5-Methyl-2(1h) pyridone derivatives and their preparation methods and uses
A technology for pyridone and derivatives, which is applied in the field of 5-methyl-2-pyridone derivatives and its preparation, and can solve the problem of preparation of 5-methyl-2(1H)pyridone derivatives that have not been seen or have not been seen Methods and uses, etc., to achieve the effect of simple steps, low cost, and mild reaction conditions
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Embodiment 1
[0081]
[0082] Among them, "rf" is the abbreviation of reflux, and its Chinese meaning is "reflux".
[0083] In a 25ml reaction bottle, first add 3.4ml from 17ml H 2 O and the solution (50%, volume fraction) that 17ml concentrated sulfuric acid forms, then add 1g (0.01mol) 2-amino-5-picoline, cool to below 10 ℃ with ice-salt bath, after stirring several minutes, reaction solution Turned milky white. Then slowly drop by (1.72g NaNO 2 with 3mLH 2 O) the mixed solution, during dropwise addition, produces irritating gas, after dropwise addition, the reaction solution turns into a light yellow solution, and TCL (thin layer chromatography) monitors until the reaction is complete (about 40min). Then add 8mL H 2 O, reflux stirring reaction 15min, cooling, add anhydrous Na under stirring 2 CO 3 , make the reaction solution neutral (produce yellow-brown solid), filter, the gained filtrate is spin-dried, then dissolve and filter with absolute ethanol, and the gained filtrate is...
Embodiment 2
[0093]
[0094] According to the method described in Example 1, replacing "p-methylacetophenone" with "p-chloroacetophenone", the compound shown in formula Ib was obtained.
[0095] Compound represented by formula Ib: yellow solid (yellow solid), melting point (mp) is 66-67°C;
[0096] 1 H NMR (400MHz, DMSO-d6) δ: 8.02 (d, J = 8.8Hz, 4H, ArH), 7.62 (d, J = 8.4Hz, 4H, ArH), 7.51 (d, J = 8.4Hz, 2H, ArH), 7.37~7.40(m, 2H, CH), 7.30(d, J=8.4Hz, 2H, ArH), 6.43(d, J=10.0Hz, 1H, CH), 3.97~4.03(m, 2H, CH), 3.55(d, J=6.8Hz, 4H, CH 2 ),2.06(s,6H,CH 3 );
[0097] 13 C NMR (100MHz, DMSO-d6) 197.40, 160.34, 143.95, 139.04, 136.02, 135.26, 129.84, 129.76, 126.31, 120.11, 113.91, 44.21, 39.53, 35.53, 16.23; IR (KBr, n, cm -1 ):3429,1673,1590,1400,1262,1091,804,590;
[0098] HRMS (ESI) calcd for C 29 h 23 Cl 2 NO 3 [M+Na] + 503.1055found 526.0963.
Embodiment 3
[0100]
[0101] According to the method described in Example 1, replacing "p-methylacetophenone" with "p-fluoroacetophenone", the compound represented by formula Ic was obtained.
[0102] Compound represented by formula Ic: gray solid (gray solid), melting point (mp) is 60-62°C;
[0103] 1 H NMR (400MHz, DMSO-d6) δ: 8.06(dd, J1=6.0Hz, J2=8.4Hz, 4H, ArH), 7.48(d, J=8.4Hz, 2H, CH), 7.26~7.35(m, 8H, ArH), 6.40(d, J=10.0Hz, 1H, CH), 3.97~4.04(m, 1H, CH), 3.52(d, J=6.8Hz, 4H, CH 2 ),2.02(s,6H,CH 3 );
[0104] 13 C NMR (100MHz, DMSO-d6) 196.93, 166.24, 163.74, 160.35, 144.06, 142.81, 139.02, 136.01, 133.37, 130.95, 128.14, 126.30, 120.11, 115.73, 158.91, 494.17, 3IR ,n,cm -1 ):2925,1675,1596,1506,1410,1364,1277,1230,1156,990,832,586;
[0105] HRMS (ESI) calcd for C 29 h 23 f 2 NO 3 [M+Na] + 471.1646found 494.1549.
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