* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference:
[1] Journal of Medicinal Chemistry, 1991, vol. 34, # 4, p. 1243 - 1252
2
[ 123158-76-9 ]
[ 7439-89-6 ]
[ 83171-49-7 ]
Reference:
[1] Patent: US5270309, 1993, A,
3
[ 123158-75-8 ]
[ 83171-49-7 ]
Reference:
[1] Journal of Medicinal Chemistry, 1991, vol. 34, # 4, p. 1243 - 1252
4
[ 89-63-4 ]
[ 83171-49-7 ]
Reference:
[1] Journal of Medicinal Chemistry, 1991, vol. 34, # 4, p. 1243 - 1252
5
[ 146512-91-6 ]
[ 83171-49-7 ]
Reference:
[1] Patent: US5270309, 1993, A,
6
[ 861547-81-1 ]
[ 83171-49-7 ]
Reference:
[1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1913, vol. <5> 22 I, p. 823[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1914, vol. <5> 23 I, p. 283 Anm.
7
[ 99-54-7 ]
[ 83171-49-7 ]
Reference:
[1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1913, vol. <5> 22 I, p. 823[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1914, vol. <5> 23 I, p. 283 Anm.
8
[ 861609-74-7 ]
[ 83171-49-7 ]
Reference:
[1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1913, vol. <5> 22 I, p. 823[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1914, vol. <5> 23 I, p. 283 Anm.
9
[ 121-87-9 ]
[ 83171-49-7 ]
Reference:
[1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1913, vol. <5> 22 I, p. 823[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1914, vol. <5> 23 I, p. 283 Anm.
Cis-2-carboxy-7-chloro-5-iodo-4-methoxycarbonyl-1,2,3,4-tetrahydroquinoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 24 Cis-2-carboxy-7-chloro-5-iodo-4-methoxycarbonyl-1,2,3,4-tetrahydroquinoline This compound was prepared by the route outlined in Example 15 using <strong>[83171-49-7]3-chloro-5-iodoaniline</strong> as starting material (m.p. 188 C. dec., dichlormethane/hexane); delta (360 MHz, CDCl3) 2.29 (1H, m, CHA CHB HC CHD), 2.92 (1H, dm, J=14.2 Hz, CHA CHB HC CHD), 3.65 (3H, s, CH3), 3.91 (1H, dd, J=6.4 and 3.4 Hz, CHA CHB HC CHD), 4.10 (1H, dd, J=6.1 and 3.3 Hz, CHA CHB HC CHD), 6.66 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.26 (1H, d, J=2.0 Hz, 6-H or 8-H); m/e 395 (M+), 290 (100%, M-H, CO2 H, CO2 Me); Found: C, 35.71; H, 2.80; N. 3.40. C12 H11 C1INO4.0.4H2 0 requires C, 35.78; H, 2.95; N, 3.48%.
Trans-2-carboxy-7-chloro-5-iodo-4-methoxycarbonyl-1,2,3,4-tetrahydroquinoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 25 Trans-2-carboxy-7-chloro-5-iodo-4-methoxycarbonyl-1,2,3,4-tetrahydroquinoline This compound was prepared by the route outlined in Example 15 and 16 using <strong>[83171-49-7]3-chloro-5-iodoaniline</strong> as starting material (colourless foam); delta (360 MHz, CDCl3), 1.95 (1H, ddd, J=14.4, 12.2 and 5.6 Hz, CHA CHB HC CHD), 2.72 (1H, dm, J=14.4 Hz, CHA CHB HC CHD), 3.76 (3H, s, CH3), 3.98 (1H, dd, J=5.6 and 2.1 Hz, CHA CHB HC CHD), 4.09 (1H, dd, J=12.2 and 3.4 Hz, CHA CHB HC CHD), 6.64 (1H, d, J=1.9 Hz, 6-H or 8-H), 7.20 (1H, d, J=1.9 Hz, 6-H and 8-H); m/e 395 (M+), 290 (100%, M-H, CO2 H, CO2 Me); Found: C, 36.88; H, 3.00; N, 3.38. C12 H11 C1INO4 requires C, 36.44; H, 2.80; N, 3.54%.
c) A solution of <strong>[123158-76-9]5-chloro-3-iodonitrobenzene</strong> (3.45 g) in acetic acid (10 ml) and ethanol (58 ml) containing iron powder (6.4 g) was refluxed for 6 h with stirring, cooled, filtered and poured into water (100 ml). The product was extracted into ethyl acetate, washed with water, dried over magnesium sulfate, filtered and solvent evaporated to yield, after column chromatography, 3-chloro-5-iodoaniline (1.5 g). delta (360 MHz, DMSO-d6) 5.58 (2H, bs, NH2) 6.57 (1H, bs, 6-H), 6.80 (1H, bs, 2-H), and 6.88 (1H, bs, 4-H).
With triethylamine; In acetone; at 20.0℃; for 6.0h;
General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.
With triethylamine; In acetone; at 20.0℃; for 6.0h;
General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.
With triethylamine; In acetone; at 20.0℃; for 6.0h;
General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.
With triethylamine; In acetone; at 20.0℃; for 6.0h;
General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.
With triethylamine; In acetone; at 20.0℃; for 6.0h;
General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.