PAPER
3,3-Disubstituted Isoindolin-1-ones
2495
Anal. Calcd for C21H16INO: C, 59.31; H, 3.79; N, 3.29. Found: C,
59.26; H, 3.90; N, 3.02.
Anal. Calcd for C17H15ClINO2: C, 47.74; H, 3.54; N, 3.28. Found:
C, 47.62; H, 3.51; N, 3.26.
2-(4-Chlorophenyl)-3-iodomethyl-3-phenylisoindolin-1-one
(3b)
3-Methylisoindolin-1-one Derivatives 4; 3-Methyl-2,3-diphe-
nylisoindolin-1-one (4a);3a Typical Procedure
White solid; mp 41–46 °C (hexane–Et2O).
IR (neat): 1686 cm–1.
1H NMR (500 MHz): d = 3.97 (1 H, d, J = 11.5 Hz), 4.05 (1 H, d,
J = 11.5 Hz), 7.32–7.41 (7 H, m), 7.47 (2 H, dd, J = 7.8, 1.8 Hz),
7.51 (1 H, d, J = 7.3 Hz), 7.55 (1 H, td, J = 7.3, 0.9 Hz), 7.62 (1 H,
td, J = 7.3, 0.9 Hz), 7.96 (1 H, d, J = 7.3 Hz).
A solution of 3a (0.33 g, 0.78 mmol) and Bu3SnH (0.42 g, 1.6
mmol) in benzene (4 mL) was stirred for 10 h at r.t. After evapora-
tion of benzene, the residue was purified by column chromatogra-
phy on silica gel to give 4a; yield: 0.18 g (75%); white solid; mp
175–176 °C (hexane–Et2O) (Lit.3a mp 174–176 °C).
IR (KBr): 1693 cm–1.
1H NMR (500 MHz): d = 2.02 (3 H, s), 7.11 (1 H, tt, J = 7.3, 1.4
Hz), 7.28 (1 H, tt, J = 7.3, 1.4 Hz), 7.32–7.36 (5 H, m), 7.41 (2 H,
dd, J = 8.7, 1.4 Hz), 7.45 (2 H, dd, J = 8.7, 1.4 Hz), 7.48 (1 H, td,
J = 7.3, 0.9 Hz), 7.53 (1 H, tt, J = 7.3, 1.4 Hz), 7.97 (1 H, dd,
J = 7.3, 1.4 Hz).
MS: m/z (%) = 459 (79, [M+]), 318 (100).
Anal. Calcd for C21H15ClINO: C, 54.87; H, 3.29; N, 3.05. Found: C,
54.64; H, 3.26; N, 3.13.
2-Butyl-3-iodomethyl-3-phenylisoindolin-1-one (3c)
Colorless viscous oil; Rf 0.44 (EtOAc–hexane, 1:3).
MS: m/z (%) = 299 (100, [M+]).
Anal. Calcd for C21H17NO: C, 84.25; H, 5.72; N, 4.68. Found: C,
84.25; H, 5.77; N, 4.60.
IR (neat): 1699 cm–1.
1H NMR (500 MHz): d = 0.99 (3 H, t, J = 7.3 Hz), 1.49 (2 H, sext,
J = 7.3 Hz), 1.70–1.78 (2 H, m), 3.59–3.77 (2 H, m), 3.91 (1 H, d,
J = 11.0 Hz), 4.02 (1 H, d, J = 11.0 Hz), 7.33 (1 H, tt, J = 7.3, 1.4
Hz), 7.38 (2 H, t, J = 7.3 Hz), 7.43–7.48 (3 H, m), 7.49–7.54 (2 H,
m), 7.83 (1 H, dd, J = 7.8, 0.9 Hz).
2-(4-Chlorophenyl)-3-methyl-2-phenylisoindolin-1-one (4b)
White solid; mp 88–89 °C (hexane–Et2O).
IR (KBr): 1682 cm–1.
1H NMR (500 MHz): d = 2.02 (3 H, s), 7.28–7.31 (3 H, m), 7.32–
7.37 (5 H, m), 7.41 (2 H, dd, J = 8.2, 1.4 Hz), 7.49 (1 H, ddd,
J = 7.8, 7.3, 0.9 Hz), 7.54 (1 H, ddd, J = 7.8, 7.3, 1.4 Hz), 7.95 (1 H,
dd, J = 7.8, 0.9 Hz).
MS: m/z (%) = 405 (48, [M+]), 207 (100).
Anal. Calcd for C19H20INO: C, 56.31; H, 4.97; N, 3.46. Found: C,
56.28; H, 4.97; N, 3.56.
MS: m/z (%) = 333 (100, [M+]).
2-tert-Butyl-3-iodomethyl-3-phenylisoindolin-1-one (3d)
Pale-yellow oil; Rf 0.54 (EtOAc–hexane, 1:2).
IR (neat): 1699 cm–1.
Anal. Calcd for C21H16ClNO: C, 75.56; H, 4.83; N, 4.20. Found: C,
75.36; H, 5.00; N, 4.12.
1H NMR (400 MHz): d = 1.51 (9 H, s), 3.88 (1 H, d, J = 11.0 Hz),
4.04 (1 H, d, J = 11.0 Hz), 7.31 (1 H, tt, J = 7.3, 1.1 Hz), 7.35–7.41
(3 H, m), 7.42 (1 H, ddd, J = 7.6, 7.3, 1.3 Hz), 7.48 (1 H, ddd,
J = 7.6, 7.3, 1.3 Hz), 7.52 (2 H, dd, J = 6.9, 1.1 Hz), 7.79 (1 H, d,
J = 7.6 Hz).
2-Butyl-3-methyl-3-phenylisoindolin-1-one (4c)
Colorless oil; Rf 0.38 (THF–hexane, 1:3).
IR (neat): 1693 cm–1.
1H NMR (500 MHz): d = 0.96 (3 H, t, J = 7.3 Hz), 1.44 (2 H, sext,
J = 7.3 Hz), 1.66–1.73 (2 H, m), 1.99 (3 H, s), 3.59 (2 H, t, J = 6.9
Hz), 7.29 (2 H, d, J = 7.3 Hz), 7.34 (2 H, t, J = 7.3 Hz), 7.39 (1 H,
td, J = 7.3, 0.9 Hz), 7.41–7.47 (3 H, m), 7.83 (1 H, d, J = 7.3 Hz).
MS: m/z (%) = 406 (0.42), 405 (0.10, [M+]), 391 (100).
Anal. Calcd for C19H20INO: C, 56.31; H, 4.97; N, 3.46. Found: C,
56.55; H, 4.87; N, 3.56.
MS: m/z (%) = 279 (65, [M+]), 208 (100).
3-Iodomethyl-3-methyl-2-phenylisoindolin-1-one (3e)
White solid; mp 102–104 °C (hexane–Et2O).
Anal. Calcd for C19H21NO: C, 81.68; H, 7.58; N, 5.01. Found: C,
81.64; H, 7.59; N, 5.01.
IR (KBr): 1701 cm–1.
2-tert-Butyl-3-methyl-3-phenylisoindolin-1-one (4d)
Pale-yellow oil; Rf 0.51(THF–hexane, 1:5).
IR (neat): 1699 cm–1.
1H NMR (500 MHz): d = 1.45 (9 H, s), 1.98 (3 H, s), 7.24 (1 H, d,
J = 7.8 Hz), 7.27 (1 H, tt, J = 7.3, 1.4 Hz), 7.34 (2 H, dd, J = 7.8, 7.3
Hz), 7.36 (1 H, ddd, J = 7.8, 7.3, 0.9 Hz), 7.41 (1 H, ddd, J = 7.8,
7.3, 1.4 Hz), 7.43 (2 H, dd, J = 7.8, 1.4 Hz), 7.79 (1 H, d, J = 7.8
Hz).
1H NMR (400 MHz): d = 1.82 (3 H, s), 3.60 (1 H, d, J = 10.5 Hz),
3.68 (1 H, d, J = 10.5 Hz), 7.11–7.14 (1 H, m), 7.34–7.39 (5 H, m),
7.54 (1 H, t, J = 7.3 Hz), 7.59 (1 H, t, J = 7.3 Hz), 7.96 (1 H, d,
J = 7.3 Hz).
MS: m/z (%) = 363 (100, [M+]).
Anal. Calcd for C16H14INO: C, 52.91; H, 3.89; N, 3.86. Found: C,
52.87; H, 4.13; N, 3.86.
MS: m/z (%) = 279 (0.4, [M+]), 264 (54), 207 (100).
2-(4-Chlorophenyl)-3-iodomethyl-5-methoxy-3-methylisoindo-
lin-1-one (3f)
Pale-yellow solid; mp 121–123 °C (pentane–Et2O).
Anal. Calcd for C19H21NO: C, 81.68; H, 7.58; N, 5.01. Found: C,
81.53; H, 7.82; N, 5.13.
IR (KBr): 1697, 1611 cm–1.
3,3-Dimethyl-2-phenylisoindolin-1-one (4e)
Pale-yellow oil; Rf 0.28 (EtOAc–hexane, 1:9).
IR (neat): 1681 cm–1.
1H NMR (500 MHz): d = 1.64 (6 H, s), 7.08–7.12 (1 H, m), 7.30–
7.36 (5 H, m), 7.47 (1 H, t, J = 7.3 Hz), 7.54 (1 H, t, J = 7.3 Hz),
7.93 (1 H, d, J = 7.3 Hz).
1H NMR (400 MHz): d = 1.80 (3 H, s), 3.55 (1H, d, J = 11.0 Hz),
3.65 (1 H, d, J = 11.0 Hz), 3.91 (3 H, s), 6.80 (1 H, d, J = 2.2 Hz),
7.05 (1 H, dd, J = 8.4, 2.2 Hz), 7.29 (4 H, s), 7.83 (1 H, d, J = 8.4
Hz).
MS: m/z (%) = 427 (100, [M+]).
Synthesis 2006, No. 15, 2493–2496 © Thieme Stuttgart · New York