Md. W. Khan, A. F. G. M. Reza / Tetrahedron 61 (2005) 11204–11210
11207
13.63 (CH3), 19.03 (–CH2–), 30.47 (–CH2–), 37.75 (C-20),
57.58 (C-3), 64.97 (–O–CH2), 122.57, 123.89, 124.29,
125.95, 128.90, 129.30, 131.96, 132.30, 136.50, 144.28,
(Ar-C), 166.90 (CON) and 170.49 (–CO2–). Anal. Calcd for
C20H21NO3: C, 74.29; H, 6.54; N, 4.33. Found: C, 74.50; H,
6.65; N, 4.58.
(KBr) 1728.1, 1682.8, 1515 and 1370.3 cmK1; UV (EtOH):
lmax 247.80 (log 3 3.791) and 210.00 (log 3 3.642) nm; H
1
NMR (400 MHz, CDCl3): d 1.15 (t, 3H, JZ7.20, 14.40 Hz,
–CH3), 2.36 (s, 3H, Ar-CH3), 2.52 (dd, 1H, JZ8.40,
16.41 Hz, H-20), 2.92 (dd, 1H, JZ4.0, 16.0 Hz, H-20), 4.07
(dd, 2H, JZ2.0, 7.20 Hz, –OCH2), 5.30 (dd, 1H, JZ4.00,
8.4 Hz, H-3), 7.23 (d, 2H, JZ8.00 Hz, Ar-H), 7.41 (d, 2H,
JZ8.40 Hz, Ar-H), 7.49–7.59 (m, 3H, Ar-H), and 7.92 (d,
1H, JZ6.80 Hz, Ar-H). Anal. Calcd for C19H19NO3: C,
73.78; H, 6.19; N, 4.53. Found: C, 74.00; H, 6.35; N, 4.78.
5.2.2. N-p-methyl phenyl-3-butyl isoindolin-1-one acet-
ate 16. Light yellow liquid; IR: nmax (CCl4) 1734.9, 1707.8,
1550.7, 1515.0, 1467.7, 1376.1 and 1306.7 cmK1; UV
(EtOH): lmax 243.60 (log 3 3.828) and 208.40 (log 3 3.664)
1
nm; H NMR (400 MHz, CDCl3): d 0.89 (t, 3H, JZ7.33,
5.2.6. N-p-methoxy phenyl-3-ethyl isoindolin-1-one
acetate 20. Light yellow liquid; IR: nmax (CCl4) 1735.8,
1707.8, 1548.7, 1513.1 and 1248.8 cmK1; UV (EtOH): lmax
14.70 Hz, –CH3), 1.27 (m, 2H, –CH2), 1.47 (m, 2H, –CH2),
2.35 (s, 3H, Ar-CH3), 2.51 (dd, 1H, JZ8.45, 16.05 Hz,
H-20), 2.94 (dd, 1H, JZ4.09, 16.08 Hz, H-20), 4.03 (m, 2H,
–OCH2), 5.54 (dd, 1H, JZ4.07, 8.34 Hz, H-3), 7.24 (t, 1H,
JZ2.38, 8.05 Hz, Ar-H), 7.42 (d, 2H, JZ8.24 Hz, Ar-H),
7.49–7.58 (m, 4H, Ar-H), and 7.92 (d, 1H, JZ7.74 Hz,
Ar-H); 13C NMR (100 MHz, CDCl3): d 13.63 (CH3), 19.09
(–CH2–), 21.02 (Ar-CH3), 30.47 (–CH2–), 37.76 (C-20),
57.75 (C-3), 64.93 (O–CH2), 122.55, 124.07, 124.26,
124.22, 129.89, 132.07, 132.15, 133.82, 135.88, 144.31,
(Ar-C), 166.84 (CON) and 170.53 (–CO2–). Anal. Calcd for
C21H23NO3: C, 74.76; H, 6.87; N, 4.15. Found: C, 74.80; H,
6.65; N, 4.38.
1
243.80 (log 3 3.813) nm; H NMR (400 MHz, CDCl3): d
1.15 (t, 3H, JZ7.13, 14.28 Hz, CH3), 2.50 (dd, 1H, JZ8.20,
16.14 Hz, H-20), 2.88 (dd, 1H, JZ4.42, 16.04 Hz, H-20),
3.81 (s, 3H, OCH3), 4.07 (dd, 2H, JZ2.08, 7.17 Hz,
O–CH2), 5.4 (dd, 1H, JZ4.41, 8.08 Hz, H-3), 6.97 (d, 2H,
JZ8.96 Hz, Ar-H), 7.39–7.67 (m, 5H, Ar-H) and 7.91 (d,
1H, JZ8.18 Hz, Ar-H); 13C NMR (100 MHz, CDCl3): d
14.02 (–CH3), 37.80 (C-20), 55.50 (OCH3), 58.16 (C-3),
60.97 (–OCH2), 114.56, 122.54, 124.13, 126.06, 128.54,
128.80, 129.18, 132.06, 144.24, 157.89, (Ar-C), 166.92
(CON) and 170.35 (–CO2–). Anal. Calcd for C19H19NO4: C,
70.15; H, 5.89; N, 4.31. Found: C, 70.30; H, 5.65; N, 4.38.
5.2.3. N-p-methoxy phenyl-3-butyl isoindolin-1-one
acetate 17. Colourless solid; mp 166–167 8C; IR: nmax
(CCl4) 1734.9, 1706.9, 1549.7, 1514.0, 1249.8, 1217.0 and
1106.1 cmK1; UV (EtOH): lmax 234.60 (log 3 3.848) nm;
1H NMR (400 MHz, CDCl3): d 0.89 (m, 3H, CH3), 1.29 (m,
2H, –CH2), 1.51 (m, 2H, –CH2), 2.51 (dd, 1H, JZ8.22,
16.03 Hz, H-20), 2.89 (dd, 1H, JZ4.39, 16.05 Hz, H-20),
3.81 (s, 3H, ArOCH3), 4.03 (m, 2H, –OCH2), 5.47 (dd, 1H,
JZ4.35, 8.09 Hz, H-3), 6.97 (d, 2H, JZ8.90 Hz, Ar-H),
7.40–7.58 (m, 5H, Ar-H) and 7.91 (d, 1H, JZ7.20 Hz,
Ar-H); 13C NMR (100 MHz, CDCl3): d 13.62 (CH3), 19.02
(–CH2–), 30.45 (–CH3–), 37.79 (C-20), 55.50 (Ar-OCH3),
58.17 (C-3), 64.92 (O–CH2), 114.58, 122.53, 124.16,
126.05, 128.81, 129.18, 132.02, 132.08, 144.27, 157.90,
(Ar-C), 166.94 (CON) and 170.49 (–CO2–). Anal. Calcd for
C21H23NO4: C, 71.38; H, 6.56; N, 3.96. Found: C, 71.60; H,
6.65; N, 4.28.
5.2.7. N-p-methyl phenyl-3-methyl isoindolin-1-one
acetate 21. Light yellow liquid; IR: nmax (CCl4) 1739.7,
1707.8, 1550.7, 1515.9 and 1380.9 cmK1; UV (EtOH): lmax
245.80 (log 3 3.771) and 206.20 (log 3 3.631) nm; 1H NMR
(400 MHz, CDCl3): d 2.35 (s, 3H, Ar-CH3), 2.50 (dd, 1H,
JZ8.52, 16.06 Hz, H-20), 2.92 (dd, 1H, JZ4.1, 16.14 Hz,
H-20), 3.60 (s, 3H, OCH3), 5.52 (dd, 1H, JZ4.02, 8.4 Hz,
H-3), 7.22 (d, 2H, JZ8.9 Hz, Ar-H), 7.40 (d, 2H, JZ
8.16 Hz, Ar-H), 7.47–7.58 (m, 3H, Ar-H) and 7.91 (d, 1H,
JZ7.45 Hz, Ar-H). Anal. Calcd for C18H17NO3: C, 73.21;
H, 5.80; N, 4.74. Found: C, 73.50; H, 5.65; N, 4.88.
5.2.8. N-p-methoxy phenyl-3-methyl isoindolin-1-one
acetate 22. Light yellow liquid; IR: nmax (CCl4) 1740.6,
1707.8, 1550.7, 1514.0 cmK1; UV (EtOH): lmax 273.40
(log 3 3.674), 235.20 (log 3 3.742) and 206.00 (log 3 3.652)
nm; 1H NMR (400 MHz, CDCl3): d 2.50 (dd, 1H, JZ8.39,
16.09 Hz, H-20), 2.91 (dd, 1H, JZ4.46, 16.08 Hz, H-20),
3.60 (s, 3H, –OCH3), 3.81 (s, 3H, Ar-OCH3), 5.48 (dd, 1H,
JZ4.42, 8.31 Hz, H-3), 6.95–7.67 (m, 7H, Ar-H), and 7.90
(d, 1H, JZ7.40 Hz, Ar-H); 13C NMR (100 MHz, CDCl3): d
37.69 (C-20), 51.96 (C-3), 55.51 (Ar-O–C), 58.11 (O–CH2),
114.59, 122.50, 124.19, 126.04, 128.86, 129.16, 131.96,
132.12, 144.21, 157.90 (Ar-C), 166.89 (CON) and 170.88
(–CO2–). Anal. Calcd for C18H17NO4: C, 69.45; H, 5.50; N,
4.50. Found: C, 69.70; H, 5.65; N, 4.78.
5.2.4. N-p-chlorophenyl-3-butyl isoindolin-1-one acetate
18. Light yellow liquid; IR: nmax (CCl4) 1732.9, 1711.7,
1550.7, 1494.7, 1373.2, 1253.6, 1217.0 and 1173.6 cmK1
;
UV (EtOH): lmax 258.20 (log 3 3.854), 226.40 (log 3 3.696)
and 209.60 (log 3 3.684) nm; 1H NMR (400 MHz, CDCl3): d
0.91 (m, 3H, CH3), 1.29 (m, 2H, CH2), 1.51 (m, 2H, CH2),
2.51 (dd, 1H, JZ8.24, 16.10 Hz, H-20), 2.92 (dd, 1H, JZ
4.04, 16.10 Hz, H-20), 5.56 (dd, 1H, JZ3.98, 8.11 Hz, H-3),
7.41 (d, 2H, JZ8.72 Hz, Ar-H), 7.50–7.61 (m, 5H, Ar-H),
and 7.92 (d, 1H, JZ7.19 Hz, Ar-H); 13C NMR (100 MHz,
CDCl3): d 13.62 (CH3), 19.02 (CH2), 30.54 (CH2), 37.63
(C-20), 57.46 (C-3), 65.06 (–O–CH2), 122.57, 124.33,
124.85, 129.00, 129.39, 131.27, 131.63, 132.53, 135.10,
144.10 (Ar-C), 166.82 (CON) and 170.28 (–CO2–). Anal.
Calcd for C20H20NO3Cl: C, 67.14; H, 5.63; N, 3.92. Found:
C, 67.00; H, 5.75; N, 4.18.
5.2.9. N-p-phenyl benzamide 23. Colourless crystalline
solid; mp 134–135 8C; IR: nmax (KBr) 3273.3, 3013.6,
1
1653.8, 1641.3, 1618.2, 1598.9, 1598.9, 1488.0 cmK1; H
NMR (400 MHz, CDCl3): d 7.04–7.89 (m, 10H, Ar-H), 8.96
(br s, 1H, N–H); 13C NMR (100 MHz, CDCl3): d 119.90,
124.46, 127.16, 128.13, 128.89, 129.72, 130.21, 136.04,
137.86, 139.05 (Ar-C), 168.28 (C]O). Anal. Calcd for
C13H11NO: C, 79.16; H, 5.62; N, 7.10. Found: C, 79.28; H,
5.65; N, 7.38.
5.2.5. N-p-methyl phenyl-3-ethyl isoindolin-1-one acetate
19. Colourless crystalline solid; mp 97–98 8C; IR: nmax