Recent advances in the synthesis of fused heterocycles with new skeletons via alkyne cyclization

Balcı, Metin

doi:10.1016/j.tetlet.2020.151994

Cited by 14 publications

(8 citation statements)

References 47 publications

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“…The 3-cyano-2-aminothiophenes are key active intermediates and building blocks for various heterocyclic products. [17][18][19][20] So far, different synthetic routes towards 3-cyano-2-aminothiophenes have been reported. [21][22][23] However, the presence of both nitrile and secondary amine functions in the same molecule is efficiently used in producing hetero fused thiénopsmidines compounds.…”

Section: Synthesis Of 2-aminothiophenes 1a-bmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…As a result, synthetic chemists are very interested in redesigning the traditional syntheses in order to achieve cleaner technologies and better yields, as well as obtaining new skeletons and studying their activities. [17] Hoping that they may design more selective and safer new condensed heterocyclic compounds possessing latent functional substituent. [18] The heterocyclic annulated pyrimidine, such as thieno [2, 3-b] pyrimidine derivatives, occupy a special place and have frequently attracted a great deal of interest of chemists researchers.…”

Section: Introductionmentioning

confidence: 99%

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Green catalyst access to thieno [2, 3‐b] pyridines derivatives

Mehaoui

Boudjema

Kibou

et al. 2023

Journal of Heterocyclic Chem

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The current study focuses on the use of tungstovanadophosphoric heteropoly acid H4PW11VO40·8 H2O (PVW) with Keggin structure and supported on acid activated (PVW/AAM) in the synthesis of new substituted Thieno [2, 3‐b] pyridines derivatives. The suggested protocol is an easy, environmentally friendly method for synthesis of thieno [2,3‐b] pyrimidine derivatives obtained from 3‐cyano‐2‐aminothiophene as building blocks under solvent‐free reactions condition. Excellent product yields of substituted Thieno [2, 3‐b] pyridine derivatives (60%–97%) were achieved using the synthesized PVW/AAM catalyst. The current processes provide benefits including a quicker reaction time, an easy set‐up, and high yields. Spectroscopic data (IR, +H and 13C NMR spectra) have revealed the structural details of all target compounds. The catalyst was characterized by X‐ray diffraction, BET and Fourier‐transformed infrared spectroscopy. X‐ray diffraction showed that PVW was correctly incorporated on an acid activated clays support. In comparison to the parent, Tungstovanadophosphoric acid, the PVW supported acid activated montmorillonite provided increased Lewis acid site density, redox characteristics, and surface area. Due to the recoverability of heterogeneous catalysts, the heterogenization of homogeneous catalysts is very attractive. In addition, the produced catalysts can be simply removed from the reaction system and reused six times more effectively.

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Section: Synthesis Of 2-aminothiophenes 1a-bmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Green catalyst access to thieno [2, 3‐b] pyridines derivatives

Mehaoui

Boudjema

Kibou

et al. 2023

Journal of Heterocyclic Chem

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“…On the other hand, heterocyclic compounds are important because they have wide applications in pharmaceutical chemistry and in the fine chemical industry, which is evidenced in that more than 90% of new drugs contain heterocyclic rings, and this generates great interest in synthetic chemists for redesigning the classic syntheses towards cleaner technologies and better yields, as well as obtaining new skeletons and studying their activities [25].…”

Section: Introductionmentioning

confidence: 99%

Recent Applications of Heteropolyacids and Related Compounds in Heterocycle Synthesis. Contributions between 2010 and 2020

et al. 2021

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Over the past two decades, polyoxometalates (POM) have received considerable attention as solid catalysts, due to their unique physicochemical characteristics, since, first, they have very strong Bronsted acidity, approaching the region of a superacid, and second, they are efficient oxidizers that exhibit rapid redox transformations under fairly mild conditions. Their structural mobility is also highlighted, since they are complex molecules that can be modified by changing their structure or the elements that compose them to model their size, charge density, redox potentials, acidity, and solubility. Finally, they can be used in substoichiometric amounts and reused without an appreciable loss of catalytic activity, all of which postulate them as versatile, economic and ecological catalysts. Therefore, in 2009, we wrote a review article highlighting the great variety of organic reactions, mainly in the area of the synthesis of bioactive heterocycles in which they can be used, and this new review completes that article with the contributions made in the same area for the period 2010 to 2020. The synthesized heterocycles to be covered include pyrimidines, pyridines, pyrroles, indoles, chromenes, xanthenes, pyrans, azlactones, azoles, diazines, azepines, flavones, and formylchromones, among others.

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“…To date, reported approaches to triazepine compounds mainly focused on decarboxylative [4 + 3] annulation of benzoxazinanones with azomethine imines (Figure a, 1), alkylation strategies employing hydrazines and hydroxylamines (Figure a, 2), and metal-promoted intramolecular coupling of tributylstannyl hydrazones (Figure a, 3) . Nevertheless, these reported strategies for triazepines either need harsh reaction conditions or involve multiple steps and complex starting materials with a limited substrate scope.…”

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confidence: 99%

Radical N₂-Retention Cyclizations of Aryl Diazoniums: Access to 7/8/9-Membered Heterocycles

Ke,

Jia,

Tong

et al. 2024

Org. Lett.

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We report herein a modular approach to synthesizing diverse functionalized 7/8/9-membered poly-N-containing heterocycles via oxidative radical N 2 -retention cyclizations of allylic aryl diazonium salts using CF 3 SO 2 Na as a CF 3 radical source. A range of trifluoromethylated benzotriazepines, benzotriazocines, and benzotriazonines were obtained in moderate to good yields. This transition-metal-free protocol demonstrates atom economy, safe conditions, broad functional group tolerance, and availability of readily accessible reagents.

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Recent advances in the synthesis of fused heterocycles with new skeletons via alkyne cyclization

Cited by 14 publications

References 47 publications

Green catalyst access to thieno [2, 3‐b] pyridines derivatives

Green catalyst access to thieno [2, 3‐b] pyridines derivatives

Recent Applications of Heteropolyacids and Related Compounds in Heterocycle Synthesis. Contributions between 2010 and 2020

Radical N₂-Retention Cyclizations of Aryl Diazoniums: Access to 7/8/9-Membered Heterocycles

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Recent advances in the synthesis of fused heterocycles with new skeletons via alkyne cyclization

Cited by 14 publications

References 47 publications

Green catalyst access to thieno [2, 3‐b] pyridines derivatives

Green catalyst access to thieno [2, 3‐b] pyridines derivatives

Recent Applications of Heteropolyacids and Related Compounds in Heterocycle Synthesis. Contributions between 2010 and 2020

Radical N2-Retention Cyclizations of Aryl Diazoniums: Access to 7/8/9-Membered Heterocycles

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Radical N₂-Retention Cyclizations of Aryl Diazoniums: Access to 7/8/9-Membered Heterocycles