苯并氧杂蒽类化合物，4，4'-芳亚甲基—二（3-甲基—吡咯酮）类化合物以及手性噁唑啉类化合物的合成
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摘要
（一）苯并氧杂蒽类化合物应用范围广，这类化合物有着许多的生物和药学功效，比如作为止痛剂，抗炎药，抗菌药，抗病毒的活性体以及荧光材料等。
由于苯并氧杂蒽类化合物的应用价值，科研人员开发出了很多的催化合成方法。主要包括：Sr(OTf)_2、相转移催化剂四丁基溴化铵、NaHSO_4/SiO_2、InCl_3和P_2O_5、I2、对甲苯磺酸、分子筛、Cu/SiO_2、脯氨酸的三氟甲磺酸盐、硝酸铈铵(CAN)以及樟脑磺酸(CSA)。这些方法都有各自的优点，但是正如硬币都有两面一样，同时也有某些缺点。比如反应时间较长（5-7小时）、使用毒性较大的有机溶剂（1,2-二氯乙烷）、催化剂有毒（Cu）或者具有较强腐蚀性（P_2O_5）以及催化剂成本较高（Sr(OTf)_2，InCl_3）等。
显然，目前的这些合成方法都是不符合“绿色化学”的理念的，有必要开发出新的合成方法。我们首次使用Br nsted酸性离子液体和ZrOCl_28H_2O作为催化剂，开发出了两种高效的绿色合成方法。
我们采用三种方法以较高的产率合成了9种离子液体，并且通过实验从中选择出了最佳的催化剂---[NSPTEA][HSO_4][N-(4-sulfonic acid) propyltriethylammonium hydrosulfate]。然后分别使用[NSPTEA][HSO_4]和ZrOCl_28H_2O作为催化剂，开发出了苯并氧杂蒽类化合物的新的合成方法。
在实验中，我们以较高的产率合成了16种苯并氧杂蒽类化合物。相对于已经报道的合成方法，我们新开发的方法具有以下显著的优点：
（1）产率高，74%-87%。
（2）反应时间大幅缩短，只需要10-30min。
（3）反应过程中不需要使用溶剂，既节约了成本，又降低了污染。
（4）[NSPTEA][HSO_4]可以重复利用。
（5）[NSPTEA][HSO_4]和ZrOCl_28H_2O几乎没有腐蚀性和毒性。
（6）[NSPTEA][HSO_4]的制备非常简单，原材料廉价易得。
（7） ZrOCl_28H_2O的存量很大，价格低廉，使用成本低。
（8）[NSPTEA][HSO_4]和ZrOCl_28H_2O对水稳定，具备良好的可操作性。
（二）吡咯环是很多具有生物活性化合物的核心结构，4,4’-芳亚甲基-二(3-甲基-吡咯酮)类化合物可以用来作为杀菌剂,农药,杀虫剂,染料,以及不同的金属离子螯合剂和提取试剂使用。
4,4’-芳亚甲基-二(3-甲基-吡咯酮)类化合物的传统合成方法主要有两套路线：
(1)以醛和吡咯酮为反应物。首先一分子醛和一分子3-甲基-2-吡唑啉-5-酮通过Knoevenagel反应合成芳亚甲基吡唑酮，然后在碱的催化作用下，另外一分子3-甲基-2-吡唑啉-5-酮再和芳亚甲基吡唑酮进行Michael加成反应，最后得到4,4’-芳亚甲基-二(3-甲基-吡咯酮)类化合物。典型的反应条件是以乙醇作溶剂，哌啶作为催化剂。(2)通过一分子醛和两分子3-甲基-2-吡唑啉-5-酮在酸的作用下进行加成反应，合成4,4’-芳亚甲基-二(3-甲基-吡咯酮)类化合物。该路线的典型反应条件是以乙醇或者以苯作为溶剂，在回流的温度下进行反应。虽然这种方法的产率较高，可以达到70%-90%。然而该方法的反应时间较长：首先需要回流3-12小时，然后在室温下再进行24小时。
通过对这两套方法的思考，我们发现无论是路线(1)还是路线(2)，都需要使用3-甲基-2-吡唑啉-5-酮作为反应底物。而3-甲基-2-吡唑啉-5-酮这一化合物通常情况下不太容易从市场上购买到，需要实验人员的预先合成。根据文献所述，3-甲基-2-吡唑啉-5-酮的合成往往需要在乙醇作溶剂的情况下回流1－3小时。而且粗产品还需要经过重结晶的纯化过程。因此导致路线(1)和路线(2)的总的实验流程加长，而且操作变得繁琐，同时合成的总产率也会相应的降低。
我们组创新的运用多组分一锅法，从醛、乙酰乙酸乙酯和水合肼出发，直接合成了4,4’-芳亚甲基-二(3-甲基-吡咯酮)类化合物，我们开发的合成方法的主要优点是：
（1）使用水作为反应的溶剂，从而避免了使用有机溶剂所造成的污染。
（2）不需要预先合成3-甲基-2-吡唑啉-5-酮，减少了合成步骤，节省了人力、物力和时间。
（3）产率较高（72%-85%），反应时间缩短至6-8小时。
（4）不需要使用催化剂。
（三）含有噁唑啉环的化合物有着很重要的作用，也因此科研人员开发出了很多合成方法。然而这些合成方法也存在一些缺点，比如反应所需条件较苛刻，需要160-220℃的高温，或者是反应所需时间太长（12-18小时）以及使用昂贵的试剂等。
我们组结合前期的工作，转换合成角度，开发出了一种新的合成方法。首先将多种手性氨基酸还原成手性氨基醇，然后和N-[氯（二甲氨基）甲基]-N-甲胺盐氯(TMUCl Cl)进行反应，以较高的产率得到了手性的噁唑啉类化合物。我们开发的方法的优点如下：
（1）反应中所用到的原材料都是廉价易得的。
（2）不需要苛刻的反应条件，室温下反应即可。
（3）产率高，时间短（5小时）。
（4）纯化过程简单，经过减压蒸馏就可以得到纯品，因而适于大量制备。
(1) Benzoxanthene compounds have many applications. They have manybiological and pharmaceutical effects, such as analgesics, anti-inflammatory drugs,antibacterial drugs, anti-viral activity and the fluorescent material.
Because of the value of the benzoxanthene compounds, the researchersdeveloped many synthetic methods, including Sr(OTf)_2, phase transfer catalysttetrabutylammonium bromide, NaHSO_4/SiO_2, InCl_3and P_2O_5, I2, toluenesulfonicacid, molecular sieves, Cu/SiO_2, proline trifluoromethane sulfonate, cericammonium nitrate (CAN) and camphor sulfonic acid (CSA). These methods havetheir own advantages, but as a coin has two sides, also have some drawbacks, suchas long reaction time (5-7hours), toxic organic solvents, toxic metal catalysts,corrosive catalyst, and expensive catalyst.
Clearly, these methods are not in line with the concept of "green chemistry", itis necessary to develop new synthetic method. We developed a new syntheticmethod using [NSPTEA][HSO_4] and ZrOCl_28H_2O as catalyst for the synthesis ofbenzoxanthene compounds
Compared to the reported synthetic methods, our newly developed method hasthe following significant advantages:
a) High yield,74%-87%.
b) The reaction time is significantly shortened, only requires10-30min.
c) The reaction does not require solvents.
d)[NSPTEA][HSO_4] can be reused.
e)[NSPTEA][HSO_4], and ZrOCl_28H_2O are not corrosive or toxic at all.
f) The preparation of [NSPTEA][HSO_4] is very simple. And the rawmaterials are cheap and easy to get.
g) ZrOCl_28H_2O costs lower.
h)[NSPTEA][HSO_4] and ZrOCl_28H_2O are water stable.
(2) Pyrrole ring is the core structure of biologically active compounds, andtherefore arise widespread concern in the pharmaceutical industry. And it hasbecome one of the synthetic target molecules. Moreover, derivatives of4,4'-arylidene-bis (3-methyl-pyrazolones) can be used as fungicides, pesticides,insecticides, dyes, and different metal ion chelators and extraction reagents.
However, the overall reaction yields and time are unsatisfying and lengthy. Sothere is still need to develop a new and convenient method for the synthesis of4,4’-arylidene-bis(3-methyl-pyrazolones).
Our group developed a multi-component one-pot method, starting directly fromaldehydes, ethyl acetoacetate and hydrazine hydrate, for the synthesis of4,4'-arylidene-bis (3-methyl-pyrazolones) compounds. The advantages of our methodare:1) more simple procedure,2) high yields,3) shorter reaction time,4) avoid theuse of organic solvents which is harmful to environment.
(3) Oxazolines are important class of heterocyclic compounds with a wide rangeof pharmaceutical and biological activities. In addition, these compounds have alsovarious synthetic uses in modern day chemistry which play an important role inasymmetric synthesis. Numerous methods have been developed for the preparationof2-substituted oxazolines. However, these methods have some shortcomings,including drastic thermal conditions (160–220℃), long reaction times (12–18h),modest yields, expensive coupling reagents.
We have developed a new, simple and mild synthesis of optically active2-(N,N-dialkyl)oxazolines by only two or three steps from cheap tetraalkyl ureas andα-amino acids with good overall yields. These new2-(N, N-dialkyl)oxazolines maybe potential chiral auxiliaries or ligands, and are being investigated in our laboratoryfor further application.
由于苯并氧杂蒽类化合物的应用价值，科研人员开发出了很多的催化合成方法。主要包括：Sr(OTf)_2、相转移催化剂四丁基溴化铵、NaHSO_4/SiO_2、InCl_3和P_2O_5、I2、对甲苯磺酸、分子筛、Cu/SiO_2、脯氨酸的三氟甲磺酸盐、硝酸铈铵(CAN)以及樟脑磺酸(CSA)。这些方法都有各自的优点，但是正如硬币都有两面一样，同时也有某些缺点。比如反应时间较长（5-7小时）、使用毒性较大的有机溶剂（1,2-二氯乙烷）、催化剂有毒（Cu）或者具有较强腐蚀性（P_2O_5）以及催化剂成本较高（Sr(OTf)_2，InCl_3）等。
显然，目前的这些合成方法都是不符合“绿色化学”的理念的，有必要开发出新的合成方法。我们首次使用Br nsted酸性离子液体和ZrOCl_28H_2O作为催化剂，开发出了两种高效的绿色合成方法。
我们采用三种方法以较高的产率合成了9种离子液体，并且通过实验从中选择出了最佳的催化剂---[NSPTEA][HSO_4][N-(4-sulfonic acid) propyltriethylammonium hydrosulfate]。然后分别使用[NSPTEA][HSO_4]和ZrOCl_28H_2O作为催化剂，开发出了苯并氧杂蒽类化合物的新的合成方法。
在实验中，我们以较高的产率合成了16种苯并氧杂蒽类化合物。相对于已经报道的合成方法，我们新开发的方法具有以下显著的优点：
（1）产率高，74%-87%。
（2）反应时间大幅缩短，只需要10-30min。
（3）反应过程中不需要使用溶剂，既节约了成本，又降低了污染。
（4）[NSPTEA][HSO_4]可以重复利用。
（5）[NSPTEA][HSO_4]和ZrOCl_28H_2O几乎没有腐蚀性和毒性。
（6）[NSPTEA][HSO_4]的制备非常简单，原材料廉价易得。
（7） ZrOCl_28H_2O的存量很大，价格低廉，使用成本低。
（8）[NSPTEA][HSO_4]和ZrOCl_28H_2O对水稳定，具备良好的可操作性。
（二）吡咯环是很多具有生物活性化合物的核心结构，4,4’-芳亚甲基-二(3-甲基-吡咯酮)类化合物可以用来作为杀菌剂,农药,杀虫剂,染料,以及不同的金属离子螯合剂和提取试剂使用。
4,4’-芳亚甲基-二(3-甲基-吡咯酮)类化合物的传统合成方法主要有两套路线：
(1)以醛和吡咯酮为反应物。首先一分子醛和一分子3-甲基-2-吡唑啉-5-酮通过Knoevenagel反应合成芳亚甲基吡唑酮，然后在碱的催化作用下，另外一分子3-甲基-2-吡唑啉-5-酮再和芳亚甲基吡唑酮进行Michael加成反应，最后得到4,4’-芳亚甲基-二(3-甲基-吡咯酮)类化合物。典型的反应条件是以乙醇作溶剂，哌啶作为催化剂。(2)通过一分子醛和两分子3-甲基-2-吡唑啉-5-酮在酸的作用下进行加成反应，合成4,4’-芳亚甲基-二(3-甲基-吡咯酮)类化合物。该路线的典型反应条件是以乙醇或者以苯作为溶剂，在回流的温度下进行反应。虽然这种方法的产率较高，可以达到70%-90%。然而该方法的反应时间较长：首先需要回流3-12小时，然后在室温下再进行24小时。
通过对这两套方法的思考，我们发现无论是路线(1)还是路线(2)，都需要使用3-甲基-2-吡唑啉-5-酮作为反应底物。而3-甲基-2-吡唑啉-5-酮这一化合物通常情况下不太容易从市场上购买到，需要实验人员的预先合成。根据文献所述，3-甲基-2-吡唑啉-5-酮的合成往往需要在乙醇作溶剂的情况下回流1－3小时。而且粗产品还需要经过重结晶的纯化过程。因此导致路线(1)和路线(2)的总的实验流程加长，而且操作变得繁琐，同时合成的总产率也会相应的降低。
我们组创新的运用多组分一锅法，从醛、乙酰乙酸乙酯和水合肼出发，直接合成了4,4’-芳亚甲基-二(3-甲基-吡咯酮)类化合物，我们开发的合成方法的主要优点是：
（1）使用水作为反应的溶剂，从而避免了使用有机溶剂所造成的污染。
（2）不需要预先合成3-甲基-2-吡唑啉-5-酮，减少了合成步骤，节省了人力、物力和时间。
（3）产率较高（72%-85%），反应时间缩短至6-8小时。
（4）不需要使用催化剂。
（三）含有噁唑啉环的化合物有着很重要的作用，也因此科研人员开发出了很多合成方法。然而这些合成方法也存在一些缺点，比如反应所需条件较苛刻，需要160-220℃的高温，或者是反应所需时间太长（12-18小时）以及使用昂贵的试剂等。
我们组结合前期的工作，转换合成角度，开发出了一种新的合成方法。首先将多种手性氨基酸还原成手性氨基醇，然后和N-[氯（二甲氨基）甲基]-N-甲胺盐氯(TMUCl Cl)进行反应，以较高的产率得到了手性的噁唑啉类化合物。我们开发的方法的优点如下：
（1）反应中所用到的原材料都是廉价易得的。
（2）不需要苛刻的反应条件，室温下反应即可。
（3）产率高，时间短（5小时）。
（4）纯化过程简单，经过减压蒸馏就可以得到纯品，因而适于大量制备。
(1) Benzoxanthene compounds have many applications. They have manybiological and pharmaceutical effects, such as analgesics, anti-inflammatory drugs,antibacterial drugs, anti-viral activity and the fluorescent material.
Because of the value of the benzoxanthene compounds, the researchersdeveloped many synthetic methods, including Sr(OTf)_2, phase transfer catalysttetrabutylammonium bromide, NaHSO_4/SiO_2, InCl_3and P_2O_5, I2, toluenesulfonicacid, molecular sieves, Cu/SiO_2, proline trifluoromethane sulfonate, cericammonium nitrate (CAN) and camphor sulfonic acid (CSA). These methods havetheir own advantages, but as a coin has two sides, also have some drawbacks, suchas long reaction time (5-7hours), toxic organic solvents, toxic metal catalysts,corrosive catalyst, and expensive catalyst.
Clearly, these methods are not in line with the concept of "green chemistry", itis necessary to develop new synthetic method. We developed a new syntheticmethod using [NSPTEA][HSO_4] and ZrOCl_28H_2O as catalyst for the synthesis ofbenzoxanthene compounds
Compared to the reported synthetic methods, our newly developed method hasthe following significant advantages:
a) High yield,74%-87%.
b) The reaction time is significantly shortened, only requires10-30min.
c) The reaction does not require solvents.
d)[NSPTEA][HSO_4] can be reused.
e)[NSPTEA][HSO_4], and ZrOCl_28H_2O are not corrosive or toxic at all.
f) The preparation of [NSPTEA][HSO_4] is very simple. And the rawmaterials are cheap and easy to get.
g) ZrOCl_28H_2O costs lower.
h)[NSPTEA][HSO_4] and ZrOCl_28H_2O are water stable.
(2) Pyrrole ring is the core structure of biologically active compounds, andtherefore arise widespread concern in the pharmaceutical industry. And it hasbecome one of the synthetic target molecules. Moreover, derivatives of4,4'-arylidene-bis (3-methyl-pyrazolones) can be used as fungicides, pesticides,insecticides, dyes, and different metal ion chelators and extraction reagents.
However, the overall reaction yields and time are unsatisfying and lengthy. Sothere is still need to develop a new and convenient method for the synthesis of4,4’-arylidene-bis(3-methyl-pyrazolones).
Our group developed a multi-component one-pot method, starting directly fromaldehydes, ethyl acetoacetate and hydrazine hydrate, for the synthesis of4,4'-arylidene-bis (3-methyl-pyrazolones) compounds. The advantages of our methodare:1) more simple procedure,2) high yields,3) shorter reaction time,4) avoid theuse of organic solvents which is harmful to environment.
(3) Oxazolines are important class of heterocyclic compounds with a wide rangeof pharmaceutical and biological activities. In addition, these compounds have alsovarious synthetic uses in modern day chemistry which play an important role inasymmetric synthesis. Numerous methods have been developed for the preparationof2-substituted oxazolines. However, these methods have some shortcomings,including drastic thermal conditions (160–220℃), long reaction times (12–18h),modest yields, expensive coupling reagents.
We have developed a new, simple and mild synthesis of optically active2-(N,N-dialkyl)oxazolines by only two or three steps from cheap tetraalkyl ureas andα-amino acids with good overall yields. These new2-(N, N-dialkyl)oxazolines maybe potential chiral auxiliaries or ligands, and are being investigated in our laboratoryfor further application.
引文
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