4790
N. G. Kundu, M. W. Khan / Tetrahedron 56 (2000) 4777±4792
3-Methyl-N-p-anisyl isoindolin-1-one 80. Colourless
powder (EtOH); mp 88±908C; IR: nmax (KBr) 3000, 1680,
1640, 1515, 1470, 1440, 1390, 1300, 1230, 1180, 1040, 840,
C21H17NO: C, 84.25; H, 5.7; N, 4.65. Found: C, 84.1; H,
5.9; N, 4.65.
1
760 cm21; lmax/nm 281.6 (log e 3.98), 227.4 (4.24); H
3-Benzyl-N-p-anisyl isoindolin-1-one 86. Colourless small
needles (EtOH); mp 130±1338C; IR: nmax (KBr) 3000,
1680, 1580, 1510, 1395, 1300, 1220, 1020, 830, 760, 725,
700, 630 cm21; UV: lmax/nm 283.4 (log e 4.01), 224.2
(4.01); 1H NMR (200 MHz, CDCl3) d 2.79 (dd, 1H,
J8.4 Hz, J13.7 Hz, CH2), 3.37 (dd, 1H, J3.6,
13.7 Hz, CH2), 3.86 (s, 3H, OCH3), 5.35 (dd, 1H, J3.6,
8.4 Hz, C-3H) 6.88±7.49 (m, 12H), 7.81±7.86 (m, 1H,
Ar-H) Anal. Calcd for C22H19NO2: C, 80.2; H, 5.8; N,
4.25. Found: C, 80.35; H, 6.1; N, 3.9.
NMR (60 MHz, CDCl3) d 1.42 (d, 3H, CH3, J6 Hz),
3.85 (s, 3H, OCH3), 5.08 (q, 1H, J6 Hz, C-3H), 6.95±
8.00 (m, 8H, Ar-H). Anal. Calcd for C16H15NO2: C, 75.85;
H, 5.95; N, 5.5. Found: C, 75.75; H, 6.0; N, 5.25.
3-Methyl-N-m-chlorophenyl isoindolin-1-one 81. Colour-
less powder (EtOH); mp 108±1108C; IR: nmax (KBr) 3000,
1690, 1600, 1485, 1360, 1150, 860, 780, 760, 700, 690 cm21;
UV: lmax/nm 274.8 (log e 4.13); 1H NMR (60 MHz, CDCl3)
d 1.50 (d, 3H, J6 Hz, CH3), 5.20 (q, 1H, J6 Hz, C-3H),
7.20±8.05 (m, 8H, Ar-H). Anal. Calcd for C15H12ClNO: C,
69.9; H, 4.7; N, 5.4. Found: C, 70.2; H, 5.0; N, 5.55.
3-Benzyl-N-m-chlorophenyl isoindolinone 87. Small
colourless needles (EtOH); mp 108±1098C; IR: nmax
(KBr) 3000, 1680, 1600, 1590, 1570, 1380, 1260, 1180,
1
3-(20-Hydroxy-20-methylpropyl)-N-p-tolyl isoindolin-1-
one 82. Light yellow powder (EtOH); mp 160±1638C; IR:
800, 750, 690 cm21; UV: lmax/nm 276.2 (log e 4.09), H
NMR (60 MHz, CCl4) d 2.73 (dd, 1H, J8, 14 Hz, CH2),
3.29 (dd, 1H, J4, 14 Hz, CH2), 5.26 (dd, 1H, J4, 8 Hz,
C-3H), 6.82±7.75 (m, 13H, Ar-H). Anal. Calcd for
C21H16ClNO: C, 75.55; H, 4.8; N, 4.2. Found: C, 75.2; H,
4.8; N, 4.3.
n
max (KBr) 3480, 2980, 1690, 1610, 1510, 1470, 1400, 1150,
810 cm21; UV: lmax/nm 273.4 (log e 4.00); 225.8 (4.15); 1H
NMR (60 MHz, CDCl31CCl4) d 1.23 (s, 6H, 2£CH3), 1.97
(d, 2H, J4 Hz, CH2), 2.39 (s, 3H, CH3), 5.33 (t, J4 Hz,
1H, C-3H), 7.16±8.03 (m, 8H, Ar-H). Anal. Calcd for
C19H21NO2: C, 77.25; H, 7.15; N, 4.75. Found: C, 77.6; H,
7.3; N, 4.7.
3-p-Methoxybenzyl-N-benzyl
isoindolin-1-one
88.
Colourless small needles (EtOH); mp 112±1148C; IR:
nmax (KBr) 3000, 1670, 1600, 1420, 1290, 1160, 1750,
740, 700 cm21; UV: lmax/nm 283.3 (log e 4.00), 225.1
3-Benzyl isoindolin-1-one 83. Colourless small needles
(EtOH); mp 126±1288C; IR: nmax (KBr) 3200, 3000,
1
(4.02); H NMR (300 MHz, CDCl3) 2.78 (dd, 1H, J7.8,
1680, 1610, 1510, 1470, 1395, 1150, 830, 760, 700 cm21
;
13.8 Hz, CH2), 3.32 (dd, 1H, J4.8 Hz, 13.8 Hz, CH2), 3.77
(s, 3H, OCH3), 4.18 (d, 1H, J15 Hz, N-CH2), 4.53 (dd, 1H,
J4.8, 7.8 Hz, C-3H), 5.47 (d, 1H, J15 Hz, N-CH2), 6.81
(d, 2H, J8.7 Hz, Ar-H), 6.87±6.93 (m, 3H), 7.24±7.42 (m,
7H), 7.83±7.85 (m, 1H, Ar-H); 13C NMR (85.5 MHz,
CDCl3) d 37.73, 44.61, 55.63, 60.08, 114.28, 123.41,
124.18, 128.22, 128.32, 128.96, 129.21, 130.84, 131.49,
132.43, 137.50, 145.56, 158.95, 168.87; DEPT: 37.42,
44.32, 55.34, 59.79, 113.97, 123.13, 123.89, 127.80,
128.29, 128.93, 130.56, 131.21. Anal. Calcd for C23H21NO:
C, 80.45; H, 6.15; N, 4.1. Found: C, 80.7; H, 5.9; N,
4.35.
1
UV: lmax/nm 282.5 (log e 4.01), 225.3 (4.11); H NMR
(300 MHz, CDCl3) d 2.88 (dd, 1H, J9, 12 Hz, CH2),
3.16 (dd, 1H, J6, 12 Hz, CH2), 4.80 (dd, 1H, J6, 9 Hz,
C-3H), 7.18±7.31 (m, 6H), 7.42±7.53 (m, 2H), 7.82 (d, 1H,
J9 Hz, Ar-H), 10.35 (s, 1H, NH); 13C NMR (75.5 MHz,
CDCl3) d 41.63, 58.47, 123.20, 124.25, 127.51, 128.74,
129.17, 129.74, 132.11, 132.40, 137.26, 147.26, 171.10.
Anal. Calcd for C15H13NO: C, 80.7; H, 5.85; N, 6.25.
Found: C, 80.35; H, 5.8; N, 6.35.
N,3-Dibenzyl isoindolin-1-one 84. Colourless powder
(EtOH); mp 83±848C; IR: nmax (KBr) 3000, 1670, 1600,
1420, 1290, 1160, 750, 740, 700 cm21; UV: lmax/nm
281.7 (log e 4.02), 224.3 (4.15); 1H NMR (300 MHz,
CDCl3) d 2.84 (dd, 1H, J7.8, 13.8 Hz, CH2), 3.38 (dd,
1H, J4.8, 13.8 Hz, CH2), 4.23 (d, 1H, J15 Hz, N-CH2),
4.58 (dd, 1H, J4.8, 7.8 Hz, C-3H), 5.47 (d, 1H, J15 Hz,
N-CH2), 6.88 (d, 1H, J6.6 Hz), 7.86 (d, 1H, J2.1 Hz,
Ar-H); 13C NMR (300 MHz, CDCl3) d.38.31, 44.17,
59.52, 122.87, 123.72, 126.92, 127.57, 128.07, 128.64,
128.70, 129.59, 131.02, 131.90, 135.97, 136.97, 145.01,
168.36, DEPT: 38.51, 44.37, 59.72, 123.07, 123.93,
127.14, 127.79, 128.28, 128.69, 128.92, 129.59, 131.24.
Anal. Calcd for C22H19NO: C, 84.3; H, 6.1; N, 4.45.
Found: C, 84.25; H, 6.35; N, 4.15.
Synthesis of 3-(50-uracilyl)methylidene-N-m-chloro-
phenyl isoindolinone 89. (Z)-3-(20,40-Dimethoxypyrimi-
din-50-yl)methylidene-N-m-chlorophenyl isoindolin-1-one
58 (110 mg, 0.27 mmol) was re¯uxed in 6 N HCl (4 mL)
at 1008C for 4 h. The reaction mixture was cooled and
®ltered. The residue obtained was washed with H2O
(3£10 mL) and dried at room temperature. Crystallisation
from methanol and few drops of DMF afforded a colourless
powder (methanol-DMF) in quantitative yield, mp .2508C
1
decomp; IR: nmax (KBr) 3210, 3040, 1720, 1680 cm21; H
NMR (60 MHz, CDCl31DMSO-d6) d 6.50 (s, 1H, vCH±),
6.63 (s, 1H, vCH), 7.28±8.10 (m, 8H, Ar-H). Anal. Calcd
for C19H12ClN3O3: C, 62.4; H, 33; N, 11.5. Found: 62.02; H,
3.35; N, 11.1.
3-Benzyl-N-phenyl isoindolin-1-one 85. Colourless small
needles (EtOH); mp 122±1238C; IR: nmax (KBr) 3000,
1680, 1600, 1500, 1390, 1150, 700, 7220, 760 cm21; UV:
l
max/nm 281.3 (log e 4.00), 224.6 (4.02); 1H NMR
Acknowledgements
(60 MHz, CDCl3) d 2.76 (dd, 1H, J8, 14 Hz, CH2),
3.28 (dd, 1H, J4, 14 Hz, CH2), 5.33 (dd, 1H, J4, 8 Hz,
C-3H), 6.68±7.85 (m, 14H, Ar-H). Anal. Calcd for
We gratefully acknowledge CSIR, Government of India
(Project No. 01(1385)/95-EMR-II) for ®nancial support.