JOCR Journal of Organic Chemistry Research 2330-5231 Scientific Research Publishing 10.12677/JOCR.2016.44013 JOCR-19131 JOCR20160400000_33937638.pdf 化学与材料 磷钨酸促进的酰肼与查尔酮缩合反应的研究 Study on the Condensation Reaction of Hydrazide with Benzylideneacetophenone Catalyzed by Phosphotungstic Acid 吴 阳 2 1 邢 雪建 2 1 邢 刘桩 2 1 侯 亚东 2 1 杨 敬辉 2 1 惠 永海 2 1 新疆大学化学化工学院，新疆 乌鲁木齐 null 02 12 2016 04 04 93 99 © Copyright 2014 by authors and Scientific Research Publishing Inc. 2014 This work is licensed under the Creative Commons Attribution International License (CC BY). http://creativecommons.org/licenses/by/4.0/

本文以杂多酸–磷钨酸为催化剂，对酰肼与查尔酮的缩合反应进行了研究。经过一系列反应条件的筛选，确立了最佳反应条件，并对底物的普适性进行了考察，得到了一系列高产率的酰腙类目标产物，最高产率达到99%。本反应操作简单，条件温和，为查尔酮酰腙合成提供了一种新的方法。 The condensation of hydrazide with benzylideneacetophenone was studied by using phospho-tungstic acid as catalyst. After a series of reaction conditions, the optimal reaction conditions were established, and the universality of the substrate was investigated. A series of acylhydrazones were obtained with the high yields, up to 99%. The reaction was simple and mild, which provided a new method for the synthesis of chalcone hydrazone.

杂多酸，缩合反应，酰腙, Heteropoly Acid Condensation Reaction Acylhydrazone 磷钨酸促进的酰肼与查尔酮缩合反应的研究<sup> </sup>

吴阳，邢雪建，邢刘桩，侯亚东，杨敬辉，惠永海*

新疆大学化学化工学院，新疆 乌鲁木齐

Email: *hyhai97@126.com

收稿日期：2016年11月1日；录用日期：2016年11月28日；发布日期：2016年12月2日

 摘 要

本文以杂多酸–磷钨酸为催化剂，对酰肼与查尔酮的缩合反应进行了研究。经过一系列反应条件的筛选，确立了最佳反应条件，并对底物的普适性进行了考察，得到了一系列高产率的酰腙类目标产物，最高产率达到99%。本反应操作简单，条件温和，为查尔酮酰腙合成提供了一种新的方法。

关键词 :杂多酸，缩合反应，酰腙

 1. 引言

酰腙是一类含有−CONHN = CH−基团的人工合成的化合物，通过酰肼与醛或酮缩合反应制得。因其分子结构中含有亚胺基(−CH = N−)故又属于席夫碱。在生物活性体系中体现出突出的抗菌、抗真菌、抗癌、脲酶抑制、抗氧化和抗糖化等良好的生理活性 [ 1 ] - [ 7 ] 。另外，酰腙类化合物与过渡金属、稀土金属等有着很强的配位能力，可以衍生出很多具有较高生物活性的金属配合物 [ 8 ] [ 9 ] [ 10 ] 。所以，在农药、医药、催化、分析和材料等方面有着广泛应用 [ 11 ] [ 12 ] [ 13 ] [ 14 ] [ 15 ] ，多年来一直备受人们的广泛关注。也引起了很多化学和生物学工作者们的极大兴趣，成为越来越活跃的研究领域之一。

本文以苯甲酰肼和查尔酮为原料，通过条件筛选得到最佳反应条件。在最佳条件下，合成了一系列收率较好的查尔酮苯甲酰腙衍生物。为合成酰腙的衍生物寻找一种简单的合成方法。

 2. 实验部分 2.1. 试剂与仪器

薄层层析硅胶用GF254硅胶和300-400目柱层析硅胶(青岛海洋化工厂)。常见的显色方式有：ZF-2型三用紫外仪，碘缸，酸性溶液，茚三酮等，熔点是由X-4数字显示显微熔点仪测定。元素分析用EA-1110元素分析仪测定。核磁共振是有VARIAN INOVA-400型核磁共振波谱仪测定，核磁氢谱的内标为TMS (δ = 0.00)，核磁碳谱的内标为CDCl3 (δ = 77.00)。常用试剂：石油醚、乙酸乙酯、甲醇、无水乙醇和二氯甲烷等分析纯试剂是由市售购买而来，未经处理直接使用。苯甲醛、苯乙酮、取代芳香醛、取代芳香酮和芳香胺等是购买于阿拉丁化学厂家，其中对有些不纯的底物在做反应时经过了纯化。

 2.2. α,β-不饱和酮的合成

α,β-不饱和酮的合成参照文献 [ 16 ] 。

 2.3. 目标化合物4a~4q的合成及结构分析

化合物4a~4q的合成反应如图1所示。以化合物4a为例，向反应管中依次加入查尔酮0.0208 g (0.10 mmol)，

图1. 查尔酮苯甲酰腙衍生物(4a~4p)的合成

苯甲酰肼0.0204 g (0.15 mmol)，磷钨酸0.0042 g (0.15 mmol%)，0.5 mL甲醇，在室温反应24 h，TLC跟踪反应情况，反应完毕后减压浓缩，得粗产物，经柱层析分离纯化，得到白色固体(洗脱液为V1(石油醚):V2(乙酸乙酯) = 1:30，1:20，1:10，1:5)。目标化合物的表征如下：

4a: (Z)-Nˊ-((E)-1,3-diphenylallylidene) benzohydrazide, White solid; 96% yield; m.p. 154~157˚C; 1H NMR (400 MHz, CDCl3): δ 8.98 (s, 1H), 7.66~7.27 (m, 15H), 6.42 (d, J = 16.4 Hz, 1 H). Anal. Calcd. (%) for C22H18N2O:C, 80.96; H, 5.56; N, 8.59. Found (%): C, 81.07; H, 5.52; N, 8.49.

4b: (Z)-Nˊ-((E)-1-(4-chlorophenyl)-3-phenylallylidene)benzohydrazide, Yellow solid; 92% yield; m.p. 161-163˚C; 1H NMR (400 MHz, CDCl3):δ 8.89(s, 1 H), 7.58~7.26 (m, 14 H), 6.38 (d, J = 16.4 Hz, 1 H). Anal. Calcd. (%) for C22H17ClN2O:C, 73.23; H, 4.75; N, 7.76. Found (%): C, 73.44; H, 4.71; N, 7.69.

4c: (Z)-Nˊ-((E)-1-(4-bromophenyl)-3-phenylallylidene) benzohydrazide, White solid; 94% yield; m.p. 173-175˚C; 1H NMR (400 MHz, CDCl3):δ 8.89 (s, 1 H), 7.87~7.19 (m, 14 H), 6.37 (d, 1 H, J = 16.8 Hz). Anal. Calcd. (%) for C22H17BrN2O: C, 65.20; H, 4.23; N, 6.91. Found (%): C, 65.37; H, 4.19; N, 6.84.

4d: (Z)-Nˊ-((E)-3-phenyl-1-(p-tolyl) allylidene) benzohydrazide, Yellow oil; 83% yield; 1H NMR (400 MHz, CDCl3): δ 9.03 (s, 1 H), 7.56 (d, J = 7.2 Hz, 1 H), 7.48~7.38 (m, 10 H ), 7.34~7.27 (m, 2 H), 6.44 (d, J = 16.2 Hz, 1H), 2.49 (s, 3 H). 13C NMR (100 MHz, CDCl3) δ: 163.16, 156.79, 140.25, 138.26, 136.13, 133.21, 131.99, 130.59, 129.16, 129.06, 128.95, 128.79, 128.67, 128.41, 128.10, 127.52, 1227.12, 21.52. Anal. Calcd. (%) for C23H20N2O: C, 81.15; H, 5.92; N, 8.23. Found (%): C, 81.29; H, 5.83; N, 8.11.

4e: (Z)-Nˊ-((E)-1-(4-methoxyphenyl)-3-phenylallylidene) benzohydrazide, Yellow oil; 90% yield; 1H NMR (400 MHz, CDCl3): δ 9.07 (s, 1 H), 7.59-7.57 (m, 2 H), 7.52-7.25 (m, 10 H), 7.15-7.13 (m, 2 H), 6.46 (d, J = 16.4 Hz, 1 H), 3.90 (s, 3 H). Anal. Calcd. (%) for C23H20N2O2: C, 77.51; H, 5.66; N, 7.86. Found (%): C, 77.75; H, 5.57; N, 7.73.

4f: (Z)-Nˊ-((E)-1-(3-chlorophenyl)-3-phenylallylidene) benzohydrazide, White solid; 75% yield; m.p. 122-124˚C; 1H NMR (400 MHz, CDCl3): δ 8.88 (s, 1 H), 7.99~7.83 (m, 2 H), 7.74~7. 57 (m, 3 H), 7.53~7.26 (m, 8 H), 7.28~7.26 (m, 1 H), 6.40 (d, J = 16 Hz, 1 H). Anal. Calcd. (%) for C22H17ClN2O: C, 73.23; H, 4.75; N, 7.76. Found (%): C, 73.38; H, 4.74; N, 7.71.

4g: (Z)-Nˊ-((E)-3-phenyl-1-(m-tolyl)allylidene) benzohydrazide, Yellow oil; 67% yield; 1H NMR (400 MHz, CDCl3): δ 9.01 (s, 1 H), 7.59 (d, J = 7.2 Hz, 1 H), 7.42-7.38 (m, 10 H ), 7.30~7.24 (m, 2 H), 6.42 (d, J = 16.6 Hz, 1 H), 2.42 (s, 3 H). Anal. Calcd. (%) for C23H20N2O: C, 81.15; H, 5.92; N, 8.23. Found(%): C, 81.26; H, 5.85; N, 8.17.

4h: (Z)-Nˊ-((E)-3-(4-fluorophenyl)-1-phenylallylidene) benzohydrazide, White solid; 85% yield; m.p. 114~116˚C; 1H NMR (400 MHz, CDCl3): δ 8.98 (s, 1 H), 7.98~7.88 (m, 1 H), 7.74~7.27 (m, 9 H), 7.12~6.99 (m, 2 H), 6.38 (d, J = 16.4 Hz, 1 H), 2.42 (s, 3 H). Anal. Calcd.(%) for C22H17FN2O: C, 76.73; H, 4.98; N, 8.13. Found (%):C, 76.88; H, 4.74; N, 8.21.

4i: (Z)-Nˊ-((E)-3-(4-chlorophenyl)-1-phenylallylidene)benzohydrazide A White solid; 87% yield; m.p. 118~121˚C; 1H NMR (400 MHz, CDCl3): δ 8.99 (s, 1 H), 8.01~7.94 (m, 1 H), 7.74~7.58 (m, 2 H), 7.53~7.52 (m, 9 H), 6.37 (d, J = 16.4 Hz, 1 H). Anal. Calcd.(%) for C22H17ClN2O: C, 73.23; H, 4.75; N, 7.76. Found(%): C, 73.41; H, 4.66; N, 7.62.

4j: (Z)-Nˊ-((E)-3-(4-bromophenyl)-1-phenylallylidene) benzohydrazide, Yellow solid; 65% yield; m.p. 112~114˚C; 1H NMR (400 MHz, CDCl3): δ 8.99 (s, 1 H), 7.65-7.62 (m, 3 H), 7.55~7.53 (m, 2 H), 7.50~7.44 (m, 3 H), 7.39-7.33 (m, 4 H), 7.27~7.25 (m, 2 H), 6.35 (d, J = 16.8 Hz, 1 H). Anal. Calcd. (%) for C22H17BrN2O: C, 65.20; H, 4.23; N, 6.91. Found (%): C, 65.34; H, 4.12; N, 6.88.

4k: (Z)-Nˊ-((E)-3-(4-methoxyphenyl)-1-phenylallylidene) benzohydrazide, Yellow solid; 88% yield; m.p. 106~109˚C; 1H NMR (400 MHz, CDCl3): δ 8.94 (s, 1 H), 7.65~7.46 (m, 6 H), 7.38~7.27 (m, 6 H), 6.86 (d, J = 8.8 Hz, 2 H), 6.37 (d, J = 16 Hz, 1 H), 3.86 (s, 3H). Anal. Calcd. (%) for C23H20N2O2: C, 77.51; H, 5.66; N, 7.86. Found (%): C, 77.68; H, 5.59; N, 7.78.

4l: (E)-Nˊ-((E)-4-(4-methoxyphenyl)but-3-en-2-ylidene)benzohydrazide, White solid; 92% yield; m.p. 202~204˚C; 1H NMR (400 MHz, CDCl3) δ: 9.01 (s, 1 H), 7.85 (s, 2 H), 7.55-7.36 (m, 5 H), 7.16-7.01 (m, 2 H), 6.99~6.88 (m, 2 H), 3.84 (s, 3 H), 2.18 (s, 3 H). 13C NMR (100 MHz, CDCl3) δ: 165.21, 161.20, 153.58, 134.42, 133.04, 129.90, 127.87, 128.49, 127.53, 126.76, 114.47, 55.36, 29.34. MS (ESI m/z) 317.1 [(M + Na+, 100%)]. Anal. Calcd. (%) for C18H18N2O2: C, 73.45; H, 6.16; N, 9.52. Found (%): C, 73.52; H, 6.09; N, 9.39.

4m: (Z)-4-chloro-Nˊ-((E)-1,3-diphenylallylidene)benzohydrazide, Yellow solid; 99% yield; m.p. 175~176˚C; 1H NMR (400 MHz, CDCl3) δ: 8.91 (s, 1 H), 8.02 (s, 1 H), 7.65~7.60 (m, 3 H), 7.46-7.39 (m, 5 H), 9.34~7.26 (m, 5 H), 7.23 (s, 1 H), 7.43 (d, J = 16 Hz, 1 H). Anal. Calcd. (%) for C22H17ClN2O: C, 73.23; H, 4.75; N, 7.76. Found (%): C, 73.36; H, 4.68; N, 7.65.

4n: (Z)-4-bromo-Nˊ-((E)-1,3-diphenylallylidene) benzohydrazide, Yellow solid; 98% yield; m.p. 124~126˚C; 1H NMR (400 MHz, CDCl3) δ: 8.91 (s, 1 H), 8.02 (s, 1 H), 7.71~7.55 (m, 3 H), 7.53~7.50 (m, 2 H), 7.44~7.27 (m, 8 H), 6.43 (d, J = 16.4 Hz, 1 H). Anal. Calcd. (%) for C22H17BrN2O: C, 65.20; H, 4.23; N, 6.91. Found (%): C, 65.33; H, 4.18; N, 6.82.

4o: (Z)-Nˊ-((E)-1,3-diphenylallylidene)-4-methoxybenzohydrazide, Yellow solid; 78% yield; m.p. 204~207˚C; 1H NMR (400 MHz, CDCl3) δ: 8.92 (s, 1 H), 7.66-7.57 (m, 3 H), 7.52-7.49 (m, 2 H), 7.44-7.39 (m, 3 H), 7.35~7.27 (m, 4 H), 6.86 (d, J = 6 Hz, 2 H), 6.40 (d, J = 16.4 Hz, 1 H). Anal. Calcd. (%) for C23H20N2O2: C, 77.51; H, 5.66; N, 7.86. Found (%): C, 77.61; H, 5.53; N, 7.69.

4p: (Z)-2-chloro-Nˊ-((E)-1,3-diphenylallylidene) benzohydrazide, White solid; 86% yield; m.p. 163~165˚C; 1H NMR (400 MHz, CDCl3) δ: 9.26 (s, 1 H), 7.87~7.84 (m, 1 H), 7.60~7.52 (m, 4 H), 7.47~7.36 (m, 3 H), 7.32-7.29 (m, 6 H), 6.91 (d, J = 16.4 Hz, 1 H). Anal. Calcd.(%) for C22H17ClN2O: C, 73.23; H, 4.75; N, 7.76. Found(%): C, 73.41; H, 4.57; N, 7.59.

4q: (Z)-Nˊ-((E)-1,3-diphenylallylidene)-2-methylbenzohydrazide, Yellow oil; 85% yield; 1H NMR (400 MHz, CDCl3) δ:8.57 (s, 1 H), 7.60~7.51 (m, 3 H), 7.46~7.24 (m, 9 H), 7.21~7.13 (m, 2 H), 6.40 (d, J = 16.4 Hz, 1 H). Anal. Calcd. (%) for C23H20N2O: C, 81.15; H, 5.92; N, 8.23. Found (%): C, 81.31; H, 5.79; N, 8.12.

 3. 结果与讨论 3.1. 最优反应条件的筛选

以查尔酮与苯甲酰肼反应为标准反应，分别进行了催化剂种类和用量、反应溶剂种类和用量、底物配比和反应时间等条件进行了优化，结果见表1。

从表1中可以看出，在没有加入催化剂时，反应不发生(表1，Entry 1)；用杂多酸磷钨酸和磷钼酸分别催化时，磷钨酸表现出了较好的产率(表1，Entry 2)；当用MCM-41固载的磷钨酸(磷钼酸)催化反应时，产率有所降低，所以我们选定磷钨酸作为催化剂。然后进行了催化剂的量筛选，实验结果表明磷钨酸量为0.15 mmol%产率最高。在对反应溶剂筛选时，发现甲醇作为溶剂，反应产率最高，89%。为了得到更高的产率，随后考察了其它溶剂对产率的影响。结果表明其它溶剂没有醇类溶剂的效果好，而在醇类溶剂中，反应产率依然在甲醇中得到最高。确定上述反应条件后，我们对底物比例进行了考察，分别对底物查尔酮：苯甲

Optimization of reaction conditions
Entry Catalyst Solvent (n) chalcone/(n) hydrazide Temperature Time Yield(%)b
1 - CH3OH 1:1.2 R.T. 24 N.R.c
2 PWA (0.15 mmol%) CH3OH 1:1.2 R.T. 24 89
3 PMA (0.15 mmol%) CH3OH 1:1.2 R.T. 24 78
4 50 wt% PWA/MCM-41 (0.15 mmol%) CH3OH 1:1.2 R.T. 24 55
5 50 wt% PMA/MCM-41 (0.15 mmol%) CH3OH 1:1.2 R.T. 24 65
6 PWA (0.10 mmol%) CH3OH 1:1.2 R.T. 24 52
7 PWA (0.05 mmol%) CH3OH 1:1.2 R.T. 24 60
8 PWA (0.20 mmol%) CH3OH 1:1.2 R.T. 24 88
9 PWA (0.15 mmol%) CH2Cl2 1:1.2 R.T. 24 60
10 PWA (0.15 mmol%) CH3CN 1:1.2 R.T. 24 52
11 PWA (0.15 mmol%) CH3C6H5 1:1.2 R.T. 24 58
12 PWA (0.15 mmol%) CH3COOEt 1:1.2 R.T. 24 64
13 PWA (0.15 mmol%) THF 1:1.2 R.T. 24 43
14 PWA (0.15 mmol%) C2H5OH 1:1.2 R.T. 24 75
15 PWA (0.15 mmol%) CH3OH 1:1 R.T. 24 75
16 PWA (0.15 mmol%) CH3OH 1:1.5 R.T. 24 96
17 PWA (0.15 mmol%) CH3OH 1:2 R.T. 24 80
18 PWA (0.15 mmol%) CH3OH 1:1.5 R.T. 12 73
19 PWA (0.15 mmol%) CH3OH 1:1.5 R.T. 18 82
20 PWA (0.15 mmol%) CH3OH 1:1.5 R.T. 36 83

表1. 反应条件的优化a

a反应条件：查尔酮0.1 mmol，酰肼0.15 mmol催化剂量为0.15 mmol%在0.5 mL甲醇中室温反应24 h。b柱层析产率。cN.R = No Reaction。

酰肼为1:1，1:1.2，1:1.5，1:2等比例下进行了筛选，结果见表1的Entries 14-17。从表中可以看到，随着酰肼量的增加，产率有所上升，在1:1.5时，达到96%的产率，当继续增加酰肼的量(比例为1:2)时，产率有所下降，所以最有底物比例为1:1.5。实验在常温条件下进行，这属于理想反应条件范畴。最后对反应时间进行了考察，结果列于表1的Entries 17-20。反应中，当反应时间延长到24 h时，反应产率得到最高值96%，继续延长反应时间，产率处于下降趋势。通过对实验条件的筛选，最佳反应条件为：室温下以0.15 mmol%的磷钨酸为催化剂，0.5 mL甲醇为溶剂，底物配比(查尔酮:苯甲酰肼)为1:1.5，反应24 h。

 3.2. 底物结构对反应的影响

在最佳反应条件下，对底物进行了普适性的研究，结果详见表1。

从表2中，可以看到R2上的取代基无论是吸电子基团还是供电子基团，都能够很好地得到相应的目

Substrate scope
Entry R1 R2 R3 Product Yield(%)b
1 Ph Ph Ph 4a 96
2 Ph p-ClPh Ph 4b 92
3 Ph p-BrPh Ph 4c 94
4 Ph p-CH3Ph Ph 4d 83
5 Ph p-OCH3Ph Ph 4e 90
6 Ph m-ClPh Ph 4f 75
7 Ph m-CH3Ph Ph 4g 67
8 p-FPh Ph Ph 4h 85
9 p-ClPh Ph Ph 4i 87
10 p-BrPh Ph Ph 4j 65
11 p-OCH3Ph Ph Ph 4k 88
12 p-OCH3Ph CH3 Ph 4l 92
13 Ph Ph p-ClPh 4m 99
14 Ph Ph p-BrPh 4n 98
15 Ph Ph p-OCH3Ph 4o 78
16 Ph Ph o-ClPh 4p 86
17 Ph Ph o-CH3Ph 4q 85

表2. 底物结构的拓展a

a反应条件：查尔酮0.1 mmol，酰肼0.15 mmol催化剂量为0.004 g在0.5 mL甲醇中室温反应24 h。b柱层析产率。

标产物；当同种取代基苯环上的位置不同时，其产率也有很大的变化，而且对位取代的产率要高于间位取代，如R2，氯取代对位时的产率要高于其间位取代(Entries 2, 6)，对甲基比间甲基的产率高(Entries 4, 7)。对于R1苯环上的取代基，除了Br取代产率较低外，其它产率都能达到85%以上。在酰肼R3取代基的改变中，从表中可以看出，对位和邻位取代的酰肼都获得了较高的产率。

 4. 结论

本文研究了查尔酮和酰肼的缩合反应。通过优化实验，最终得出了最优反应条件：0.004 g磷钨酸为催化剂、底物配比为1:1.5(查尔酮:酰肼)，甲醇为溶剂，室温下反应24 h。在该反应条件下，获得了一系列高产率的酰腙类目标产物，最高产率达到99%。本反应具有反应条件温和，催化剂廉价易得等优点。

 基金项目

国家自然科学基金(Nos. 21161026, 21362036)。

 文章引用

吴 阳,邢雪建,邢刘桩,侯亚东,杨敬辉,惠永海. 磷钨酸促进的酰肼与查尔酮缩合反应的研究 Study on the Condensation Reaction of Hydrazide with Benzylideneacetophenone Catalyzed by Phosphotungstic Acid[J]. 有机化学研究, 2016, 04(04): 93-99. http://dx.doi.org/10.12677/JOCR.2016.44013

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