CN105017333A - 一种催化剂催化二氢嘧啶酮类化合物的合成方法 - Google Patents
一种催化剂催化二氢嘧啶酮类化合物的合成方法 Download PDFInfo
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
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Abstract
本发明提供了一种合成含苯磺酸的金属配位聚合物(MCPs)的合成方法并由单晶X-射线确定其晶体结构。而且进一步研究了其对二氢嘧啶酮类化合物的催化活性。采用简便、易操作的方法催化合成了系列二氢嘧啶酮类化合物并且催化产率可高达99%。
Description
技术领域
本发明属于无机化学,有机化学和药物化学领域,涉及金属配位聚合物的合成及其催化合成二氢嘧啶酮类化合物的实验方法。
背景技术
自从Biginelli反应被发现以来,在近几十年中吸引着越来越多的人关注并得到了迅速地发展。这是因为其产品及其衍生物在生物和药理和医学方面有着很大的应用价值,例如它们可以用作抗高血压药的钙离子通道阻滞剂、抗菌、抗病毒、消炎和α1a-拮抗等药理活性(K. S. Atwal, G. C. Rovnyak, S. D. Kimball, D. M. Floyd, S. Moreland, B. N. Swanson, J. Z. Gougoutas, J. Schwartz, K. M. Smillie and M. F. Malley, J. Med. Chem., 1990, 33, 2629; G. C. Rovnyak, K. S. Atwal, A. Hedberg, S. D. Kimball, S. Moreland, J. Z. Gougoutas, R. B. C. O, J. Schwartz and M. F. Malley, J. Med. Chem., 1992, 35, 3254)。尽管利用固相反应、包含离子液体的液相反应、金属及路易斯酸碱催化和利用其它催化剂催化的方法得到了很好的进步,但是仍然还存在一些不足,比如需要较长的反应时间,昂贵的试剂,较强的路易斯酸碱及有时会用到有害的有机溶剂。
最近,金属配位聚合物(MCPs)的设计和合成也逐渐引起化学家及材料学家的关注。这是由于这种材料在催化、气体吸收或存储、荧光、传感和药物运输方面有着潜在的应用价值。尤其MCPs在催化方面已经得到了很好的发展(I. Luz, F. X. Llabres i Xamena and A. Corma, J. Catal., 2012, 285, 285)。由于苯磺酸及过渡金属离子(Co2+, Fe3+和Cu2+)都曾经被用来催化有机物的合成(P. Li, S. Regati, R. J. Butcher, H. D. Arman, Z. Chen, S. Xiang, B. Chen and C. G. Zhao, Tetrahedron Lett., 2011, 52, 6220; S. H. A. M. Leenders, R. Gramage-Doria, B. de Bruin and J. N. H. Reek, Chem. Soc. Rev., 2015, 44, 433)。因此本发明同时考虑到以上两者的优点,采用苯磺酸和钴离子及有机配体配位形成MCPs。
考虑到二氢嘧啶酮类化合物拥有较高的生物活性,而且经常能作为有机合成的重要中间体,因此本发明公开使用上述的MCPs催化剂实现了对二氢嘧啶酮类化合物的高效制备。这对将来合成二氢嘧啶酮类化合物具有重要的指导意义。
发明内容
本发明提供了一种合成具有高效催化活性的金属有机配位聚合物的合成方法,并用来高效催化合成二氢嘧啶类化合物。本发明达到了减少催化剂的用量、缩短反应时间、简化实验操作的绿色合成方法。
为实现上述目的,将苯磺酸、氢氧化钠、硝酸钴、及DPP (1,3-二(吡啶-4-基)丙烷)溶于水和甲醇的混合溶液中,其中DPP的结构式见图1。然后将溶液转移到反应釜中加热120度5小时后,降温过滤析出得到红色晶体的配位聚合物1。将所得产品1经单晶X-射线衍射分析确定其分子结构,见图2。最后将产物1研磨作为催化剂,采用一锅法催化系列苯甲醛、乙酰乙酸乙酯和尿素的反应得到二氢嘧啶类化合物。其中催化结果如下表一所示:
本发明的具体合成步骤为。
实施例一、产品1的合成。
将0.037g的苯磺酸(0.2mmol)、0.008g氢氧化钠(0.2mmol)、0.040g DPP (0.2mmol)和0.029g硝酸钴(0.1mmol)溶于水(2mL)和甲醇(3mL)的混合溶液中。将反应混合液转移到反应釜中加热120度5小时后以5度每小时的速率缓慢降至室温、过滤、静置、析出红色的目标产物1并确定其晶体结构图。
实施例二、催化合成二氢嘧啶酮类化合物的方法。
取0.02mmol的产品1作为催化剂加入到1mmol苯甲醛、2mmol乙酰乙酸乙酯和1.5mmol的混合物中,在80摄氏度的的油浴锅中加热2小时,得到无色产品,最后用水和甲醇洗剂纯化得到目标产品。最后选用不同的醛在相同的条件下催化得到系列的二氢嘧啶酮类化合物。
附图说明
图1、DPP (1,3-二(吡啶-4-基)丙烷)的分子结构图。
图2、化合物1的晶体结构图。
具体实施方式
本发明提供了一种合成具有高效催化活性的金属有机配位聚合物的合成方法,并用来高效催化合成二氢嘧啶类化合物。本发明达到了减少催化剂的用量、缩短反应时间、简化实验操作的绿色合成方法。
为实现上述目的,将苯磺酸、氢氧化钠、硝酸钴、及DPP (1,3-二(吡啶-4-基)丙烷)溶于水和甲醇的混合溶液中,其中DPP的结构式见图1。然后将溶液转移到反应釜中加热120度5小时后,降温过滤析出得到红色晶体的配位聚合物1。将所得产品1经单晶X-射线衍射分析确定其分子结构,见图2。最后将产物1研磨作为催化剂,采用一锅法催化系列苯甲醛、乙酰乙酸乙酯和尿素的反应得到二氢嘧啶类化合物。其中催化结果如下表一所示:
本发明的具体合成步骤为。
实施例一、产品1的合成。
将0.037g的苯磺酸(0.2mmol)、0.008g氢氧化钠(0.2mmol)、0.040g DPP (0.2mmol)和0.029g硝酸钴(0.1mmol)溶于水(2mL)和甲醇(3mL)的混合溶液中。将反应混合液转移到反应釜中加热120度5小时后以5度每小时的速率缓慢降至室温、过滤、静置、析出红色的目标产物1并确定其晶体结构图。
实施例二、催化合成二氢嘧啶酮类化合物的方法。
取0.02mmol的产品1作为催化剂加入到1mmol苯甲醛、2mmol乙酰乙酸乙酯和1.5mmol的混合物中,在80摄氏度的的油浴锅中加热2小时,得到无色产品,最后用水和甲醇洗剂纯化得到目标产品。最后选用不同的醛在相同的条件下催化得到系列的二氢嘧啶酮类化合物。
Claims (5)
1.一种含磺酸基的金属配位聚合物的合成及其高效催化合成二氢嘧啶酮类化合物的合成方法,其特征在于合成步骤为:
(1) 实施例一、配合物1的合成
将一定比例的苯磺酸、氢氧化钠、DPP (1,3-二(吡啶-4-基)丙烷)和硝酸钴溶于一定量的水和有机溶剂中,然后将反应混合液转移到反应釜中加热完成后缓慢降至室温、过滤、静置、析出红色的目标产物1并确定其晶体结构图;
(2) 实施例二、催化合成二氢嘧啶酮类化合物的方法
其制备过程是以目标产物1为催化剂,取适量的产品1作为催化剂在适当温度下催化如下的反应式一段时间后,得到目标产品,最后用水和有机溶剂洗剂纯化得到纯净的产品;其反应式为:
式中:R1选自H、卤素、硝基、氰基、三氟甲基、C1~C9的烷基或C1~C9的烷氧基;R2是C1-10烷基、OR未取代的C3-8环烷基或单- 、二- 或三- 取代的C3-8环烷基,其中在环烷基上的取代基独立地的选自羟基、C1-8烷基、卤代C1-8烷基、烷C1-8烷氧基或卤代的C1-8烷氧基;R3、R4和R5每一个都独立地选自氢、卤素、卤代C1-10烷基、未取代或取代的芳基或未取代或取代的C1-10烷基,其中烷基上的取代基选自C1-7烷氧基、卤代C1-7烷氧基或芳基;R6和R7每一个都独立的选自氢或C1-10烷基。
2.根据权利要求书1所述的配合物1的合成,其特征在于所使用的苯磺酸、氢氧化钠、DPP (1,3-二(吡啶-4-基)丙烷)和硝酸钴的比例为0.1~3.5:0.1~3.5:0.1~3.5:0.1~3.5。
3.根据权利要求书1所述的配合物1的合成和催化合成二氢嘧啶酮类化合物的方法,其特征在于所选的温度范围从室温到200摄氏度。
4.根据权利要求书1所述的配合物1的合成和催化合成二氢嘧啶酮类化合物的方法,其特征在于所需要的反应时间范围从0.4小时到168小时。
5.根据权利要求书1所述的配合物1的合成和催化合成二氢嘧啶酮类化合物的方法,其特征在于所选的有机溶剂为含碳原子数为1-10的单醇、双醇、三醇、四醇或多羟基醇、丙酮、乙酸乙酯、二甲基亚砜、N,N-二甲基甲酰胺、二氯甲烷、三氯甲烷、四氯化碳、硝基甲烷、四氢呋喃、N-甲基吡咯烷酮、石油醚、苯、甲苯的单一溶剂或混合溶剂。
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