共查询到20条相似文献,搜索用时 140 毫秒
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异腈是一种含有稳定二价碳原子的重要活性反应物,在含氮化合物的构建、新药物的研发以及天然产物的合成中得到了广泛的应用.在过去的十年中,以Passerini和Ugi反应为基础,化学家们致力于研究异腈参与的多组分反应.最近,过渡金属催化异腈参与的氧化偶联反应得到广泛的发展,而使用的催化剂主要集中在一些贵重的过渡金属(Pd、Rh、Ag等)化合物,如何利用廉价过渡金属Co来催化异腈参与的偶联反应具有非常重要的意义.在这里我们概述了近年来Co催化异腈参与的偶联反应的最新研究进展. 相似文献
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《有机化学》2021,(4)
以Ugi四组分反应为关键步骤,建立了一种合成结构多样、色牢度性能优异新型分散染料的新方法.从简单易得的原料出发,经过4-氧代丁酸衍生物合成,酸、苯胺、苯甲醛和环己基异氰的Ugi四组分反应以及Ugi产物与重氮盐偶合等步骤合成了15个新颖的分散染料.用~1H NMR、~(13)C NMR、红外光谱、质谱和高分辨质谱对Ugi产物和新染料的结构进行了表征,并测试了他们的可见光吸收和摩尔消光系数.在聚酰胺和聚酯纤维上色牢度的研究发现,新型分散染料的色牢度比已知分散染料红1和红13有了很大提高.色牢度的提高与分散染料中引入的两个酰胺基和一个酯基以及染料分子量/体积的适当提高相关.这是一个合成新型高性能分散染料分子库的有效方法. 相似文献
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《高分子学报》2020,(7)
报道了基于Ugi多组分反应的N_(α-)叔丁氧羰基_(-L-)赖氨酸、糠醛与叔丁基异腈的聚合.聚合条件温和,无需使用催化剂,且所得聚合物的相对数均分子量M_n最高可达10.0 kg/mol.特别是,聚合在水中也可顺利进行,可以避免有毒溶剂的使用,符合绿色化学发展理念.核磁共振氢谱(~1H-NMR)、核磁共振碳谱(~(13)C-NMR)及基质辅助激光解吸电离飞行时间质谱(MALDI-TOF-MS)的结果证实所得聚合物具有类肽的结构.在此基础上,推测N_(α-)叔丁氧羰基_(-L-)赖氨酸、糠醛与叔丁基异腈的聚合符合Ugi反应的一般机理,即糠醛首先与氨基缩合形成亚胺,再经过两次的亲核加成、Mumm重排以及酰基转移反应,最终形成具有类肽结构的聚合物. DSC测试结果表明聚合物玻璃化转变温度(T_g)为116℃,无明显熔点.所获得的聚合物在生物降解材料及生物医用材料等领域具有潜在的应用价值,这为赖氨酸和糠醛的直接聚合以及可再生资源的高附加值利用开辟了一条新路径. 相似文献
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α-acyloxyaminoamides can be prepared, with yields ranging from fair to very good (up to 89%), through an Ugi four component reaction by mixing a carbonyl component, a carboxylic acid, an isocyanide and an N-alkylated hydroxylamine in methanol. Preformed nitrones furnish the same final compounds with comparable yields. 相似文献
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《Tetrahedron letters》2004,45(21):3999-4001
A new application of the Ugi reaction in the synthesis of heterocyclic compounds is described. Substituted quinolin-2-(1H)-ones are formed in one-pot sequential Ugi four-component condensation and intramolecular Knoevenagel cyclization between o-acylanilines, aldehydes, malonic or tosylacetic acids and cyclohexyl isocyanide. 相似文献
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《Mendeleev Communications》2022,32(6):747-749
The glutarimide moiety, common in many immuno-modulatory drugs, was decorated with lactam and diamide side chains via two variants of the Ugi reaction, namely, with isocyanide, aldehyde and acid or with isocyanide and oxo acid. The resulting diastereomerically pure compounds were evaluated for their affinity towards the E3 ubiquitin ligase substrate receptor Cereblon. 相似文献
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Morteza Shiri Mohammad Ali Zolfigol Ardeshir Khazaei Toktam Faal-Rastegar Hendrik G. Kruger 《Journal of the Iranian Chemical Society》2014,11(1):85-90
Multicomponent condensation of ethyl 3-formylindole 2-carboxylate, amines, isocyanide and (S)-N-boc-alanine or (S)-N-boc-serine is described. This Ugi four-component condensation (Ugi-4CC) reaction yielded a series of novel dipeptides containing an indolyl moiety. These compounds exhibit potential biological activity. 相似文献
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Ahmad Shaabani Sajjad Keshipour Shabnam Shaabani Mojtaba Mahyari 《Tetrahedron letters》2012,53(13):1641-1644
The ability of zinc chloride as a catalyst to promote the three-component Ugi reaction of 2-aminophenols, aliphatic or aromatic aldehydes, and cyclohexyl isocyanide in methanol at room temperature is described. The N-cyclohexyl-2-(2-hydroxyphenylamino) amide products are obtained in high yields. When N,N-dimethylformamide dimethyl acetal and triethyl orthoformate, as two new components of the three-component Ugi reaction are used instead of the aldehyde the reaction gives N-cyclohexyl-2-(dimethylamino)-2-(2-hydroxyphenylamino)acetamide and N-cyclohexyl-2-(2-hydroxyphenylamino)-2-ethoxyacetamide derivatives, respectively. 相似文献
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Nádia R. Aguiam Vânia I. CastroAna I.F. Ribeiro Rui D.V. FernandesCarina M. Carvalho Susana P.G. CostaSílvia M.M.A. Pereira-Lima 《Tetrahedron》2013
The multicomponent Ugi reaction is a straightforward method that can be used for the synthesis of highly hindered C-tetrasubstituted amino acids by reacting an amine, a ketone or aldehyde, a carboxylic acid and an isocyanide. In the present work, the synthesis of several α,α-dialkylglycines (α,α-diethylglycine, Deg; α,α-dipropylglycine, Dpg; 1-amino-1-cyclohexanecarboxylic acid, Ac6c) was achieved by solid phase Ugi reaction using resins functionalized with the isocyanide group. Since no resins with these features were available commercially, the functionalization of an aminomethylated resin started by the use of glycine (Gly), β-alanine (β-Ala) and γ-aminobutyric acid (GABA) as spacers. After spacer N-formylation, followed by dehydration, isocyanide functionalised resins were obtained. The resins were then used in solid phase Ugi reaction, using phenylacetic acid as the acid component, 4-methoxybenzylamine as the amine component and different ketones, to afford the desired N-acylated α,α-dialkylglycines in good overall yields (60–80%), after acidolytic cleavage from the resin, thus proving the feasibility of this approach. 相似文献
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Jonathan G. Rudick 《Journal of polymer science. Part A, Polymer chemistry》2013,51(19):3985-3991
Isocyanide multicomponent reactions assemble more than two reaction components by exploiting the reactivity of the isocyanide carbon atom toward addition of electrophiles and nucleophiles. Reactions such as the Passerini three‐component and Ugi four‐component coupling reactions have a long and successful history in organic synthesis, which has only recently been explored in polymer chemistry. In a short time, this class of multicomponent reactions has been established as a viable method for the synthesis of linear polymers as well as more complex architectures such as miktoarm star polymers and dendrimers. This highlight discusses the recent accomplishments made with regard to innovative syntheses of polymers and dendrimers via the Passerini and Ugi reactions. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013 , 51, 3985–3991 相似文献
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Oswald Lockhoff 《Angewandte Chemie (International ed. in English)》1998,37(24):3436-3439
Four-component reactions : The Ugi reaction of four suitably functionalized carbohydrate derivatives (as a per-O-benzylated amine, an aldehyde, a carboxylic acid, and an isocyanide) allow the effective assembly of diverse compound libraries. The complex glycoconjugates formed can be deprotected (see the picture for an example), and the resulting glycomimetics are of high interest for screening purposes. 相似文献
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The development of a new convertible isocyanide, indole-isocyanide, for ready access to pyroglutamic acids culminated in the formal total synthesis of the proteasome inhibitor omuralide featuring a stereocontrolled Ugi reaction. Indole-isocyanide was named after the facilitation of hydrolysis of the resulting 2-(2,2-dimethoxyethyl)anilide via an N-acylindole intermediate obtained by the Ugi multicomponent condensation reaction followed by the indole formation. 相似文献
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2-Nitrophenyl isocyanide is introduced as a convertible isocyanide with demonstration of its feasibility and applicability in an efficient synthesis of the fused gamma-lactam beta-lactone bicycle of proteasome inhibitor omuralide. Starting from a linear keto acid precursor, the fused gamma-lactam beta-lactone bicycle was prepared in four steps by a sequential biscyclization strategy; a stereocontrolled Ugi reaction and the concomitant direct beta-lactonization following the formation of an N-acylbenzotriazole intermediate. The N-acylbenzotriazole is amenable to intra- or intermolecular attack from a variety of nucleophiles with a catalytic amount of base to form the pyroglutamic acid derivatives. 相似文献