Dehydroabietyl 2-amino-3-cyanopyridine derivatives, preparation method and application thereof
A cyanopyridine and derivative technology, applied in antiviral agents, organic chemistry and other directions, can solve the problems of complex post-processing procedures, high cost of reaction raw materials, harsh reaction conditions, etc., and achieve good antiviral effect, good inhibitory effect, Easy post-processing effects
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Embodiment 1
[0030] The preparation of compound a:
[0031]
[0032] 1mmol of benzaldehyde, 1mmol of methyl 12-acetyl dehydroabietate, 1mmol of malononitrile, 2mmol of ammonium acetate and 10mL of trifluoroethanol were sequentially added into a 25mL single-necked flask, and the temperature was raised to 80°C, and reacted for 12h under stirring. After the reaction solution was cooled to 42°C, it was filtered to obtain a solid. The solid was recrystallized with 4 mL of tetrahydrofuran, and the recrystallized solid was vacuum-dried at a vacuum degree of 0.1 MPa and a temperature of 50°C for 12 hours to obtain a dehydroabietyl 2-amino-3-cyanopyridine derivative product a. Yield: 76%, white powder; mp 210-214°C; 1 H NMR (400MHz, DMSO) δ7.64(d, J=5.4Hz, 2H), 7.54(d, J=5.6Hz, 2H), 7.38(s, 1H), 7.15(s, 1H), 7.05(s ,1H),6.98(s,1H),6.68(s,1H),3.61(s,3H),3.49–3.39(m,1H),3.17(dd,J=13.5,6.7Hz,1H),2.85( ddd, J=27.7, 18.4, 8.0Hz, 2H), 2.30(d, J=12.8Hz, 1H), 2.04(d, J=11.9Hz, 1H), 1.86–1.53(m, 6H), ...
Embodiment 2
[0034] Preparation of compound b:
[0035]
[0036] Add 1mmol of 2-methoxybenzaldehyde, 1mmol of methyl 12-acetyl dehydroabietate, 1mmol of malononitrile, 2mmol of ammonium acetate and 10mL of trifluoroethanol successively in a 25mL single-necked flask, heat up to 70°C, and stir Under reaction 14h. After cooling the reaction solution to 48°C, the solid was obtained by filtration. The solid was recrystallized with 4 mL of tetrahydrofuran, and the recrystallized solid was vacuum-dried at a vacuum degree of 0.1 MPa and a temperature of 50°C for 12 hours to obtain the dehydroabietyl 2-amino-3-cyanopyridine derivative product b. Yield: 78%, white powder; mp 216-218°C; 1 H NMR (400MHz, DMSO) δ7.65 (dd, J = 7.5, 2.0Hz, 2H), 7.58–7.52 (m, 2H), 7.39 (s, 1H), 7.16 (s, 1H), 7.06 (s, 1H),7.00(s,2H),6.68(s,1H),4.39(t,J=5.1Hz,1H),3.62(s,3H),3.45(qd,J=7.0,5.1Hz,2H), 3.28–3.12(m,1H),2.96–2.74(m,1H),2.31(d,J=12.6Hz,1H),2.05(d,J=10.7Hz,1H),1.86–1.72(m,2H) ,1.65(dd,J=25.0,11.7Hz,4H),1.33...
Embodiment 3
[0038] Preparation of compound c:
[0039]
[0040] Add 1mmol of 3-methoxybenzaldehyde, 1mmol of methyl 12-acetyl dehydroabietate, 1mmol of malononitrile, 2mmol of ammonium acetate and 10mL of trifluoroethanol successively in a 25mL single-necked flask, heat up to 60°C, and stir Under reaction 15h. After cooling the reaction solution to 45°C, the solid was obtained by filtration. The solid was recrystallized with 4 mL of tetrahydrofuran, and the recrystallized solid was vacuum-dried for 12 hours at a vacuum degree of 0.1 MPa and a temperature of 50° C. to obtain the dehydroabietyl 2-amino-3-cyanopyridine derivative product c. Yield: 73%, white powder; mp 215-218°C; 1 H NMR (400MHz, DMSO) δ7.45 (t, J = 7.9Hz, 1H), 7.22–7.17 (m, 2H), 7.15 (s, 1H), 7.09 (dd, J = 8.2, 1.9Hz, 1H) ,7.05(s,1H),6.97(s,2H),6.70(s,1H),3.85–3.80(m,3H),3.75(d,J=8.1Hz,1H),3.61(s,3H), 3.22–3.13(m,1H),2.95–2.74(m,2H),2.30(d,J=12.8Hz,1H),2.09–1.99(m,1H),1.85–1.54(m,6H),1.33( d,J=7.5Hz,3H).MS(M+Na + )...
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