一种2-吡啶酮类化合物的绿色高效合成方法与流程

本发明属于化工技术领域，具体涉及一种高效绿色合成2-吡啶酮类化合物的方法。

背景技术：

吡啶酮化合物是一类重要的含氮杂环化合物，根据n原子所处位置的差别以及含−c=o数量的不同分为2-吡啶酮、4-吡啶酮、2,4-二吡啶酮化合物。同时，该类化合物广泛存在于众多的天然产物中，其结构是多种天然生物碱母核，是药物和功能性材料的主要结构单元。许多具有药理活性的合成药物分子、天然药物分子中都含有吡啶酮母体结构，如下所示：

由于2-吡啶酮类化合物具有广泛的生物活性，同时具有合成药物分子的应用价值。迄今为止已有各种方法来制备2-吡啶酮化合物，包括guareschi-thorpecondensation，transition-metal-catalyzedreactions，tandem-blasisereaction，directing-group-assistedintermolecularc−hannulation等。然而，在现有的2-吡啶酮合成方法中，大部分以有毒过渡金属作催化剂，并在有机极性溶剂中反应，后处理繁琐，对环境污染不可逆转。

研究表明，微波条件下一些反应的反应能垒降低导致反应更容易进行。同时利用微波加热快速、均质等优点可大幅度的缩短有机反应时间和减少催化剂的使用从而使反应条件变得更加绿色温和。因此，设计构建微波条件下合成2-吡啶酮类化合物是实现绿色高效制备该类化合物重要途径。

技术实现要素：

本发明的目的在于提供一种绿色高效合成2-吡啶酮类化合物的方法。

本发明的目的是这样实现的，是以二羰基化合物、丙二酸二乙酯、n,n-二甲基甲酰胺二甲基缩醛和胺类化合物为原料，同时经历condensation反应，n-nucleophilicaddition反应，再通过substitutionreaction和intramolecularcyclization反应制备得到2-吡啶酮，其反应原理如下：

与现有技术相比，本发明具有以下突出优点:

本发明所述的高效绿色合成2-吡啶酮类化合物的方法是在微波条件下以简单易得的二羰基化合物、丙二酸二乙酯、n,n-二甲基甲酰胺二甲基缩醛和胺类化合物四组分化合物一锅投料，降低原料成本，且反应过程无任何溶剂和催化剂的使用，从根本上解决了原路线污染较大、操作难度高等问题。

本发明的有益效果主要体现为：

1.反应在微波条件下进行，反应速度快，反应过程安全；

2.原料简单，市场可以买到，价格便宜；

3.四组分原料一起投料一锅操作，中间体不需要分离操作，反应过程高效省力；

4.整个转变过程效率高，最终产物通过简单色谱处理就可得到纯净化合物；

5.绿色的反应程序，副产物只有乙醇，原子经济性高；

6.2-吡啶酮化合物实用价值高，重要的天然产物、合成药物、化工材料等的组成结构。

附图说明

图1-1、图1-2为本发明实施例1中1号化合物核磁图谱；

图2-1、图2-2为本发明实施例2中1号化合物核磁图谱；

图3-1、图3-2为本发明实施例3中1号化合物核磁图谱。

具体实施方式

下面结合实施例和附图对本发明作进一步的说明，但不以任何方式对本发明加以限制，基于本发明教导所作的任何变换或替换，均属于本发明的保护范围。

本发明所述的绿色高效合成2-吡啶酮类化合物的方法，是本发明公开了吡啶酮类化合物及其新颖的四组分一锅投料绿色合成方法。方法如下：在微波反应器中以二羰基化合物、丙二酸二乙酯，n,n-二甲基甲酰胺二甲基缩醛与胺类化合物四组分原料在无溶剂和催化剂条件下加热到100℃保温反应2.0h，停止反应萃取洗涤，重结晶得到2-吡啶酮化合物，产物的纯度高达98.8%；

其反应原理如下：

本发明所述的高效绿色合成2-吡啶酮类化合物的方法制备得到吡啶酮化合物产品的纯度能达到98.9%以上。

本发明所述的目标物2-吡啶酮类化合物结构通式为：

其中，r¹为甲基，甲氧基；r²为苯，含三氟甲基、氰基、硝基、卤素、甲基、甲氧基、叔丁基、乙基等烷基或芳基取代的苯，甲基、乙基、丁基、环丙基等烷基。

本发明所述的高效绿色合成2-吡啶酮化合物的技术路线如下：

下面以具体实施案例对本发明做进一步说明：

本发明实施例中所用的材料或试剂的规格及检测仪器如无特别说明均为市售。

微波反应器：cemdiscover-sp微波合成仪

核磁仪：brukeravanceiii400mhz核磁仪

红外波谱仪：thermonicolets10ft-ir红外波谱仪

质谱仪：agilentlc/msdtofinstrument质谱仪器

熔点仪器：北京泰克techx-5熔点仪器

实施例1

实施例反应式如下：

该制备方法包括以下步骤：

微波条件下下，以甲酰乙酸乙酯或乙酰丙酮、乙酰乙酸乙酯、n,n-二甲基甲酰胺二甲基缩醛、苯胺类化合物为原料，四组分一起投入反应器中，升温到100℃保温反应2.0h，待有大量固体析出后停止反应，多次萃取后用石油醚、乙酸乙酯重结晶，过滤晶体洗涤，干燥得到2-吡啶酮化合物。

实施例中胺类化合物变化制备得到2-吡啶酮类化合物的得率情况如下：

上述化合物数据如下：

3-ethyl5-methyl6-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3,5-dicarboxylate5a:yield88%,264.87mg;paleyellowsolid;mp:111.2-111.7^oc.¹hnmr(cdcl3,400mhz,tms)δ8.80(s,1h,ch),7.55-7.47(m,3h,ph-h),7.14(d,j=7.6hz,2h,ph-h),4.35(q,j=7.2hz,2h,och2),3.86(s,3h,och3),2.43(s,3h,ch3),1.35(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.2,164.7,159.8,158.9,145.7,138.1,130.0,129.3,127.5,117.5,108.2,61.4,52.2,21.2,20.4,14.2.ir(kbr)(vmax,cm^-1):3446,1746,1710,1678,1603,1529,1490,1436,1370,1313,1254,1219,1091,863,778,708,597.hrms(esi-tof)m/zcalcdforc17h17nnao5⁺[m+na]⁺338.0999,found338.1002.

3-ethyl5-methyl1-(4-bromophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5b:yield52%,165.57mg;paleyellowsolid;mp:161.1-161.2^oc.¹hnmr(cdcl3,400mhz,tms)δ8.80(s,1h,ch),7.68(d,j=8.4hz,2h,ph-h),7.04(d,j=8.4hz,2h,ph-h),4.36(q,j=7.2hz,2h,och2),3.87(s,3h,och3),2.44(s,3h,ch3),1.35(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.1,164.5,159.6,158.5,145.9,137.0,133.4,129.3,123.5,117.6,108.4,61.5,52.3,20.4,14.2.ir(kbr)(vmax,cm^-1):3454,1705,1603,1533,1485,1429,1365,1314,1264,1213,1124,1067,1025,849,775,725,580.hrms(esi-tof)m/zcalcdforc17h16brnnao5⁺[m+na]⁺416.0104,found416.0109.

3-ethyl5-methyl1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5c:yield79%,229.98mg;paleyellowsolid;mp:105.3-105.6^oc.¹hnmr(cdcl3,400mhz,tms)δ8.78(s,1h,ch),7.26-7.19(m,2h,ph-h),7.13-7.10(m,2h,ph-h),4.36(q,j=7.2hz,2h,och2),2.43(s,3h,och3),1.39(t,j=7.2hz,3h,ch3),1.35(s,3h,ch3).¹³cnmr(cdcl3,100mhz)δ164.7,163.9(d,j=76.2hz),159.8,158.6,145.7,133.9(d,j=3.5hz),129.5(d,j=8.7hz),129.4,117.2,117.0,108.7,61.3,20.4,14.2.ir(kbr)(vmax,cm^-1):3410,1708,1606,1508,1442,1267,1031,860,571.hrms(esi-tof)m/zcalcdforc17h17nfo5⁺[m+h]⁺334.1088,found334.1085.

3-ethyl5-methyl6-methyl-2-oxo-1-(4-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3,5-dicarboxylate5d:yield72%,237.65mg;paleyellowsolid;mp:168.1-170.1^oc.¹hnmr(cdcl3,400mhz,tms)δ8.83(s,1h,ch),7.84(d,j=8hz,2h,ph-h),7.32(d,j=8hz,2h,ph-h),4.38(q,j=7.2hz,2h,och2),3.89(s,3h,och3),2.45(s,3h,ch3),1.37(t,j=6.8hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ164.6,164.5,159.6,157.9,146.0,141.3,128.5,127.3,127.2,117.8,109.0,61.5,61.4,20.4,14.2.ir(kbr)(vmax,cm^-1):3454,1717,1658,1532,1441,1322,1232,1192,1065,852,579.hrms(esi-tof)m/zcalcdforc18h16f3nnao5⁺[m+na]⁺406.0873,found406.0879.

3-ethyl5-methyl6-methyl-1-(4-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5e:yield49%,140.52mg;paleyellowsolid;mp:116.1-116.8^oc.¹hnmr(cdcl3,400mhz,tms)δ8.83(s,1h,ch),8.44(d,j=8.4hz,2h,ph-h),7.39(d,j=8.8hz,2h,ph-h),4.38(q,j=7.2hz,2h,och2),3.90(s,3h,och3),2.45(s,3h,ch3),1.35(t,j=6.8hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ164.5,157.2,148.2,145.5,129.6,125.4,124.1,61.7,53.6,20.8,14.2.ir(kbr)(vmax,cm^-1):3435,2324,1733,1661,1525,1441,1383,1238,1067,1010,863,647,548.hrms(esi-tof)m/zcalcdforc17h17n2o7⁺[m+h]⁺361.1030,found361.1035.

3-ethyl5-methyl6-methyl-2-oxo-1-(p-tolyl)-1,2-dihydropyridine-3,5-dicarboxylate5f:yield89%,260.18mg;paleyellowsolid;mp:158.2-162.4^oc.¹hnmr(cdcl3,400mhz,tms)δ8.81(s,1h,ch),7.34(d,j=8.0hz,2h,ph-h),7.02(d,j=7.6hz,2h,ph-h),4.36(q,j=7.2hz,2h,och2),3.88(s,3h,och3),2.45(s,3h,ch3),2.42(s,3h,ch3),1.36(t,j=8.0hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.3,159.2,145.7,139.4,135.4,130.7,127.2,117.3,108.1,61.4,52.2,21.2,20.4,14.2.ir(kbr)(vmax,cm^-1):3725,1703,1605,1535,1402,1370,1314,1263,1218,1091,1028,863,775,614.hrms(esi-tof)m/zcalcdforc18h19nnao5⁺[m+na]⁺352.1155,found352.1158.

3-ethyl5-methyl1-(4-ethylphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5g:yield80%,250.36mg;paleyellowsolid;mp:41.8-42.9^oc.¹hnmr(cdcl3,400mhz,tms)δ8.79(s,1h,ch),7.35(d,j=8.4hz,2h,ph-h),7.03(d,j=8.4hz,2h,ph-h),4.36(q,j=7.2hz,2h,och2),3.86(s,3h,och3),2.72(q,j=7.6hz,2h,ch2),2.44(s,3h,ch3),1.34(t,j=7.2hz,3h,ch3),1.27(t,j=7.6hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.3,164.8,159.8,159.2,145.6,145.5,135.6,129.4,127.2,117.4,108.1,61.3,52.1,28.5,20.4,15.2,14.2.ir(kbr)(vmax,cm^-1):3412,1707,1678,1604,1531,1437,1367,1265,1220,1063,862,798,774,686,549.hrms(esi-tof)m/zcalcdforc19h22no5⁺[m+h]⁺344.1489,found344.1492.

3-ethyl5-methyl1-(4-isopropylphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5h:yield85%,268.05mg;paleyellowsolid;mp:162.1-163.7^oc.¹hnmr(cdcl3,400mhz,tms)δ8.79(s,1h,ch),7.38(d,j=8.4hz,2h,ph-h),7.04(d,j=8.4hz,2h,ph-h),4.35(q,j=7.2hz,2h,och2),3.86(s,3h,och3),2.98(m,1h,ch),2.44(s,3h,ch3),1.35(t,j=7.2hz,3h,ch3),1.28-1.27(m,6h,ch3).¹³cnmr(cdcl3,100mhz)δ165.3,164.9,159.8,159.2,150.1,145.6,135.6,128.0,127.2,117.4,108.0,61.3,52.1,33.8,23.8,20.4,14.2.ir(kbr)(vmax,cm^-1):3412,2959,1698,1677,1602,1581,1427,1371,1314,1258,1220,1033,844,800,688,571.hrms(esi-tof)m/zcalcdforc20h24no5⁺[m+h]⁺358.1648,found358.1649.

3-ethyl5-methyl1-(4-(tert-butyl)phenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5i:yield78%,252.57mg;paleyellowsolid;mp:189.1-191.2^oc.¹hnmr(cdcl3,400mhz,tms)δ8.79(s,1h,ch),7.53(d,j=8.4hz,2h,ph-h),7.05(d,j=8.4hz,2h,ph-h),4.35(q,j=7.2hz,2h,och2),3.86(s,3h,och3),2.44(s,3h,ch3),1.36-1.33(m,12h,ch3).¹³cnmr(cdcl3,100mhz)δ165.3,164.9,159.8,159.3,152.4,145.6,135.3,126.9,117.4,108.0,61.3,52.1,34.8,31.2,20.4,14.2.ir(kbr)(vmax,cm^-1):3414,1705,1432,1272,1029,861,774,569.hrms(esi-tof)m/zcalcdforc21h26no5⁺[m+h]⁺372.1803,found372.1805.

3-ethyl5-methyl1-(4-methoxyphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5j:yield86%,262.46mg;paleyellowsolid;mp:128.9-130^oc.¹hnmr(cdcl3,400mhz,tms)δ8.79(s,1h,ch),7.03(m,4h,ph-h),4.36(q,j=8.0hz,2h,och2),3.87(s,3h,och3),3.85(s,3h,och3),2.45(s,3h,ch3),1.37(t,j=8.0hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.3,159.9,159.5,145.7,145.6,130.6,128.5,117.3,115.2,108.5,108.1,61.4,55.5,20.5,14.2.ir(kbr)(vmax,cm^-1):3451,2983,1700,1607,1510,1441,1369,1315,1260,1216,1144,1091,1027,830,775,684,562.hrms(esi-tof)m/zcalcdforc18h20no6⁺[m+h]⁺346.1285,found346.1293.

3-ethyl5-methyl1-(3-bromophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5k:yield57%,185.28mg;paleyellowsolid;mp:147.3-148.3^oc.¹hnmr(cdcl3,400mhz,tms)δ8.84(s,1h,ch),8.44(d,j=8.4hz,2h,ph-h),7.40(d,j=8.4hz,2h,ph-h),4.38(q,j=7.2hz,2h,och2),3.90(s,3h,och3),2.45(s,3h,ch3),1.37(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ164.7,164.6,159.6,158.3,146.0,139.2,132.6,131.2,130.9,126.5,123.4,117.7,108.8,61.5,61.4,20.4,14.3,14.2.ir(kbr)(vmax,cm^-1):3405,1705,1579,1533,1438,1357,1254,1032,859,796,773,676,552.hrms(esi-tof)m/zcalcdforc17h16brnnao5⁺[m+na]⁺416.0104,found416.0110.

3-ethyl5-methyl6-methyl-2-oxo-1-(m-tolyl)-1,2-dihydropyridine-3,5-dicarboxylate5l:yield90%,263.48mg;paleyellowsolid;mp:45.1-46.5^oc.¹hnmr(cdcl3,400mhz,tms)δ8.79(s,1h,ch),7.42-7.26(m,2h,ph-h),6.94-6.91(m,2h,ph-h),4.34(q,j=7.2hz,2h,och2),2.44(s,3h,och3),2.38(s,3h,ch3),1.39(t,j=7.2hz,3h,ch3),1.33(s,3h,ch3),.¹³cnmr(cdcl3,100mhz)δ164.9,164.8,159.8,158.8,145.7,140.2,138.1,130.0,129.8,128.0,124.4,117.5,108.5,61.4,61.2,21.3,20.4,14.3,14.2.ir(kbr)(vmax,cm^-1):3418,2987,1698,1603,1532,1448,1372,1266,1237,1033,861,798,775,709,574.hrms(esi-tof)m/zcalcdforc18h20no5⁺[m+h]⁺330.1338,found330.1336.

3-ethyl5-methyl1-(3-methoxyphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5m:yield81%,245.20mg;paleyellowsolid;mp:132.6-133.4^oc.¹hnmr(cdcl3,400mhz,tms)δ8.78(s,1h,ch),7.43-7.26(m,h,ph-h),7.00-6.97(m,h,ph-h),6.71-6.64(m,2h,ph-h),4.33(q,j=7.2hz,2h,och2),3.85(s,3h,och3),3.78(s,3h,och3),2.45(s,3h,ch3),1.33(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)165.2,164.7,160.9,159.7159.0,145.7,139.0,130.8,119.5,117.3,115.2,113.0,108.1,61.4,55.4,52.2,29.6,20.2,14.2.ir(kbr)(vmax,cm^-1):δ3392,2827,1720,1632,1531,1438,1260,1214,1071,860,755,560.hrms(esi-tof)m/zcalcdforc18h20no6⁺[m+h]⁺346.1291,found346.1294.

3-ethyl5-methyl6-methyl-2-oxo-1-(o-tolyl)-1,2-dihydropyridine-3,5-dicarboxylate5n:yield86%,250.30mg;paleyellowsolid;mp:134.8-137^oc.¹hnmr(cdcl3,400mhz,tms)δ8.84(s,1h,ch),7.38-7.35(m,3h,ph-h),7.04-7.02(m,1h,ph-h),4.38(q,j=7.2hz,2h,och2),3.89(s,3h,och3),2.40(s,3h,ch3),2.06(s,3h,ch3),1.41-1.35(t,j=7.6hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.2,164.7,159.1,158.9,145.8,137.3134.7,131.5,129.5,127.7,117.4,108.1,61.4,52.2,19.6,17.2,14.2.ir(kbr)(vmax,cm^-1):3785,3382,2315,1696,1438,1261,1068,1023,861,549.hrms(esi-tof)m/zcalcdforc18h19nnao5⁺[m+na]⁺352.1155,found352.1157.

3-ethyl5-methyl1-(2-isopropylphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5o:yield60%,178.70mg;paleyellowsolid;mp:49.1-50.6^oc.¹hnmr(cdcl3,400mhz,tms)δ8.79(s,1h,ch),7.47-7.45(m,2h,ph-h),7.33-6.96(m,2h,ph-h),4.35(q,j=7.2hz,2h,och2),3.87(s,3h,och3),2.51-2.44(m,1h,ch),2.39(s,3h,ch3),1.35(t,j=7.2hz,3h,ch3),1.17-1.14(m,6h,ch3).¹³cnmr(cdcl3,100mhz)δ165.3,164.7,159.3,159.1,145.4,145.1,135.8,129.9,127.4,127.3,117.6,107.8,61.3,52.1,28.2,24.0,23.1,20.1,14.2.ir(kbr)(vmax,cm^-1):3400,2963,2960,1698,1680,1599,1528,1488,1434,1371,1255,1227,1033,860,762,687,570.hrms(esi-tof)m/zcalcdforc20h24no5⁺[m+h]⁺358.1646,found358.1649.

3-ethyl5-methyl1-(2-methoxyphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5p:yield85%,259.01mg;paleyellowsolid;mp:134.7-139.5^oc.¹hnmr(cdcl3,400mhz,tms)δ8.79(s,1h,ch),7.41(m,1h,ph-h),7.06-7.01(m,3h,ph-h),4.33(q,j=7.2hz,2h,och2),3.84(s,3h,och3),3.73(s,3h,och3),2.40(s,3h,ch3),1.37(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.3,164.8,159.9,159.3,154.0,145.8,130.9,128.7,126.5,121.3,117.1,112.1,107.9,61.2,55.7,52.1,19.3,14.2.ir(kbr)(vmax,cm^-1):3430,2925,1713,1602,1531,1438,1320,1260,1071,860,802,755,573.hrms(esi-tof)m/zcalcdforc18h19nnao6⁺[m+na]⁺368.1105,found368.1109.

3-ethyl5-methyl1-(4-methoxy-3-methylphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate5q:yield86%,272.94mg;paleyellowsolid;mp:108.2-110.8^oc.¹hnmr(cdcl3,400mhz,tms)δ8.78(s,1h,ch),6.92-6.88(m,3h,ph-h),4.36(q,j=7.2hz,2h,och2),3.87(s,6h,och3),2.47(s,3h,ch3),2.22(s,3h,ch3),1.36(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.3,164.9,159.6,158.1,145.5,130.1,129.2,128.8,125.6,117.4,110.7,108.0,61.3,55.5,52.1,20.4,16.3,14.2.ir(kbr)(vmax,cm^-1):3450,2579,1720,1607,1514,1441,1395,1315,1270,1206,1091,1027,830,785,684,560.hrms(esi-tof)m/zcalcdforc19h22no6⁺[m+h]⁺360.1447,found360.1448.

ethyl5-acetyl-6-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate5r:yield85%,224.49mg;paleyellowsolid;mp:113.2-115.5^oc.¹hnmr(cdcl3,400mhz,tms)δ8.70(s,1h,ch),7.56-7.49(m,3h,ph-h),7.15-7.13(m,2h,ph-h),4.39(q,j=6.8hz,2h,och2),2.59(s,3h,ch3),2.38(s,3h,ch3),1.37(t,j=6.8hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.3,165.0,159.4,158.7,145.3,138.0,130.1,129.3,127.4,116.7,116.2,61.6,29.3,20.8,14.2.ir(kbr)(vmax,cm^-1):3404,2386,2026,1667,1588,1441,1361,1262,1071,860,794,689,548.hrms(esi-tof)m/zcalcdforc17h17nnao4⁺[m+na]⁺322.1050,found322.1049.

ethyl5-acetyl-1-(4-bromophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate5s:yield47%,139.94mg;paleyellowsolid;mp:173.2-181.3^oc.¹hnmr(cdcl3,400mhz,tms)δ8.69(s,1h,ch),7.69(d,j=7.6hz,2h,ph-h),7.03(d,j=8.4hz,2h,ph-h),4.38(q,j=7.2hz,2h,och2),2.58(s,3h,ch3),2.39(s,3h,ch3),1.37(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ195.1,163.7,158.2,157.2,144.3,135.9,132.3,128.2,122.6,115.9,115.3,60.6,30.9,28.6,21.6,13.0.ir(kbr)(vmax,cm^-1):3407,1701,1666,1587,1519,1440,1378,1261,1224,1040,863,797,573.hrms(esi-tof)m/zcalcdforc17h16brnnao4⁺[m+na]⁺400.0155,found400.0159.

ethyl5-acetyl-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate5t:yield76%,209.43mg;paleyellowsolid;mp:111.9-112.6^oc.¹hnmr(cdcl3,400mhz,tms)δ8.67(s,1h,ch),7.24-7.20(m,2h,ph-h),7.13-7.09(m,2h,ph-h),4.37(q,j=7.2hz,2h,och2),2.56(s,3h,ch3),2.37(s,3h,ch3),2.39(s,3h,ch3),1.35(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ195.2,163.8,160.5,158.4,157.5,144.3,132.8(d,j=3.5hz),132.7,128.4(d,j=8.7hz),128.3,116.3,116.3(d,j=23.0hz),115.360.6,28.3,19.8,13.2.ir(kbr)(vmax,cm^-1):3410,3074,2985,1710,1661,1587,1504,1441,1374,1258,1136,1021,953,846,796,590,544.hrms(esi-tof)m/zcalcdforc17h17nfo4⁺[m+h]⁺318.1132,found318.1136.

ethyl5-acetyl-6-methyl-2-oxo-1-(4-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxylate5u:yield89%,290.18mg;palewhitesolid;mp:195.4-197.4^oc.¹hnmr(cdcl3,400mhz,tms)δ8.71(s,1h,ch),7.84(d,j=8hz,2h,ph-h),7.31(d,j=7.6hz,2h,ph-h),4.39(q,j=6.8hz,2h,och2),2.60(s,3h,ch3),2.38(s,3h,ch3),1.37(t,j=6.8hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.1,164.6,159.1,157.8,145.5,141.4,128.4,127.3,117.1,116.5,61.7,29.3,20.8,14.2.ir(kbr)(vmax,cm^-1):3130,2301,1667,1441,1380,1325,1263,1122,1066,1010,863,797,739,549.hrms(esi-tof)m/zcalcdforc18h16f3nnao4⁺[m+na]⁺390.0924,found390.0926.

ethyl5-acetyl-6-methyl-1-(4-nitrophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate5v:yield50%,137.73mg;paleyellowsolid;mp:192.5-194.7^oc.¹hnmr(cdcl3,400mhz,tms)δ8.72(s,1h,ch),8.44(d,j=8.8hz,2h,ph-h),7.39(d,j=8.4hz,2h,ph-h),4.40(q,j=7.2hz,2h,och2),2.60(s,3h,ch3),2.38(s,3h,ch3),1.38(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.0,164.4,157.2,148.2,145.5,143.5,129.2,125.4,117.3,116.7,61.8,29.4,20.8,14.2.ir(kbr)(vmax,cm^-1):3378,2300,1698,1662,1592,1527,1441,1351,1261,1120,1067,1009,862,738,549.hrms(esi-tof)m/zcalcdforc17h16n2nao6⁺[m+na]⁺367.0901,found367.0909.

ethyl5-acetyl-6-methyl-2-oxo-1-(p-tolyl)-1,2-dihydropyridine-3-carboxylate5w:yield87%,241.28mg;paleyellowsolid;mp:148.1-150.6^oc.¹hnmr(cdcl3,400mhz,tms)δ8.69(s,1h,ch),7.34(d,j=7.2hz,2h,ph-h),7.02(d,j=7.6hz,2h,ph-h),4.38(q,j=6.8hz,2h,och2),2.58(s,3h,ch3),2.42(s,3h,ch3),2.39(s,3h,ch3),1.37(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.3,165.0,159.5,158.9,145.2,139.4,135.3,130.7,127.1,116.6,116.1,61.5,29.3,21.2,20.9,14.2.ir(kbr)(vmax,cm^-1):3385,1709,1668,1588,1504,1440,1371,1262,1070,862,733,549.hrms(esi-tof)m/zcalcdforc18h19nnao4⁺[m+na]⁺336.1206,found336.1208.

ethyl5-acetyl-1-(4-ethylphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate5x:yield80%,229.16mg;paleyellowsolid;mp:183.1-184.3^oc.¹hnmr(cdcl3,400mhz,tms)δ8.68(s,1h,ch),7.35(d,j=8.4hz,2h,ph-h),7.03(d,j=8.4hz,2h,ph-h),4.36(q,j=7.2hz,2h,och2),2.72(q,j=7.6hz,2h,ch2),2.57(s,3h,ch3),2.38(s,3h,ch3),1.35(t,j=7.2hz,3h,ch3),1.26(t,j=7.6hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.3,165.1,159.5,158.9,145.5,145.2,135.4,129.5,127.1,116.6,116.1,61.5,29.3,28.5,20.9,15.2,14.2.ir(kbr)(vmax,cm^-1):3412,2960,1704,1664,1589,1503,1453,1374,1297,1254,1216,1053,866,796,695,649,572,554.hrms(esi-tof)m/zcalcdforc19h22no4⁺[m+h]⁺328.1539,found328.1543.

ethyl5-acetyl-1-(4-isopropylphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate5y:yield70%,204.84mg;paleyellowsolid;mp:181.5-182.2^oc.¹hnmr(cdcl3,400mhz,tms)δ8.68(s,1h,ch),7.38(d,j=8.4hz,2h,ph-h),7.03(d,j=8.4hz,2h,ph-h),4.37(q,j=7.2hz,2h,och2),2.98(m,1h,ch),2.57(s,3h,ch3),2.38(s,3h,ch3),1.35(t,j=7.2hz,3h,ch3),1.28-1.26(m,6h,ch3).¹³cnmr(cdcl3,100mhz)δ196.3,165.1,159.5,159.0,150.1,145.2,135.5,128.0,127.1,126.8,116.6,116.1,61.5,33.8,31.2,29.3,23.8,20.9,14.2.ir(kbr)(vmax,cm^-1):3413,2958,1701,1663,1587,1500,1442,1373,1252,1218,1029,866,796,570.hrms(esi-tof)m/zcalcdforc20h24no4⁺[m+h]⁺342.1695,found342.1700.

ethyl5-acetyl-1-(4-(tert-butyl)phenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate5z:yield86%,270.1249mg;paleyellowsolid;mp:78.1-79.6^oc.¹hnmr(cdcl3,400mhz,tms)δ8.68(s,1h,ch),7.53(d,j=8.8hz,2h,ph-h),7.04(d,j=8.8hz,2h,ph-h),4.36(q,j=7.2hz,2h,och2),2.57(s,3h,ch3),2.38(s,3h,ch3),1.37-1.33(m,12h,ch3).¹³cnmr(cdcl3,100mhz)δ196.3,165.1,159.5,159.0,152.4,145.2,135.2,127.0,126.8,116.6,116.1,61.5,34.8,31.2,29.3,20.9,14.2.ir(kbr)(vmax,cm^-1):3413,2965,1701,1664,1588,1502,1443,1373,1256,1217,1029,866,795,571.hrms(esi-tof)m/zcalcdforc21h26no4⁺[m+h]⁺356.1851,found356.1856.

ethyl5-acetyl-1-(4-methoxyphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate6a:yield90%,263.48mg;paleyellowsolid;mp:179.7-180.6^oc.¹hnmr(cdcl3,400mhz,tms)δ8.68(s,1h,ch),7.03(m,4h,ph-h),4.38(q,j=7.2hz,2h,och2),3.85(s,3h,och3),2.58(s,3h,ch3),2.40(s,3h,ch3),1.37(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.3,165.0,160.0,159.7,159.2,145.2,130.4,116.6,116.1,115.3,61.5,55.5,29.3,20.9,14.2.ir(kbr)(vmax,cm^-1):3383,2026,1702,1664,1588,1506,1439,1376,1257,1219,1069,1031,863,796,550.hrms(esi-tof)m/zcalcdforc18h19nnao5⁺[m+na]⁺352.1155,found352.1158.

ethyl5-acetyl-1-(3-bromophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate6b:yield45%,132.38mg;paleyellowsolid;mp:118.9-126.3^oc.¹hnmr(cdcl3,400mhz,tms)δ8.68(s,1h,ch),7.64(m,h,ph-h),7.42(m,h,ph-h),7.33(m,h,ph-h)7.10(m,h,ph-h)4.38(q,j=7.2hz,2h,och2),2.57(s,3h,ch3),2.39(s,3h,ch3)1.36(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.1,164.7,159.2,158.1,145.4,139.0,132.7,131.2,130.8,126.3,123.5,116.9,116.4,61.7,29.3,20.8,14.2.ir(kbr)(vmax,cm^-1):3402,1704,1663,1587,1509,1440,1376,1253,1219,1039,862,797,741,671,572,550.hrms(esi-tof)m/zcalcdforc17h16brnnao4⁺[m+na]⁺400.0155,found400.0162.

ethyl5-acetyl-1-(3-methoxyphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate6c:yield81%,233.84mg;paleyellowsolid;mp:178.2-179.6^oc.¹hnmr(cdcl3,400mhz,tms)δ8.69(s,1h,ch),7.46-7.00(m,2h,ph-h),6.73-6.65(m,2h,ph-h),4.38(q,j=7.2hz,2h,och2),3.81(s,3h,och3),2.58(s,3h,ch3),2.42(s,3h,ch3),1.37(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.2,165.0,160.9,159.3,158.7,145.3,139.0,130.8,119.5,116.1,115.2,113.1,61.6,55.4,29.3,20.7,14.2.ir(kbr)(vmax,cm^-1):3379,2310,1679,1654,1593,1502,1436,1237,1217,1067,866,762,551.hrms(esi-tof)m/zcalcdforc18h20no5⁺[m+h]⁺330.1336,found330.1338.

ethyl5-acetyl-6-methyl-2-oxo-1-(o-tolyl)-1,2-dihydropyridine-3-carboxylate6d:yield86%,238.14mg;paleyellowsolid;mp:129.9-131.3^oc.¹hnmr(cdcl3,400mhz,tms)δ8.73(s,1h,ch),7.38-7.35(m,3h,ph-h),7.03-7.01(m,1h,ph-h),4.39(q,j=6.8hz,2h,och2),2.59(s,3h,ch3),2.34(s,3h,ch3),2.05(s,3h,ch3),1.37(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.2,165.0,158.7,145.4,137.2,134.6,131.6,129.6,127.7,127.2,116.7,116.1,61.6,29.3,20.0,17.2,14.2.ir(kbr)(vmax,cm^-1):3130,2987,2317,1704,1662,1584,1511,1444,1374,1255,1219,1138,1037,862,798,742,548.hrms(esi-tof)m/zcalcdforc18h19nnao4⁺[m+na]⁺336.1206,found336.1205.

ethyl5-acetyl-1-(2-isopropylphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate6e:yield69%,201.43mg;paleyellowsolid;mp:171.9-173.1^oc.¹hnmr(cdcl3,400mhz,tms)δ8.68(s,1h,ch),7.49-7.43(m,2h,ph-h),7.33-6.95(m,2h,ph-h),4.37(q,j=7.2hz,2h,och2),2.58(s,3h,ch3),2.50-2.43(m,1h,ch),2.34(s,3h,ch3),1.35(t,j=7.2hz,3h,ch3),1.17-1.14(m,6h,ch3).¹³cnmr(cdcl3,100mhz)δ196.1,165.0,159.0,145.1,135.7,129.9,127.4,127.3,116.8,115.7,61.4,29.3,28.2,24.0,23.1,20.6,14.2.ir(kbr)(vmax,cm^-1):3403,2994,2960,1700,1664,1588,1509,1486,1449,1376,1310,1257,1222,1032,950,862,761,706,558.hrms(esi-tof)m/zcalcdforc20h24no4⁺[m+h]⁺342.1696,found342.1700.

ethyl5-acetyl-1-(2-methoxyphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate6f:yield85%,247.01mg;paleyellowsolid;mp:177.5-178.7^oc.¹hnmr(cdcl3,400mhz,tms)δ8.71(s,1h,ch),7.47-7.43(m,1h,ph-h),7.09-7.04(m,3h,ph-h),4.38(q,j=6.8hz,2h,och2),3.77(s,3h,och3),2.58(s,3h,ch3),2.38(s,3h,ch3),1.37(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.3,165.1,159.7,158.9,153.9,145.5,130.9,128.6,126.4,121.4,116.4,115.9,112.1,61.5,55.7,29.3,19.7,14.3.ir(kbr)(vmax,cm^-1):3381,2319,1698,1665,1593,1502,1442,1375,1262,1217,1067,862,741,548.hrms(esi-tof)m/zcalcdforc18h19nnao5⁺[m+na]⁺352.1155,found352.1157.

ethyl5-acetyl-1-(4-methoxy-3-methylphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate6g:yield85%,257.53mg;paleyellowsolid;mp:126.1-127.2^oc.¹hnmr(cdcl3,400mhz,tms)δ8.68(s,1h,ch),6.92-6.88(m,3h,ph-h),4.37(q,j=7.2hz,2h,och2),3.87(s,3h,och3),2.57(s,3h,ch3),2.41(s,3h,ch3),2.21(s,3h,ch3),1.36(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.4,165.2,159.8,158.1,145.3,129.9,129.1,128.8,125.5,116.4,116.1,110.7,61.6,55.5,29.4,21.0,16.3,14.2.ir(kbr)(vmax,cm^-1):3376,2041,1789,1662,1576,1506,1420,1272,1209,1069,1022,853,796,557.hrms(esi-tof)m/zcalcdforc19h22no5⁺[m+h]⁺344.1498,found344.1499.

实施例2

实施例反应式如下：

该制备方法包括以下步骤：

微波条件下下，以甲酰乙酸乙酯或乙酰丙酮、乙酰乙酸乙酯、n,n-二甲基甲酰胺二甲基缩醛、烷胺类化合物为原料，四组分一起投入反应器中，升温到100℃保温反应2.0h，待有大量固体析出后停止反应，多次萃取后用石油醚、乙酸乙酯重结晶，过滤晶体洗涤，干燥得到2-吡啶酮化合物。

实施例中胺类化合物变化制备得到2-吡啶酮类化合物的得率情况如下：

上述化合物数据如下：

3-ethyl5-methyl1,6-dimethyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate7a:yield75%,164.61mg;paleyellowsolid;mp:100.8-102.6^oc.¹hnmr(cdcl3,400mhz,tms)δ8.67(s,1h,ch),4.73(s,1h,nch),4.38(q,j=7.2hz,2h,och2),3.86(s,3h,och3),3.64(s,3h,nch3)2.85(s,3h,ch3),1.38(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.4,164.7,159.6,158.3,144.4,116.3,108.2,61.3,52.2,32.1,18.6,14.3.ir(kbr)(vmax,cm^-1):3419,2026,1662,1601,1587,1523,1442,1371,1252,1059,860,549.hrms(esi-tof)m/zcalcdforc12h15nnao5⁺[m+na]⁺276.0842,found276.0844.

3-ethyl5-methyl1-isopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate7b:yield78%,191.29mg;palewhitesolid;mp:144-148.4^oc.¹hnmr(cdcl3,400mhz,tms)δ8.55(s,1h,ch),4.73(s,1h,nch),4.36(q,j=7.2hz,2h,och2),3.83(s,3h,och3),2.82(s,3h,ch3),1.68-1.62(m,6h,ch3,ch3).¹³cnmr(cdcl3,100mhz)δ165.9,164.6,159.9,144.1,108.6,61.2,52.2,19.5,18.4,14.3.ir(kbr)(vmax,cm^-1):3406,1697,1669,1603,1534,1431,1361,1299,1253,1030,860,801,775,550.hrms(esi-tof)m/zcalcdforc14h19nnao5⁺[m+na]⁺304.1155,found304.1160.

3-ethyl5-methyl1-butyl-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate7c:yield72%,183.11mg;viscousliquid;¹hnmr(cdcl3,400mhz,tms)δ8.59(s,1h,ch),4.32(q,j=6.8hz,2h,och2),4.08(s,2h,nch2)3.80(s,3h,och3),2.81(s,3h,ch3)1.62(s,2h,ch2),1.34(m,5h,ch2,ch3)0.91(m,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.4,164.7,159.2,157.8,144.4,116.3,108.2,61.2,52.1,45.3,30.0,20.2,17.9,14.3,13.5.ir(kbr)(vmax,cm^-1):3435,2961,1715,1668,1603,1536,1436,1370,1300,1232,1148,1069,1033,959,861,804,778,685,547.hrms(esi-tof)m/zcalcdforc15h21nnao5⁺[m+na]⁺318.1312,found318.1317.

3-ethyl5-methyl1-cyclopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate7d:yield80%,195.50mg;palewhitesolid;mp:122.8-124.4^oc.¹hnmr(cdcl3,400mhz,tms)δ8.61(s,1h,ch),4.37(q,j=7.2hz,2h,och2),3.85(s,3h,och3),2.92(m,4h,nch,ch3),1.37(t,j=6.8hz,3h,ch3),0.84(m,4h,2ch2).¹³cnmr(cdcl3,100mhz)δ165.3,164.6,161.2,160.7,144.2,117.2,108.1,61.2,52.0,29.7,19.5,14.3,11.2.ir(kbr)(vmax,cm^-1):3403,1736,1708,1662,1599,1533,1433,1311,1223,1132,1037,861,779,571.hrms(esi-tof)m/zcalcdforc14h17nnao5⁺[m+na]⁺302.0999,found302.1003.

3-ethyl5-methyl1-cyclohexyl-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate7e:yield85%,241.03mg;paleyellowsolid;mp:155.9-156.5^oc.¹hnmr(cdcl3,400mhz,tms)δ8.54(s,1h,ch),4.35(q,j=7.2hz,2h,och2),3.83(s,3h,och3),2.81(s,3h,ch3),1.88-1.86(m,4h,ch2),1.65(s,1h,nch),1.37-1.33(m,7h,ch2ch3).¹³cnmr(cdcl3,100mhz)δ165.9,164.7,160.1,144.0,108.7,61.2,52.2,28.0,26.5,25.0,14.4.ir(kbr)(vmax,cm^-1):3394,1696,1575,1536,1441,1366,1242,1035,861,800,548.hrms(esi-tof)m/zcalcdforc17h24no5⁺[m+h]⁺322.1644,found322.1649.

ethyl5-acetyl-1,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate7f:yield72%,147.10mg;paleyellowsolid;mp:93.4-95.3^oc.¹hnmr(cdcl3,400mhz,tms)δ8.55(s,1h,ch),4.40(q,j=7.2hz,2h,och2),3.64(s,3h,nch3),2.77(s,3h,ch3)2.54(s,3h,ch3),1.40(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.5,164.9,159.2,158.0,143.9,116.4,115.5,61.4,32.1,29.3,18.9,14.3.ir(kbr)(vmax,cm^-1):3386,2321,1734,1703,1659,1590,1521,1427,1371,1305,1254,1223,1113,1023,865,796,739,655,550.hrms(esi-tof)m/zcalcdforc12h15nnao4⁺[m+na]⁺260.0893,found260.0894.

ethyl5-acetyl-1-isopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate7g:yield68%,153.88mg;palewhitesolid;mp:133.4-133.7^oc.¹hnmr(cdcl3,400mhz,tms)δ8.45(s,1h,ch),4.40(q,j=6.8hz,2h,och2),2.75(s,3h,ch3)2.53(s,3h,ch3),1.65-1.63(m,6h,2ch3),1.39(t,j=6.8hz,3h,ch3),1.25(s,1h,nch).¹³cnmr(cdcl3,100mhz)δ197.1,164.8,159.5,143.5,116.9,61.3,29.6,19.5,18.8,14.3.ir(kbr)(vmax,cm^-1):3407,2026,1659,1587,1519,1442,1378,1245,1071,860,549.hrms(esi-tof)m/zcalcdforc14h19nnao4⁺[m+na]⁺288.1206,found288.1210.

ethyl5-acetyl-1-butyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate7h:yield68%,162.01mg;viscousliquid;¹hnmr(cdcl3,400mhz,tms)δ8.47(s,1h,ch),4.33(m,2h,och2),4.08(s,2h,nch2)2.73(s,3h,ch3),2.48(s,3h,ch3)1.61(s,2h,ch2),1.36(m,5h,ch2,ch3)0.91(m,3h,ch3).¹³cnmr(cdcl3,100mhz)δ196.6,164.9,158.8,157.5,144.0,129.7,117.1,116.4,115.5,61.3,45.3,30.0,29.3,20.2,18.214.3,13.5.ir(kbr)(vmax,cm^-1):3389,2964,1737,1658,1593,1526,1424,1372,1297,1233,1129,1069,1030,862,802,752,551.hrms(esi-tof)m/zcalcdforc15h21nnao4⁺[m+na]⁺302.1363,found302.1368.

ethyl5-acetyl-1-cyclopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate7i:yield70%,157.97mg;paleyellowsolid;mp:86.9-88.1^oc.¹hnmr(cdcl3,400mhz,tms)δ8.51(s,1h,ch),4.39(q,j=7.2hz,2h,och2),2.92(s,1h,nch),2.87(s,3h,ch3),2.52(s,3h,ch3),1.40-1.37(m,5h,ch2ch3),0.84-0.83(m,2h,ch2).¹³cnmr(cdcl3,100mhz)δ196.2,164.8,161.1,160.3,144.0,116.3,116.1,61.4,29.7,29.3,20.1,14.3,11.2.ir(kbr)(vmax,cm^-1):3388,1667,1585,1523,1443,1259,1070,860,549.hrms(esi-tof)m/zcalcdforc14h17nnao4⁺[m+na]⁺286.1050,found286.1052.

ethyl5-acetyl-1-cyclohexyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate7j:yield82%,219.87mg;paleyellowsolid;mp:126.1-127.4^oc.¹hnmr(cdcl3,400mhz,tms)δ8.42(s,1h,ch),4.39(m,2h,och2),2.74(s,3h,ch3),2.52(s,3h,ch3),1.89-1.88(m,4h,ch2),1.66(s,1h,nch3),1.39-1.37(m,9h,ch2ch3).¹³cnmr(cdcl3,100mhz)δ197.1,164.9,159.7,143.4,117.0,61.3,29.5,26.4,24.9,14.3.ir(kbr)(vmax,cm^-1):3138,1697,1663,1590,1448,1294,1242,1035,862,797,740,550.hrms(esi-tof)m/zcalcdforc17h24no4⁺[m+h]⁺306.1692,found306.1700.

实施例3

实施例反应式如下：

该制备方法包括以下步骤：

微波条件下下，以甲酰乙酸乙酯或乙酰丙酮、乙酰乙酸乙酯、n,n-二甲基甲酰胺二甲基缩醛、其他胺类化合物为原料，四组分一起投入反应器中，升温到100℃保温反应2.0h，待有大量固体析出后停止反应，多次萃取后用石油醚、乙酸乙酯重结晶，过滤晶体洗涤，干燥得到2-吡啶酮化合物。

实施例中胺类化合物变化制备得到2-吡啶酮类化合物的得率情况如下：

上述化合物数据如下：

3-ethyl5-methyl1-benzyl-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate8a:yield73%,207.49mg;paleyellowsolid;mp:115.4-116.8^oc.¹hnmr(cdcl3,400mhz,tms)δ8.73(s,1h,ch),7.33-7.28(m,3h,ph-h),7.15-7.13(d,2h,ph-h),5.48(s,2h,nch2),4.42(q,j=7.0hz,2h,och2),3.85(s,3h,och3),2.78(s,3h,ch3),1.40(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.4,164.6,159.7,158.8,145.0,135.0,128.9,127.7,126.4,126.8,116.8,108.6,61.4,52.3,48.1,18.4,14.3.ir(kbr)(vmax,cm^-1):3379,2315,1707,1528,1369,1241,1068,862,740,547.hrms(esi-tof)m/zcalcdforc18h19nnao5⁺[m+na]⁺352.1155,found352.1156.

3-ethyl5-methyl1-benzhydryl-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate8b:yield65%,222.99mg;paleyellowsolid;mp:135.4-136.9^oc.¹hnmr(cdcl3,400mhz,tms)δ8.75(s,1h,ch),8.25(s,1h,nch),7.36-7.30(m,6h,ph-h),7.22-7.21(m,4h,ph-h),4.39(q,j=6.4hz,2h,och2),3.83(s,3h,och3),2.44(s,3h,ch3),1.38(t,j=6.8hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.2,164.6,160.3,159.9,145.0,137.0,128.6,127.9,127.6,116.9,109.1,61.4,52.2,22.0,14.3,14.2.ir(kbr)(vmax,cm^-1):3419,2986,1698,1671,1602,1524,1440,1373,1248,1143,1029,861,800,777,698,581.hrms(esi-tof)m/zcalcdforc24h23nnao5⁺[m+na]⁺428.1468,found428.1463.

3-ethyl5-methyl6-methyl-1-(naphthalen-1-yl)-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate8c:yield62%,190.00mg;paleyellowsolid;mp:113.9-116.7^oc.¹hnmr(cdcl3,400mhz,tms)δ8.93(s,1h,ch),7.96-7.90(m,2h,ph-h),7.58-7.44(m,3h,ph-h),7.32-7.26(m,2h,ph-h),4.37(q,j=7.2hz,2h,och2),3.90(s,3h,och3),2.36(s,3h,ch3),1.34(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ165.2,164.8,159.8,159.7,146.0,134.7,134.5,129.9,128.7,128.0,126.9,125.7,125.6,121.2,117.6,108.4,61.5,52.2,19.6,14.2.ir(kbr)(vmax,cm^-1):3411,1699,1677,1604,1532,1438,1370,1313,1255,1231,1042,861,802,778,737,550.hrms(esi-tof)m/zcalcdforc21h19nnao5⁺[m+na]⁺388.1155,found388.1163.

3-ethyl5-methyl1-(furan-2-ylmethyl)-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylate8d:yield88%,249.06mg;whiteyellowsolid;mp:98.2-99.6^oc.¹hnmr(cdcl3,400mhz,tms)δ8.47(s,1h,ch),7.26-7.21(m,1h,ch),6.40-6.25(m,2h,ch),5.31(s,2h,nch2),4.33(q,j=7.2hz,2h,och2),2.88(s,3h,ch3),2.47(s,3h,ch3),1.32(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ195.6,163.6,157.7,158.9,156.9,147.3,143.2,141.3,115.7,115.0,109.7,109.4,60.4,40.2,28.4,17.5,13.3.ir(kbr)(vmax,cm^-1):3145,3123,2989,1713,1662,1589,1521,1439,1380,1247,1028,860,802,778,569.hrms(esi-tof)m/zcalcdforc16h18no6⁺[m+h]⁺320.1125,found320.1129.

ethyl5-acetyl-1-benzhydryl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate8e:yield60%,194.72mg;paleyellowsolid;mp:158.3-161.7^oc.¹hnmr(cdcl3,400mhz,tms)δ11.69(s,1h,nch),8.69(s,1h,ch),7.26(m,10h,ph-h),4.42(q,j=7.2hz,2h,och2),2.77(s,3h,och3),2.54(s,3h,ch3),1.41(t,j=6.8hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ195.1,164.2,161.7,158.1,147.0,116.2,61.4,28.6,20.8,14.2.ir(kbr)(vmax,cm^-1):3383,1696,1652,1583,1445,1366,1245,1070,1007,861,800,741,547.hrms(esi-tof)m/zcalcdforc24h24no4⁺[m+h]⁺390.1700,found390.1707.

ethyl5-acetyl-1-(furan-2-ylmethyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate8f:yield88%,236.58mg;whitesolid;mp:114.2-114.8^oc.¹hnmr(cdcl3,400mhz,tms)δ8.47(s,1h,ch),7.26-7.21(m,1h,ch),6.40-6.25(m,2h,ch),5.31(s,2h,nch2),4.33(q,j=7.2hz,2h,och2),2.88(s,3h,ch3),2.47(s,3h,ch3),1.32(t,j=7.2hz,3h,ch3).¹³cnmr(cdcl3,100mhz)δ195.6,163.6,157.7,158.9,156.9,147.3,143.2,141.3,115.7,115.0,109.7,109.4,60.4,40.2,28.4,17.5,13.3.ir(kbr)(vmax,cm^-1):3413,1713,1662,1589,1521,1439,1380,1247,1028,860,802,778,569.hrms(esi-tof)m/zcalcdforc16h18no5⁺[m+h]⁺304.1174,found304.1179。