Air-oxidized products of multi-component reactions between 3-amino-1,2,4-triazole, aromatic aldehydes and isonitriles

Parchinsky, Vladislav; Koleda, Vladimir V.; Shuvalova, Olga; Kravchenko, Dmitry V.; Krasavin, Mikhail

doi:10.1016/j.tetlet.2006.07.037

Cited by 28 publications

(10 citation statements)

References 8 publications

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“…All the solvents used in the GBB-3CR. ,26-28,30,39,45,51,54-56,61,66,68,74,75,78,87,96-100,103,108,110,118,120,123, 51 1:1 EtOH:H 2 O [165,180] 2125,126,128,130,136,141,142,150,153,154,156,[166][167][168]177,181,[183][184][185]187,188] …”

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confidence: 99%

The Groebke‐Blackburn‐Bienaymé Reaction

2019

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Imidazo[1,2‐a]pyridine is a well‐known scaffold in many marketed drugs, such as Zolpidem, Minodronic acid, Miroprofen and DS‐1 and it also serves as a broadly applied pharmacophore in drug discovery. The scaffold revoked a wave of interest when Groebke, Blackburn and Bienaymé reported independently a new three component reaction resulting in compounds with the imidazo[1,2‐a]‐heterocycles as a core structure. During the course of two decades the Groebke Blackburn Bienaymé (GBB‐3CR) reaction has emerged as a very important multicomponent reaction (MCR), resulting in over a hundred patents and a great number of publications in various fields of interest. Now two compounds derived from GBB‐3CR chemistry received FDA approval. To celebrate the first 20 years of GBB‐chemistry, we present an overview of the chemistry of the GBB‐3CR, including an analysis of each of the three starting material classes, solvents and catalysts. Additionally, a list of patents and their applications and a more in‐depth summary of the biological targets that were addressed, including structural biology analysis, is given.

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confidence: 99%

The Groebke‐Blackburn‐Bienaymé Reaction

2019

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“…Multicomponent reactions are the reactions in which sequential assembling of two or more starting materials in a single reaction vessel forms the final product. Multicomponent reactions are the useful platform for the synthesis of simple to complex heterocyclic molecules in minimum number of steps to get diversity‐oriented products and having much important in chemical as well as biological aspects . The advantages of MCRs are atom economy, simplicity, and time‐saving process .…”

Section: Introductionmentioning

confidence: 99%

Multicomponent Efficient Synthesis of New [1,2,4]Triazolo[3,4]thiadiazines

Sujatha

Vedula

2019

Journal of Heterocyclic Chem

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A series of novel triazolo thiadiazines were synthesized by a simple, highly efficient, one‐pot pseudo four component approach involving the condensation of 4‐amino‐5‐hydrazinyl‐4H‐1,2,4‐triazole‐3‐thiol (1), aromatic aldehydes (2), and various phenacyl bromides (3) with good yields. The structures of compounds were confirmed by analytical and spectral (IR, 1H NMR, 13C NMR) data.

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“…In fact, the development of simple, elegant and facile methodologies for the synthesis of heterocycles is one of the most important aspects in organic synthesis. Multicomponent reactions (MCRs), reactions involving at least three starting materials in a one-pot reaction, have brought some of the most efficient syntheses of heterocycles (Adib et al, 2011;Schwerkoske et al, 2005;Rousseau et al, 2007;Parchinsky et al, 2006). Isocyanide-based MCRs (IMCRs), such as the Passerini, the Ugi reactions and the GroebkeBlackburn-Bienaymé, are very useful for the diversity oriented synthesis of collections of compounds (El Kaim and Grimaud, 2009;Sadjadi and Heravi, 2011;Khan et al, 2012; NMR and 13 C NMR were recorded in solution in CDCl 3 on a Bruker spectrometer ( 1 H at 400 MHz, 13 C at 100 MHz) and high-resolution mass spectra (HRMS).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial and antioxidant activities of imidazotriazoles and new multicomponent reaction toward 5-amino-1-phenyl[1,2,4]triazole derivatives

Aouali

Mhalla²,

Allouche³

et al. 2015

Med Chem Res

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International audienceThe Groebke-type multicomponent reaction between 5-amino-1,2,4-triazole derivatives, aromatic aldehydes and isocyanides has been studied from the viewpoint of convenient generation of combinatorial arrays of imidazo[2,1-c][1,2,4]triazoles. The reaction is considered to proceed via the formation of an iminium species followed by a [4 + 1] cyclo addition with the isocyanides using scandium triflate as a Lewis acid catalyst. The synthesized imidazo[2,1-c][1,2,4]triazole derivatives 4a, 4b, 4f and 4g were screened for antibacterial, antifungal and antioxidant activities. Among the tested compounds, 4b followed by 4f showed potent antibacterial and antifungal activities. All of these compounds were also screened in vitro for the antioxidant activity using DPPH assay. Most of them have shown very significant antioxidant activity

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Air-oxidized products of multi-component reactions between 3-amino-1,2,4-triazole, aromatic aldehydes and isonitriles

Cited by 28 publications

References 8 publications

The Groebke‐Blackburn‐Bienaymé Reaction

The Groebke‐Blackburn‐Bienaymé Reaction

Multicomponent Efficient Synthesis of New [1,2,4]Triazolo[3,4]thiadiazines

Synthesis, antimicrobial and antioxidant activities of imidazotriazoles and new multicomponent reaction toward 5-amino-1-phenyl[1,2,4]triazole derivatives

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