. Org. Chem.
1977, 42, 4217; (c) Grigg, R.; Gunaratne, H. Q. N.; Sridharan, V. J.
Chem. Soc., Chem. Commun. 1985, 1183; (d) Takahashi, I.; Kawakami,
T.; Hirano, E.; Yokota, H.; Kitajima, H. Synlett 1996, 353; (e) Takahashi,
I.; Hatanaka, M. Heterocycles 1997, 45, 2475.
(Z)-5-Benzylidene-6-phenyl-5,6-dihydropyrrolo[3,
4-b]pyridin-7-one (5s) White solid, m.p. 130-132
1
℃; H NMR (300 MHz, CDCl3) δ: 8.86 (d, J=4.7 Hz,
1H), 8.22 (d, J=7.7 Hz, 1H), 7.46 (dd, J=8.4, 5.7 Hz,
2H), 7.13 (s, 5H), 6.94 (dt, J=17.5, 7.2 Hz, 5H); 13C
NMR (75 MHz, CDCl3) δ: 165.93, 156.99, 153.95,
135.55, 133.41, 133.24, 132.23, 129.61, 128.61, 127.51,
127.33, 124.16, 121.68, 110.41; HRMS calcd for
C20H14N2O (M+) 298.1106, found 298.1013.
[14] Wilkinson, G.; Stone, F. G. A.; Abel, E. W. Comprehensive Organometal-
lic Chemistry, 1st ed., Pergamon, Oxford, 1982, p. 1.
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Acknowledgement
This work was supported by the Team Innovation
Project of Suzhou University.
[18] Sarkar, S.; Dutta, S.; Dey, R.; Naskar, S. Tetrahedron Lett. 2012, 53,
6789.
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(Pan, B.; Fan, Y.)
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