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Search for "four-component reaction" in Full Text gives 56 result(s) in Beilstein Journal of Organic Chemistry.

New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives

  • Yuriy I. Horak,
  • Roman Z. Lytvyn,
  • Andrii R. Vakhula,
  • Yuriy V. Homza,
  • Nazariy T. Pokhodylo and
  • Mykola D. Obushak

Beilstein J. Org. Chem. 2025, 21, 444–450, doi:10.3762/bjoc.21.31

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  • derivatives. Also, benzoisoindoles have been synthesized via the pseudo-four-component reaction of 3-phenylallylamines with maleic anhydride [35]. Finally, furfural was utilized in the Ugi reactions with unsaturated acids leading to the intramolecular Diels–Alder furan (IMDAF) reaction (Figure 1) [36]. In the
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Published 26 Feb 2025

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

  • Lucía Campos-Prieto,
  • Aitor García-Rey,
  • Eddy Sotelo and
  • Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

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  • single step. The oxazepine scaffold can be easily accessed using the Ugi four-component reaction. By modifying this scaffold, the researchers aimed to reduce the hydrogen-bond donating properties. The Passerini reaction, employing bifunctional salicylaldehydes and isocyanides successfully yielded
  • /intramolecular Ullmann-type C–N coupling reactions. Azido-Ugi 4CR/cyclization (AU-4CR) strategy: The azido-Ugi four-component reaction (AU-4CR) is an elegant and atom economical approach for obtaining substituted tetrazoles, which are very relevant in medicinal chemistry [64]. When combined with suitable post
  • active oxoindole-β-lactam compounds developed by Brãndao et al. [33]. The most promising hybrids synthesized via the Ugi-azide multicomponent reaction reported by Kushwaha et al. [34]. Most potent antioxidant compounds obtained through the Ugi four-component reaction developed by Pachón-Angona et al. [35
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Published 03 Dec 2024

Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

  • Marzieh Norouzi,
  • Mohammad Taghi Nazeri,
  • Ahmad Shaabani and
  • Behrouz Notash

Beilstein J. Org. Chem. 2024, 20, 2870–2882, doi:10.3762/bjoc.20.241

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  • electrophilic sites simultaneously in their structure, these zwitterions are able to participate in various cyclization processes, especially for the synthesis of pyrroles [37][38][39][40]. For example, Li et al. developed a one-pot four-component reaction (4-CR) of malononitrile, aldehydes, and isocyanides
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Published 11 Nov 2024

5th International Symposium on Synthesis and Catalysis (ISySyCat2023)

  • Anthony J. Burke and
  • Elisabete P. Carreiro

Beilstein J. Org. Chem. 2024, 20, 2704–2707, doi:10.3762/bjoc.20.227

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  • a new family of isatin-based α-acetamide carboxamide oxindole hybrids using the versatile Ugi four-component reaction [18]. Sixteen hybrids were prepared by reacting 5-amino-1-benzyl-3,3-dimethoxyindolin-2-one, benzyl isocyanide, carboxylic acids, and aldehyde/ketone derivatives, catalyzed by ZnF2
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Published 28 Oct 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

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  • tolerated in this consecutive four-component reaction, as the 1,3,4-thiadiazine synthesis competes with the thiazole synthesis. Salicylaldehydes 14 and 4-hydroxy-6-methyl-2H-pyran-2-one (16) can also be used to produce 1,3-dicarbonyl compounds 18 by Knoevenagel condensation and subsequent cyclization. This
  • -component reaction, with a concluding cyclocondensation employing Boc hydrazine, 1,5-diacyl-5-hydroxypyrazoline 127 is formed, as later confirmed by isolation [149]. Upon alkaline workup, this gives 3-acylpyrazole 128 in good yield (Scheme 45) [147]. Ynediones are also accessible from α-ketocarboxylic acids
  • gives access to polyfunctional ynedione 129 [147]. In contrast to Sonogashira alkynylation, where glyoxyl substrates furnish ynones with concomitant decarbonylation [145], Stephens–Castro alkynylation preserves the dicarbonyl functionality in the product [148]. Embedded within a consecutive four
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Published 16 Aug 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

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Published 01 Aug 2024

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

  • Alexander V. Tsygankov,
  • Vladyslav O. Vereshchak,
  • Tetiana O. Savluk,
  • Serhiy M. Desenko,
  • Valeriia V. Ananieva,
  • Oleksandr V. Buravov,
  • Yana I. Sakhno,
  • Svitlana V. Shishkina and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

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  • 1, which contains a chlorine atom in the β-position, with convertible isocyanides 4a–d, para-substituted anilines 2a–e and monochloroacetic acid (3) as the smallest building blocks in a four-component reaction leads to the formation of the Ugi bisamides 5–8 (Table 1). Their structures offer several
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Published 26 Jul 2024

The Ugi4CR as effective tool to access promising anticancer isatin-based α-acetamide carboxamide oxindole hybrids

  • Carolina S. Marques,
  • Aday González-Bakker and
  • José M. Padrón

Beilstein J. Org. Chem. 2024, 20, 1213–1220, doi:10.3762/bjoc.20.104

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  • , 38200, La Laguna, Spain 10.3762/bjoc.20.104 Abstract Considering early-stage drug discovery programs, the Ugi four-component reaction is a valuable, flexible, and pivotal tool, facilitating the creation of two new amide bonds in a one-pot fashion to effectively yield the desired α-aminoacylamides. Here
  • urgent need to find novel, effective and safe drugs for cancer therapy. Recently, focusing on the design of more potent anticancer drug candidates using more sustainable synthetic processes, we report a new Ugi four-component reaction approach for easy access to Ugi-derived isatin-peptoids in moderate to
  • obtained using an Ugi four-component reaction (Ugi4CR). (B) The synthetic strategy reported in this work. Library of α-acetamide carboxamide oxindole hybrids 5 accessed via the Ugi4CR. Microwave-assisted CuAAC reaction to access α-acetamide carboxamide 1,2,3-triazole oxindole hybrid 7. Library of α
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Published 27 May 2024

Innovative synthesis of drug-like molecules using tetrazole as core building blocks

  • Jingyao Li,
  • Ajay L. Chandgude,
  • Qiang Zheng and
  • Alexander Dömling

Beilstein J. Org. Chem. 2024, 20, 950–958, doi:10.3762/bjoc.20.85

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  • developed building block approach, we decided to incorporate an oxo-tetrazole into an Ugi four-component reaction, the most studied and versatile MCR in organic synthesis and drug discovery [31][32]. Despite tremendous exploration, finding novel substrates or bioisosteres as a starting material in the Ugi
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Published 29 Apr 2024

One-pot Ugi-azide and Heck reactions for the synthesis of heterocyclic systems containing tetrazole and 1,2,3,4-tetrahydroisoquinoline

  • Jiawei Niu,
  • Yuhui Wang,
  • Shenghu Yan,
  • Yue Zhang,
  • Xiaoming Ma,
  • Qiang Zhang and
  • Wei Zhang

Beilstein J. Org. Chem. 2024, 20, 912–920, doi:10.3762/bjoc.20.81

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  • schistosomiasis [22][23][24][25]. The combination of the privileged heterocycles tetrazole and tetrahydroisoquinoline in one molecule generates new molecules which could have biological activities. A standard Ugi four-component reaction (Ugi-4CR) of an aldehyde, amine, isocyanide, and a carboxylic acid produces
  • highly diverse peptidic structures A with up to four points of substitution (Scheme 1) [26][27]. By replacing the carboxylic acid with a nucleophilic azide reagent XN3 (generally TMSN3), the Ugi-azide four-component reaction (UA-4CR) of an aldehyde, amine, isocyanide, and azide gives 1,5-disubstituted 1H
  • . The initial Ugi-azide four-component reaction constructs the tetrazole motif while the subsequent intramolecular Heck reaction assembles the tetrahydroisoquinoline. The one-pot reaction avoids the intermediate purification which has favorable PASE in the synthesis of heterocyclic compounds
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Published 23 Apr 2024

Catalytic multi-step domino and one-pot reactions

  • Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25

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  • acetaldehyde dimethyl acetal as a masked form of acetaldehyde, which is hydrolyzed in situ, allowing for a higher product yield and fewer byproducts [15]. The group of Müller describes an elegant consecutive four-component reaction involving an alkynylation–cyclization–iodination–alkylation sequence toward
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Published 08 Feb 2024

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

  • Xiaofeng Zhang,
  • Xiaoming Ma and
  • Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

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  • pseudo-four-component reaction for the synthesis of tetrahydropyrrolothiazole derivatives. The reaction of cysteine with two equiv of arylaldehydes and one equiv of maleimides in EtOH at 90 °C for 12 h afforded tetrahydropyrrolothiazoles 29 in 66–79% yields with up to 7:1 dr (Scheme 17) [76]. Using
  • ]isoquinolines. Pseudo-four-component reaction for the synthesis of tetrahydropyrrolothiazoles 29 and 30 (>4:1 dr). One-pot two-step synthesis of spirooxindole-pyrrolothiazoles 31 (>4:1 dr). Acknowledgements We would like to thank all our co-workers who worked on the research projects highlighted in this paper
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Published 06 Nov 2023

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

  • Nadia Ledermann,
  • Alae-Eddine Moubsit and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

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  • generated by a consecutive four-component reaction starting from ortho-haloanilines, terminal alkynes, N-iodosuccinimide, and alkyl halides in yields of 11–69%. Initiated by a copper-free alkynylation, followed by a base-catalyzed cyclizive indole formation, electrophilic iodination, and finally
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Published 14 Sep 2023

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

  • Chandra Sekhar Tekuri,
  • Pargat Singh and
  • Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

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  • present study discloses an easy and first synthetic approach to build highly π-conjugated copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins through a trichloroacetic acid-catalyzed one-pot four-component reaction of 2,3-diamino-5,10,15,20-tetraarylporphyrins, 2-hydroxynaphthalene-1,4-dione, aromatic
  • ]chromeno[2,3-h]quinoxalinoporphyrins 3–8. For the optimization of the reaction conditions, a model four-component reaction of copper(II) 2,3-diamino-5,10,15,20-tetra(p-tolyl)porphyrin with 2-hydroxynaphthalene-1,4-dione (2), benzaldehyde and dimedone was carried out in the presence of 20 mol % p
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Published 11 Aug 2023

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

  • Oleksandr V. Kolomiiets,
  • Alexander V. Tsygankov,
  • Maryna N. Kornet,
  • Aleksander A. Brazhko,
  • Vladimir I. Musatov and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

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  • 24 hours at room temperature in DMF with catalytic amounts of HClO4. The yield of compound 4a in this case was 76%. Then new heterocyclic acids were used as reagents for the Ugi four-component reaction. Due to the rather low solubility of the acids in methanol, it was necessary to increase the
  • heterocyclic acid 8a was obtained by a three-component reaction of 2-amino-5-chloropyridine (1a), 4-formylbenzoic acid (5f), and tert-butyl isocyanide (3a) according to the procedure described above (Scheme 3). In another step, we attempted to introduce the acid 8a into the Ugi four-component reaction with 4
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Published 26 May 2023

One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles

  • Juan Lu,
  • Bin Yao,
  • Desheng Zhan,
  • Zhuo Sun,
  • Yun Ji and
  • Xiaofeng Zhang

Beilstein J. Org. Chem. 2022, 18, 1607–1616, doi:10.3762/bjoc.18.171

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  • 10.3762/bjoc.18.171 Abstract A novel four-component reaction in one pot as an atom- and step-economic process was developed to synthesize diastereoselectively spirooxindolepyrrolothiazoles through sequential N,S-acetalation of aldehydes with cysteine and decarboxylative [3 + 2] cycloaddition with olefinic
  • results using ᴅ- and ʟ-cysteine to synthesize compound 5a (Scheme 5). We conferred green chemistry metrics to evaluate the process efficiency of four-component reaction via comprehensive and quantitative calculation. The metrics analysis is carried out for the two-step synthesis with intermediate
  • -component reaction (4-CR) with 2.2:1.1:1.0 of 1a/2/4a at 90 °C for 9 h in EtOH after variations of solvents, reaction time and temperature with one operational step (Table 1, entries 7–12). This 4-CR is the first example of double annulations with sequential N,S-acetalation and [3 + 2] cycloaddition for
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Published 28 Nov 2022

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

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  • dialkyl but-2-ynedioate. Thus, a quasi-four-component reaction led to the final product. There are two chiral carbon atoms in the molecules, thus two diastereoisomers would be formed in the reaction. However, the 1H and 13C NMR spectra gave only one set of resonances for the characteristic groups, which
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Published 08 Aug 2022

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

  • Shao-Cong Zhan,
  • Ren-Jie Fang,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 796–808, doi:10.3762/bjoc.18.80

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  • dienophiles, 5-arylidene-1,3-dimethylbarbituric acids, could be in situ generated by aromatic aldehydes and 1,3-dimethylbarbituric acid under the standard conditions. Therefore, the four-component reaction was carried out by using two molecular aromatic aldehydes, 1,3- dimethylbarbituric acid and 2
  • '-indolines] 2a–h, in which the two phenyl groups exist in cis-position. This result clearly indicated that this reaction has a similar outcome of stereochemistry. Based on the success of the four-component reaction through in situ generation of dienes and dienophiles, we further considered whether more
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Published 07 Jul 2022

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

  • Shivani Gulati,
  • Stephy Elza John and
  • Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

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  • 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
  • acids 37. Likewise, the four-component reaction comprised of isatin 35, but-2-ynedioates 39, amino acids 37 and phenacyl bromides 41 to yield the N-acylated spirooxindoles 42 in good yields (Scheme 13). The reaction effectively explored the 1,3 dipolar compound generated with isatin and amino acids
  • -component reaction whereas a further reaction with phenacyl bromide 41 results the product of the four-component reaction 42. Recently, our group [52] efficiently employed the synergistic approach of MWA-MCR to deliver pyrrolidinyl spirooxindole 44. The isatin 35, primary amino acids 37 and 3
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Published 19 Apr 2021

Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition

  • Maryna O. Mazur,
  • Oleksii S. Zhelavskyi,
  • Eugene M. Zviagin,
  • Svitlana V. Shishkina,
  • Vladimir I. Musatov,
  • Maksim A. Kolosov,
  • Elena H. Shvets,
  • Anna Yu. Andryushchenko and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2021, 17, 678–687, doi:10.3762/bjoc.17.57

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  • to a large number of diverse heterocyclic compounds [10][11]. Over the past decade, several cases of using an Ugi four-component reaction (Ugi-4CR) in combination with intramolecular azide–alkyne cycloaddition (IAAC) for the synthesis of 1,2,3-triazolobenzodiazepines were reported [3][7][12][13][14
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Published 08 Mar 2021

Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts through the cinchona alkaloid-promoted electrophilic fluorination

  • Yuqing Wang,
  • Gaigai Wang,
  • Anatoly A. Peshkov,
  • Ruwei Yao,
  • Muhammad Hasan,
  • Manzoor Zaman,
  • Chao Liu,
  • Stepan Kashtanov,
  • Olga P. Pereshivko and
  • Vsevolod A. Peshkov

Beilstein J. Org. Chem. 2020, 16, 1963–1973, doi:10.3762/bjoc.16.163

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  • structure of (S)-12e (slow enantiomer). Post-transformations of 2-oxo-aldehyde-derived Ugi adducts 8. Synthesis of 2-oxo-aldehyde-derived Ugi adducts. Asymmetric protocols for Passerini three-component reaction (P-3CR). Asymmetric protocols for Ugi four-component reaction (U-4CR) by Houk, Tan and co-workers
  • -component reaction (U-4CR) a carboxylic acid 1, an aldehyde 2, and an isocyanide 3 are complemented by a primary amine 5 that altogether undergo a condensation into a peptide-like adduct 6. These reactions are typically conducted in polar protic solvents such as methanol or water. Several examples of
  • stereocontrol was achieved with the aid of different Lewis acid promoters bearing chiral ligands, while the most recent and at the same time the most general procedure developed by Liu, Tan and co-workers relied on the stereoinduction by a chiral phosphoric acid (Table 1) [40]. In the standard Ugi four
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Published 11 Aug 2020

Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones

  • Valeria Nori,
  • Antonio Arcadi,
  • Armando Carlone,
  • Fabio Marinelli and
  • Marco Chiarini

Beilstein J. Org. Chem. 2020, 16, 1084–1091, doi:10.3762/bjoc.16.95

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  • palladium-catalyzed regioselective cascade cyclization of propargylamides/coupling with ArB(OH)2 in dioxane/water, to give trisubstituted arylidene-isoquinolinones [44] was published. However, the Ugi four-component reaction used to construct the starting building blocks was limited to the preparation of
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Published 20 May 2020

Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction

  • Yong Li,
  • Zheng Huang,
  • Jia Xu,
  • Yong Ding,
  • Dian-Yong Tang,
  • Jie Lei,
  • Hong-yu Li,
  • Zhong-Zhu Chen and
  • Zhi-Gang Xu

Beilstein J. Org. Chem. 2020, 16, 663–669, doi:10.3762/bjoc.16.63

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  • [35][36][37]. These new processes improved the overall efficiency with shorter reaction times and lower costs of synthetic preparations, and minimized the amount of waste generated. In recent years, we used the Ugi four-component reaction as a main tool to generate nitrogen-containing heterocycles [38
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Published 09 Apr 2020

Ultrasonic-assisted unusual four-component synthesis of 7-azolylamino-4,5,6,7-tetrahydroazolo[1,5-a]pyrimidines

  • Yana I. Sakhno,
  • Maryna V. Murlykina,
  • Oleksandr I. Zbruyev,
  • Anton V. Kozyryev,
  • Svetlana V. Shishkina,
  • Dmytro Sysoiev,
  • Vladimir I. Musatov,
  • Sergey M. Desenko and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2020, 16, 281–289, doi:10.3762/bjoc.16.27

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  • -pyrazole-4-carbonitrile with aromatic aldehydes and pyruvic acid or its esters under ultrasonication led to the formation of 4,5,6,7-tetrahydroazolo[1,5-a]pyrimidines 4a–u (Scheme 4) containing an azolylamino substituent in the 7-position via an unusual pseudo four-component reaction, rather than two
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Published 27 Feb 2020

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

  • Gerardo M. Ojeda,
  • Prabhat Ranjan,
  • Pavel Fedoseev,
  • Lisandra Amable,
  • Upendra K. Sharma,
  • Daniel G. Rivera and
  • Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

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  • prospect of the tetrazole hybridization strategy in drug discovery. Among the most versatile methods for obtaining tetrazoles are the Ugi-azide four-component reaction (Ugi-azide-4CR) [14][15][16] and the 1,3-dipolar cycloaddition of azides with (acyl)cyanides [17][18]. The Ugi-azide-4CR enables the
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Published 16 Oct 2019
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