Preparation and characterization of a novel DABCO based tetra cationic ionic liquid as a reusable catalyst for the multi-component synthesis of 2H-indazolo[2,1-b]phthalazine-trione and [1,2,4]triazoloquinazolinone derivatives under solvent-free condition

Safari, Niloufar; Shirini, Farhad; Tajik, Hassan

doi:10.1016/j.molstruc.2019.127143

Cited by 17 publications

(6 citation statements)

References 43 publications

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“…Several articles address different DABCO-based IL to promote similar three-component heterocyclizations; [127][128][129][130] the last article by Seyyedi et al also contains a comparison of the efficiency of DABCO-based IL (reaction times, yields, TON) with other types of catalysts in similar reactions, and the authors pointed out that their new catalysts have advantages in terms of simplicity of operation, high yields, formation of byproducts, and ease of processing because no column chromatography is required for isolation.…”

Section: Reactions Of Aminotriazolesmentioning

confidence: 99%

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Desenko,

Gorobets,

Lipson

et al. 2023

The Chemical Record

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Dihydroazolopyrimidines are an important class of heterocycles that are isosteric to natural purines and are therefore of great interest primarily as drug‐like molecules. In contrast to the heteroaromatic analogs, synthetic approaches to these compounds were developed much later, and their chemical properties and biological activity have not been studied in detail until recently. In the review, different ways to build dihydroazolopyrimidine systems from different building blocks are described – via the initial formation of a partially hydrogenated pyrimidine ring or an azole ring, as well as a one‐pot assembly of azole and azine fragments. Special attention is given to modern approaches: multicomponent reactions, green chemistry, and the use of non‐classical activation methods. Information on the chemical properties of dihydroazolopyrimidines and the prospects for their use in the design of drugs of various profiles are also summarized in this review.

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Section: Reactions Of Aminotriazolesmentioning

confidence: 99%

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Desenko,

Gorobets,

Lipson

et al. 2023

The Chemical Record

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“…A common way for the preparation of these important target molecules is the multi-component reaction of aldehydes with 3-amino-1,2,4-triazole or 2-aminobenzimidazole, and a β-diketone in the presence of a variety of catalysts. 31–36…”

Section: Introductionmentioning

confidence: 99%

“…A common way for the preparation of these important target molecules is the multi-component reaction of aldehydes with 3-amino-1,2,4triazole or 2-aminobenzimidazole, and a b-diketone in the presence of a variety of catalysts. [31][32][33][34][35][36] Although the use of these catalysts causes an improvement, harsh reaction conditions, long reaction times, expensive reagents, low yields of the products and the use of a large quantity of volatile organic solvents are important limitations associated with these methods. Furthermore, during most of the existing methods, the catalyst cannot be recovered or reused.…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of triazolo/benzazolo[2,1-b]quinazolinone derivatives catalyzed by a new deep eutectic mixture based on glucose, pregabalin and urea

Rahro,

Shirini,

Gilani

2023

RSC Adv.

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“…Recently presented routes for the synthesis of quaternary salts of DABCO, both monoalkylated − and dialkylated, , have made DABCO an unexplored source of new ionic liquids (DABCO ILs) in the field of their utilization. Thus, ionic liquids containing a DABCO cation in their structure, have found application as electrolytes for electrochemical, , catalysts, − surfactants. − They were used in synthesis of functionalized magnetic nanoparticles, while deep eutectic solvents, DABCO ILs, were used as the reaction medium . In biology, they can be used in peptide coupling or as potent alkaline phosphatase inhibitors .…”

Section: Introductionmentioning

confidence: 99%

Mono N-Alkylated DABCO-Based Ionic Liquids and Their Application as Latent Curing Agents for Epoxy Resins

Zielinski

Szpecht

Hinc

et al. 2021

ACS Appl. Polym. Mater.

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Research on ionic liquids is constantly providing information on their new and more advanced applications. Undoubtedly, the use of latent curing agents for epoxy resins is one of the most interesting applications of this group of compounds. In this work, a detailed description of the synthesis and physicochemical studies of DABCO-based (1,4-diazabicylo[2.2.2]octane) ionic liquids is presented. Their most valuable feature is that they can be latent curing agents for polymerization of epoxy resins, which in turn can be used, when combined with fibers, as composites with special, new properties. The research includes detailed discussion of synthesis of new DABCO-ILs, focusing on obtaining pure compounds and expanding current knowledge on the subject. Thermal (DSC) and chromatographic (IC) properties have been discussed for all presented salts. Furthermore, ionic liquids with dicyanamide and triflate anion have demonstrated the ability to initiate polymerization of epoxy resins. Subsequently, all mixtures were cured into cubical shape and were subjected to the Shore hardness test (SHT). The main advantages of the obtained ILs are (i) the ability to store ionic liquids/epoxy resin mixture for prolonged periods of time without deterioration of curing properties and (ii) a significantly lower quantity of ionic liquids used in the process of curing epoxy resins.

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Preparation and characterization of a novel DABCO based tetra cationic ionic liquid as a reusable catalyst for the multi-component synthesis of 2H-indazolo[2,1-b]phthalazine-trione and [1,2,4]triazoloquinazolinone derivatives under solvent-free condition

Cited by 17 publications

References 43 publications

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Facile synthesis of triazolo/benzazolo[2,1-b]quinazolinone derivatives catalyzed by a new deep eutectic mixture based on glucose, pregabalin and urea

Mono N-Alkylated DABCO-Based Ionic Liquids and Their Application as Latent Curing Agents for Epoxy Resins

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