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CN113004215B - 一种2,4,5-三取代噁唑类化合物的合成方法 - Google Patents

一种2,4,5-三取代噁唑类化合物的合成方法 Download PDF

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CN113004215B
CN113004215B CN202011529222.4A CN202011529222A CN113004215B CN 113004215 B CN113004215 B CN 113004215B CN 202011529222 A CN202011529222 A CN 202011529222A CN 113004215 B CN113004215 B CN 113004215B
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oxazole compound
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trisubstituted oxazole
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CN113004215A (zh
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吕宁宁
戴玲
于书玲
陈久喜
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Wenzhou University
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    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract

本发明公开了一种简便高效的2,4,5‑三取代噁唑类化合物的合成方法，包括如下步骤：将氰基取代酯类化合物、简单芳烃、乙酰丙酮钯、二甲基亚砜加入到有机溶剂三氟乙酸中，空气条件下油浴加热至100℃进行反应6小时，反应完全后，后处理得到所述的2,4,5‑三取代噁唑类化合物。该方法利用光普的简单芳烃作为反应原料，在钯催化剂的作用下，通过与氰基取代的酯类化合物之间的串联环合反应一步合成2,4,5‑三取代噁唑类化合物，转化效率高，原子经济性好；同时合成方法操作简单，反应收率高，同时底物适应性广。

Description

一种2,4,5-三取代噁唑类化合物的合成方法
技术领域
本发明属于有机合成领域，具体涉及一种2,4,5-三取代噁唑类化合物的合成方法。
背景技术
2,4,5-三取代噁唑类化合物是一类非常重要的结构骨架，其结构广泛存在于药物分子、天然产物以及功能性材料中。传统的2,4,5-三取代噁唑类化合物的合成方法需要冗长的反应步骤以及苛刻的反应条件才能够实现该类化合物的高效构建。从而寻求发展新的简便高效的2,4,5-三取代噁唑类化合物的合成方法显得尤为重要。
近年来，在Larock课题组利用过渡金属钯催化下通过芳基钯物种对氰基底物的亲核加成，高效实现腈类化合物的官能团转化。此后，以官能团化的腈类化合物作为反应底物，在过渡金属的催化下，通过串联环合反应能够成功实现一系列重要的含氮杂环化合物骨架的构筑。然而在这些转化中，往往需要利用高活性的芳基硼酸试剂作为反应底物来实现芳基钯物种的制备，导致反应底物需要额外的预官能团化的步骤同时也使得反应的原子经济性大大降低。
从原子经济性的角度以及环境的角度来看，利用惰性的碳氢键作为潜在的官能团，通过其与钯催化剂之间直接的亲电钯化作用形成的金属钯物种，继而与官能团化腈类化合物的转化，来实现2,4,5-三取代噁唑类化合物的制备显示出了优越的原子经济性以及步骤经济性。我们课题组首次发展了一种利用乙酰丙酮钯作为催化剂，简单芳烃作为反应底物，以二甲基亚砜作为反应的配体，在以三氟乙酸作为反应溶剂在空气的反应氛围下，通过与取代的腈类化合物的反应能够顺利合成2,4,5-三取代噁唑类化合物，该方法条件温和，反应适应性广，并且无需额外的氧化剂，为合成不同官能团取代的2,4,5-三取代噁唑类化合物提供了一种简单有效的方法。
发明内容
本发明提供了一种新颖且高效的2,4,5-三取代噁唑类化合物的合成方法，该合成方法底物适用性广，化学选择性好，反应活性高。
一种新颖且高效的2,4,5-三取代噁唑类化合物的合成方法，包括如下步骤：将简单芳烃、氰基取代酯类化合物、乙酰丙酮钯、DMSO加入到有机溶剂中，空气条件下加热到100℃进行反应，反应6h，反应完全后，后处理(萃取以及柱层色谱分离)得到所述的2,4,5-三取代噁唑类化合物；
所述的氰基取代酯类化合物的结构如式(II)所示：
Figure BDA0002851722860000021
所述的简单芳烃的结构如式(III)所示：
Figure BDA0002851722860000022
所述的2,4,5-三取代噁唑类化合物的结构如式(I)所示：
Figure BDA0002851722860000023
式(I)～(III)中，R1选自H、烷基、芳基、杂芳基；R2选自烷基、芳基、杂芳基；R3选自甲基、甲氧基、氟、溴。
本发明中，不需要利用预官能团化的芳基化试剂，可直接由简单的芳烃与氰基取代的酯类化合物之间的串联环合反应在一锅法中顺利实现2,4,5-三取代噁唑类化合物的制备，目标产物中的氮原子来自氰基中的氮原子。
作为优选，所述的有机溶剂为三氟乙酸(TFA)。
作为优选，反应温度为100℃，反应时间为6小时。
同现有技术相比，本发明的有益效果体现在：
(1)本发明通过简单易得的原料直接利用惰性的碳氢键与钯金属催化剂之间的亲电取代形成金属物种，随后发生一系列的串联环合反应在一锅中成功过实现2,4,5-三取代噁唑类化合物的制备，转化效率高，原子经济性好；
(2)本发明的合成方法操作简单，反应活性高，同时底物适应范围广泛。
附图说明
图1为实施例1得到的化合物的氢谱和碳谱谱图；
图2为实施例2得到的化合物的氢谱和碳谱谱图；
图3为实施例3得到的化合物的氢谱和碳谱谱图；
图4为实施例4得到的化合物的氢谱和碳谱谱图；
图5为实施例5得到的化合物的氢谱和碳谱谱图；
图6为实施例6得到的化合物的氢谱和碳谱谱图；
图7为实施例7得到的化合物的氢谱和碳谱谱图；
图8为实施例8得到的化合物的氢谱和碳谱谱图；
图9为实施例9得到的化合物的氢谱和碳谱谱图；
图10为实施例10得到的化合物的氢谱和碳谱谱图；
图11为实施例11得到的化合物的氢谱和碳谱谱图；
图12为实施例12得到的化合物的氢谱和碳谱谱图；
图13为实施例13得到的化合物的氢谱和碳谱谱图；
图14为实施例14得到的化合物的氢谱和碳谱谱图；
其中，氢谱在500MHz核磁仪器上进行测试。碳谱在125MHz核磁仪器上进行测试。测试条件均为室温下使用四甲基硅烷作内标，样品用氘代氯仿溶解。
具体实施方式
下面结合具体实施例对本发明做进一步的描述，以下具体实施例都是本发明的最优实施方式。
实施例1～14
按照表1的原料配比在10mL封管中加入氰基取代的酯类化合物(II，0.3mmol)、简单芳烃底物(III，2.1mmol)、乙酰丙酮钯(0.03mmol)、二甲基亚砜(0.6mmol)和有机溶剂TFA(2mL)，混合搅拌均匀，在空气氛围下，在油浴(100℃)下反应6h。按照表2的反应条件反应完成后，冷却，用饱和的碳酸钠溶液(1mol/L)进行洗涤，饱和食盐水洗，收集有机相用硫酸钠干燥，硅胶拌样，经过柱层析纯化得到相应的2,4,5-三取代噁唑类化合物(Ⅰ)，反应过程如下式所示：
Figure BDA0002851722860000041
表1实施例1～14的原料配比
Figure BDA0002851722860000042
表2实施例1～14的反应条件和反应结果
Figure BDA0002851722860000043
Figure BDA0002851722860000051
表1和表2中，T为反应温度，t为反应时间，Me为甲基，CF3为三氟甲基，Ph为苯基，2-COOMe为2-甲酸甲酯基。
实施例1～14制备得到部分化合物的结构确认数据：
Figure BDA0002851722860000052
4-Mesityl-2,5-diphenyloxazole(I-1)
Yellow solid(96.6mg,95％).mp:120-121℃.Column chromatography onsilica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500MHz,CDCl3)δ8.25(d,J＝6.4Hz,2H),7.56-7.50(m,5H),7.36-7.33(m,2H),7.30-7.26(m,1H),7.04(s,2H),2.40(s,3H),2.18(s,6H).13C NMR(125MHz,CDCl3)δ160.1,146.0,138.4,137.7,135.6,130.3,129.1,129.0,128.9,128.7,127.8,127.7,126.5,124.3,21.3,20.1.HRMS(ESI-TOF)calcd for C24H21NONa+[M+Na]+:362.1515,found 362.1528.
Figure BDA0002851722860000053
5-(Furan-2-yl)-4-mesityl-2-phenyloxazole(I-2)
Yellow oil(83.9mg,85％).Column chromatography on silica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500MHz,CDCl3)δ7.65-7.64(m,1H),7.49-7.46(m,2H),7.36-7.32(m,2H),7.30-7.28(m,1H),7.19-7.18(m,1H),7.02(s,2H),6.62(dd,J＝1.8Hz,J＝3.5Hz,1H),2.40(s,3H),2.16(s,6H).13C NMR(125MHz,CDCl3)δ153.0,145.5,144.4,143.3,138.5,137.7,135.3,128.9,128.7,128.6,128.0,124.3,112.0,111.6,21.3,20.1.HRMS(ESI-TOF)calcd for C22H20NO2 +[M+H]+:330.1489,found330.1480.
Figure BDA0002851722860000061
4-Mesityl-2-phenyloxazole(I-3)
Colourless oil(69.4 mg,88％).Column chromatography on silica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ8.12(d,J＝6.9 Hz,2H),7.59(s,1H),7.48-7.47(m,3H),6.95(s,2H),2.32(s,3H),2.22(s,6H).13C NMR(125 MHz,CDCl3)δ161.6,139.7,138.3,138.0,136.0,130.4,128.9,128.5,127.9,127.7,126.6,21.2,20.7.HRMS(ESI-TOF)calcd for C18H18NO+[M+H]+:264.1383,found 264.1387.
Figure BDA0002851722860000062
4-Mesityl-2-phenyl-5-propyloxazole(I-4)
Yellow solid(80.5 mg,88％).mp:120-121℃.Column chromatography onsilica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ8.12-8.09(m,2H),7.49-7.41(m,3H),6.95(s,2H),2.54(t,J＝7.4Hz,2H),2.34(s,3H),2.17(s,6H),1.75-1.66(m,2H),0.97(t,J＝7.4 Hz,3H).13C NMR(125 MHz,CDCl3)δ159.9,148.8,138.1,138.0,134.7,129.9,128.8,128.3,128.2,126.2,27.2,21.3,21.2,20.3,13.9.HRMS(ESI-TOF)calcd for C21H24NO+[M+H]+:306.1852,found 306.1848.
Figure BDA0002851722860000063
4-Mesityl-5-phenethyl-2-phenyloxazole(I-5)
Yellow oil(88.1 mg,80％).Column chromatography on silica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ8.16-8.14(m,2H),7.54-7.49(m,3H),7.32-7.29(m,2H),7.26-7.19(m,3H),6.97(s,2H),3.06(t,J＝7.4 Hz,2H),2.93(t,J＝7.1 Hz,2H),2.37(s,3H),2.10(s,6H).13C NMR(125 MHz,CDCl3)δ160.0,147.7,140.7,138.1,138.0,135.2,130.0,128.8,128.6,128.5,128.3,128.2,128.0,126.3,126.2,33.9,27.2,21.2,20.2.HRMS(ESI-TOF)calcd for C26H26NO+[M+H]+:368.2009,found 368.2015.
Figure BDA0002851722860000071
4-Mesityl-2-(naphthalen-1-yl)-5-phenyloxazole(I-6)
Yellow oil(105.0 mg,90％).Column chromatography on silica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ9.55(d,J＝8.7 Hz,1H),8.48-8.46(m,1H),8.02(d,J＝8.2 Hz,1H),7.96(d,J＝8.0 Hz,1H),7.71-7.57(m,5H),7.40-7.37(m,2H),7.33-7.30(m,1H),7.09(s,2H),2.45(s,3H),2.26(s,6H).13C NMR(125 MHz,CDCl3)δ160.1,145.7,138.5,137.9,135.6,134.2,131.2,130.4,129.4,129.0,128.9,128.8,128.6,128.0,127.8,127.7,126.8,126.4,125.1,124.4,124.2,21.4,20.3.HRMS(ESI-T OF)calcd for C28H24NO+[M+H]+:390.1852,found 390.1855.
Figure BDA0002851722860000072
4-Mesityl-5-phenyl-2-(thiophen-2-yl)oxazole(I-7)
Yellow solid(88.0 mg,85％).mp:122-123℃.Column chromatography onsilica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ7.86-7.85(m,1H),7.49-7.46(m,3H),7.36-7.32(m,2H),7.30-7.27(m,1H),7.21-7.18(m,1H),7.02(s,2H),2.40(s,3H),2.18(s,6H).13C NMR(125 MHz,CDCl3)δ156.4,145.4,138.5,137.7,135.4,130.3,128.9,128.7,128.3,128.1,127.9,127.8,127.7,124.2,21.3,20.1.HRMS(ESI-TOF)calcd for C22H20NOS+[M+H]+:346.1260,found 346.1270.
Figure BDA0002851722860000081
4-Mesityl-5-phenyl-2-(pyridin-3-yl)oxazole(I-8)
Yellow solid(86.7 mg,45％).mp:121-122℃.Column chromatography onsilica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ9.43-9.42(m,1H),8.72-8.71(m,1H),8.46-8.43(m,1H),7.48-7.43(m,3H),7.35-7.28(m,3H),7.01(s,2H),2.38(s,3H),2.13(s,6H).13C NMR(125 MHz,CDCl3)δ157.8,151.0,147.8,146.8,138.7,137.6,135.8,133.6,129.0,128.8,128.7,128.6,128.3,124.4,124.0,123.7,21.3,20.1.HRMS(ESI-TOF)calcd for C23H21N2O+[M+H]+:341.1648,found341.1651.
Figure BDA0002851722860000082
4-Mesityl-2-methyl-5-phenyloxazole(I-9)
Yellow oil(59.0 mg,71％).Column chromatography on silica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ7.38(d,J＝7.2 Hz,2H),7.32-7.29(m,2H),7.26-7.22(m,1H),7.00(s,2H),2.62(s,3H),2.39(s,3H),2.12(s,6H).13C NMR(125 MHz,CDCl3)δ160.0,145.7,138.2,137.6,134.0,129.2,128.8,128.6,127.5,124.0,21.3,20.1,14.2.HRMS(ESI-TOF)calcd for C19H20NO+[M+H]+:278.1539,found 278.1544.
Figure BDA0002851722860000091
4-Mesityl-2-phenethyl-5-phenyloxazole(I-10)
Yellow oil(99.1 mg,90％).Column chromatography on silica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ7.38-7.35(m,3H),7.34-7.32(m,4H),7.31-7.26(m,3H),7.00(s,2H),3.27(s,4H),2.39(s,3H),2.09(s,6H).13C NMR(125 MHz,CDCl3)δ162.7,145.6,140.4,138.3,137.6,133.7,129.1,128.9,128.8,128.6,128.5,127.6,126.5,124.1,33.4,30.2,21.3,20.0.HRMS(ESI-TOF)calcd forC26H26NO+[M+H]+:368.2009,found 368.2015.
Figure BDA0002851722860000092
2,4,5-Triphenyloxazole(I-11)
Colourless oil(28.5 mg,32％).Column chromatography on silica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ8.20(d,J＝7.9 Hz,2H),7.79-7.77(m,2H),7.72(d,J＝7.8 Hz,2H),7.53-7.48(m,3H),7.46-7.37(m,6H).13C NMR(125 MHz,CDCl3)δ160.3,145.7,136.9,132.8,130.4,129.2,128.9,128.8,128.7,128.6,128.3,128.2,127.6,126.7,126.6.Spectroscopic data for the titlecompound were consistent with those reported in the literature.
Figure BDA0002851722860000101
2,5-Diphenyl-4-(2,4,6-trimethoxyphenyl)oxazole(I-12)
Yellow solid(59.2 mg,51％).mp:135-136℃.Column chromatography onsilica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ8.24-8.22(m,2H),7.60-7.58(m,2H),7.54-7.48(m,3H),7.37-7.28(m,3H),6.29(s,2H),3.93(s,3H),3.74(s,6H).13C NMR(125 MHz,CDCl3)δ162.4,160.0,159.7,147.2,130.1,130.0,129.5,128.7,128.5,128.0,127.5,126.6,124.8,103.6,91.3,56.0,55.5.HRMS(ESI-TOF)calcd for C24H22NO4 +[M+H]+:388.1543,found 388.1552.
Figure BDA0002851722860000102
4-(3-Fluoro-2,4,6-trimethylphenyl)-2,5-diphenyloxazole(I-13)
Yellow oil(83.5 mg,78％).Column chromatography on silica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ8.18-8.16(m,2H),7.50-7.46(m,3H),7.43-7.42(m,2H),7.32-7.29(m,2H),7.26-7.24(m,1H),6.97(d,J＝7.6Hz,1H),2.30(s,3H),2.07-2.05(m,6H).13C NMR(125 MHz,CDCl3)δ160.3,158.5(C-F,1JC-F＝241.0 Hz),146.3,134.6,132.8,131.1,130.5,130.4(C-F,3JC-F＝5.3 Hz),129.0,128.9,128.7,128.1,127.5,126.6,125.0(C-F,2JC-F＝18.5 Hz),124.6,124.4,19.7,14.9,12.2.HRMS(ESI-TOF)calcd for C24H21FNO+[M+H]+:358.1602,found 358.1602.
Figure BDA0002851722860000111
4-(3-Bromo-2,4,6-trimethylphenyl)-2,5-diphenyloxazole(I-14)
Yellow oil(96.3 mg,77％).Column chromatography on silica gel(Eluent:petroleum ether/ethyl acetate,16/1).1H NMR(500 MHz,CDCl3)δ8.22-8.19(m,2H),7.54-7.49(m,3H),7.46-7.44(m,2H),7.35-7.32(m,2H),7.29-7.26(m,1H),7.10(s,1H),2.49(s,3H),2.32(s,3H),2.09(s,3H).13C NMR(125MHz,CDCl3)δ160.3,146.2,139.0,137.9,136.7,135.4,131.1,130.6,130.2,129.0,128.9,128.6,128.2,127.5,126.6,125.8,124.4,24.3,21.4,20.0.HRMS(ESI-TOF)calcd for C24H21BrNO+[M+H]+:418.0801,found 418.0806.

Claims (5)

1.一种2,4,5-三取代噁唑类化合物的合成方法，其特征在于，包括如下步骤：将氰基取代酯类化合物、简单芳烃、钯催化剂、配体添加剂加入到有机溶剂中，空气条件下，将温度控制在90~110℃下反应4~10 h，反应完全后，后处理得到所述的2,4,5-三取代噁唑类化合物；
所述的氰基取代酯类化合物的结构如式（II）所示：
Figure DEST_PATH_IMAGE001
（II）；
所述的简单芳烃的结构如式（III）所示：
Figure 929409DEST_PATH_IMAGE002
（III）
所述的2,4,5-三取代噁唑类化合物的结构如式（I）所示：
Figure DEST_PATH_IMAGE003
（I）
式（I）~（III）中，R1选自H、烷基、甲氧基、芳基、杂芳基、三氟甲基、卤素以及酯基；
R2选自H、烷基、芳基或杂芳基；
R3 选自甲基、甲氧基、卤素中的一个或者多个；
所述的有机溶剂为三氟乙酸；
所述的钯催化剂为乙酰丙酮钯；
所述的配体为二甲基亚砜。
2.根据权利要求1所述的2,4,5-三取代噁唑类化合物的合成方法，其特征在于，所述的R1选自H、丙基、苯基、呋喃基或吡啶基；R2选自甲基、苯基、萘基、呋喃基或者吡啶基；R3 选自甲基、甲氧基、氟、溴中的一个或者多个。
3.根据权利要求1所述的2,4,5-三取代噁唑类化合物的合成方法，其特征在于，所述的反应条件无需金属氧化剂的引入。
4.根据权利要求1所述的2,4,5-三取代噁唑类化合物的合成方法，其特征在于，反应温度为100℃，空气反应条件下，反应时间为6小时。
5.根据权利要求1所述的2,4,5-三取代噁唑类化合物的合成方法，其特征在于，所述的2,4,5-三取代噁唑类化合物为以下化合物中的一种：
Figure 315391DEST_PATH_IMAGE004
。
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