A new method for c-h activation of tetrazolium-directed meta-nitration
A technology of phenyltetrazolium and nitration, applied in the direction of organic chemistry, can solve the problems of poor meta-selectivity, intolerance of various functional groups, etc.
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Embodiment 1
[0018] Example 1: Synthesis of Compound 1
[0019]
[0020] Add 2-methyl-5-phenyl-2 to a clean pressure bottle H - Tetrazolium (32 mg, 0.20 mmol), Ru 3 (CO) 12 (4.8 mg, 0.015 mmol), PPh 3 (7.9 mg, 0.060 mmol), iodobenzene trifluoroacetate (95 mg, 0.22 mmol), hexafluoroisopropanol (2 mL) and copper nitrate trihydrate (36 mg, 0.30 mmol) and then placed in an oil bath at 100 °C Stir for 24h;
[0021] After the reaction was completed, the solvent was removed under reduced pressure, and the product was directly separated and purified by silica gel column chromatography to obtain 38.5 mg of the product as a white solid, the yield was 94%, the melting point was 96-100 o C; 1 H NMR (400 MHz, Chloroform- d ) δ 8.97 (s, 1H), 8.47 (d, J = 8.0 Hz, 1H), 8.31 (d, J = 8.0 Hz, 1H), 7.68 (t, J = 8.0 Hz, 1H), 4.44 (s, 3H); 13 C NMR (100 MHz, Chloroform- d ) δ 163.5, 148.8, 132.5, 130.2, 129.2, 125.0, 121.9, 39.9; HRMS (ESI): Calculated C 22 H 16 ClN 2 [M+H] + : 206.0673, mea...
Embodiment 2
[0022] Example 2: Synthesis of Compound 2
[0023]
[0024] Add 2-methyl-5-(3-methyl-5-phenyl)-2 to a clean pressure bottle H - Triazole (34.8 mg, 0.20 mmol), Ru 3 (CO) 12 (4.8 mg, 0.015 mmol), P(o-Tol) 3 (18.2 mg, 0.060 mmol), iodobenzene trifluoroacetate (95 mg, 0.22 mmol), hexafluoroisopropanol (2 mL) and Cu(NO 3 ) 2 •3H 2 O (36 mg mg, 0.30 mmol) and then stirred in an oil bath at 100 °C for 24 h;
[0025] After the reaction was completed, the solvent was removed under reduced pressure, and the product was directly separated and purified by silica gel column chromatography to obtain 40.8 mg of the product as a gray solid, yield 65%, melting point 90-92 o C; 1 H NMR (400 MHz, Chloroform- d ) 8.77 (s, 1H), 8.29 (s, 1H), 8.13 (s, 1H), 4.43 (s, 3H), 2.55 (s, 3H); 13 C NMR (100 MHz, Chloroform- d ) δ 163.7, 148.8, 140.9, 133.2, 128.8, 125.4, 119.2, 39.8, 21.5; HRMS (ESI): m / z measured value: C 9 H 9 N 5 O 2 [M+H] + : 220.0829, Found: 220.0835.
Embodiment 3
[0026] Example 3: Synthesis of Compound 3
[0027]
[0028] Add 2-(4-Methoxy-phenyl)-2 to a clean pressure bottle H -1,2,3-Triazole (56.8 mg, 0.20 mmol), Ru 3 (CO) 12 (4.8 mg, 0.015 mmol), P(o-furyl) 3 (13.9 mg, 0.060 mmol), iodobenzene trifluoroacetate (95 mg, 0.22 mmol), hexafluoroisopropanol (2 mL) and AgNO3 (61.1 mg, 0.36 mmol) and then stirred in an oil bath at 100 °C for 24 h;
[0029] After the reaction was completed, the solvent was removed under reduced pressure, and the product was directly separated and purified by silica gel column chromatography to obtain 40.8 mg of the product, a pale yellow solid, yield 92%, melting point 122-124 mg o C; 1 H NMR (400 MHz, Chloroform- d ) δ 8.60 (s,1H), 8.27 (d, J = 8.0 Hz, 1H), 7.82 (s, 2H), 7.21 (d, J = 8.0 Hz, 1H), 4.02(s, 3H); 13 C NMR (150 MHz, Chloroform- d ) δ 152.0, 139.7, 136.1, 132.9, 124.2, 116.6, 114.3, 57.1; HRMS (ESI): m / z calculated value C 9 H 8 N 4 O 3 [M+H] + : 221.0669, found: 221.0676.
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