Int. J. Mol. Sci. 2018, 19, 408
10 of 14
162.7, 160.6, 148.2, 143.5, 137.9, 133.2, 132.3, 131.6, 128.4, 125.0, 124.6, 118.5, 115.4, 111.7 (Ar-C, C=O),
44.1 (CH2), HR-MS (ESI) m/z: calculated for C19H15FN2O3 (M + H)+: 338.1067, found: 338.1062.
3.3.4. N-{2-[(4-Chlorobenzyl)carbamoyl]phenyl}furan-2-carboxamide (4d)
◦
This compound was obtained in 72% yield (from ethanol), mp 213–215 C. ν
max (KBr)/cm−1 3358,
2955 (N–H), 1710 (C=O), 1698 (C=O); 1H NMR (DMSO-d6) δH 10.6 (bs, 1H, NHCO), 7.1–8.2 (m, 11H,
Ph-H, furoyl-H and benzyl-H), 7.3 (bs, 1H, NHCH2), 3.9 (s, 2H, CH2); 13C NMR (DMSO-d6) δC 168.2,
161.9, 160.2, 148.2, 143.7, 138.2, 133.8, 131.7, 131.6, 128.4, 125.6, 123.3, 117.5, 115.8, 111.2 (Ar-C, C=O),
44.1 (CH2), HR-MS (ESI) m/z: calculated for C19H15ClN2O3 (M + H)+: 354.0771, found: 354.0778.
3.3.5. N-{2-[(4-Methylbenzyl)carbamoyl]phenyl}furan-2-carboxamide (4e)
◦
This compound was obtained in 70% yield (from ethanol), mp 175–178 C. ν
max (KBr)/cm−1 3358,
2955 (N–H), 1713 (C=O), 1688 (C=O); 1H NMR (DMSO-d6) δH 10.5 (bs, 1H, NHCO), 6.9–8.4 (m, 11H,
Ph-H, furoyl-H and benzyl-H), 7.2 (bs, 1H, NHCH2), 4.0 (s, 2H, CH2), 2.3 (s, 3H, CH3); 13C NMR
(DMSO-d6) δC 167.8, 162.7, 160.6, 149.2, 142.5, 138.1, 133.2, 132.3, 131.6, 129.4, 125.5, 124.9, 118.9, 114.8,
112.1 (Ar-C, C=O), 44.5 (CH2), 21.5 (CH3), HR-MS (ESI) m/z: calculated for C20H18N2O3 (M + H)+:
334.1317, found: 334.1311.
3.3.6. N-{2-[(4-Sulfamoylphenyl)carbamoyl]phenyl}furan-2-carboxamide (6a)
This compound was obtained in 75% yield (from 1,4-dioxan), mp 188–189 ◦C. max (KBr)/cm−1
ν
3357, 3203 (N–H), 1678 (C=O), 1632 (C=O), 1341, 1152 (S=O); 1H NMR (DMSO-d6) δH 11.5 (bs, 1H,
NHCO), 10.2 (bs, 1H, NHCO), 8.6–6.7 (m, 11H, Ph-H, furoyl-H and aminosulphonyl ph-H), 3.4 (bs, 2H,
NH2); 13C NMR (DMSO-d6) δC 168.2, 162.9, 148.2, 143.5, 141.3, 137.2, 136.3, 132.6, 129.4, 127.7, 124.6,
123.4, 120.2, 118.5, 115.9, 112.1 (Ar-C, C=O), HR-MS (ESI) m/z: calculated for C18H15N3O5S (M + H)+:
385.0732, found: 385.0741.
3.3.7. N-{2-[(4-(N-(Pyridin-2-Yl)sulfamoyl]phenyl)carbamoyl)phenyl}furan-2-carboxamide (6b)
◦
−1
(KBr)/cm
max
This compound was obtained in 64% yield (from acetonitraile), mp 209–211 C.
ν
3357, 3203 (N–H), 1675 (C=O), 1640 (C=O), 1341, 1152 (S=O); 1H NMR (DMSO-d6) δH 11.3 (bs, 1H,
NHCO), 10.8 (bs, 1H, SO2NH), 10.5 (bs, 1H, NHCO), 6.7–8.6 (m, 15H, Ph-H, furoyl-H and
aminosulphonyl ph-H, pyridinyl-H); 13C NMR (DMSO-d6) δC 167.1, 162.4, 148.1, 143.4, 141.2, 137.5,
135.3, 132.6, 129.7, 127.9, 124.1, 123.2, 119.5, 118.2, 115.6, 111.3, 109.5 (Ar-C, C=O), HR-MS (ESI) m/z:
calculated for C23H18N4O5S (M + H)+: 462.0998, found: 462.0992.
3.3.8. N-{2-[(4-(N-(Thiazol-2-Yl)sulfamoyl)phenyl)carbamoyl]phenyl}furan-2-carboxamide (6c)
◦
This compound was obtained in 62% yield (from ethanol), mp 217–219 C. ν
max (KBr)/cm−1 3348,
3205 (N–H), 1681 (C=O), 1642 (C=O), 1341, 1152 (S=O); 1H NMR (DMSO-d6) δH 11.2 (bs, 1H, NHCO),
10.8 (bs, 1H, SO2NH), 10.3 (bs, 1H, NHCO), 6.3–8.6 (m, 13H, Ph-H, furoyl-H and aminosulphonyl ph-H,
thiazole-H); 13C NMR (DMSO-d6) δC 170.4, 167.3, 161.7, 147.9, 143.8, 140.7, 137.9, 136.8, 134.6, 133.1,
129.4, 128.1, 123.8, 122.7, 119.2, 118.0, 116.1, 113.1, 111.7 (Ar-C, C=O), HR-MS (ESI) m/z: calculated for
C23H18N4O5S (M + H)+: 462.0998, found: 462.0991.
3.4. Synthesis and Characterization of N-[2-(Hydrazinecarbonyl)phenyl]furan-2-carboxamide (7)
A mixture of methyl-2-(furan-2-carboxamido)benzoate (2) (1 mmol) and hydrazine hydrate
(5 mmol) in ethanol (20 mL) was refluxed for 8 h. After cooling, the mixture was poured into crushed
ice and the formed solid was filtered off. The crude product was recrystallized from hot water to give
◦
compound (7) in 95% yield, mp 210–212 C. ν
max (KBr)/cm−1 3204–3210 (NH2, NH), 1689 (C=O), 1657
(C=O); 1H NMR (DMSO-d6) δH 12.4 (bs, 1H, NHNH2), 10.2 (bs, 1H, NHCO), 6.7–8.6 (m, 7H, Ph-H
and furoyl-H), 4.7 (s, 2H, NH2); 13C NMR (DMSO-d6) δC 168.0, 156.1, 148.0, 146.5, 139.1, 132.5, 128.3,