M. Pal et al. / Tetrahedron 60 (2004) 3987–3997
3995
4.4.1. Parallel synthesis of V. Parallel synthesis was carried
out using eight reaction flasks simultaneously each con-
taining the appropriate amide III and powdered K2CO3. To
a solution of phenacyl amide III (0.8 mmol) in 1:1 EtOH–
H2O (20 mL) was added powder K2CO3 (1.2 mmol) and the
mixture was stirred at 25 8C for 10–15 min. The mixture
was then heated to 75–80 8C for 2.5 h. After completion of
the reaction each mixture was cooled and poured into water
(25 mL) with stirring. In all cases products appeared as
solid, and the filtered solid, after washing with cold hexane
(2£5 mL), was analytically pure.
(2C), 129.36 (2C), 128.75 (2C), 128.45 (2C), 128.29, 120.32
(2C), 115.54, 52.11 (CH2); HPLC: 99%, INERTSIL ODS
3V (150£4.6 mm), 0.01 M KH2PO4/CH3CN 0/40, 10/40,
30/85, 40/85, 45/40, 50/40, 1.0 mL/min, 240 nm, reten-
tion time 32.73 min; found C, 62.47; H, 3.59; N, 3.01;
C22H15BrNOCl requires C, 62.21; H, 3.56; N, 3.30%.
4.4.6. 4-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-phe-
nyl-2,5-dihydro-1H-2-azolone (Ve). White solid; yield
89%; DSC 154.86 8C; dH (200 MHz, CDCl3) 7.70 (d, J¼
8.9 Hz, 2H), 7.43–7.28 (m, 9H), 6.94 (d, J¼8.9 Hz, 2H),
4.69 (s, 2H, CH2), 3.82 (s, 3H, OCH3); nmax (KBr) 1681,
1594 cm21; m/z (CI, i-Butane) 376 (100, MHþ); 13C NMR
(50 MHz, DMSO-d6): 168.06 (CvO), 155.72, 146.64,
134.04, 132.43, 131.69, 131.35, 129.47 (2C), 129.37 (2C),
128.73 (2C), 128.40 (2C), 128.17 (2C), 120.53 (2C), 114.05
(2C), 55.18 (OCH3), 52.51 (CH2); HPLC: 98%, INERTSIL
ODS 3V (250£4.6 mm), 0.01 M KH2PO4/CH3CN 0/40. 10/
40, 30/85, 40/85, 45/40, 50/40, 1.0 mL/min, 240 nm,
retention time 28.38 min; found C, 73.54; H, 4.99; N,
3.61; C23H18NO2Cl requires C, 73.50; H, 4.83; N, 3.73%.
4.4.2. 1-(4-Chlorophenyl)-3,4-diphenyl-2,5-dihydro-1H-
2-azolone (Va). Off white solid; yield 82%; DSC 178.27 8C;
dH (200 MHz, CDCl3) 7.80 (d, J¼8.8 Hz, 2H), 7.40–7.35
(m, 12H), 4.74 (s, 2H, CH2); nmax (KBr) 1677, 1595 cm21
;
m/z (CI, i-Butane) 346 (100, MHþ); 13C NMR (50 MHz,
DMSO-d6): 168.76 (CvO), 148.59, 138.14, 132.20, 131.72,
129.55, 129.36 (2C), 128.74 (2C), 128.61 (2C), 128.34 (2C),
128.10 (2C), 127.71 (2C), 127.36, 120.03 (2C), 52.25
(CH2); HPLC: 95%, HICHROM RPB (250£4.6 mm),
0.01 M KH2PO4/CH3CN 0/40, 5/40, 20/80, 30/80, 35/40,
40/40, 1.0 mL/min, 242 nm, retention time 23.91 min;
found C, 76.22; H, 4.69; N, 3.87; C22H16NOCl requires C,
76.41; H, 4.66; N, 4.05%.
4.4.7. 1-(4-Bromophenyl)-4-(4-methylphenyl)-3-phenyl-
2,5-dihydro-1H-2-azolone (Vf). Yellow solid; yield 97%;
DSC 167.72 8C; dH (200 MHz, CDCl3) 7.76 (d, J¼8.8 Hz,
2H), 7.50 (d, J¼8.8 Hz, 2H), 7.40–7.22 (m, 7H), 7.12 (d,
J¼7.8 Hz, 2H), 4.71 (s, 2H, CH2), 2.35 (s, 3H, CH3); nmax
(KBr) 1680, 1598 cm21; m/z (CI, i-Butane) 404 (100,
MHþ), 406 (100, Mþ2); 13C NMR (50 MHz, DMSO-d6):
168.91 (CvO), 148.56, 139.49, 138.62, 131.93, 131.66
(2C), 131.03, 129.40 (2C), 129.26, 129.22 (2C), 128.39
(2C), 128.06, 127.64 (2C), 120.34 (2C), 115.35, 52.10
(CH2), 20.86 (CH3); HPLC: 99%, INERTSIL ODS 3V
(150£4.6 mm), 0.01 M KH2PO4/CH3CN 0/75, 10/75,
15/80, 25/80, 30/75, 35/75, 1.0 mL/min, 210 nm, retention
time 13.30 min; found C, 68.54; H, 4.39; N, 3.31;
C23H18NOBr requires C, 68.33; H, 4.49; N, 3.46%.
4.4.3. 1-(4-Bromophenyl)-3,4-diphenyl-2,5-dihydro-1H-
2-azolone (Vb). Light yellow solid; yield 87%; DSC
173.31 8C; dH (200 MHz, CDCl3) 7.76 (d, J¼9.1 Hz, 2H),
7.50 (d, J¼9.1 Hz, 2H), 7.41–7.34 (m, 10H), 4.73 (s, 2H,
CH2); nmax (KBr) 1678, 1588 cm21; m/z (CI, i-Butane) 392
(100, Mþ2), 390 (100, Mþ); 13C NMR (50 MHz, DMSO-
d6): 168.78 (CvO), 148.60, 138.56, 132.20, 131.72, 131.65,
129.56 (2C), 129.37 (2C), 128.62 (2C), 128.35 (2C), 128.11
(2C), 127.72 (2C), 120.38 (2C), 115.42, 52.20 (CH2);
HPLC: 99%, INERTSIL ODS 3V (150£4.6 mm), 0.01 M
KH2PO4/CH3CN 0/40, 10/40, 30/85, 40/85, 45/40, 50/40,
1.0 mL/min, 240 nm, retention time 30.06 min; found C,
67.50; H, 4.34; N, 3.71; C22H16NOBr requires C, 67.71; H,
4.13; N, 3.59%.
4.4.8. 1-(4-Chlorophenyl)-4-(4-fluorophenyl)-3-phenyl-
2,5-dihydro-1H-2-azolone (Vg). Light yellow solid; yield
94%; DSC 163.04 8C; dH (200 MHz, CDCl3) 7.80 (d, J¼
9.0 Hz, 2H), 7.39–7.30 (m, 9H), 7.01 (t, J¼8.5 Hz, 2H),
4.71 (s, 2H, CH2); nmax (KBr) 1668, 1603 cm21; m/z (CI,
i-Butane) 364 (100, MHþ); 13C NMR (50 MHz, DMSO-d6):
168.64 (CvO), 165.01, 160.08, 147.34, 138.07, 131.62,
131.54, 130.09, 129.92, 129.34, 129.02, 128.70, 128.60,
128.39 (2C), 128.15, 127.37, 119.86 (2C), 115.88, 115.45,
52.21 (CH2); HPLC: 99%, INERTSIL ODS 3V
(250£4.6 mm), 0.01 M KH2PO4/CH3CN 0/75, 10/75, 15/
80, 25/80, 30/75, 35/75, 1.0 mL/min, 210 nm, retention time
9.04 min; found C, 72.84; H, 3.98; N, 3.79; C22H15NOClF
requires C, 72.63; H, 4.16; N, 3.85%.
4.4.4. 1,4-Di(4-chlorophenyl)-3-phenyl-2,5-dihydro-1H-
2-azolone (Vc). Yellow solid; yield 85%; DSC 190.90 8C;
dH (200 MHz, CDCl3) 7.79 (d, J¼9.0 Hz, 2H), 7.38–7.25
(m, 11H), 4.70 (s, 2H, CH2); nmax (KBr) 1668, 1594 cm21
;
m/z (CI, i-Butane) 380 (100, MHþ); 13C NMR (50 MHz,
DMSO-d6): 168.58 (CvO), 147.37, 138.10, 134.25, 132.27,
131.43, 131.11, 129.54 (2C), 129.35 (2C), 128.78 (4C),
128.49 (2C), 128.30, 127.48, 120.09 (2C), 52.21 (CH2);
HPLC: 99%, INERTSIL ODS 3V (150£4.6 mm), 0.01 M
KH2PO4/CH3CN 0/70, 5/70, 15/85, 25/85, 30/70, 35/70,
1.0 mL/min, 240 nm, retention time 13.79 min; found C,
69.81; H, 3.99; N, 3.41; C22H15NOCl2 requires C, 69.49; H,
3.98; N, 3.68%.
4.4.9. 1-(4-Methoxyphenyl)-3,4-diphenyl-2,5-dihydro-
1H-2-azolone (Vh). White solid; yield 85%; DSC
139.94 8C; dH (200 MHz, CDCl3) 7.73 (d, J¼8.9 Hz, 2H),
7.42–7.33 (m, 10H), 6.94 (d, J¼8.9 Hz, 2H), 4.73 (s, 2H,
CH2), 3.82 (s, 3H, OMe); nmax (KBr) 1689 cm21; m/z (CI,
i-Butane) 342 (80, MHþ), 341 (100); 13C NMR (50 MHz,
DMSO-d6): 168.0 (CvO), 156.28, 146.57, 132.77, 132.61,
131.63, 129.59 (2C), 129.34 (2C), 128.72 (2C), 128.38 (2C),
128.18 (2C), 127.62 (2C), 120.64 (2C), 114.28, 55.44
(OCH3), 53.0 (CH2); HPLC: 97%, INERTSIL ODS 3V
4.4.5. 1-(4-Bromophenyl)-4-(4-chlorophenyl)-3-phenyl-
2,5-dihydro-1H-2-azolone (Vd). Off white solid; yield
85%; DSC 170.45 8C; dH (200 MHz, CDCl3) 7.75 (d, J¼
7.3 Hz, 2H), 7.50 (d, J¼7.1 Hz, 2H), 7.48–7.25 (m, 9H),
4.70 (s, 2H, CH2); nmax (KBr) 1669, 1590 cm21; m/z (CI,
i-Butane) 426 (100, Mþ2), 424 (80, Mþ); 13C NMR
(50 MHz, DMSO-d6): 168.59 (CvO), 147.21, 138.49,
134.49, 134.30, 132.28, 131.66, 131.40, 131.04, 129.50