有机碱催化的基于贫电子炔的有机反应研究
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摘要
贫电子炔与有机碱形成的两性离子是一类重要的活性中间体。本文通过对一些试剂如β-二羰基化合物,醛,甘氨酸酯的衍生物等和这类活性中间体发生和促进的一些反应进行了研究。通过活泼亚甲基化合物与这类两性离子反应的研究,我们发展了多取代苯和α,β-脱氢氨基酸酯衍生物制备方法;通过醛,贫电子炔和β-二羰基化合物在有机碱催化下研究,我们发展了三苯基膦催化的一类多组分反应和DMAP催化的乙炔基酮与醛的环化反应。全文主要包括以下几个部分:
1.研究了三苯基膦催化的β-二羰基化合物与乙炔基酮的α-加成反应,通过这种方法合成了一系列含有端位烯的多羰基化合物。这种方法操作简单,条件温和。
2.研究了三苯基膦催化的β-二羰基化合物,乙炔基酮和醛的多分子反应,通过这种方法合成了一系列多羰基化合物;提出了三苯基膦催化的这类多分子反应机理。
3.研究了在水相中三苯基膦催化的α,β-不饱和炔酮的异构化反应,通过这种方法合成了一系列共轭的(E,E)-二烯酮。
4.研究了在2,4-戊二酮作为添加物,DMAP催化的炔基酮的自身苯环化反应,通过这种方法合成了一系列1,3,5-三取代的苯,这种方法条件温和,产率高。并研究了在这种条件下炔基酮的交叉环化反应。
5.研究了两分子丙炔酸酯与各种β-二羰基化物的苯环化,通过这种方法合成了一系列多取代的苯。根据实验结果,提出了苯环化反应的机理。
6.初步探讨了DMAP催化的乙炔基酮与醛的环化反应,通过这种方法合成了几种3,4,5-三取代的4H-吡喃,并提出了一个反应机理。
7.研究了三乙胺促进的甘氨酸酯衍生物与贫电子炔的加成反应,通过这种方法合成了一系列α,β-脱氢氨基酸酯衍生物。反应是通过共轭加成及分子内氢的转移来完成的。
通过这些研究,我们扩展了贫电子炔与有机碱形成的两性离子的应用范围,为合成多取代苯以及α,β-脱氢氨基酸酯衍生物等提供了新的方法。
The zwitterions formed from the addition of organic base to electron-defecient alkyne are a class of important dipolar species. We have pursued some reactions based on the zwitterions withβ-dicarbonyl moieties, aldehydes, benzophenone Schiff base derivatives of glycine esters. We developed the approach of synthesis of highly substituted benzenes andα,β-dehydroamino acid derivatives through the reaction of activated methenes with the zwitterions; and developed a multi-component reaction ofβ-dicarbonyl moieties, acetylenic ketones and aldehydes catalyzed by triphenylphosphine; and a cycloaddition of aldehydes with acetylenic ketones catalyzed by DMAP. This article is made up of seven sections.
1. A facile and mild process for synthesis of olefins bearingβ-dicarbonyl moieties based onα-addition ofβ-dicarbonyl moieties to acetylenic ketones catalyzed by triphenylphosphine was developed.
2. A multi-component reaction ofβ-dicarbonyl moieties, acetylenic ketones and aldehydes catalyzed by triphenylphosphine was developed. The method supplies a facile way to synthesis multi-carbonyl compounds. A plausible mechanism is proposed for this multi-component reaction.
3. An efficient isomerization of alkynyl ketones to (E,E)-diene ketones was developed. The reaction catalyzed by triphenylphosphine in aqueous media gave the desired products.
4. A new organocatalytic process of cyclotrimerization of acetylenic ketones was developed, which procedure catalyzed by DMAP in the presence of 2,4-pentanedione as co-catalyst gave 1,3,5-trisubstituted-benzenes with almost quantitative yields under mild conditions. And cross cyclotrimerization of two different acetylenic ketones was investigated.
5. DMAP-catalyzed benzannulation reaction of ethyl propiolate withβ-dicarbonyl compounds at room temperature providing highly substituted benzenes was developed. A possible mechanism for the benzannulation reaction is proposed.
6. A cycloaddition of aldehydes with acetylenic ketones catalyzed by DMAP was developed. The method supplies a facile way to synthesis 3,4,5-trisubstituted-4H-pyrans in moderate to good yields. A plausible mechanism is proposed for this process.
7. A mild and efficient process for synthesis ofα,β-dehydroamino acid derivatives through Et_3N-promoted michael addition of activated alkynes with benzophenone Schiff base derivatives of glycine esters was developed.
Through these rsearches, we extened the appliacation of the zwitterions formedfrom the addition of organic base to electron-defecient alkyne and developed newapproach to synthesis of highly substituted benzenes andα,β-dehydroamino acidderivatives.
1.研究了三苯基膦催化的β-二羰基化合物与乙炔基酮的α-加成反应,通过这种方法合成了一系列含有端位烯的多羰基化合物。这种方法操作简单,条件温和。
2.研究了三苯基膦催化的β-二羰基化合物,乙炔基酮和醛的多分子反应,通过这种方法合成了一系列多羰基化合物;提出了三苯基膦催化的这类多分子反应机理。
3.研究了在水相中三苯基膦催化的α,β-不饱和炔酮的异构化反应,通过这种方法合成了一系列共轭的(E,E)-二烯酮。
4.研究了在2,4-戊二酮作为添加物,DMAP催化的炔基酮的自身苯环化反应,通过这种方法合成了一系列1,3,5-三取代的苯,这种方法条件温和,产率高。并研究了在这种条件下炔基酮的交叉环化反应。
5.研究了两分子丙炔酸酯与各种β-二羰基化物的苯环化,通过这种方法合成了一系列多取代的苯。根据实验结果,提出了苯环化反应的机理。
6.初步探讨了DMAP催化的乙炔基酮与醛的环化反应,通过这种方法合成了几种3,4,5-三取代的4H-吡喃,并提出了一个反应机理。
7.研究了三乙胺促进的甘氨酸酯衍生物与贫电子炔的加成反应,通过这种方法合成了一系列α,β-脱氢氨基酸酯衍生物。反应是通过共轭加成及分子内氢的转移来完成的。
通过这些研究,我们扩展了贫电子炔与有机碱形成的两性离子的应用范围,为合成多取代苯以及α,β-脱氢氨基酸酯衍生物等提供了新的方法。
The zwitterions formed from the addition of organic base to electron-defecient alkyne are a class of important dipolar species. We have pursued some reactions based on the zwitterions withβ-dicarbonyl moieties, aldehydes, benzophenone Schiff base derivatives of glycine esters. We developed the approach of synthesis of highly substituted benzenes andα,β-dehydroamino acid derivatives through the reaction of activated methenes with the zwitterions; and developed a multi-component reaction ofβ-dicarbonyl moieties, acetylenic ketones and aldehydes catalyzed by triphenylphosphine; and a cycloaddition of aldehydes with acetylenic ketones catalyzed by DMAP. This article is made up of seven sections.
1. A facile and mild process for synthesis of olefins bearingβ-dicarbonyl moieties based onα-addition ofβ-dicarbonyl moieties to acetylenic ketones catalyzed by triphenylphosphine was developed.
2. A multi-component reaction ofβ-dicarbonyl moieties, acetylenic ketones and aldehydes catalyzed by triphenylphosphine was developed. The method supplies a facile way to synthesis multi-carbonyl compounds. A plausible mechanism is proposed for this multi-component reaction.
3. An efficient isomerization of alkynyl ketones to (E,E)-diene ketones was developed. The reaction catalyzed by triphenylphosphine in aqueous media gave the desired products.
4. A new organocatalytic process of cyclotrimerization of acetylenic ketones was developed, which procedure catalyzed by DMAP in the presence of 2,4-pentanedione as co-catalyst gave 1,3,5-trisubstituted-benzenes with almost quantitative yields under mild conditions. And cross cyclotrimerization of two different acetylenic ketones was investigated.
5. DMAP-catalyzed benzannulation reaction of ethyl propiolate withβ-dicarbonyl compounds at room temperature providing highly substituted benzenes was developed. A possible mechanism for the benzannulation reaction is proposed.
6. A cycloaddition of aldehydes with acetylenic ketones catalyzed by DMAP was developed. The method supplies a facile way to synthesis 3,4,5-trisubstituted-4H-pyrans in moderate to good yields. A plausible mechanism is proposed for this process.
7. A mild and efficient process for synthesis ofα,β-dehydroamino acid derivatives through Et_3N-promoted michael addition of activated alkynes with benzophenone Schiff base derivatives of glycine esters was developed.
Through these rsearches, we extened the appliacation of the zwitterions formedfrom the addition of organic base to electron-defecient alkyne and developed newapproach to synthesis of highly substituted benzenes andα,β-dehydroamino acidderivatives.
引文
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