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Yield: 90%; white powder, m.p. 165-167 oC, IR (KBr) (νmax/cm-1): 3230 (OH), 1710 and 1665 (C=O). 1H NMR (500 MHz, d6-DMSO): δ 1.49 (9 H, 3 CH3), 7.52 – 7.90 (5 H, m, 5 CH aromatic), 7.74 (1 H, s, CH), 12.18 (1 H, broad s, OH). 13C NMR (125.8 MHz, d6-DMSO): δ 28.5 (3 CH3), 82.4 (C), 102.3 (C-4), 140.0 (C-3), 133.5 (C-5), 128.8, 129.4, 133.2 and 135.0 (aromatic), 163.1 (CO), 164.5 (CO). Anal. Calcd for C15H16N2O4: C, 62.49; H, 5.59; N, 9.72%. Found: C, 62.6; H, 5.4; N, 9.9%.

Methyl- 1- (furan-2-carbonyl) -5- hydroxy -1H –pyrazole -3-carboxylate (3d).
Yield: 82%; white powder, m.p. 180-182 oC, IR (KBr) (νmax/cm-1): 3210 (OH), 1739 and 1668 (C=O). 1H NMR (250.1 MHz, d6-DMSO): δ 3.85 (3 H, OCH3), 6.59 (1H, m, CH furan), 7.57 (1H, s, CH furan), 7.65 (1H, d, 3JHH = 2 HZ, CH furan), 7.83 (1 H, s, CH pyrazole), 12.07 (1 H, broad s, OH). 13C NMR (62.89 MHz, d6-DMSO): δ 55.9 (OCH3), 116.0 (C-4), 149.3 (C-3), 137.0 (C-5), 111.2, 120.1,140.0 and 142.8 (furan), 164.9 (CO), 167.6 (CO). Anal. Calcd for C10H8N2O5: C, 50.85; H, 3.41; N, 11.86%. Found: C, 50.7; H, 3.5; N, 11.7%.

Ethyl- 1- (furan-2-carbonyl) -5- hydroxy- 1H- pyrazole -3-carboxylate (3e).
Yield: 80%; white powder, m.p. 143-145 oC, IR (KBr) (νmax/cm-1): 3203 (OH), 1730 and 1668 (C=O). 1H NMR (500 MHz, CDCl3): δ 1.28 (3 H, d 3JHH = 7 HZ, CH3), 4.37 (2 H, d 3JHH = 7 HZ, OCH2), 6.60 (1H, m, CH furan), 7.58 (1H, s, CH furan), 7.65 (1H, d, 3JHH = 2 HZ, CH furan), 7.86 (1 H, s, CH pyrazole), 13.43 (1 H, broad s, OH). 13C NMR (125.8 MHz, CDCl3): δ 14.3 (CH3), 62.7 (CH2), 112.9 (C-4), 145.8 (C-3), 137.3 (C-5), 111.5, 120.3,140.2 and 142.6 (furan), 165.1 (CO), 169.9 (CO). Anal.Calcd for C11H10N2O5: C, 52.80; H, 4.03; N, 11.20%. Found: C, 52.9; H, 4.1; N, 11.1%.

t-butyl- 1- (furan-2-carbonyl) -5- hydroxy- 1H- pyrazole -3-carboxylate (3f).
Yield: 84%; white powder, m.p. 158-160 oC, IR (KBr) (νmax/cm-1): 3220 (OH), 1710 and 1669 (C=O). 1H NMR (500 MHz, d6-DMSO): δ 1.49 (9 H, 3 CH3), 6.72 (1H, m, CH furan), 7.41 (1H, s, CH furan), 7.67 (1H, d, 3JHH = 2 HZ, CH furan), 7.98 (1 H, s, CH pyrazole), 12.19 (1 H, broad s, OH). 13C NMR (125.8 MHz, d6-DMSO): δ 28.6 (3 CH3), 82.4 (C), 113.2 (C-4), 147.6 (C-3), 135.0 (C-5), 110.9, 120.3,140.3 and 142.5 (furan), 162.9 (CO), 167.1 (CO). Anal. Calcd for C13H14N2O5: C, 56.11; H, 5.07; N, 10.07%. Found: C, 56.2; H, 4.9; N, 10.2%.

مطلب مرتبط :   مقاله درمورد ایجاد تغییر و روش ترکیبی

Dimethyl 2- (benzoyl-hydrazono) -succinate (4a).
Yield: 95%; white powder, m.p. 141-143 oC, IR (KBr) (νmax/cm-1): 3185 (NH), 1727 and 1671 (C=O). 1H NMR (500.1 MHz, d6-DMSO): δ 3.61 and 3.73 (6H, 2OCH3), 3.87 (2H, s, CH2), 7.47 – 7.81 (5 H, m, 5 CH aromatic), 11.38 (1 H, broad s, NH).13C NMR (125.8 MHz, d6-DMSO): δ 33.3 (CH2), 53.0 and 53.3 (2OCH3), 129.1, 129.6, 133.0 and 133.9 (aromatic), 154.2 (C=N), 165.4, 169.2 and 169.4 (3CO). Anal. Calcd for C13H14N2O5: C, 56.11; H, 5.07; N, 10.07%. Found: C, 56.3; H, 4.9; N, 10.2%.

Dimethyl 2-[(furan – 2- carbonyl) –hydrazono] – succinate (4b).
Yield: 90%; white powder, m.p. 133-135 oC, IR (KBr) (νmax/cm-1): 3275 (NH), 1735 and 1661 (C=O). 1H NMR (500.1 MHz, d6-DMSO): δ 3.61 and 3.76 (6H, 2OCH3), 3.81 (2H, s, CH2), 6.69 (1H, m, CH furan), 7.63 (1H, s, CH furan), 7.96 (1H, d, 3JHH = 2 HZ, CH furan), 11.45 (1 H, broad s, NH). 13C NMR (125.8 MHz, d6-DMSO): δ 32.8 (CH2), 53.0 and 53.5 (2OCH3), 113.1, 120.2,145.8 and 147.9 (furan), 154.3 (C=N), 165.2, 168.9 and 169.1 (3CO). Anal. Calcd for C11H12N2O6: C, 49,26; H, 4.51; N, 10.44%. Found: C, 49.1; H, 4.4; N, 10.6%.

Diethyl 2-[ (furan-2-carbonyl) –hydrazono]-succinate (4c).
Yield: 91%; white powder, m.p. 143-145 oC, IR (KBr) (νmax/cm-1): 3214 (NH), 1728 and 1665 (C=O). 1H NMR (500 MHz, d6-DMSO): δ 0.68 (3 H, d 3JHH = 7 HZ, CH3), 1.34 (3 H, d 3JHH = 7 HZ, CH3), 3.78 (2H, s, CH2), 4.17-4.32 (4 H, m, 2OCH2), 6.63 (1H, m, CH furan), 7.44 (1H, s, CH furan), 7.52 (1H, d, 3JHH = 2 HZ, CH furan), 13.2 (1 H, broad s, NH). 13C NMR (125.8 MHz, d6-DMSO): δ 13.9 and 14.4 (2CH3), 32.6 (CH2), 61.9 and 62.1 (2OCH2), 113.3, 119.9,145.3 and 147.5 (furan), 154.1 (C=N), 165.6, 169.5 and 169.9 (3CO). Anal.Calcd for C13H16N2O6: C, 52.70; H, 5.44; N, 9.46%. Found: C, 52.8; H, 5.6; N, 9.3%.

مطلب مرتبط :   پایان نامه قابلیت اطمینان و تولیدکنندگان

Di t-butyl 2-[ (furan-2-carbonyl) –hydrazono]-succinate (4d).
Yield: 88%; white powder, m.p. 158-160 oC, IR (KBr) (νmax/cm-1): 3223 (NH), 1714 and 1658 (C=O). 1H NMR (500 MHz, d6-DMSO): δ 0.85 (9 H, s, t-Bu), 1.47 (9 H, s, t-Bu), 3.89 (2H, s, CH2), 6.61 (1H, m, CH furan), 7.38 (1H, s, CH furan), 7.52 (1H, d, 3JHH = 2 HZ, CH furan), 12.02 (1 H, broad s, NH). 13C NMR (125.8 MHz, d6-DMSO): δ 28.6 and 28.8 (6 CH3 of 2 t-Bu), 32.1 (CH2), 78.4 and 82.7 (2C), 113.7, 119.8,145.0 and 146.9 (furan), 154.6 (C=N), 165.2, 169.0 and 169.6 (3CO). Anal. Calcd for C17H24N2O6: C, 57.94; H, 6.86; N, 7.95%. Found: C, 57.8; H, 6.7; N, 8.1%.

Di t-butyl 2- (benzoyl-hydrazono) -succinate (4e).
Yield: 90%; white powder, m.p. 141-143 oC, IR (KBr) (νmax/cm-1): 3260 (NH), 1726 and 1688 (C=O). 1H NMR (500.1 MHz, d6-DMSO): δ 1.45 (9 H, s, t-Bu), 1.54 (9 H, s, t-Bu), 3.55 (2H, s, CH2), 7.44 – 7.93 (5 H, m, 5 CH aromatic), 13.54 (1 H, broad s, NH).13C NMR (125.8 MHz, d6-DMSO): δ 28.6 and 28.8 (6 CH3 of 2 t-Bu), 32.3 (CH2), 79.3 and 82.1 (2 C), 129.3, 129.7, 132.9 and 133.7 (aromatic), 154.5 (C=N), 165.6, 169.4 and 169.9 (3CO). Anal. Calcd for C19H26N2O5: C, 62.97; H, 7.23; N, 7.73%. Found: C, 62.8; H, 7.4; N, 7.8%.

دسته بندی : علمی