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Chapter-5
Synthesis of highly substituted pyrroles
Spectral data of synthesized compounds
2-acetyl-N-(4-ethylphenyl)-4-(4-fluorophenyl)-4-oxo-3-phenylbutanamide ADD-
05. White solid, yield 82%, mp 190-192 ° C; R f 0.42 (9:1 Chloroform: Methanol); IR
(KBr): 3473, 3072, 2895, 2828, 1694, 1635, 1482, 850, 780 cm -1 ; 1 H NMR (300
MHz, DMSO): δ 1.06-1.11 (t, 3H, CH 3 ), 2.22 (s, 3H, CH 3 ), 2.44-2.47 (q, 2H CH 2 ),
4.70-4.73 (d, 1H, CH, j=10.8Hz), 5.36–5.39 (d, 1H, CH, j=10.8Hz), 7.03-7.15 (m,
3H, Ar), 7.18-7.35 (m, 8H, Ar), 8.09-8.13 (t, 2H, Ar), 10.16 (s, 1H, NH); MS (m/z):
417 [M + ]; Anal. Calcd for C 26 H 24 FNO 3 : C, 74.80; H, 5.79; N, 3.36; Found: C, 74.82;
H, 5.75; N, 3.33.
N-(4-chlorophenyl)-2-(cyclopropanecarbonyl)-4-(4-fluorophenyl)-4-oxo-3-phenyl
butanamide ADD-23. White solid, yield 85%, mp 220-222 ° C; R f 0.42 (9:1
Chloroform: Methanol); IR (KBr): 3430, 3045, 2895, 1635, 1482, 1343, 1298, 980,
783, 732 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 0.90-0.93 (m, 2H, CH 2 ), 1.05-1.13 (m,
2H, CH 2 ), 2.18-2.23 (m, 1H, CH), 4.77-4.80 (d, 1H, CH, j=10.84Hz), 4.49–5.51 (d,
1H, CH, j=10.84Hz), 6.84-6.89 (m, 2H, Ar), 7.00-7.09 (m, 4H, Ar), 7.18-7.27 (m,
3H, Ar), 7.34-7.40 (m, 2H, Ar); 13 C NMR (100 MHz, CDCl 3 ): δ 11.82, 13.12. 20.34,
53.10, 66.10, 115.42, 115.90, 121.83, 122.56, 128.13, 128.70, 129.03, 129.25, 129.39,
131.66, 131.75, 123.16, 132.19, 132.92, 132.95, 160.94, 167.04, 196.70, 205.50; MS
(m/z): 449 [M + ]; Anal. Calcd for C 26 H 21 ClFNO 3 : C, 69.41; H, 4.70; N, 3.11; Found:
C, 69.43; H, 4.75; N, 3.13.
tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-methyl-3-phenyl-4-(p-tolylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-01. White
solid, mp 167-169 ° C; R f 0.42 (9:1 Chloroform: Methanol); IR (KBr): 3412, 3032,
2977, 2872, 1731, 1659, 1479, 1029, 792, 737, 709 cm -1 ; MS (m/z): 625 [M + ]; Anal.
Calcd for C 38 H 42 FN 2 O 5 : C, 72.94; H, 6.77; N, 4.48; Found: C, 72.95; H, 6.78; N, 4.50.
tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-4-((4-methoxyphenyl)carbamoyl)-
5-methyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-02. White solid, mp 153-155 ° C; R f 0.47 (9:1 Chloroform: Methanol); IR (KBr):
3477, 3037, 2981, 2928, 2878, 1729, 1665, 1567, 1542, 1482, 1288, 1083, 1035, 837,
789, 741, 711 cm -1 ; MS (m/z): 656 [M + ]; Anal. Calcd for C 38 H 42 FN 2 O 6 : C, 71.32; H,
6.91; N, 4.27; Found: C, 71.35; H, 6.92; N, 4.28.
Department of Chemistry, Saurashtra University, Rajkot-360005 180