联烯酸酯和β-邻卤芳基杂环烯酮缩胺的反应研究
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摘要
联烯因其累积二烯结构,在有机合成中具有独特的反应活性。在联烯的两端,可以引入丰富多样的取代基,包括烷基,芳基,烯丙基,氰基,乙酰基和酯基。为有机合成方法学的多样性提供了无限机会。
β-邻卤芳基杂环烯酮缩胺有着极高的反应活性,是有机化学中形成碳-碳键和碳-氮键的一种很好合成子。它是一类重要的有机合成中间体,在杂环化合物的合成中有着广泛的应用。
本文以杂环烯酮缩胺和联烯酸酯进行反应,构筑和发展新型1,8-二氮杂萘类杂环体系的合成方法,合成了25个新型的咪唑并吡啶类化合物和23个新型苯并咪唑并二氮杂萘二酮类化合物。
论文第一章首先介绍了联烯以及杂环烯酮缩胺的独特性质和它们在有机合成领域中的广泛应用;第二章介绍了联烯酸酯和β-邻卤芳基杂环烯酮缩在DABCO和K_2CO_3催化下进行反应,生成咪唑并吡啶类化合物和1,8-二氮杂萘类化合物。在反应中研究了溶剂,温度,催化剂及其用量等条件对反应的影响,确定了最佳反应条件。整个系列反应条件温和,操作简便,溶剂用量少,产品易于纯化。这种方法合成二氮杂萘类化合物迄今未见文献报道,是一种环境友好的方法。
在这个反应中,共有9个不同活性位点参与反应,经历了一系列Knoevenagel缩合、氮杂烯反应、环化和分子内亲核取代反应,生成了两个新环、三个新键,充分体现了“原子经济性”。所合成的化合物均经IR、~1H NMR、~(13)C NMR和高分辨质谱分析表征。其中对化合物4a和6g进行了X-单晶衍射分析,确定了其精确的空间结构。
Allenes, which are endowed with features by the presence of the cumulated diene structural unit, show unique reactivity in organic synthesis. Different kinds of substituent group including aryl, alkyl, allyl, cyano, acetyl ethoxycarbonyl and methoxycarbonyl is successfully introduced into both ends of the allenes, which provides unlimited opportunities for diversity of methodology of organic synthesis.β-(2-Haloaryl)-heterocyclic ketene aminals are good synthons in the form of C-C bond and C-N bond because of its high reactivity.β-(2-Haloaryl)-heterocyclic ketene aminals are powerful and versatile intermediates for the synthesis of a wide variety of new heterocycles and fused heterocycles.
This thesis focus on building new frame work of [1, 8]naphthyridine,twenty five new imidazo(pyrido)[1,2-a]pyridines and twenty three imidazo(pyrido)[3,2,1-ij]- [1,8]naphthyridines compounds were synthesized via the reaction of allenic acid esters and heterocyclic ketene aminals.
In the first chapter, allenes and polarized heterocyclic ketene aminals as very useful synthons in organic synthesis were reviewed in brief. In the second chapter, imidazo(pyrido)[1,2-a]pyridines and imidazo(pyrido)[3,2,1-ij][1,8]naphthyridines derivatives unreported in the literatures have been synthesised withβ-(2-haloaryl)- heterocyclic ketene aminals and allenic esters reactions in the presence of DABCO and K_2CO_3 as catalyst. The reaction conditions including solvent, catalyst and molar ratio were also investigated. These reactions were very mild, convenient and effective.
In this reaction, nine different active sites were involved; three new bonds and two new rings were constructed with all reactants which efficiently utilized via a sequence of Knoevenagel condensation, aza-ene reaction, cyclization and intramolecular nucleophilic substitution reactions. It fully reflects the“atom economy” in this reaction.
The structures of all the target compounds were confirmed by IR, 1H NMR, 13C NMR, and HRMS, and the plausible mechanism was also presented. The unambiguous molecular structure of 4a and 6g were determined by X-ray diffraction analysis.
β-邻卤芳基杂环烯酮缩胺有着极高的反应活性,是有机化学中形成碳-碳键和碳-氮键的一种很好合成子。它是一类重要的有机合成中间体,在杂环化合物的合成中有着广泛的应用。
本文以杂环烯酮缩胺和联烯酸酯进行反应,构筑和发展新型1,8-二氮杂萘类杂环体系的合成方法,合成了25个新型的咪唑并吡啶类化合物和23个新型苯并咪唑并二氮杂萘二酮类化合物。
论文第一章首先介绍了联烯以及杂环烯酮缩胺的独特性质和它们在有机合成领域中的广泛应用;第二章介绍了联烯酸酯和β-邻卤芳基杂环烯酮缩在DABCO和K_2CO_3催化下进行反应,生成咪唑并吡啶类化合物和1,8-二氮杂萘类化合物。在反应中研究了溶剂,温度,催化剂及其用量等条件对反应的影响,确定了最佳反应条件。整个系列反应条件温和,操作简便,溶剂用量少,产品易于纯化。这种方法合成二氮杂萘类化合物迄今未见文献报道,是一种环境友好的方法。
在这个反应中,共有9个不同活性位点参与反应,经历了一系列Knoevenagel缩合、氮杂烯反应、环化和分子内亲核取代反应,生成了两个新环、三个新键,充分体现了“原子经济性”。所合成的化合物均经IR、~1H NMR、~(13)C NMR和高分辨质谱分析表征。其中对化合物4a和6g进行了X-单晶衍射分析,确定了其精确的空间结构。
Allenes, which are endowed with features by the presence of the cumulated diene structural unit, show unique reactivity in organic synthesis. Different kinds of substituent group including aryl, alkyl, allyl, cyano, acetyl ethoxycarbonyl and methoxycarbonyl is successfully introduced into both ends of the allenes, which provides unlimited opportunities for diversity of methodology of organic synthesis.β-(2-Haloaryl)-heterocyclic ketene aminals are good synthons in the form of C-C bond and C-N bond because of its high reactivity.β-(2-Haloaryl)-heterocyclic ketene aminals are powerful and versatile intermediates for the synthesis of a wide variety of new heterocycles and fused heterocycles.
This thesis focus on building new frame work of [1, 8]naphthyridine,twenty five new imidazo(pyrido)[1,2-a]pyridines and twenty three imidazo(pyrido)[3,2,1-ij]- [1,8]naphthyridines compounds were synthesized via the reaction of allenic acid esters and heterocyclic ketene aminals.
In the first chapter, allenes and polarized heterocyclic ketene aminals as very useful synthons in organic synthesis were reviewed in brief. In the second chapter, imidazo(pyrido)[1,2-a]pyridines and imidazo(pyrido)[3,2,1-ij][1,8]naphthyridines derivatives unreported in the literatures have been synthesised withβ-(2-haloaryl)- heterocyclic ketene aminals and allenic esters reactions in the presence of DABCO and K_2CO_3 as catalyst. The reaction conditions including solvent, catalyst and molar ratio were also investigated. These reactions were very mild, convenient and effective.
In this reaction, nine different active sites were involved; three new bonds and two new rings were constructed with all reactants which efficiently utilized via a sequence of Knoevenagel condensation, aza-ene reaction, cyclization and intramolecular nucleophilic substitution reactions. It fully reflects the“atom economy” in this reaction.
The structures of all the target compounds were confirmed by IR, 1H NMR, 13C NMR, and HRMS, and the plausible mechanism was also presented. The unambiguous molecular structure of 4a and 6g were determined by X-ray diffraction analysis.
引文
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[2] Schuter, H. F., Coppola, G. M., Application of isatoic anhydride chemistry to the synthesis of racemic paraensine. J. Heterocycl. Chem., 1984, 21, 1409-1410.
[3] Ficini, J., Pouliquen, J., Cycloaddition of ynamines with carbon dioxide. Route to diamides of allene-1,3-dicarboxylic acids. J. Am. Chem. Soc., 1971, 93, 3295-3297.
[4] Ma, S., Wei, Q., Wang, H., Unique selectivity of iodohydroxylation reaction of allenyl phenyl sulfoxides in aqueous MeCN. A stereodefined synthesis of (E)-2-Iodo-3-hydroxy- 1-alkenyl sulfoxides. Org. Lett., 2000, 2, 3893-3895.
[5] Zens, A. P., Elis, P. D., Dtchfield, R., Carbon-13 nuclear magnetic resonance chemical shifts of the fluoroallenes. Comparison between theory and experiment. J. Am.Chem. Soc., 1974, 96, 1309-1312.
[6] Knoth, W. H., Coffman, D. D., Synthesis and chemistry of 1,1-difluoroallene. J. Am. Chem. Soc., 1960, 82, 3873-3875.
[7] Back, T. G., Muralidharan, K. R., Formation and electrophilic reactions of benzeneselenenyl p-toluenesulfonate. Preparation and properties of addition products with acetylenes. J. Org. Chem., 1991, 56, 2781-2787.
[8] Kakiuchi, K., Ue, M., Tsukahara, H., et. Al., Novel rearrangement of 5,6-disubstituted bicyclo[4.2.0]octan-2-ones with AlCl3. Application to total synthesis of (±)-5-oxosilphiperfol-6-ene and (±)-silphiperfol-6-ene. J. Am. Chem. Soc., 1989, 111, 3707-3712.
[9] Zhao, G. L., Huang, J. W., Shi, M., Abnormal aza-Baylis?Hillman reaction of N-tosylated imines with ethyl 2,3-butadienoate and penta-3,4-dien-2-one. Org. Lett., 2003, 5, 4737- 4739.
[10] Yasukouchi, T., Kanematsu, K., For intermolecular [4+2] cycloaddition of chloromethyl- sulfonyl(or trichloromethylsulfonyl)-1,2-propadiene with different 1,3-dienes, Tetrahedron Lett., 1989, 30, 6559-6562.
[11] Kanematsu, K., Kinoyama, I., One-pot access to benzosulfolenes(1,3-dihydrobenzo[c] thiophene S,S-dioxides) via allenyl furfuryl(2-furylmethyl)sulfone intramolecular cycloaddition strategy. Chem. Commun., 1992: 735-736.
[12] Padwa, A., Meske, M., Ni, Z. J., Intramolecular (3 + 2) cycloaddition of nitrones with allenesand alkynes. Tetrahedron Lett., 1993, 34, 5047-5050.
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