A method for synthesizing α-cyclic amine maleimide hybrids
A technology of maleimide and cyclic amine, which is applied in the field of organic synthesis, can solve problems such as insufficient research, and achieve the effects of good selectivity, mild reaction conditions, and easy operation
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Embodiment 1
[0019]
[0020] Add 1a, organic solvent, catalyst, oxidizing agent, TEMPO and 2a into a 15mL pressure-resistant tube in sequence, cover with a stopper and seal it, and place it in an oil bath to heat up and stir for reaction. After the reaction was completed, it was quenched with saturated brine, extracted with ethyl acetate, anhydrous Na 2 SO 4 dry. Spin-dry and separate on a silica gel column (petroleum ether / ethyl acetate=20 / 1) to obtain the product 3a.
[0021] Various reaction results were obtained by changing the catalyst, oxidant, organic solvent, temperature and dosage ratio of the reaction, as shown in Table 1.
[0022] Synthesis of 3a under different reaction conditions in table 1 a
[0023]
[0024]
Embodiment 2
[0026]
[0027] Add 1a (81mg, 0.5mmol), toluene (2mL), anhydrous ferric chloride (8mg, 0.05mmol), dicumyl peroxide (135mg, 0.5mmol) and 2,2 to a 15mL pressure tube in sequence. , 6,6-tetramethylpiperidine nitrogen oxide (78mg, 0.5mmol) and 2a (86mg, 0.5mmol), under air atmosphere, cover the stopper and seal it, place it in an oil bath at 80°C and stir for 12 hours . After the reaction, cool to room temperature, quench with saturated brine, extract with ethyl acetate (10mL×3), combine the organic phases, anhydrous Na 2 SO 4 dry. After spin-drying, silica gel column separation (petroleum ether / ethyl acetate=20 / 1) gave product 3a (121 mg, 73%) as a yellow oil. 1 H NMR (400MHz, CDCl 3 ): δ7.44(t, J=8.0Hz, 2H), 7.34(d, J=7.6Hz, 1H), 7.31(d, J=8.0Hz, 2H), 7.23-7.27(m, 2H), 6.95 (d, J=8.4Hz, 2H), 6.89(d, J=7.2Hz, 1H), 6.34(d, J=1.2Hz, 1H), 4.80(t, J=4.8Hz, 1H), 3.30-3.33 (m,2H),2.09-2.17(m,1H),1.97-2.05(m,1H),1.83-1.92(m,1H),1.71-1.81(m,1H),1.61-1.69(m,2H) . 13 C{1H}NMR (1...
Embodiment 3
[0029] According to the method and steps of Example 2, various α-cyclic amine maleimide hybrids 3 were synthesized by changing reactants 1 and 2 a,b , the specific results are as follows:
[0030]
[0031] Representative product characterization data are as follows:
[0032] 1-Phenyl-3-(1-(p-tolyl)piperidin-2-yl)-1H-pyrrole-2,5-dione(3b)
[0033] Yellow oil (149mg, 86%). 1 H NMR (400MHz, CDCl 3 ): δ7.43(t, J=8.0Hz, 2H), 7.34(d, J=7.6Hz, 1H), 7.30(dd, J 1 =8.4Hz,J 2 =1.2Hz, 2H), 7.05(d, J=8.0Hz, 2H), 6.87(d, J=8.0Hz, 2H), 6.32(d, J=1.2Hz, 1H), 4.64(t, J=5.2 Hz,1H),3.28-3.34(m,1H),3.10-3.16(m,1H),2.26(s,3H),2.09-2.17(m,1H),1.82-1.93(m,2H),1.70- 1.78(m,1H),1.60-1.69(m,2H). 13 C{ 1 H}NMR (150MHz, CDCl 3 ): δ170.0, 169.3, 150.1, 148.7, 131.5, 131.0, 129.9, 129.1, 128.3, 127.7, 125.9, 119.2, 53.7, 51.3, 31.3, 25.9, 21.9, 20.6. HRMS (ESI) m / z: [M+H ] + Calcd for C 22 h 23 N 2 o 2 + 347.1754; Found: 347.1749.
[0034]1-Phenyl-3-(1-(4-(trifluoromethyl)phenyl)piperidi...
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