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Search for "Ugi reaction" in Full Text gives 48 result(s) in Beilstein Journal of Organic Chemistry.
One-pot Ugi-azide and Heck reactions for the synthesis of heterocyclic systems containing tetrazole and 1,2,3,4-tetrahydroisoquinoline
Beilstein J. Org. Chem. 2024, 20, 912–920, doi:10.3762/bjoc.20.81
- reaction of isonitriles were synthesized in moderate yields (58–60%). For the Ugi reaction involving isocyanoacetate, lactamination occurred spontaneously to provide the ring-fused tetrazolo[1,5-a]pyrazin-6(5H)-one adducts 5 which after intramolecular Heck reaction gave functionalized tetracyclic tetrazolo
- the Ugi reaction products 5 could affect the yield of the Heck reaction. To address the issue, compounds 5 were N-alkylated to afford intermediates 7 which were used in the subsequent Heck reaction step. Thus, an alternative one-pot Ugi-azide/N-alkylation/Heck reaction procedure was developed (Scheme
Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions
Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53
- –Bienaymé reaction; imidazo[1,2-a]pyridine; isocyanide; multicomponent reaction; peptidomimetic; Ugi reaction; Introduction The use of isocyanide multicomponent reactions (IMCR) to prepare biologically active compounds is one of the most promising tools in modern organic and medicinal chemistry. Therefore
- attention to another isocyanide multicomponent reaction – the Ugi reaction [21], which is one of the most important methods for the synthesis not only of peptidomimetics but also of other types of complex organic compounds. The presence of several diversity points and modification of starting components for
- peptidomimetic chain was already described in 2010 [32]. Thus, the corresponding acid components were synthesized with GBB-3CR and used in Ugi and Paserini reactions with various aldehydes, amines (for Ugi) and isocyanides. Moreover, in 2016 [33], an alternative route to use GBB-3CR products in Ugi reaction as
Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects
Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71
- azepinone 22 and exemplified a modified Ugi reaction (four-component reaction). The aldehyde and acid component of the Ugi reaction was functionalized on the same biaryl ring employing a Suzuki–Miyaura coupling. The authors advocated the use of microwave as it consistently increased the yield from 49% to 82
Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition
Beilstein J. Org. Chem. 2021, 17, 678–687, doi:10.3762/bjoc.17.57
- Chemistry, University of Nebraska – Lincoln, 639 N 12th St, Lincoln, NE 68588, USA 10.3762/bjoc.17.57 Abstract A novel catalyst-free synthetic approach to 1,2,3-triazolobenzodiazepinones has been developed and optimized. The Ugi reaction of 2-azidobenzaldehyde, various amines, isocyanides, and acids
- harder while the microwave-assisted catalyst-free conditions were effective for both terminal and non-terminal alkynes. Keywords: click chemistry; microwave chemistry; multicomponent reactions; triazolobenzodiazepines; Ugi reaction; Introduction Benzannulated heterocycles are among the most important
- a few steps and constitutes one of the most actual and promising synthetic routes of modern organic chemistry. Among a wide variety of tandem strategies combination of an isocyanide-based multicomponent Ugi reaction with secondary transformations is one of the most powerful tools and provides access
Menthyl esterification allows chiral resolution for the synthesis of artificial glutamate analogs
Beilstein J. Org. Chem. 2021, 17, 540–550, doi:10.3762/bjoc.17.48
- studies will straightforwardly focus on the enantioselective synthesis of only the (2R)-isomer. The asymmetric Ugi reaction recently developed [29] is of interest for the selective preparation of (2R)-6 (Scheme 1 and Scheme 5) [6][8]. Studies are in progress to develop an asymmetric Ugi/Diels–Alder
Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts through the cinchona alkaloid-promoted electrophilic fluorination
Beilstein J. Org. Chem. 2020, 16, 1963–1973, doi:10.3762/bjoc.16.163
- Ugi reaction we have attempted to stereodefine the chiral center at the peptidyl position through the post-Ugi functionalization. In order to achieve this, we chose to study 2-oxo-aldehyde-derived Ugi adducts many of which partially or fully exist in the enol form that lacks the aforementioned chiral
- alkaloid-promoted electrophilic fluorination producing enantioenriched post-Ugi adducts fluorinated at the peptidyl position. Keywords: cinchona alkaloids; electrophilic fluorination; enantioselective synthesis; 2-oxo-aldehydes; Ugi reaction; Introduction Multicomponent reactions (MCRs) [1][2][3][4][5][6
- diastereoselective U-4CR have been described [48][49][50][51][52][53][54]. Yet, the Ugi reaction turned out to be a rather challenging chemical transformation in terms of establishing the asymmetric version [33][34][35]. Apart from the two asymmetric three-component modifications lacking the acid component [55][56
Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction
Beilstein J. Org. Chem. 2020, 16, 663–669, doi:10.3762/bjoc.16.63
- has the potential to produce a large number of tetramic acid analogues, which cannot be easily accessed by the classic synthetic methods. Keywords: Dieckmann cyclization; multicomponent reactions; nitrogen heterocycles; one-pot reaction; Ugi reaction; Introduction Nitrogen-containing heterocycles
- medicinal chemistry. Multicomponent reactions (MCRs) [22][23][24] are emerging tools for assembling complex molecules in a rapid and efficient manner. The four-component Ugi reaction followed by a suitable post modification of [25][26] has become a popular research field for diversity-oriented synthesis [27
Efficiency Effsyn of complex syntheses as multicomponent reactions, its algorithm and calculations based on concrete criteria
Beilstein J. Org. Chem. 2019, 15, 1425–1433, doi:10.3762/bjoc.15.142
- components for linking, and also generates its own structure which is capable of extensions like the domino reaction types [5]. An Ugi reaction is used in the total synthesis of the extremely potent antitumor agent ecteinascidin-743 (Et-743, 1) by Fukuyama to form a large part of the skeleton 2 (Scheme 5
- ). All data for the U-4CR are available in the literature [14]. The precursors of the Ugi reaction consist of 3 reaction chains of 6, 6 and 2 links, respectively. Calculation by means of the algorithm The calculation of the overall yield yoa of 2 is based on the data basis for the total synthesis of
- significant difference is due to the MCR itself and primarily the linked parallel reactions of the 3 precursors, as can be clearly seen in Scheme 5. These results favour the use of the MCR strategy with the Ugi reaction and provide an increase in yield by 2.6 times that of a linear solution. MCR strategy
Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction
Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126
- available starting materials including scaffold diversity. A small focused compound library of 23 Ugi products was created and screened for antibacterial activity. Keywords: antibacterial activity; Doebner reaction; pyrazolo[3,4-b]pyridine carboxylic acids; Ugi reaction; Introduction Modern medicinal
- diversity-oriented synthetic (DOS) approaches. First, by using CBD and MCR strategies in a Doebner-type reaction we synthesized pyrazolopyridine carboxylic acids which were subsequently applied in the Ugi reaction, thus, combining two multicomponent procedures. Results and Discussion As mentioned above, the
- -type condensation of aminopyrazoles, aldehydes and pyruvic acid [45][46] with the isocyanide-based four-component Ugi reaction. As we have shown before [47][48] the application of the CBD strategy to multicomponent Doebner-type condensations involving aminoazoles allowed the synthesis of several
Steroid diversification by multicomponent reactions
Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121
- -lactam, albeit functionalized in the side chain. The one-pot synthesis of the β-lactam steroid was achieved via the Ugi 3-component-4-center reaction using the dehydrocholic aldehyde 1 as carbonyl component. This variation of the Ugi reaction including a β-amino acid component allows the formation of the
- carbonyl is far away from the rigid chiral steroid, the Ugi reaction shows no significant diastereoselectivity, while the carbonyl component directly linked to the bulky steroidal nucleus – especially in α-position of a stereocenter – provides a very good diastereocontrol in the MCR. Dar et al. [18
- structural characteristics of both compounds are the presence of a phenyl moiety as R1 and a t-Bu group at the terminal amide. Thus, using the same synthetic strategy as shown in Scheme 5, Dávola et al. [23] synthetized a family of new Ugi reaction-derived androstanic azasteroids with a much more diverse
Ugi reaction-derived prolyl peptide catalysts grafted on the renewable polymer polyfurfuryl alcohol for applications in heterogeneous enamine catalysis
Beilstein J. Org. Chem. 2019, 15, 1210–1216, doi:10.3762/bjoc.15.118
- Abstract The multicomponent synthesis of prolyl pseudo-peptide catalysts using the Ugi reaction with furfurylamines or isocyanides is described. The incorporation of such a polymerizable furan handle enabled the subsequent polymerization of the peptide catalyst with furfuryl alcohol, thus rendering
- employ a three-component, diastereoselective variant of the Ugi reaction for the synthesis of a prolyl pseudo-peptide catalyst, which proved effective in an organocatalytic conjugate addition reaction [6]. Later, our groups developed an Ugi reaction-based multicomponent approach enabling the structure
- produced by means of an initial Ugi reaction followed by an acid-catalyzed polymerization. They catalytic polymers were screened in the heterogeneous catalytic Michael addition in batch, proving that catalyst 3 is more effective and provides better stereoselectivity. A continuous-flow organocatalytic
Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams
Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104
- . Proposed mechanism for the formation of isoindolinones 36. Three-component reaction of formylbenzoic acid 33, amines 2 and fluorinated silyl ethers 39. Three-component Ugi reaction of 2-formylbenzoic acid (33), diamines 41 and isocyanides 42. Non-catalysed (A, B) and chiral phosphoric acid promoted (C
Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions
Beilstein J. Org. Chem. 2019, 15, 906–930, doi:10.3762/bjoc.15.88
- macroheterocycles in a reduced number of steps. Keywords: consecutive/repetitive multicomponent reactions; isocyanide; isocyanide-based multicomponent reactions; (macro)heterocycles; Passerini reaction; Ugi reaction; Introduction Isocyanide (isonitrile) chemistry was first described by Lieke in 1859 [1] and forms
- , which is able to undergo both electrophilic and nucleophilic reactions at the carbon atom. The Ugi reaction, firstly reported by Ugi et al. in 1959 [14], involves an amine, a ketone or aldehyde, an isocyanide, and a carboxylic acid to form a dipeptide product. It is undoubtedly one of the most important
- IMCRs known and has found many applications in synthetic organic chemistry [2][3][9][10]. Among the IMCRs the Ugi reaction has been the most used in the repetitive/consecutive strategy for the synthesis of (macro)heterocycles. The union of different types of MCRs for the synthesis of more complex
Synthesis of a novel category of pseudo-peptides using an Ugi three-component reaction of levulinic acid as bifunctional substrate, amines, and amino acid-based isocyanides
Beilstein J. Org. Chem. 2019, 15, 852–857, doi:10.3762/bjoc.15.82
- synthesis of a novel category of pseudo-peptides via intramolecular Ugi reaction of levulinic acid (4-oxopentanoic acid), aromatic and aliphatic amines, and amino acid-based isocyanides is reported. Levulinic acid was applied as a bifunctional substrate containing both carbonyl and acid moieties suitable
- for the Ugi reaction. This article provides a facile and convenient one-pot procedure for the synthesis of peptide-like heterocyclic molecules containing 2-pyrrolidone (γ-lactam), amide and ester functional groups with good to excellent yields. Keywords: amino acid-based isocyanides; levulinic acid
- ; multicomponent; pseudo-peptides; Ugi reaction; Introduction The multistep synthesis of complex molecules normally requires a large number of repetitive synthetic operations, such as extraction, separation, chromatography and other purification steps. These disadvantages encouraged chemists to synthesize complex
Design of indole- and MCR-based macrocycles as p53-MDM2 antagonists
Beilstein J. Org. Chem. 2019, 15, 513–520, doi:10.3762/bjoc.15.45
- for p53-MDM2 inhibition by fluorescence polarization and 1H,15N HSQC NMR measurements confirm MDM2 binding. Keywords: 1H,15N HSQC NMR; indole; macrocycles; multicomponent; p53-MDM2; Ugi reaction; Introduction Macrocycles are the chemical entities that are consisting of a 12-membered or even bigger
Synthesis of a tubugi-1-toxin conjugate by a modulizable disulfide linker system with a neuropeptide Y analogue showing selectivity for hY1R-overexpressing tumor cells
Beilstein J. Org. Chem. 2019, 15, 96–105, doi:10.3762/bjoc.15.11
- triple-negative breast cancer MDA-MB-468 cells. Keywords: drug targeting; neuropeptide Y; PDC; peptide–drug conjugate; targeted tumor therapy; tubugi; tubulysin A; Ugi reaction; Introduction Until recently, the medication of tumor diseases was primarily based on more or less unspecific
- three cell lines was determined as proof for targeted delivery. Results and Discussion Synthesis of tubugi-1 building blocks We established the Ugi reaction as a powerful tool for peptide synthesis and ligation, including the first syntheses of tubulysine derivatives by us and later also others [44][53
- ][55][56]. In a single step, the Ugi reaction permits the introduction of different functionalities which may be followed with additional modifications on the side chain (e.g., via ring-closing metathesis or Click reaction) [53]. For tubugi conjugates we learned that alkyl amide bonds and several types
Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones
Beilstein J. Org. Chem. 2018, 14, 2572–2579, doi:10.3762/bjoc.14.234
- University, 53 Kabanbay Batyr Ave, Block 7, Astana, 010000, Republic of Kazakhstan 10.3762/bjoc.14.234 Abstract A series of propargylamides containing an electron-rich benzene ring was prepared through the Ugi reaction of 3,5-dimethoxyaniline with various propiolic acids, aldehydes and isocyanides
- . Subjecting these adducts to a gold-catalyzed intramolecular alkyne hydroarylation process allowed to efficiently construct the 2-quinolone core bearing a branched substituent on the nitrogen atom. Keywords: gold catalysis; hydroarylation; 2-quinolones; Ugi reaction; Introduction Quinoline and its oxidized
- address this issue by employing propargylamides 7 obtained by a four-component Ugi reaction of propiolic acids 3, aldehydes 4, isocyanides 5 and 3,5-dimethoxyaniline (6a) (Scheme 2). We anticipated that the resulting adducts 7 would readily produce 2-quinolones 8 bearing a branched substituent on the
Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry
Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179
- an organophotocatalytic version of the Ugi reaction. These procedures were undertaken in a flow chemistry set-up, using irradiation by green LEDs and Rose Bengal as the photocatalyst (Scheme 13) [56]. The scope of the reaction is fairly broad, especially considering the method was developed in a flow
Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins
Beilstein J. Org. Chem. 2018, 14, 626–633, doi:10.3762/bjoc.14.49
- (CSIR-NIIST), Thiruvananthapuram-19, India 10.3762/bjoc.14.49 Abstract A practical three-step protocol for the assembly of triazolobenzodiazepine-fused diketopiperazines and hydantoins has been developed. The synthesis of these tetracyclic ring systems was initiated by an Ugi reaction, which brought
- ; hydantoin; intramolecular azide–alkyne cycloaddition; Ugi reaction; Introduction The versatile bioactivities of multiring-fused heterocyclic scaffolds continue to attract significant attention in developing new methods for their synthesis. A plethora of functionalized fused heterocycles can be easily
- multiring-fused derivatives incorporating all these heterocyclic moieties. We hypothesized that 2,5-diketopiperazine-fused triazolobenzodiazepine could be obtained by proper functionalization of building blocks starting with an Ugi reaction; followed by two ring-closing steps, one being a base-induced
Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles
Beilstein J. Org. Chem. 2017, 13, 2596–2602, doi:10.3762/bjoc.13.256
- 1,5-disubstituted tetrazoles due to the intrinsic generation of molecular diversity [11][12][13][14][15]. As the Ugi reaction also requires an amine component, we envisaged that reactions of hydrazino compounds (RNHNH2) with TMSN3 could furnish useful compounds bearing both the hydrazino and the
Mechanochemical synthesis of small organic molecules
Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186
- reaction of electron-rich arenes [88][98]. Mechanochemical aryl halogenation reaction using trihaloisocyanuric acids [100]. Mechanochemical fluorination reaction by LAG method [102]. Mechanochemical Ugi reaction [116]. Mechanochemical Passerine reaction [116]. Mechanochemical synthesis of α-aminonitriles
Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid
Beilstein J. Org. Chem. 2017, 13, 1478–1485, doi:10.3762/bjoc.13.146
- prehalogenation [16]. iii) The multicomponent method: only two strategies have been reported to the best of our knowledge. One is a combination of the Ugi reaction, which uses 2,4-dimethoxybenzylamine, arylglyoxal, carboxylic acid, and isonitrile as components, and a subsequent Robinson–Gabriel reaction [17]. The
A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline
Beilstein J. Org. Chem. 2017, 13, 1413–1424, doi:10.3762/bjoc.13.138
- non-classical inputs for the Joullié–Ugi reaction and for subsequent preparation [28] of sterically encumbered, constrained peptidomimetic frameworks. Diversely substituted indolenines 9 are easy to prepare via the Fischer indole synthesis [26] and their use in the CCR can be expected to result in
New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized
Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104
- -aryl-1H-pyrazole-4-carboxamides; antibacterial activity; Groebke–Blackburn–Bienaymé reaction; isocyanide Ugi reaction; Introduction An intensive progress in pharmaceutical and medicinal chemistry, as well as in the generation and improvement of medicinal technologies has led to defeating a wide scope
A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy
Beilstein J. Org. Chem. 2017, 13, 817–824, doi:10.3762/bjoc.13.82
- conditions and a broad substrate scope, allowing for the rapid construction of structurally complex and diverse heterocycles in moderate to good yields. Keywords: Groebke–Blackburn–Bienaymé reaction; imidazo[1,2-a]pyridines; isoquinolines; multicomponent reaction; Ugi reaction; Introduction Imidazo[1,2-a
- discovery [22][23][24][25][26][27]. The Ugi reaction [28], an elegant pioneer of a multicomponent reaction, represents a powerful synthetic tool to assemble versatile peptide-like compounds. It has found many applications in the facile synthesis of natural products and biologically interesting molecules [29
- combination of the Ugi reaction with other transformations proved to be powerful strategies for the efficient synthesis of novel heterocycles. In 1998, the Groebke–Blackburn–Bienaymé (GBB) reaction, an Ugi-3CR variant was discovered by three groups independently [36][37][38]. The GBB reaction of an amidine
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