共查询到19条相似文献,搜索用时 109 毫秒
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以丙二酸和二氯亚砜为起始原料,经氯代、环合、催化氢化及烷基化反应合成了新化合物——N-甲基-5-苯基-4-羟基-2-吡啶酮,总收率38.7%,其结构经1H NMR,IR和EI-MS表征. 相似文献
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N-酰亚甲基-2-吡啶酮是一类非常重要的结构单元, 广泛存在于天然产物和其它具有生物活性的化合物中. 其合成通常是通过2-羟基吡啶与相应的亲电试剂发生分子间亲核取代反应. 然而, 由于2-羟基吡啶的双亲核特性, 这一方法往往面临着N/O化学选择性难以控制的问题. 报道了一例钯催化三组分烯丙基取代反应, 化学专一性地合成难以构建的大位阻N-酰亚甲基-2-吡啶酮衍生物, 收率最高可达98%, 未见有O-烷基化副产物的生成. 该反应可以在克级规模下进行, 依然取得98%的收率. 本方法所得到的N-酰亚甲基-2-吡啶酮产物经过简单转化, 可方便地制得含吡啶酮结构的非天然氨基酸类化合物. 实验结果显示, 该三组分反应是经过一个串联的亲核取代和烯丙基取代反应而专一性地合成N-酰亚甲基-2-吡啶酮衍生物. 相似文献
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以甲基麦芽酚为原料,1,3,5-苯三甲酰氯为三角架分子,合成了一种新的以苯环为骨架的3-羟基-4-吡啶酮六齿螯合剂TMC(BuHP)3,其结构经1H NMR、 FT-IR和MS表征,并通过MS分析证实了其与三价铁离子的配位。 相似文献
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Fatma El-Mariah Ekhlass Nassar 《Phosphorus, sulfur, and silicon and the related elements》2013,188(12):3145-3155
Dimethyl 4-(methoxymethylene)-2-pentenedioate 2 was selected as the starting material for the synthesis of some novel 2-pyridones containing sulfonamide moiety, which we expected to have biological activities such as bactericidal and fungicidal or other applications of certain interest. 相似文献
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E. V. Verbitskiy E. M. Cheprakova P. A. Slepuhin M. G. Pervova M. A. Samorukova O. N. Zabelina G. L. Rusinov V. N. Charushin 《Chemistry of Heterocyclic Compounds》2011,47(6):710-718
The reaction of 5-(het)aryl-1-ethyl-2(1H)-pyrazinones with terminal arylacetylenes, leading to a mixture of two isomeric 4-aryl- and 5-aryl-substituted 2(1H)-pyridones has been investigated. The regioselectivity of this reaction has been shown on the basis of reaction mixtures
study by chromato-mass spectrometry. A crystallographic investigation of the synthesized 2(1H)-pyridones and also a forecast of their potential biological activity have been carried out. 相似文献
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Aberg V Norman F Chorell E Westermark A Olofsson A Sauer-Eriksson AE Almqvist F 《Organic & biomolecular chemistry》2005,3(15):2817-2823
A reagent-free microwave-assisted decarboxylation procedure for carboxylic acid functionalized bicyclic 2-pyridones has been developed. This new method, based on microwave heating at 220 degrees C for 600 seconds in N-methyl pyrrolidone (NMP), proved to be practical and very efficient, resulting in decarboxylated 2-pyridones in near-quantitative yields. The decarboxylated products and the intermediate 2-pyridones in the form of carboxylic acid methyl esters and carboxylic acids were screened for their effect on Abeta-peptide aggregation. Two out of the 21 2-pyridones described in this study inhibited amyloid formation of the Alzheimer Abeta(1-40) peptide. The effect was seen even at a 4 : 1 ratio of 2-pyridone and monomeric Abeta-peptide. 相似文献
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The N-H...O H-bonding enthalpy between 4-pyridones connected in a chain of H-bonds can achieve 23 kcal/mol for the most central H-bonds, while that between two 4-pyridones is 9.90 kcal/mol based upon DFT calculations on the counterpoise-corrected potential energy surfaces. That the range of enthalpies for N-H...O H-bonds can vary from as little as 2 to as much 23 kcal/mol depends primarily upon the polarizability of whatever internally connects the N-H and C=O within the H-bonding molecule, which are two parallel -C=C- entities in 4-pyridone. The contribution of covalent or charge-transfer interactions between the pi-systems of adjacent 4-pyridones is small. 相似文献
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Mediated by sodium persulfate (Na(2)S(2)O(8)), a series of polysubstituted 4-pyridones were synthesized via self-condensation of N-aryl acetoacetamides, during which a novel N to C 1,3-acyl migration should be involved. The structure of 4-pyridone was unequivocally confirmed by X-ray diffraction analysis. However, the self-condensation of N-benzyl acetoacetamides under the same condition gave polysubstituted 2-pyridones instead of 4-pyridones. 相似文献
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Erik Chorell 《Tetrahedron letters》2010,51(18):2461-2463
Improved procedures to synthesize enantioselectively analogues of a peptidomimetic scaffold with high biological relevance have been developed. Experimental design led to a general method for the preparation of dihydrooxazolo ring-fused 2-pyridones in good yields and high enantiomeric purity. The knowledge gained from this was also used to improve the microwave-accelerated synthesis of dihydrothiazolo ring-fused 2-pyridones to give complete stereo retention and high yields. 相似文献
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Upadysheva A. V. Grigor'eva N. D. Znamenskaya A. P. 《Chemistry of Heterocyclic Compounds》1977,13(11):1240-1243
Intramolecular rearrangement of two-ring 2,3-disubstituted 4-oxo-1,2,3,4-tetrahydropyrimidines to pyridine derivatives, which takes place under the influence of polyphosphoric acid, was observed. It is shown that cycloalkanopyrimidones are converted primarily to two- or three-ring 2-pyridones and to small amounts of the corresponding 4-pyridones and 4-aminopyridines. A possible mechanism that enables one to explain the difference in the occurrence of the rearrangements primarily to 2- or 4-pyridones as a function of the absence or presence of aromatic character of the ring condensed with the pyrimidine ring is proposed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1549–1553, November, 1977. 相似文献
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Schiff's bases 1 derived from ketones and t-butylamine reacted with diphenyl malonate, diphenyl methyl-malonate and diphenyl phenylmalonate to give 4-hydroxy-2-pyridones 4–6 . Schiff's bases b on reaction with trimethyl methanetricarboxylate afforded 4-hydroxy-3-methoxycarbonyl-2-pyridones 12 . 相似文献
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Dihydrothiazolo ring-fused 2-pyridones have previously been shown to inhibit pilus assembly in uropathogenic Escherichia coli. Methods have now been developed to synthesize both dihydroimidazolo and dihydrooxazolo ring-fused 2-pyridones. To obtain the nitrogen analogs, Cbz-protected imidazolines were reacted with an acyl-Meldrum's acid derivative under acidic conditions. To prepare the oxygen analogs, a one-pot procedure was developed that allowed synthesis of dihydrooxazolo ring-fused 2-pyridones starting from acylated serine derivatives. After hydrolysis to their corresponding carboxylic acids and lithium carboxylates, biological evaluation revealed that the sulfur could be replaced by an oxygen atom and still maintains the ability to inhibit pilus assembly in uropathogenic E. coli. However, introducing a secondary amine instead of oxygen resulted in a substantial decrease in biological activity. 相似文献