微波辐射下取代三芳基杂环化合物的合成及反应研究
摘要
近年来，MORE化学技术在有机合成中的应用越来越广泛。与传统加热反应相比，微波辐射下的有机合成具有反应速度快、产率高、副反应少、产品易纯化等优点，还可以节约能源，实现原子经济性合成和生态友好绿色合成。杂环化合物不仅广泛地存在于自然产物中，而且由于其特殊的生物、药理活性，在现有的药物和农药品种中，一半以上是杂环化合物。有关杂环化合物的合成，一直是有机合成化学家关注的焦点问题。将微波辐射技术用于杂环化合物的合成是微波应用于有机合成的一个方面。随着微波合成技术的不断完善和发展，有关利用此技术合成不同类型杂环化合物的报道也越来越多。
本论文的研究目的主要在于探索微波辐射下2，4，6-三芳基吡喃盐的合成及其与一系列亲核体的开环、关环及消除反应。希望能够从简单的原料出发，在温和的条件下经过简单的步骤，发展高效、高选择性的“原子经济性”反应，拓展绿色的MORE化学技术。本文提供了2，4，6-三芳基吡喃盐与Na_2CO_3／I_2、Na_2S／I_2、NH_2OH·HCl、NH_2NH_2·H_2O的快速、简便的反应和方法，合成了多芳基取代的呋喃、噻吩、异噁唑及二氮杂(艹卓)类化合物，从而扩大了MORE化学技术在合成杂环化合物方面的应用。
本论文分为五章：
第一章：微波辐射在杂环化合物合成中的应用研究进展
本部分综述了一百多篇文献，介绍了近几年微波辐射技术在合成杂环化合物中的应用研究进展。主要从不同的杂环类型分别加以概括，概述了微波技术在合成四、五、六、七元杂环方面的应用。
第二章：微波辐射下2-芳酰基-3，5-二芳基呋喃类化合物的合成研究
2，4，6-三芳基吡喃盐是一类非常有用的有机合成中间体，其可与许多亲核试剂在不同的介质中发生转化，生成不同类型的杂环化合物，为合成多芳基取代的杂环化合物提供了一条途径。
本章在微波辐射下，以芳乙酮和芳香醛为起始原料合成了含不同取代基的2，4，6-三芳基吡喃盐，重点研究了2，4，6-三芳基吡喃盐与Na_2CO_3／I_2在微波辐射下的反应情况，发现当微波辐射功率P=450W，辐照时间T=8～10min时，可以以最大收率得到2-芳酰基-3，5-二芳基呋喃。共合成了十种化合物，产物经现代波谱分析及元素分析表征了其结构。本法具有反应时间短、操作简便、收率高等优点。
第三章：微波辐射下2-芳酰基-3，5-二芳基噻吩类化合物的合成研究
本章研究了微波辐射下2，4，6一三芳基毗喃盐与NaZS/I:及常规条件下2，4，6一三芳基
硫代毗喃盐与NaZs/I:的反应，都以不同收率得到了2一芳酞基一3，5一二芳基噬吩类化合物。
考察了诸如微波辐射功率、时间、溶剂及原料等因素对反应的影响，比较了两种反应各
自的优劣。在实验中我们发现，较2，4，6一三芳基毗喃盐，2，4，6一三芳基硫代毗喃盐更易
与N处S/几反应转化成2一芳酞基一3，5一二芳基噬吩，且常规条件下反应时间短，产物后处
理更加简单。利用两种方法共合成了十种化合物，产物结构都用现代波谱分析及元素分
析进行了表征。
第四章:微波辐射下2，4，6一三芳基毗喃盐与盐酸经胺的反应研究
本章中我们首次将微波辐射技术用于2，4，6一三芳基毗喃盐与盐酸轻胺的转化反应
中，非预期的一步得到了常规条件下需要二步反应才能得到的3，5一二芳基异嗯哇类化合
物，并且以水作为反应介质，实现了微波辐射下水相中的有机合成反应。与常规反应相
比，此方法不但实现了一步转化反应，简化了操作步骤，提高了收率，大大的缩短了反
应时间，而且避免了使用文献方法中对环境有严重危害的高氯酸和有机溶剂，无论从节
省能源还是从环境保护来说均可以说是一种“绿色”的合成方法。利用此方法我们共合
成了十二种不同芳基取代的3，5一二芳基异嗯哇衍生物。通过实验发现，2，4，6一三芳基毗
喃盐与盐酸经胺在NaoH的水溶液中在600W的功率下微波辐射6一smin即可完成反应，
比常规反应速度快315礴00倍。实验中我们考察了微波辐射功率、时间、溶剂、反应体
系酸碱性等因素对反应的影响，从而优选出较佳的反应条件，并根据文献推断出反应机
理。本反应操作简便、收率高、后处理简单，且环境友好，是一种合成3，5一二芳基异德
哇的较佳合成方法。
第五章:微波辐射下2，4，6一三芳基毗喃盐及硫代毗喃盐与水合脐的反应
研究
本章中我们研究了微波辐射下2，4，6一三芳基毗喃盐及硫代毗喃盐与水合脐反应生
成3，5，7一三芳基一1，2一二氮杂革的反应情况。在实验中，我们重点考察了反应体系酸碱性
对反应的影响，发现此反应在中性水介质中几乎能以定量收率生成3，5，7一三芳基一1，2-
二氮杂革衍生物;而当反应体系为强碱性时，却发生其他转化，得不到目标产物。通过
对溶剂的考察还发现，此反应也可以在水溶剂中顺利进行，虽然目标产物收率由于溶解
性影响较在乙醇/水(v;v=l:1)体系中略有下降。但从环境保护、节省能源、操作安
全性方面考虑，我们仍优先选择水为反应最佳溶剂。另外，我们还考察了微波辐射功率、
时间等对反应的影响。利用本法共合成了十一种化合物，产物均经现代波谱分析表?
The application of microwave irradiation to organic synthesis has been the focus of considerable attention in recent years and becoming an emerging technology that could make industrially important organic syntheses more eco-friendly than conventional reactions. Enhancement of a chemical reaction as compared to conventional chemistry can manifest itself in several ways including the following: (1) highly accelerated reaction rates for various types of reactions; (2) improved yield in many cases; (3) stereo- or regioselectivity in some cases; (4) reduction in side products;
(5) limited amounts of solvents (or no solvents in special cases) needed as reaction media;
(6) successful product formation in some reactions that fail under conventional conditions; (7) increase in the rate of some chemoenzymatic reactions; and (8) simplification and improvement of classical synthetic methods. MORE chemistry techniques are potentially valuable as increase 'atom economy' by reducing organic solvents, improving product selectivity and chemical yields. Furthermore, heterocyclic compounds continue to attract significant synthetic efforts due to their important performance in a variety of disciplines. Under the framework of 'Green Chemistry' the chemists have developed MORE chemistry approach for the synthesis of variety of heterocyclic compounds. With the developing microwave equipment, more and more publications have appeared on microwave mediated chemical reactions.
The destination of this thesis is to study the ring expand and closure of 2,4,6-triarylpyrylium salts with a series of nucleophiles under microwave irradiation conditions, it is expected that synthesis of the aimed products under mild condition from commercially available materials and expand the application of microwave irradiation in organic synthesis. This thesis provided the rapid, facile reaction of 2,4,6-triarylpyryliums with Na2CO3/I2, Na2S/I2, NH2OH-HC1, NH2NH2-H2O and obtained furan, thiophene, isoxazole, diazepine derivatives. We broaden the scope of the microwave technology in heterocyclic compounds synthesis. The thesis includes five chapters.
Chapter one: The advance of heteocyclic compounds synthesis under
microwave irradiation.
This part covers the new advance of the microwave-assisted four-, five-, six-, seven-membered heterocyclic compounds synthesis. We emphases on the synthesis of five-, six-membered heterocyclic compounds under microwave irradiation conditions.
Chapter two: The synthesis of 2-aroyl-3,5-diarylfuran derivatives under microwave irradiation
2,4,6-TriarylpyryIiums are very useful intermediates in organic synthesis and react readily with practically many nucleophilic reagents. In this section, we focused on the investigation of the reaction of different aryl substituted pyrylium salts with NaiCOij/h under microwave irradiation and obtained the excellent yield 2-aroyl-3,5-diarylfuran derivatives when using acetone as solvent at 450W continuing 8~10min. We also present a probable reaction mechanism according to the literatures and experiment. This method is simple, fast and affords good yields.
Chapter three: Microwave-promoted synthesis of 2-aroyl-3,5-diaryI-
thiophene derivatives
This chapter includes a description of the conversion 2,4,6-triarylpyryliums with NazS/Ij under microwave irradiation and the reaction of 2,4,6-triarylthiopyryliums with NaiS/Ij under conventional condition. The results are shown that the same products obtained by using these two approaches. We examined the irradiation power, time, solvent and different salts on the yields. It was found that 2,4,6-triarylthiopyryliums are more easily converted into the products than the corresponding 2,4,6-triarylpyryliums. Using these methods, we obtained ten kinds of compounds. The products were characterized by modern spectral data.
Chapter four: The study of the conversion of 2,4,6-triarylpyryliums
with hydroxylamine hydrochloride under microwave irradiation
In this chapter, we firstly used the microwave technology to accel
本论文的研究目的主要在于探索微波辐射下2，4，6-三芳基吡喃盐的合成及其与一系列亲核体的开环、关环及消除反应。希望能够从简单的原料出发，在温和的条件下经过简单的步骤，发展高效、高选择性的“原子经济性”反应，拓展绿色的MORE化学技术。本文提供了2，4，6-三芳基吡喃盐与Na_2CO_3／I_2、Na_2S／I_2、NH_2OH·HCl、NH_2NH_2·H_2O的快速、简便的反应和方法，合成了多芳基取代的呋喃、噻吩、异噁唑及二氮杂(艹卓)类化合物，从而扩大了MORE化学技术在合成杂环化合物方面的应用。
本论文分为五章：
第一章：微波辐射在杂环化合物合成中的应用研究进展
本部分综述了一百多篇文献，介绍了近几年微波辐射技术在合成杂环化合物中的应用研究进展。主要从不同的杂环类型分别加以概括，概述了微波技术在合成四、五、六、七元杂环方面的应用。
第二章：微波辐射下2-芳酰基-3，5-二芳基呋喃类化合物的合成研究
2，4，6-三芳基吡喃盐是一类非常有用的有机合成中间体，其可与许多亲核试剂在不同的介质中发生转化，生成不同类型的杂环化合物，为合成多芳基取代的杂环化合物提供了一条途径。
本章在微波辐射下，以芳乙酮和芳香醛为起始原料合成了含不同取代基的2，4，6-三芳基吡喃盐，重点研究了2，4，6-三芳基吡喃盐与Na_2CO_3／I_2在微波辐射下的反应情况，发现当微波辐射功率P=450W，辐照时间T=8～10min时，可以以最大收率得到2-芳酰基-3，5-二芳基呋喃。共合成了十种化合物，产物经现代波谱分析及元素分析表征了其结构。本法具有反应时间短、操作简便、收率高等优点。
第三章：微波辐射下2-芳酰基-3，5-二芳基噻吩类化合物的合成研究
本章研究了微波辐射下2，4，6一三芳基毗喃盐与NaZS/I:及常规条件下2，4，6一三芳基
硫代毗喃盐与NaZs/I:的反应，都以不同收率得到了2一芳酞基一3，5一二芳基噬吩类化合物。
考察了诸如微波辐射功率、时间、溶剂及原料等因素对反应的影响，比较了两种反应各
自的优劣。在实验中我们发现，较2，4，6一三芳基毗喃盐，2，4，6一三芳基硫代毗喃盐更易
与N处S/几反应转化成2一芳酞基一3，5一二芳基噬吩，且常规条件下反应时间短，产物后处
理更加简单。利用两种方法共合成了十种化合物，产物结构都用现代波谱分析及元素分
析进行了表征。
第四章:微波辐射下2，4，6一三芳基毗喃盐与盐酸经胺的反应研究
本章中我们首次将微波辐射技术用于2，4，6一三芳基毗喃盐与盐酸轻胺的转化反应
中，非预期的一步得到了常规条件下需要二步反应才能得到的3，5一二芳基异嗯哇类化合
物，并且以水作为反应介质，实现了微波辐射下水相中的有机合成反应。与常规反应相
比，此方法不但实现了一步转化反应，简化了操作步骤，提高了收率，大大的缩短了反
应时间，而且避免了使用文献方法中对环境有严重危害的高氯酸和有机溶剂，无论从节
省能源还是从环境保护来说均可以说是一种“绿色”的合成方法。利用此方法我们共合
成了十二种不同芳基取代的3，5一二芳基异嗯哇衍生物。通过实验发现，2，4，6一三芳基毗
喃盐与盐酸经胺在NaoH的水溶液中在600W的功率下微波辐射6一smin即可完成反应，
比常规反应速度快315礴00倍。实验中我们考察了微波辐射功率、时间、溶剂、反应体
系酸碱性等因素对反应的影响，从而优选出较佳的反应条件，并根据文献推断出反应机
理。本反应操作简便、收率高、后处理简单，且环境友好，是一种合成3，5一二芳基异德
哇的较佳合成方法。
第五章:微波辐射下2，4，6一三芳基毗喃盐及硫代毗喃盐与水合脐的反应
研究
本章中我们研究了微波辐射下2，4，6一三芳基毗喃盐及硫代毗喃盐与水合脐反应生
成3，5，7一三芳基一1，2一二氮杂革的反应情况。在实验中，我们重点考察了反应体系酸碱性
对反应的影响，发现此反应在中性水介质中几乎能以定量收率生成3，5，7一三芳基一1，2-
二氮杂革衍生物;而当反应体系为强碱性时，却发生其他转化，得不到目标产物。通过
对溶剂的考察还发现，此反应也可以在水溶剂中顺利进行，虽然目标产物收率由于溶解
性影响较在乙醇/水(v;v=l:1)体系中略有下降。但从环境保护、节省能源、操作安
全性方面考虑，我们仍优先选择水为反应最佳溶剂。另外，我们还考察了微波辐射功率、
时间等对反应的影响。利用本法共合成了十一种化合物，产物均经现代波谱分析表?
The application of microwave irradiation to organic synthesis has been the focus of considerable attention in recent years and becoming an emerging technology that could make industrially important organic syntheses more eco-friendly than conventional reactions. Enhancement of a chemical reaction as compared to conventional chemistry can manifest itself in several ways including the following: (1) highly accelerated reaction rates for various types of reactions; (2) improved yield in many cases; (3) stereo- or regioselectivity in some cases; (4) reduction in side products;
(5) limited amounts of solvents (or no solvents in special cases) needed as reaction media;
(6) successful product formation in some reactions that fail under conventional conditions; (7) increase in the rate of some chemoenzymatic reactions; and (8) simplification and improvement of classical synthetic methods. MORE chemistry techniques are potentially valuable as increase 'atom economy' by reducing organic solvents, improving product selectivity and chemical yields. Furthermore, heterocyclic compounds continue to attract significant synthetic efforts due to their important performance in a variety of disciplines. Under the framework of 'Green Chemistry' the chemists have developed MORE chemistry approach for the synthesis of variety of heterocyclic compounds. With the developing microwave equipment, more and more publications have appeared on microwave mediated chemical reactions.
The destination of this thesis is to study the ring expand and closure of 2,4,6-triarylpyrylium salts with a series of nucleophiles under microwave irradiation conditions, it is expected that synthesis of the aimed products under mild condition from commercially available materials and expand the application of microwave irradiation in organic synthesis. This thesis provided the rapid, facile reaction of 2,4,6-triarylpyryliums with Na2CO3/I2, Na2S/I2, NH2OH-HC1, NH2NH2-H2O and obtained furan, thiophene, isoxazole, diazepine derivatives. We broaden the scope of the microwave technology in heterocyclic compounds synthesis. The thesis includes five chapters.
Chapter one: The advance of heteocyclic compounds synthesis under
microwave irradiation.
This part covers the new advance of the microwave-assisted four-, five-, six-, seven-membered heterocyclic compounds synthesis. We emphases on the synthesis of five-, six-membered heterocyclic compounds under microwave irradiation conditions.
Chapter two: The synthesis of 2-aroyl-3,5-diarylfuran derivatives under microwave irradiation
2,4,6-TriarylpyryIiums are very useful intermediates in organic synthesis and react readily with practically many nucleophilic reagents. In this section, we focused on the investigation of the reaction of different aryl substituted pyrylium salts with NaiCOij/h under microwave irradiation and obtained the excellent yield 2-aroyl-3,5-diarylfuran derivatives when using acetone as solvent at 450W continuing 8~10min. We also present a probable reaction mechanism according to the literatures and experiment. This method is simple, fast and affords good yields.
Chapter three: Microwave-promoted synthesis of 2-aroyl-3,5-diaryI-
thiophene derivatives
This chapter includes a description of the conversion 2,4,6-triarylpyryliums with NazS/Ij under microwave irradiation and the reaction of 2,4,6-triarylthiopyryliums with NaiS/Ij under conventional condition. The results are shown that the same products obtained by using these two approaches. We examined the irradiation power, time, solvent and different salts on the yields. It was found that 2,4,6-triarylthiopyryliums are more easily converted into the products than the corresponding 2,4,6-triarylpyryliums. Using these methods, we obtained ten kinds of compounds. The products were characterized by modern spectral data.
Chapter four: The study of the conversion of 2,4,6-triarylpyryliums
with hydroxylamine hydrochloride under microwave irradiation
In this chapter, we firstly used the microwave technology to accel
引文
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